Discovery and development of antiandrogens

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have great effect on the antagonist activities of current small molecule antiandrogens and make them less efficient in blocking AR function via indirect modulation from inside of the LBP. Recent studies with circulating tumor cells, suggest that the mutation frequency is higher than previously assumed based on tumor

892:, isolated from marine sponges that effectively inhibits AR N-terminal domain-activated reporter gene transcription, see figure 8. The evidence presented was not sufficient to support the conclusion that sintokamide A directly inhibits the function of AR NTD, and the mechanism of action needs further investigation. 685:, where the binding affinity of sulfone was 3-fold higher than that of sulfide. These results indicate that substituents of the B-ring largely determine the effect of the X-linkage in AR binding. Researchers have proposed that the tertiary hydroxyl group is involved in direct interaction with AR because when an 876:

Functionally, AR NTD plays the primary role in regulating target gene transcription activation and mediating various receptor-protein and intra-receptor N-terminal and C-terminal interactions. Therefore, modulation of NTD function is considered an efficient strategy to target AR action. Among various

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expresses AR with a T877A point mutation that causes proliferation in the presence of the antiandrogens hydroxyflutamide and cyproterone acetate. This mutation has also been discovered in patients with antiandrogen withdrawal syndrome being treated with these compounds. In another study, bicalutamide

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in the LBD that alter ligand specificity and/or functional activity exist and are thought to contribute to the conversion of some AR antagonists into agonists, which explains the paradoxical temporary improvement sometimes observed in patients when antiandrogen therapy is stopped. These mutations can

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assays have shown them both to be selective AR agonists and that they inhibit proliferation of several prostate cancer cell lines. Atraric acid also hinders extracellular matrix invasion and both compounds are able to prevent androgen-induced nuclear translocation of the AR. More potent derivatives

812:

Steroid receptors have similarities in gene sequences and protein structures, leading often to functional crosstalk among steroid receptors. One of the criteria for AR NTD antagonists is to achieve high degree of specificity for the AR. It is though important to realize that AR specificity does not

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Antagonists of the N-terminal domain (NTD) of the AR have been proposed to overcome the limitations of current antiandrogens regarding mutant ARs, by directly blocking AR function from protein surface, outside of the LBP. This direct blockade is thought to provide a more efficient strategy to avoid

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secretion. It thereby reduces androgen, estrogen and LH levels. Cyproterone acetate acts both directly as an antiandrogen in prostate cancer cells and also functions to indirectly decrease serum testosterone levels. The latter causes the limitations of cyproterone acetate, which are central effects

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Cyproterone acetate is a 6-chloro-1,2-methylene derivative of 17α-acetoxyprogesterone. It shows major antiandrogenic activity together with androgenic activities. Cyproterone acetate displays high affinity for AR in rats which increases when the 1,2-methylene group is removed from the compound. If

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For hydroxyflutamide, a group of compounds that differed in the aromatic ring did not bind to the AR. This suggests that the bisubstitution in the hydroxyflutamide ring is essential for high AR binding affinity. It has also been demonstrated that hydroxyflutamide requires the strong hydrogen bond

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ring of W741. In non-mutant AR, the presence of the W741 side chain probably forces bicalutamide to protrude out thus precluding the active position of H12 on the AR receptor. However, hydroxyflutamide worked as an antagonist for W741 mutant ARs. This concurs with the theory that flutamide and

877:

functional domains in different nuclear receptors, NTD is the least conserved and so could maybe become the best target site for NTD antagonists to achieve AR specificity. However the structural features of the NTD are undetermined due to a high degree of flexibility in its conformation. Both

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to the N3 atom, the receptor binding and biological activity of the compound increases 100 times that of NSAAs. Also the compound does not bind to other steroid receptors. If a methyl group is changed for the butylalcohol group, the compound shows 3 and 10 times more antiandrogenic activity

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is an arylpropionamide analog, seen in figure 6. It has replaced flutamide and nilutamide as the first choice antiandrogen for prostate cancer treatment. Bicalutamide is not as hepatotoxic as flutamide and nilutamide and has a longer half-life, of 6 days in humans, that allows once a day

743:

and/or signal transduction pathways. This antiandrogen resistance may also be linked to the relative weakness of current antiandrogens as they have an affinity 50 times or more lower than that of DHT for the AR. This may also explain why compensatory AR overexpression is often observed.

739:(AWS) and is one of the major drawbacks of existing antiandrogens. AWS is defined as tumor regression or symptomatic relief observed upon discontinuation of the antiandrogen therapy. The mechanism for this is not fully understood but current theories include alterations of the AR gene, 582: 904:(SARMs) has been proposed as a novel approach for the treatment of prostate cancer. These ligands should behave as antagonists in the prostate with either no activity or agonist activity in other target tissues, so as to have little or no effects in the anabolic tissues or 594: 388:

Flutamide became the first NSAA to be tested clinically. Later the NSAAs bicalutamide and nilutamide were developed. The alleged advantages of these compounds were that they did not affect libido or potency like the other centrally acting compounds under development,

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Sadar MD, Williams DE, Mawji NR, Patrick BO, Wikanta T, Chasanah E, et al. (November 2008). "Sintokamides A to E, chlorinated peptides from the sponge Dysidea sp. that inhibit transactivation of the N-terminus of the androgen receptor in prostate cancer cells".

606: 2382:

Hamann LG, Higuchi RI, Zhi L, Edwards JP, Wang XN, Marschke KB, et al. (February 1998). "Synthesis and biological activity of a novel series of nonsteroidal, peripherally selective androgen receptor antagonists derived from 1,2-dihydropyridonoquinolines".

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Kawata H, Arai S, Nakagawa T, Ishikura N, Nishimoto A, Yoshino H, et al. (September 2011). "Biological properties of androgen receptor pure antagonist for treatment of castration-resistant prostate cancer: optimization from lead compound to CH5137291".

856:

Even though small molecule antagonists and NTD antagonist targeting AF2 surface differ in binding sites, they both inhibit AR function by disrupting AF2 function. Therefore, mechanistically, these NTD antagonists may also be classified as ‘AF2 antagonists’.

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functions of the imidazolinedione was identified, it is much less susceptible to hepatic metabolism than the amide bond in hydroxuflutamide. This results in a longer half-life of nilutamide in humans of 2 days. Nevertheless, the nitro anion-free

366:

Cyproterone acetate was developed to overcome this problem. It is formed by adding an acetate group to cyproterone, see figure 3. Cyproterone acetate has a dual mode of action as it competes directly with DHT for binding to AR, but also inhibits

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administration at lower dosage. Bicalutamide shares the amide bond structure with flutamide. Even so, the amide bond hydrolysis was discovered in rats, not in humans, which could explain the prolonged half life of bicalutamide in humans.

384:

gave pharmaceutical companies the incentive to search for alternative, "pure" NSAAs that would not have these side effects. Pure antiandrogens block the androgen receptor without exerting any agonistic or any other hormonal activity.

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Williams L, Thompson LD, Seethala RR, Weinreb I, Assaad AM, Tuluc M, et al. (May 2015). "Salivary duct carcinoma: the predominance of apocrine morphology, prevalence of histologic variants, and androgen receptor expression".

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Yoshino H, Sato H, Shiraishi T, Tachibana K, Emura T, Honma A, et al. (December 2010). "Design and synthesis of an androgen receptor pure antagonist (CH5137291) for the treatment of castration-resistant prostate cancer".

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Cyproterone is a steroidal antiandrogen that competitively inhibits the binding of testosterone or DHT to AR. Cyproterone binds to ARs that are expressed by prostate cancer cells as well as to the AR that are expressed in the

131:

in men, which could be reversed by re-administration of androgen. In 1941 Huggins treated prostate cancer patients by androgen ablation with either castration or estrogen therapy; the beneficial effect of androgen ablation on

730:

or antiandrogen therapy. This suggests that long term use of these antiandrogens during prostate cancer can lead to the development of androgen-independent prostate cancer cells or the ability of adrenal androgens to support

853:, and X = any amino acid residue), whereas other nuclear receptors have a highly similar binding mechanism for ‘LxxLL’ type of binding motifs. This provides a unique opportunity for the development of AR-specific peptides. 782:

treatment of LNCaP cells resulted in two LBD mutations, W741L and W741C, causing bicalutamide to acquire agonist activity to both mutant ARs. The W741L mutation generates additional space such that the sulfonyl-linked

635:

ring structure. The structures can be seen in figure 7, where the anilide ring is coloured red. These three compounds require an electron-deficient aromatic ring for efficient AR binding. Replacing the anilide with an

2335:

Battmann T, Branche C, Bouchoux F, Cerede E, Philibert D, Goubet F, et al. (January 1998). "Pharmacological profile of RU 58642, a potent systemic antiandrogen for the treatment of androgen-dependent disorders".

692:

Nilutamide has very low affinity for AR when tested on castrated rat prostate. Modifications such as replacing the N3 atom with oxygen has little effect on affinity of the compound for prostate AR. By replacing the

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that may directly block the AF2 in AR LBD from protein surface. Even in bound mutant AR, NTD antagonists would be able to block the AF2 function via direct surface interaction, regardless of the ligand bound.

2070:

Suzuki H, Akakura K, Komiya A, Aida S, Akimoto S, Shimazaki J (September 1996). "Codon 877 mutation in the androgen receptor gene in advanced prostate cancer: relation to antiandrogen withdrawal syndrome".

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High binding affinity to AR. Unlike bicalutamide, it does not promote nuclear translocation and impairs both DNA binding to androgen response elements and recruitment of coactivators. Induces tumor cell

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Small molecule antiandrogens that are available today have undesirable side effects caused by complete, non-selective inhibition of AR action. To minimize these side effects, a new class of tissue

2999: 359:(LH) serum levels. This rise in LH levels causes an increase in serum testosterone levels and ultimately diminishes the ability of cyproterone to compete for AR binding and to block androgenic 3084: 3029: 2915: 338:

might be crucial for the agonist or antagonist activity of AR ligands. Binding of DNA is also required for AR-regulated gene expression, also known as classic genomic gene function of AR.

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Hara T, Miyazaki J, Araki H, Yamaoka M, Kanzaki N, Kusaka M, et al. (January 2003). "Novel mutations of androgen receptor: a possible mechanism of bicalutamide withdrawal syndrome".

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than cyproterone acetate. Hydroxyflutamide has relatively low binding affinity to AR and is therefore generally used at high doses in order to achieve complete AR blockage in therapy.

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Foster WR, Car BD, Shi H, Levesque PC, Obermeier MT, Gan J, et al. (April 2011). "Drug safety is a barrier to the discovery and development of new androgen receptor antagonists".

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Antiandrogens that are currently on the market are particularly useful for the treatment of prostate cancer during the early stages. However, prostate cancer often progresses to a

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activation function 2 (AF2). AF1 is ligand-independent and plays the primary role in target gene transactivation. The AF2 is a ligand-dependent and only shows limited function.

2984: 2782: 3034: 677:. The sulfides showed in most cases at least 2-fold higher binding affinity than corresponding sulfones. However, this relationship was reversed when the R3 group was NHSO 551:. (R)-bicalutamide has an almost fourfold higher affinity for the prostate AR than hydroxyflutamide and has a better side-effect profile compared to other antiandrogens. 4647: 2989: 2964: 915:. 5-alpha reductase is only expressed in specific tissues and could therefore be a unique contributor to tissue selectivity. Specific inhibition of the type 2 enzyme by 791:

nilutamide antagonize AR through the mechanism of “passive antagonism”, as they are of a more modest size then bicalutamide. These drugs may therefore be effective as a

232:

androgens are mainly testosterone and DHT. AR is expressed in cells of a wide range of tissues, throughout the entire body, beyond primary and secondary sexual organs.

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AR activation requires the formation of a functional activation function 2 (AF2) region in AR LBD that mediates the interactions between AR and various transcription

3059: 3054: 3098: 2744:"The natural compounds atraric acid and N-butylbenzene-sulfonamide as antagonists of the human androgen receptor and inhibitors of prostate cancer cell growth" 2699:

Schleich S, Papaioannou M, Baniahmad A, Matusch R (July 2006). "Extracts from Pygeum africanum and other ethnobotanical species with antiandrogenic activity".

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or overcome abnormal AR action during AWS, as well as allowing for more flexibility in structural modification without the space limitations of the rigid LBP.

3019: 3004: 1060:

Orally available, strong antagonistic activity in the prostate without raising plasma levels of LH and testosterone. Seems to be more potent than LG120907.

2939: 2930: 2910: 60:. Antiandrogens are mainly used for the treatment of prostate diseases. Research from 2010 suggests that ARs could be linked to the disease progression of 4208: 4177: 543:

carbon in its structure (labeled with an asterisk in figure 6), which is connected to the hydroxyl and methyl groups . It is therefore administered as a

6462: 3124: 501:

in humans, especially when using relatively high dosage employed for androgen blockage. Nilutamide causes side-effects which limit its usage, such as

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Poyet P, Labrie F (October 1985). "Comparison of the antiandrogenic/androgenic activities of flutamide, cyproterone acetate and megestrol acetate".

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instead of a nitro group like flutamide and nilutamide. This change in groups avoids the nitro reduction observed in nilutamide. Bicalutamide has a

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co-factors (including co-activators and co-repressors) and general transcriptional machinery further ensures the transactivation of AR-regulated

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ring of these drugs have not shown higher binding to the AR receptor, compared to compounds which have a chloro or trifluoromethyl group at the

2211: 908:(CNS). However discovering this new class of ligands might be challenging because the molecular mechanism of AR action is not well understood. 2043: 6457: 5409: 4201: 4167: 4134: 3049: 2835: 1769: 901: 137: 911:

Several mechanisms have been proposed to achieve this tissue selectivity of AR ligands. The most definitive evidence exists for the role of

6452: 4448: 4172: 3117: 3039: 1190:

Completely inhibits AR-mediated transactivation and proliferation of the CRPC xenograft model LNCaP-BC2, which is bicalutamide-resistant.

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donor ability of the tertiary hydroxyl group and fixed conformers involved in intramolecular hydrogen binding, to bind effectively to AR.

5204: 5199: 4797: 4182: 3392: 334:. All these complicated processes are initiated by the ligand-induced conformational changes in the LBD. Ligand specific recruitment of 4637: 2084: 143:

It became evident that androgen ablation alone was insuffient to cure patients with advanced prostate cancer. In the late 1960s, the

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Singh SM, Gauthier S, Labrie F (February 2000). "Androgen receptor antagonists (antiandrogens): structure-activity relationships".

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analysis suggest that AR NTD is highly disordered under native conditions, making it a difficult target for drug discovery.

573:

the binding slightly decreases, whereas further removal of the C6 double bond modifies the binding kinetics, see figure 7.

4308: 4288: 3910: 3722: 2529:"Phase I dose-escalation study of the novel antiandrogen BMS-641988 in patients with castration-resistant prostate cancer" 61: 481:

analog of flutamide, as seen in figure 5. Nilutamide is eliminated exclusively by metabolism, mainly by reduction of the

6447: 6417: 5982: 5276: 5137: 4664: 4490: 4303: 4079: 3671: 421: 168: 41: 5354: 4716: 4318: 4151: 4087: 3612: 3366: 3191: 2883: 653: 536: 393:(LHRH) agonists and cyproterone acetate. But this theory did not prove to be true. These NSAAs eventually crossed the 5339: 5334: 5142: 1574:

Haendler B, Cleve A (April 2012). "Recent developments in antiandrogens and selective androgen receptor modulators".

5644: 4876: 4495: 4037: 3271: 5986: 4706: 4527: 4485: 4433: 4379: 3863: 3852: 3246: 3221: 2828: 1182: 941:

The development status of other small molecule antiandrogens undergoing research in 2011 can be seen in table 1.

335: 84: 4273: 454:. By reversing the stimulatory effect of DHT on ventral prostate weight, flutamide is approximately 2-fold more 6493: 6149: 5296: 5265: 4985: 4926: 4659: 4437: 4313: 4263: 3442: 3267: 1239: 984: 926:

Inactive parent compounds that are activated by type 2 5-alpha reductase in the prostate to form antiandrogens.

327: 323: 303: 205: 5634: 5369: 5349: 4517: 1242:

are natural compounds with antiandrogen properties which have been purified from the bark of the African tree

394: 95:

use despite the fact that a very large variety of antiandrogen compounds have been discovered and researched.

2011:"Detection of androgen receptor mutations in circulating tumor cells in castration-resistant prostate cancer" 6498: 6165: 5092: 4836: 4746: 4654: 4554: 4542: 4443: 4139: 4029: 3358: 3313: 3303: 3263: 3251: 2873: 826: 221: 116: 1966:

Miyamoto H, Rahman MM, Chang C (January 2004). "Molecular basis for the antiandrogen withdrawal syndrome".

922:

Several approaches might make use of the potential tissue-specific conversion to develop SARMs, including:

547:. Post-approval investigation revealed that its antiandrogenic activity resides almost entirely in the (R)- 6488: 6157: 5629: 5292: 4931: 4841: 4802: 4674: 4522: 4391: 4340: 3447: 3353: 3259: 3255: 3196: 1093: 1052: 1011: 905: 455: 432:

product, 3-trifluoromethyl-4-nitroaniline. Hydroxyflutamide is a more potent AR antagonist than flutamide

49: 1251:

are currently being synthesized in hope of improving the pharmacological profile of these two compounds.

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in a patient. Led to the findings that several antiandrogens produce off-target antagonist binding to

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Gucalp A, Traina TA (Jan–Feb 2010). "Triple-negative breast cancer: role of the androgen receptor".

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to the nucleus. The translocated receptor then binds to the androgen-response elements (ARE) on the

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of the androgen responsive gene, a consensus sequence located either upstream or downstream of the

270:

Two functions have been identified in AR that have critical roles in the regulation of target gene

160: 33: 21: 5535: 5525: 5968: 5209: 5072: 5032: 5010: 4943: 4846: 4819: 4787: 4620: 4510: 4362: 4227: 4021: 3983: 3452: 3387: 3343: 3333: 3308: 3236: 3211: 2774: 2724: 2645: 2601: 2527:

Rathkopf D, Liu G, Carducci MA, Eisenberger MA, Anand A, Morris MJ, et al. (February 2011).

2361: 2096: 1991: 1894: 1599: 1500: 1457: 932:

AR agonists that are converted to antiandrogens only by type 2 5-alpha reductase in the prostate.

882: 319: 291: 257: 6009: 6004: 5789: 5565: 5555: 1157:

Showed increased potency compared to bicalutamide. Phase I trial was discontinued because of an

6308: 6243: 6238: 6188: 6019: 5933: 5545: 2288:"Expanding the therapeutic use of androgens via selective androgen receptor modulators (SARMs)" 1170: 6303: 6223: 6178: 6129: 5953: 5938: 5869: 5839: 5799: 5664: 5580: 5490: 5440: 5359: 5162: 5067: 4886: 4603: 4465: 4374: 4357: 4325: 4278: 4235: 4224: 4091: 3915: 3772: 3762: 3700: 3206: 3172: 2766: 2716: 2681: 2637: 2593: 2558: 2509: 2460: 2400: 2353: 2317: 2268: 2189: 2130: 2088: 2035: 1983: 1948: 1886: 1851: 1816: 1765: 1729: 1661: 1591: 1541: 1492: 1449: 1413: 1363: 1323: 1158: 912: 689:

group is introduced to that hydroxyl moiety, the receptor binding affinity greatly decreases.

447: 425: 417: 352: 315: 213: 188: 144: 25: 5769: 5764: 5754: 5595: 5425: 260:(DBD) which recognises and binds to androgen response elements (ARE) in target gene sequence. 6298: 6119: 6109: 6089: 5470: 5374: 5037: 4901: 4460: 4298: 4258: 4033: 3964: 3287: 2944: 2868: 2758: 2708: 2673: 2629: 2585: 2548: 2540: 2499: 2491: 2450: 2442: 2392: 2345: 2307: 2299: 2260: 2179: 2169: 2080: 2025: 1975: 1938: 1930: 1878: 1843: 1806: 1798: 1719: 1711: 1653: 1583: 1531: 1484: 1441: 1405: 1355: 1313: 1305: 1215: 740: 209: 148: 2480:"Antitumour activity of MDV3100 in castration-resistant prostate cancer: a phase 1-2 study" 2423:"Development of a second-generation antiandrogen for treatment of advanced prostate cancer" 1040: 770: 766: 762: 397:, like cyproterone acetate, leading to a subsequent increase in serum testosterone levels. 6034: 5919: 5774: 5460: 5445: 5112: 5087: 4938: 4891: 4701: 4561: 4057: 3622: 3532: 3417: 2478:

Scher HI, Beer TM, Higano CS, Anand A, Taplin ME, Efstathiou E, et al. (April 2010).

1243: 723: 544: 420:

with pure antiandrogenic properties, seen in figure 4. It is completely absorbed from the

331: 311: 271: 104: 57: 37: 2212:"Functional and structural analysis of androgen receptors for anti-cancer drug discovery" 2438: 2165: 64:

and salivary duct carcinoma and that antiandrogens can potentially be used to treat it.

5879: 5704: 5679: 5307: 5283: 5256: 5219: 5152: 5077: 4980: 4765: 4736: 4593: 4536: 4475: 4470: 4145: 4041: 4003: 3991: 3950: 3787: 3596: 3588: 3580: 3552: 3537: 3482: 3298: 2878: 2858: 2553: 2528: 2504: 2479: 2455: 2422: 2312: 2287: 2184: 2149: 1943: 1918: 1811: 1786: 1724: 1699: 1318: 1293: 1162: 1151: 845:. ARs seem to have a distinct preference for ‘FxxLF’ type of binding motifs (where F = 842: 498: 485: 88: 68: 2495: 2349: 6482: 6288: 6233: 6208: 5784: 5182: 5082: 4293: 3522: 2728: 1917:

Yin D, He Y, Perera MA, Hong SS, Marhefka C, Stourman N, et al. (January 2003).

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gives weakly active compounds, which can be attributed to the lack of intramolecular

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and sexual potency. Several reports also state that cyproterone acetate causes liver

307: 45: 2778: 2649: 2605: 2100: 1898: 1603: 1461: 581: 263:

Ligand binding domain (LBD) which is responsible for ligand recognition and binding.

36:(DHT). Antiandrogens are important for men with hormonally responsive diseases like 6427: 6283: 6213: 6114: 6104: 6069: 6039: 5973: 5948: 5899: 5854: 5819: 5794: 5739: 5694: 5530: 5312: 5229: 5117: 5047: 5022: 4970: 4960: 4906: 4753: 4686: 4571: 4566: 4549: 4500: 4047: 3935: 3842: 3827: 3817: 3812: 3802: 3757: 3752: 3691: 3658: 3644: 3630: 3542: 3507: 3472: 3462: 3427: 3372: 3323: 3318: 3144: 2150:"Structural basis for antagonism and resistance of bicalutamide in prostate cancer" 1995: 1504: 1235: 1101: 1085: 1032: 991: 878: 837:

Research on these NTD antagonists are usually carried out by affinity screening of

783: 778: 645: 570: 524: 443: 368: 348: 244: 172: 76: 29: 17: 2544: 2365: 2303: 2030: 1700:"Pharmacokinetics and pharmacodynamics of nonsteroidal androgen receptor ligands" 1488: 1445: 6412: 6293: 6278: 6273: 6203: 6139: 6094: 5998: 5994: 5990: 5943: 5889: 5884: 5864: 5804: 5749: 5719: 5709: 5699: 5669: 5654: 5570: 5550: 5455: 5379: 5271: 5224: 5189: 5107: 5097: 5042: 5000: 4965: 4911: 4896: 4861: 4856: 4610: 4581: 4067: 4051: 3999: 3995: 3987: 3972: 3945: 3886: 3881: 3876: 3871: 3837: 3797: 3652: 3592: 3576: 3502: 3497: 3467: 3432: 3422: 3407: 3402: 3328: 3275: 2863: 2844: 1787:"Selective androgen receptor modulators in preclinical and clinical development" 1065: 916: 593: 502: 482: 381: 377: 360: 193: 152: 4193: 2154:

Proceedings of the National Academy of Sciences of the United States of America

1657: 1359: 438:, with higher binding affinity for the AR. Hydroxyflutamide has an elimination 6382: 6349: 6198: 6193: 6173: 6144: 6064: 6029: 6024: 6014: 5909: 5844: 5779: 5729: 5585: 5480: 5435: 5394: 5302: 5251: 5102: 5052: 5005: 4995: 4814: 4782: 4741: 4691: 4681: 4627: 4615: 4576: 4428: 4423: 4418: 4413: 4408: 4330: 4061: 4017: 3940: 3920: 3832: 3807: 3777: 3584: 3567: 3527: 3512: 3492: 3241: 3226: 3109: 2762: 2677: 1715: 1587: 1134: 1108: 817:, since NTD antagonists may also interact with protein targets other than AR. 548: 451: 429: 298:

or antagonists, position themselves in the ligand-binding pocket (LBP) of the

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Tran C, Ouk S, Clegg NJ, Chen Y, Watson PA, Arora V, et al. (May 2009).

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AR agonists that are inactivated by type 2 5-alpha reductase in the prostate.

6403: 6377: 6357: 6353: 6341: 6218: 6183: 6124: 6084: 6079: 5978: 5958: 5894: 5859: 5834: 5829: 5814: 5734: 5684: 5605: 5540: 5485: 5475: 5465: 5399: 5246: 5234: 4990: 4881: 4809: 4770: 4696: 4669: 4598: 4352: 4335: 4025: 4007: 3930: 3822: 3747: 3727: 3638: 3634: 3572: 3487: 3201: 2446: 2174: 2085:

10.1002/1097-0045(199609)29:3<153::aid-pros2990290303>3.0.co;2-5

1847: 1536: 1519: 1122: 1088:, it does not promote nuclear translocation and impairs both DNA binding to 702: 605: 540: 478: 439: 287: 164: 83:

chemistry. Steroidal antiandrogens share a similar steroid structure, while

53: 2770: 2720: 2685: 2641: 2597: 2562: 2513: 2464: 2321: 2272: 2193: 2134: 2039: 1987: 1952: 1855: 1820: 1733: 1665: 1595: 1545: 1496: 1453: 1417: 1367: 1327: 860: 726:

state in which the cancer progresses in the presence of continued androgen

3393:

Trenbolone hexahydrobenzylcarbonate (trenbolone cyclohexylmethylcarbonate)

2712: 2404: 2357: 2092: 1890: 1202: 631:

Hydroxyflutamide and its analogues, bicalutamide and nilutamide, share an

513: 6389: 6268: 6263: 6258: 6253: 6248: 6054: 5809: 5744: 5560: 5515: 5510: 5505: 5500: 5495: 5450: 5389: 5384: 5324: 4505: 4347: 4111: 4013: 3602: 3279: 3152: 3140: 1934: 1089: 1024: 999: 753: 727: 673: 566: 489: 229: 124: 112: 108: 1072: 6345: 6134: 6074: 5874: 5759: 5600: 5575: 5430: 5172: 5122: 5062: 4723: 3562: 3180: 2633: 2589: 1140: 1126: 967: 850: 830: 792: 706: 668: 664: 649: 632: 532: 466: 434: 299: 295: 290:, like a typical steroid receptor, and is associated with a complex of 225: 156: 128: 72: 2396: 2264: 1979: 1834:

Gelmann EP (July 2002). "Molecular biology of the androgen receptor".

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of androgens at the hypothalamic-pituitary level leading to increased

302:

AR and bind to the LBD, see figure 2. The AR goes through a series of

171:(FDA) approved it for use the treatment of prostate cancer. In 1995, 103:

At the beginning of the twentieth century, a relationship between the

6396: 6337: 6322: 6228: 795:

for refractory prostate cancer previously treated with bicalutamide.

787: 758: 698: 694: 686: 656:(R1) and either a cyano or nitrogen group at the para position (R2). 637: 373: 243:. Only one AR gene has been identified in humans which is located on 92: 1005: 786:

ring of bicalutamide is accommodated at the location of the missing

2809:

The androgen receptor gene mutations database world wide web server

1346:

Gao W (October 2010). "Androgen receptor as a therapeutic target".

1309: 973: 829:. Therefore, most of the research on NTD AR antagonists focuses on 644:

or to poor hydrogen-bond donor capability. Various combinations of

5928: 5610: 5520: 774: 732: 465: 404: 306:

changes and HSP dissociate from AR. The transformed AR undergoes

6361: 5674: 1518:

Urban D, Rischin D, Angel C, D'Costa I, Solomon B (March 2015).

1046: 236: 151:

for AR blockers led to the discovery of the first antiandrogen,

4197: 3113: 2817: 2808: 2009:

Jiang Y, Palma JF, Agus DB, Wang Y, Gross ME (September 2010).

6044: 2813: 1785:

Narayanan R, Mohler ML, Bohl CE, Miller DD, Dalton JT (2008).

919:

blocks the conversion of testosterone to DHT in the prostate.

5451:

Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4)

5410: 4294:

Adrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione)

1644:

Gao W (2010). "Peptide antagonist of the androgen receptor".

497:

formed during nitro reduction could still be associated with

2205: 2203: 2148:

Bohl CE, Gao W, Miller DD, Bell CE, Dalton JT (April 2005).

990:

Orally active and more potent than current small molecular

136:

prostate cancer was realised, for which he was awarded the

3025:

Nucleoside and nucleotide reverse-transcriptase inhibitors

841:

libraries that express random peptides containing various

2338:

The Journal of Steroid Biochemistry and Molecular Biology

5135:

17α-Alkylated 5α-dihydro-19-nortestosterone derivatives:

4638:

7α-Methyl-19-norandrostenedione (MENT dione, trestione)

773:

mutations are examples of known AR LBD mutations. The

294:(HSP) through interactions with LBD. Androgens, either 91:. Only a limited number of compounds are available for 5332:

5α-Dihydro-17α-ethynyl-19-nortestosterone derivatives:

239:

is more than 90kb long and codes for a protein of 919

2970:

Dual serotonin and norepinephrine reuptake inhibitors

1569: 1567: 1565: 1563: 1561: 1559: 1557: 1555: 888:

In 2008 there were reports of a chlorinated peptide,

274:, the N-terminal activation function 1 (AF1) and the 6418: 3672: 3299:

Androstanolone (stanolone, dihydrotestosterone, DHT)

2416: 2414: 1764:(5th ed.). Baltimore : Williams & Wilkins. 1524:

Journal of the National Comprehensive Cancer Network

1341: 1339: 1337: 1261:

Discovery and development of 5α-reductase inhibitors

147:(AR) was discovered and characterized. Screening of 6330: 6321: 5619: 5408: 4766:

Normethandrone (methylestrenolone, normethisterone)

4248: 4234: 4101: 3963: 3900: 3862: 3851: 3699: 3690: 3621: 3538:

Normethandrone (methylestrenolone, normethisterone)

3314:

Drostanolone propionate (dromostanolone propionate)

3171: 3158: 3151: 2896: 2851: 1520:"Abiraterone in metastatic salivary duct carcinoma" 663:For bicalutamide, the antiandrogenic activities of 2116: 2114: 2112: 2110: 1693: 1691: 1689: 1687: 1685: 1683: 1681: 1679: 1677: 1675: 424:after oral administration and undergoes extensive 4978:17α-Alkylated 5α-dihydrotestosterone derivatives: 1912: 1910: 1908: 351:and pituitary. Therefore, cyproterone blocks the 28:(AR) and thereby block the biological effects of 3428:Metandienone (methandienone, methandrostenolone) 714:than bicalutamide and nilutamide, respectively. 326:(TSS) of AR target genes. Recruitment of other 247:. It comprises four main regions, see figure 1: 159:group was then added to cyproterone and created 5197:5α-Dihydro-17α-ethynyltestosterone derivatives: 3015:Non-nucleoside reverse-transcriptase inhibitors 1639: 1637: 1635: 1633: 1391: 1389: 1387: 1385: 1383: 1381: 1379: 1377: 372:on androgen secretion, with subsequent loss of 4648:11β-Methyl-19-nortestosterone dodecylcarbonate 3480:17α-Alkylated dihydrotestosterone derivatives: 1631: 1629: 1627: 1625: 1623: 1621: 1619: 1617: 1615: 1613: 442:of about 8 hours in humans. Hydrolysis of the 212:superfamily. Its function is regulated by the 200:The four main regions of the androgen receptor 5415:Tooltip Selective androgen receptor modulator 5060:17α-Alkylated 19-nortestosterone derivatives: 4209: 3520:17α-Alkylated 19-nortestosterone derivatives: 3125: 2829: 266:A small hinge region between the DBD and LBD. 8: 5466:Enobosarm (ostarine, MK-2866, GTx-024, S-22) 3339:Metenolone enanthate (methenolone enanthate) 2377: 2375: 2065: 2063: 428:to its active form, 2-hydroxyflutamide, and 5217:17α-Ethynyl-19-nortestosterone derivatives: 3663: 671:substitutions of the X-linkage were tested 167:was discovered. In 1989 the United States 20:was discovered in the 1960s. Antiandrogens 6327: 4939:Methylclostebol (chloromethyltestosterone) 4834:5α-Dihydro-19-nortestosterone derivatives: 4245: 4216: 4202: 4194: 3859: 3696: 3168: 3132: 3118: 3110: 2836: 2822: 2814: 1434:The American Journal of Surgical Pathology 987: – no further developments since 1998 115:had been established. American physician 87:(NSAAs) may have structurally distinctive 5160:17α-Vinyl-19-nortestosterone derivatives: 4776:Oxabolone cipionate (oxabolone cypionate) 4392:DHEA (androstenolone, prasterone; 5-DHEA) 4236: 3701: 3383:Oxabolone cipionate (oxabolone cypionate) 3227:Prasterone (dehydroepiandrosterone, DHEA) 3173: 2552: 2503: 2454: 2311: 2183: 2173: 2029: 1942: 1810: 1723: 1535: 1317: 1287: 1285: 1283: 1281: 1279: 1277: 1275: 620:Basic structures of current antiandrogens 254:(NTD) which serves a modulatory function. 216:of androgens, which initiates sequential 4867:Chlorodehydromethylandrostenediol (CDMA) 3334:Metenolone acetate (methenolone acetate) 1762:Foye's principles of medicinal chemistry 1294:"A history of prostate cancer treatment" 1214: 1201: 943: 859: 512: 488:. Although the hydrolysis of one of the 192: 6468:List of androgens and anabolic steroids 4854:17α-Alkylated testosterone derivatives: 3400:17α-Alkylated testosterone derivatives: 2975:Selective serotonin reuptake inhibitors 1755: 1753: 1751: 1749: 1747: 1745: 1743: 1698:Gao W, Kim J, Dalton JT (August 2006). 1271: 4872:Chlorodehydromethyltestosterone (CDMT) 4628:Testifenon (testiphenon, testiphenone) 3413:Chlorodehydromethyltestosterone (CDMT) 902:selective androgen receptor modulators 896:Selective androgen receptor modulators 5153:Norvinisterone (vinylnortestosterone) 4687:Bolmantalate (nandrolone adamantoate) 4682:Bolandione (19-nor-4-androstenedione) 4397:DHEA enanthate (prasterone enanthate) 3553:Norvinisterone (vinylnortestosterone) 3232:Prasterone enanthate (DHEA enanthate) 2742:Roell D, Baniahmad A (January 2011). 1092:response elements and recruitment of 391:luteinizing-hormone-releasing hormone 138:Nobel Prize in Physiology or Medicine 7: 6423:Tooltip Sex hormone-binding globulin 5170:17α-Ethynyltestosterone derivatives: 4449:Polytestosterone phloretin phosphate 3677:Tooltip human chorionic gonadotropin 3560:17α-Ethynyltestosterone derivatives: 2751:Molecular and Cellular Endocrinology 2666:Bioorganic & Medicinal Chemistry 1871:Molecular and Cellular Endocrinology 1576:Molecular and Cellular Endocrinology 1084:High binding affinity to AR. Unlike 821:Ligand binding domain as target site 286:Unbound AR is mainly located in the 5093:Methylhydroxynandrolone (MOHN, MHN) 4798:Trenbolone hexahydrobenzylcarbonate 4458:5α-Dihydrotestosterone derivatives: 4326:Androstenedione (4-androstenedione) 4183:List of androgens/anabolic steroids 3163:Tooltip anabolic–androgenic steroid 1292:Denmeade SR, Isaacs JT (May 2002). 555:Structure and activity relationship 5150:17α-Vinyltestosterone derivatives: 4912:Methandriol (methylandrostenediol) 4112:Androvax (androstenedione albumin) 3550:17α-Vinyltestosterone derivatives: 3433:Methandriol (methylandrostenediol) 3065:Bcr-Abl tyrosine-kinase inhibitors 937:Other small-molecule antiandrogens 735:growth. This phenomenon is called 505:and delayed adaption to darkness. 14: 5190:Ethisterone (ethynyltestosterone) 4907:Metandienone (methandrostenolone) 4737:Methoxydienone (methoxygonadiene) 4348:Boldione (1,4-androstadienedione) 4299:Androstenediol (5-androstenediol) 4264:4-Dehydroepiandrosterone (4-DHEA) 4178:Progestogens and antiprogestogens 3577:ethisterone (ethynyltestosterone) 3237:Prasterone sulfate (DHEA sulfate) 3080:Neurokinin 1 receptor antagonists 2955:Dipeptidyl peptidase-4 inhibitors 1027:without raising plasma levels of 416:Flutamide is an arylpropionamide 163:. In the 1970s, the antiandrogen 6463:Progesterone receptor modulators 4954:Methyltestosterone 3-hexyl ether 4917:Methandriol bisenanthoyl acetate 4877:Chloromethylandrostenediol (CMA) 4712:Dimethandrolone dodecylcarbonate 4471:1-Androsterone (1-andro, 1-DHEA) 3458:Methyltestosterone 3-hexyl ether 3438:Methandriol bisenanthoyl acetate 3296:Dihydrotestosterone derivatives: 3070:Cannabinoid receptor antagonists 1968:Journal of Cellular Biochemistry 1175: 1139: 1107: 1071: 1045: 1004: 972: 872:N-Terminal domain as target site 748:Androgen receptor gene mutations 737:antiandrogen withdrawal syndrome 718:Antiandrogen withdrawal syndrome 604: 592: 580: 127:administration led to glandular 4635:19-Nortestosterone derivatives: 3351:19-Nortestosterone derivatives: 2899:and development of drug classes 2788:from the original on 2019-10-01 2286:Gao W, Dalton JT (March 2007). 2049:from the original on 2017-08-17 883:circular dichroism spectroscopy 701:atom at the C2 position of the 228:and receptor-DNA interactions. 5650:15β-Hydroxycyproterone acetate 5541:OPK-88004 (LY-2452473, TT-701) 4117:Ovandrotone albumin (Fecundin) 3589:norethisterone (norethindrone) 2385:Journal of Medicinal Chemistry 1760:Lemke TL, Williams DA (2002). 1348:Advanced Drug Delivery Reviews 1183:Chugai Pharmaceutical Co. Ltd. 944: 477:Nilutamide is a nitroaromatic 1: 6448:Receptor/signaling modulators 5205:17α-Ethynyl-3β-androstanediol 5200:17α-Ethynyl-3α-androstanediol 4643:11β-Methyl-19-nortestosterone 2916:Angiotensin receptor blockers 2545:10.1158/1078-0432.CCR-10-2955 2496:10.1016/S0140-6736(10)60172-9 2350:10.1016/S0960-0760(97)00151-9 1646:Current Pharmaceutical Design 804:N-Terminal domain antagonists 67:As of 2010 antiandrogens are 62:triple-negative breast cancer 6458:Estrogen receptor modulators 5905:Trimethyltrienolone (R-2956) 5277:Lynestrenol phenylpropionate 4665:19-Nordehydroepiandrosterone 4168:Androgen receptor modulators 4080:hydroxyprogesterone caproate 3543:Propetandrol (propethandrol) 3473:Tiomesterone (thiomesterone) 2304:10.1016/j.drudis.2007.01.003 2031:10.1373/clinchem.2010.143297 1883:10.1016/0303-7207(85)90059-0 1836:Journal of Clinical Oncology 1489:10.1097/PPO.0b013e3181ce4ae1 1446:10.1097/pas.0000000000000413 342:Development of antiandrogens 169:Food and Drug Administration 42:benign prostatic hyperplasia 6453:Androgens and antiandrogens 6224:Ralaniten acetate (EPI-506) 5640:7α-Thiomethylspironolactone 5355:Medroxyprogesterone acetate 4717:Dimethandrolone undecanoate 4528:Dihydromethylandrostenediol 4319:Androstenediol dipropionate 4173:Estrogens and antiestrogens 4109:Androstenedione immunogens: 4088:medroxyprogesterone acetate 3668:Tooltip luteinizing hormone 3613:Medroxyprogesterone acetate 3367:nandrolone phenylpropionate 3272:testosterone ester mixtures 3192:Androstenediol dipropionate 3094:Melatonin receptor agonists 3045:Thalidomide and its analogs 3000:Memantine and related drugs 2950:Cyclooxygenase 2 inhibitors 1398:Current Medicinal Chemistry 6515: 4543:Dihydrotestosterone esters 4496:11-Ketodihydrotestosterone 4309:Androstenediol 17β-acetate 4289:11β-Hydroxyandrostenedione 4274:4,17α-Dimethyltestosterone 4038:ethinylestradiol sulfonate 2960:Direct thrombin inhibitors 2897:Case studies of discovery 1791:Nuclear Receptor Signaling 1658:10.2174/138161210790963850 1360:10.1016/j.addr.2010.08.002 627:Nonsteroidal antiandrogens 186: 85:nonsteroidal antiandrogens 6440: 5347:Progesterone derivatives: 5138:5α-Dihydronorethandrolone 4707:Dimethandrolone buciclate 4537:androstanolone, stanolone 4533:Dihydrotestosterone (DHT) 4491:7β-Hydroxyepiandrosterone 4380:Cloxotestosterone acetate 4304:Androstenediol 3β-acetate 4256:Testosterone derivatives: 4241:Tooltip Androgen receptor 4129: 3706:Tooltip Androgen receptor 3610:Progesterone derivatives: 3222:Cloxotestosterone acetate 3189:Testosterone derivatives: 3178:Tooltip Androgen receptor 3075:CCR5 receptor antagonists 2763:10.1016/j.mce.2010.09.013 2678:10.1016/j.bmc.2010.10.023 2225:: 439–444. Archived from 1716:10.1007/s11095-006-9024-3 1588:10.1016/j.mce.2011.06.002 1240:N-butylbenzenesulfonamide 1222:N-butylbenzenesulfonamide 6153:-Butylbenzenesulfonamide 5340:5α-Dihydronorethisterone 5335:5α-Dihydrolevonorgestrel 5297:norethisterone enanthate 5266:levonorgestrel butanoate 5143:5α-Dihydronormethandrone 4996:Mebolazine (dimethazine) 4986:Desoxymethyltestosterone 4927:Methandriol dipropionate 4724:LS-1727 (nandrolone 17β- 4660:19-Nor-5-androstenedione 4518:Dihydroethyltestosterone 4314:Androstenediol diacetate 3493:Mebolazine (dimethazine) 3443:Methandriol dipropionate 3268:testosterone undecanoate 3010:Neuraminidase inhibitors 2533:Clinical Cancer Research 1410:10.2174/0929867003375371 1246:, see figures 9 and 10. 1154: – trial terminated 324:transcription start site 6284:Topilutamide (fluridil) 5645:11α-Hydroxyprogesterone 4655:19-Nor-5-androstenediol 4555:Drostanolone propionate 3843:Topilutamide (fluridil) 3264:testosterone propionate 2985:HIV-protease inhibitors 2906:5α-Reductase inhibitors 2447:10.1126/science.1168175 2175:10.1073/pnas.0500381102 1848:10.1200/jco.2002.10.018 1704:Pharmaceutical Research 1537:10.6004/jnccn.2015.0040 560:Steroidal antiandrogens 179:followed a year later. 117:Charles Brenton Huggins 6169:-Desmethylenzalutamide 5875:SC-5233 (spirolactone) 5293:norethisterone acetate 4932:Methandriol propionate 4803:Trenbolone undecanoate 4675:Bolandiol dipropionate 4523:Dihydrofluoxymesterone 4486:5α-Androst-2-en-17-one 4341:Boldenone undecylenate 3448:Methandriol propionate 3354:Bolandiol dipropionate 3260:testosterone enanthate 3256:testosterone cypionate 3197:Boldenone undecylenate 3035:Proton pump inhibitors 1923:Molecular Pharmacology 1298:Nature Reviews. Cancer 1223: 1210: 1053:Ligand Pharmaceuticals 1019:Orally active, strong 1012:Ligand Pharmaceuticals 906:central nervous system 868: 813:necessarily translate 569:atom is replaced by a 521: 474: 422:gastrointestinal tract 413: 224:that affects receptor- 204:The AR belongs to the 201: 6161:-Desmethylapalutamide 5690:Chlormadinone acetate 5635:7α-Thiospironolactone 5506:LGD-2941 (LGD-122941) 5496:LG121071 (LGD-121071) 5370:3-Keto-5α-abiraterone 5350:6α-Methylprogesterone 5289:Norethisterone esters 5262:Levonorgestrel esters 5178:Ethinylandrostenediol 5028:Methyl-1-testosterone 4948:+esterified estrogens 4922:Methandriol diacetate 4587:Mesterolone cipionate 4269:4-Hydroxytestosterone 4072:chlormadinone acetate 3733:Chlormadinone acetate 3304:Androstanolone esters 2713:10.1055/s-2006-946638 1231:Natural antiandrogens 1218: 1205: 863: 648:substitutions in the 516: 469: 446:represents the major 426:first pass metabolism 408: 196: 187:Further information: 5850:Potassium canrenoate 5318:Quingestanol acetate 5128:Tetrahydrogestrinone 5016:Metenolone enanthate 4842:5α-Dihydrotrestolone 4837:5α-Dihydronandrolone 4825:Trestolone enanthate 4793:Trenbolone enanthate 4759:Norclostebol acetate 4368:Clostebol propionate 4084:gestonorone caproate 3892:Saw palmetto extract 3783:Potassium canrenoate 3378:Norclostebol acetate 3363:nandrolone decanoate 3217:Clostebol propionate 2990:Integrase inhibitors 2965:Direct Xa inhibitors 2292:Drug Discovery Today 1935:10.1124/mol.63.1.211 1147:Bristol-Myers Squibb 959:Stage of development 741:coregulator proteins 646:electron-withdrawing 218:conformation changes 6373:Dihydrotestosterone 6368:Dehydroandrosterone 6219:Ralaniten (EPI-002) 6100:Inocoterone acetate 5825:Nomegestrol acetate 5725:Delmadinone acetate 5715:Cyproterone acetate 5660:Abiraterone acetate 5630:7α-Thioprogesterone 5240:Etynodiol diacetate 4444:Testosterone esters 4387:Dehydroandrosterone 4284:11-Ketotestosterone 4076:cyproterone acetate 3984:prolactin releasers 3926:Cyproterone acetate 3908:Abiraterone acetate 3768:Nomegestrol acetate 3743:Delmadinone acetate 3738:Cyproterone acetate 3720:Abiraterone acetate 3252:Testosterone esters 2439:2009Sci...324..787T 2166:2005PNAS..102.6201B 946: 793:second-line therapy 531:Bicalutamide has a 395:blood–brain barrier 357:luteinizing hormone 292:heat shock proteins 282:Mechanism of action 161:cyproterone acetate 34:dihydrotestosterone 5210:Dihydroethisterone 5073:Dimethyltrienolone 5033:Methylepitiostanol 5011:Metenolone acetate 4944:Methyltestosterone 4847:19-Norandrosterone 4820:Trestolone acetate 4788:Trenbolone acetate 4732:-nitrosocarbamate) 4621:Stenbolone acetate 4511:Bolazine capronate 4363:Clostebol caproate 4156:Never to phase III 4022:diethylstilbestrol 3649:GnRH (gonadorelin) 3453:Methyltestosterone 3388:Trenbolone acetate 3344:Stenbolone acetate 3309:Bolazine capronate 3212:Clostebol caproate 3060:Tubulin inhibitors 2634:10.1002/pros.21351 2590:10.1002/pros.21263 2018:Clinical Chemistry 1224: 1211: 962:Other information 869: 724:hormone-refractory 522: 475: 414: 258:DNA-binding domain 202: 175:was approved, and 149:chemical libraries 71:and can be either 6476: 6475: 6436: 6435: 6406: 6399: 6392: 6385: 6317: 6316: 5840:Osaterone acetate 5800:Megestrol acetate 5665:Allyltestosterone 5441:Acetothiolutamide 5360:Megestrol acetate 5163:Vinyltestosterone 5068:Dimethyldienolone 4887:Ethyltestosterone 4815:Trestolone (MENT) 4747:Nandrolone esters 4728:-(2-chloroethyl)- 4604:Nisterime acetate 4481:3α-Androstanediol 4466:1-Androstenedione 4375:Cloxotestosterone 4358:Clostebol acetate 4279:5-Androstenedione 4225:Androgen receptor 4191: 4190: 4125: 4124: 4092:megestrol acetate 3965:Antigonadotropins 3959: 3958: 3916:Aminoglutethimide 3773:Osaterone acetate 3763:Megestrol acetate 3686: 3685: 3359:Nandrolone esters 3207:Clostebol acetate 3107: 3106: 3055:TRPV1 antagonists 2995:Lipase inhibitors 2490:(9724): 1437–46. 2397:10.1021/jm970699s 2265:10.1021/ol802021w 2210:Nahleh Z (2008). 1980:10.1002/jcb.10757 1803:10.1621/nrs.06010 1771:978-0-683-30737-5 1228: 1227: 1196: 1195: 1159:epileptic seizure 913:5-alpha reductase 448:metabolic pathway 353:negative feedback 252:N-terminal domain 208:subfamily of the 189:androgen receptor 183:Androgen receptor 145:androgen receptor 58:androgen alopecia 26:androgen receptor 6506: 6424: 6420: 6404: 6397: 6390: 6383: 6328: 6110:Ketodarolutamide 6090:Hydroxyflutamide 6047:(via metabolite 5416: 5412: 5367:Others/unsorted: 5038:Methylstenbolone 4902:Hydroxystenozole 4461:1-Androstenediol 4259:4-Androstenediol 4246: 4242: 4238: 4218: 4211: 4204: 4195: 4058:GnRH antagonists 4034:ethinylestradiol 4030:estradiol esters 3860: 3707: 3703: 3697: 3678: 3674: 3669: 3665: 3623:Progonadotropins 3288:Testoviron Depot 3179: 3175: 3169: 3164: 3160: 3134: 3127: 3120: 3111: 3099:Renin inhibitors 2945:c-Met inhibitors 2869:Drug development 2838: 2831: 2824: 2815: 2797: 2796: 2794: 2793: 2787: 2748: 2739: 2733: 2732: 2696: 2690: 2689: 2660: 2654: 2653: 2616: 2610: 2609: 2573: 2567: 2566: 2556: 2524: 2518: 2517: 2507: 2475: 2469: 2468: 2458: 2433:(5928): 787–90. 2418: 2409: 2408: 2379: 2370: 2369: 2332: 2326: 2325: 2315: 2283: 2277: 2276: 2247: 2241: 2240: 2238: 2237: 2231: 2216: 2207: 2198: 2197: 2187: 2177: 2145: 2139: 2138: 2118: 2105: 2104: 2067: 2058: 2057: 2055: 2054: 2048: 2033: 2015: 2006: 2000: 1999: 1963: 1957: 1956: 1946: 1914: 1903: 1902: 1866: 1860: 1859: 1831: 1825: 1824: 1814: 1782: 1776: 1775: 1757: 1738: 1737: 1727: 1695: 1670: 1669: 1641: 1608: 1607: 1571: 1550: 1549: 1539: 1515: 1509: 1508: 1472: 1466: 1465: 1428: 1422: 1421: 1393: 1372: 1371: 1343: 1332: 1331: 1321: 1289: 1244:Pygeum africanum 1198: 1197: 1179: 1163:GABA-A receptors 1152:Phase I clinical 1143: 1111: 1075: 1049: 1023:activity in the 1008: 980:Roussel-Uclaf SA 976: 950:Name of compound 947: 843:signature motifs 777:prostate cancer 705:ring and adding 642:hydrogen binding 608: 596: 587:Hydroxyflutamide 584: 450:for this active 210:nuclear receptor 206:steroid receptor 6514: 6513: 6509: 6508: 6507: 6505: 6504: 6503: 6494:Cancer research 6479: 6478: 6477: 6472: 6432: 6422: 6313: 6035:Cyanonilutamide 5964:Bavdegalutamide 5775:Epitestosterone 5615: 5446:Acetoxolutamide 5414: 5404: 5113:Norethandrolone 5088:Methyldienolone 4892:Fluoxymesterone 4702:Dimethandrolone 4562:Epiandrosterone 4240: 4230: 4222: 4192: 4187: 4161: 4146:Clinical trials 4121: 4097: 3976: 3955: 3896: 3854: 3853:Steroidogenesis 3847: 3705: 3682: 3676: 3667: 3617: 3533:Norethandrolone 3418:Fluoxymesterone 3177: 3162: 3155: 3147: 3138: 3108: 3103: 3088: 3030:PDE5 inhibitors 3020:NS5A inhibitors 3005:mTOR inhibitors 2934: 2898: 2892: 2852:Steps in design 2847: 2842: 2805: 2800: 2791: 2789: 2785: 2746: 2741: 2740: 2736: 2698: 2697: 2693: 2662: 2661: 2657: 2628:(12): 1344–56. 2618: 2617: 2613: 2575: 2574: 2570: 2526: 2525: 2521: 2477: 2476: 2472: 2420: 2419: 2412: 2381: 2380: 2373: 2344:(1–2): 103–11. 2334: 2333: 2329: 2285: 2284: 2280: 2259:(21): 4947–50. 2253:Organic Letters 2249: 2248: 2244: 2235: 2233: 2229: 2214: 2209: 2208: 2201: 2147: 2146: 2142: 2123:Cancer Research 2120: 2119: 2108: 2069: 2068: 2061: 2052: 2050: 2046: 2013: 2008: 2007: 2003: 1965: 1964: 1960: 1916: 1915: 1906: 1868: 1867: 1863: 1842:(13): 3001–15. 1833: 1832: 1828: 1784: 1783: 1779: 1772: 1759: 1758: 1741: 1697: 1696: 1673: 1643: 1642: 1611: 1573: 1572: 1553: 1517: 1516: 1512: 1474: 1473: 1469: 1430: 1429: 1425: 1395: 1394: 1375: 1354:(13): 1277–84. 1345: 1344: 1335: 1291: 1290: 1273: 1269: 1257: 1233: 939: 898: 874: 823: 806: 801: 750: 720: 684: 680: 629: 624: 623: 622: 621: 614: 613: 612: 609: 601: 600: 597: 589: 588: 585: 562: 557: 511: 464: 403: 344: 332:gene expression 312:phosphorylation 284: 272:transactivation 191: 185: 119:found out that 101: 69:small molecules 38:prostate cancer 12: 11: 5: 6512: 6510: 6502: 6501: 6499:Drug discovery 6496: 6491: 6481: 6480: 6474: 6473: 6471: 6470: 6465: 6460: 6455: 6450: 6445: 6441: 6438: 6437: 6434: 6433: 6431: 6430: 6425: 6415: 6410: 6386:-α-Amino acids 6380: 6375: 6370: 6365: 6334: 6332: 6325: 6319: 6318: 6315: 6314: 6312: 6311: 6306: 6301: 6296: 6291: 6286: 6281: 6276: 6271: 6266: 6261: 6256: 6251: 6246: 6241: 6236: 6231: 6226: 6221: 6216: 6211: 6206: 6201: 6196: 6191: 6186: 6181: 6176: 6171: 6163: 6155: 6147: 6142: 6137: 6132: 6127: 6122: 6117: 6112: 6107: 6102: 6097: 6092: 6087: 6082: 6077: 6072: 6067: 6062: 6057: 6052: 6042: 6037: 6032: 6027: 6022: 6017: 6012: 6007: 6002: 5976: 5971: 5966: 5961: 5956: 5951: 5946: 5941: 5936: 5931: 5926: 5913: 5912: 5907: 5902: 5897: 5892: 5887: 5882: 5880:Spironolactone 5877: 5872: 5867: 5862: 5857: 5852: 5847: 5842: 5837: 5832: 5827: 5822: 5817: 5812: 5807: 5802: 5797: 5792: 5787: 5782: 5777: 5772: 5767: 5762: 5757: 5752: 5747: 5742: 5737: 5732: 5727: 5722: 5717: 5712: 5707: 5705:Cyproheptadine 5702: 5697: 5692: 5687: 5682: 5680:Canrenoic acid 5677: 5672: 5667: 5662: 5657: 5652: 5647: 5642: 5637: 5632: 5623: 5621: 5617: 5616: 5614: 5613: 5608: 5603: 5598: 5589: 5588: 5583: 5578: 5573: 5568: 5563: 5558: 5553: 5548: 5543: 5538: 5533: 5528: 5523: 5518: 5513: 5508: 5503: 5498: 5493: 5488: 5483: 5478: 5473: 5468: 5463: 5458: 5453: 5448: 5443: 5438: 5433: 5428: 5419: 5417: 5406: 5405: 5403: 5402: 5397: 5392: 5387: 5382: 5377: 5372: 5363: 5362: 5357: 5352: 5343: 5342: 5337: 5328: 5327: 5322: 5321: 5320: 5310: 5308:Norgestrienone 5305: 5300: 5286: 5284:Norethisterone 5281: 5280: 5279: 5269: 5259: 5257:Levonorgestrel 5254: 5249: 5244: 5243: 5242: 5232: 5227: 5222: 5213: 5212: 5207: 5202: 5193: 5192: 5187: 5186: 5185: 5175: 5166: 5165: 5156: 5155: 5146: 5145: 5140: 5131: 5130: 5125: 5120: 5115: 5110: 5105: 5100: 5095: 5090: 5085: 5080: 5078:Ethyldienolone 5075: 5070: 5065: 5056: 5055: 5050: 5045: 5040: 5035: 5030: 5025: 5020: 5019: 5018: 5013: 5003: 4998: 4993: 4988: 4983: 4981:Androisoxazole 4974: 4973: 4968: 4963: 4958: 4957: 4956: 4941: 4936: 4935: 4934: 4929: 4924: 4919: 4909: 4904: 4899: 4894: 4889: 4884: 4879: 4874: 4869: 4864: 4859: 4850: 4849: 4844: 4839: 4830: 4829: 4828: 4827: 4822: 4812: 4807: 4806: 4805: 4800: 4795: 4790: 4780: 4779: 4778: 4768: 4763: 4762: 4761: 4751: 4750: 4749: 4739: 4734: 4721: 4720: 4719: 4714: 4709: 4699: 4694: 4689: 4684: 4679: 4678: 4677: 4667: 4662: 4657: 4652: 4651: 4650: 4640: 4631: 4630: 4625: 4624: 4623: 4613: 4608: 4607: 4606: 4596: 4594:Methyldiazinol 4591: 4590: 4589: 4579: 4574: 4569: 4564: 4559: 4558: 4557: 4547: 4546: 4545: 4530: 4525: 4520: 4515: 4514: 4513: 4503: 4498: 4493: 4488: 4483: 4478: 4476:1-Testosterone 4473: 4468: 4463: 4454: 4453: 4452: 4451: 4446: 4431: 4426: 4421: 4416: 4411: 4406: 4405: 4404: 4399: 4389: 4384: 4383: 4382: 4372: 4371: 4370: 4365: 4360: 4350: 4345: 4344: 4343: 4333: 4328: 4323: 4322: 4321: 4316: 4311: 4306: 4296: 4291: 4286: 4281: 4276: 4271: 4266: 4261: 4252: 4250: 4243: 4232: 4231: 4223: 4221: 4220: 4213: 4206: 4198: 4189: 4188: 4186: 4185: 4180: 4175: 4170: 4165: 4160: 4159: 4158: 4157: 4154: 4143: 4137: 4131: 4130: 4127: 4126: 4123: 4122: 4120: 4119: 4114: 4105: 4103: 4099: 4098: 4096: 4095: 4065: 4055: 4045: 4042:paroxypropione 4011: 4004:chlorpromazine 3992:metoclopramide 3974: 3969: 3967: 3961: 3960: 3957: 3956: 3954: 3953: 3951:Spironolactone 3948: 3943: 3938: 3933: 3928: 3923: 3918: 3913: 3904: 3902: 3898: 3897: 3895: 3894: 3889: 3884: 3879: 3874: 3868: 3866: 3857: 3849: 3848: 3846: 3845: 3840: 3835: 3830: 3825: 3820: 3815: 3810: 3805: 3800: 3791: 3790: 3788:Spironolactone 3785: 3780: 3775: 3770: 3765: 3760: 3755: 3750: 3745: 3740: 3735: 3730: 3725: 3713: 3711: 3694: 3688: 3687: 3684: 3683: 3681: 3680: 3656: 3642: 3627: 3625: 3619: 3618: 3616: 3615: 3606: 3605: 3600: 3597:norgestrienone 3581:levonorgestrel 3570: 3565: 3556: 3555: 3546: 3545: 3540: 3535: 3530: 3525: 3516: 3515: 3510: 3505: 3500: 3495: 3490: 3485: 3483:Androisoxazole 3476: 3475: 3470: 3465: 3460: 3455: 3450: 3445: 3440: 3435: 3430: 3425: 3420: 3415: 3410: 3405: 3396: 3395: 3390: 3385: 3380: 3375: 3370: 3356: 3347: 3346: 3341: 3336: 3331: 3326: 3321: 3316: 3311: 3306: 3301: 3292: 3291: 3249: 3244: 3239: 3234: 3229: 3224: 3219: 3214: 3209: 3204: 3199: 3194: 3185: 3183: 3166: 3149: 3148: 3139: 3137: 3136: 3129: 3122: 3114: 3105: 3104: 3102: 3101: 3096: 3091: 3086: 3082: 3077: 3072: 3067: 3062: 3057: 3052: 3047: 3042: 3037: 3032: 3027: 3022: 3017: 3012: 3007: 3002: 2997: 2992: 2987: 2982: 2977: 2972: 2967: 2962: 2957: 2952: 2947: 2942: 2940:Cephalosporins 2937: 2932: 2928: 2923: 2918: 2913: 2911:ACE inhibitors 2908: 2902: 2900: 2894: 2893: 2891: 2890: 2889: 2888: 2887: 2886: 2876: 2866: 2861: 2859:Drug discovery 2855: 2853: 2849: 2848: 2843: 2841: 2840: 2833: 2826: 2818: 2812: 2811: 2804: 2803:External links 2801: 2799: 2798: 2734: 2691: 2672:(23): 8150–7. 2655: 2611: 2568: 2519: 2470: 2410: 2371: 2327: 2298:(5–6): 241–8. 2278: 2242: 2219:Cancer Therapy 2199: 2160:(17): 6201–6. 2140: 2106: 2059: 2001: 1958: 1904: 1861: 1826: 1777: 1770: 1739: 1710:(8): 1641–58. 1671: 1652:(9): 1106–13. 1609: 1582:(1–2): 79–91. 1551: 1510: 1477:Cancer Journal 1467: 1423: 1373: 1333: 1310:10.1038/nrc801 1270: 1268: 1265: 1264: 1263: 1256: 1253: 1232: 1229: 1226: 1225: 1212: 1194: 1193: 1191: 1188: 1185: 1180: 1173: 1167: 1166: 1155: 1149: 1144: 1137: 1131: 1130: 1118: 1115: 1112: 1105: 1098: 1097: 1082: 1079: 1076: 1069: 1062: 1061: 1058: 1055: 1050: 1043: 1037: 1036: 1017: 1014: 1009: 1002: 996: 995: 988: 982: 977: 970: 964: 963: 960: 957: 954: 951: 938: 935: 934: 933: 930: 927: 897: 894: 873: 870: 822: 819: 805: 802: 800: 799:Current status 797: 749: 746: 719: 716: 682: 678: 628: 625: 616: 615: 610: 603: 602: 598: 591: 590: 586: 579: 578: 577: 576: 575: 561: 558: 556: 553: 510: 507: 499:hepatotoxicity 463: 460: 402: 399: 343: 340: 304:conformational 283: 280: 268: 267: 264: 261: 255: 184: 181: 113:prostate gland 100: 97: 89:pharmacophores 13: 10: 9: 6: 4: 3: 2: 6511: 6500: 6497: 6495: 6492: 6490: 6489:Antiandrogens 6487: 6486: 6484: 6469: 6466: 6464: 6461: 6459: 6456: 6454: 6451: 6449: 6446: 6443: 6442: 6439: 6429: 6426: 6421: 6416: 6414: 6411: 6408: 6401: 6394: 6387: 6381: 6379: 6376: 6374: 6371: 6369: 6366: 6363: 6359: 6355: 6351: 6347: 6343: 6339: 6336: 6335: 6333: 6329: 6326: 6324: 6320: 6310: 6307: 6305: 6302: 6300: 6297: 6295: 6292: 6290: 6289:Valproic acid 6287: 6285: 6282: 6280: 6277: 6275: 6272: 6270: 6267: 6265: 6262: 6260: 6257: 6255: 6252: 6250: 6247: 6245: 6242: 6240: 6237: 6235: 6234:Rezvilutamide 6232: 6230: 6227: 6225: 6222: 6220: 6217: 6215: 6212: 6210: 6209:Proxalutamide 6207: 6205: 6202: 6200: 6197: 6195: 6192: 6190: 6187: 6185: 6182: 6180: 6177: 6175: 6172: 6170: 6168: 6164: 6162: 6160: 6156: 6154: 6152: 6148: 6146: 6143: 6141: 6138: 6136: 6133: 6131: 6128: 6126: 6123: 6121: 6118: 6116: 6113: 6111: 6108: 6106: 6103: 6101: 6098: 6096: 6093: 6091: 6088: 6086: 6083: 6081: 6078: 6076: 6073: 6071: 6068: 6066: 6063: 6061: 6058: 6056: 6053: 6050: 6046: 6043: 6041: 6038: 6036: 6033: 6031: 6028: 6026: 6023: 6021: 6018: 6016: 6013: 6011: 6008: 6006: 6003: 6000: 5996: 5992: 5988: 5984: 5980: 5977: 5975: 5972: 5970: 5967: 5965: 5962: 5960: 5957: 5955: 5952: 5950: 5947: 5945: 5942: 5940: 5937: 5935: 5932: 5930: 5927: 5925: 5924:-Bicalutamide 5923: 5918: 5917:Nonsteroidal: 5915: 5914: 5911: 5908: 5906: 5903: 5901: 5898: 5896: 5893: 5891: 5888: 5886: 5883: 5881: 5878: 5876: 5873: 5871: 5868: 5866: 5863: 5861: 5858: 5856: 5853: 5851: 5848: 5846: 5843: 5841: 5838: 5836: 5833: 5831: 5828: 5826: 5823: 5821: 5818: 5816: 5813: 5811: 5808: 5806: 5803: 5801: 5798: 5796: 5793: 5791: 5788: 5786: 5785:Guggulsterone 5783: 5781: 5778: 5776: 5773: 5771: 5768: 5766: 5763: 5761: 5758: 5756: 5753: 5751: 5748: 5746: 5743: 5741: 5738: 5736: 5733: 5731: 5728: 5726: 5723: 5721: 5718: 5716: 5713: 5711: 5708: 5706: 5703: 5701: 5698: 5696: 5693: 5691: 5688: 5686: 5683: 5681: 5678: 5676: 5673: 5671: 5668: 5666: 5663: 5661: 5658: 5656: 5653: 5651: 5648: 5646: 5643: 5641: 5638: 5636: 5633: 5631: 5628: 5625: 5624: 5622: 5618: 5612: 5609: 5607: 5604: 5602: 5599: 5597: 5594: 5591: 5590: 5587: 5584: 5582: 5579: 5577: 5574: 5572: 5569: 5567: 5564: 5562: 5559: 5557: 5554: 5552: 5549: 5547: 5544: 5542: 5539: 5537: 5534: 5532: 5529: 5527: 5524: 5522: 5519: 5517: 5514: 5512: 5509: 5507: 5504: 5502: 5499: 5497: 5494: 5492: 5489: 5487: 5484: 5482: 5479: 5477: 5474: 5472: 5469: 5467: 5464: 5462: 5459: 5457: 5454: 5452: 5449: 5447: 5444: 5442: 5439: 5437: 5434: 5432: 5429: 5427: 5424: 5423:Nonsteroidal: 5421: 5420: 5418: 5413: 5407: 5401: 5398: 5396: 5393: 5391: 5388: 5386: 5383: 5381: 5378: 5376: 5375:5α-Androstane 5373: 5371: 5368: 5365: 5364: 5361: 5358: 5356: 5353: 5351: 5348: 5345: 5344: 5341: 5338: 5336: 5333: 5330: 5329: 5326: 5323: 5319: 5316: 5315: 5314: 5311: 5309: 5306: 5304: 5301: 5298: 5294: 5290: 5287: 5285: 5282: 5278: 5275: 5274: 5273: 5270: 5267: 5263: 5260: 5258: 5255: 5253: 5250: 5248: 5245: 5241: 5238: 5237: 5236: 5233: 5231: 5228: 5226: 5223: 5221: 5218: 5215: 5214: 5211: 5208: 5206: 5203: 5201: 5198: 5195: 5194: 5191: 5188: 5184: 5183:Ethandrostate 5181: 5180: 5179: 5176: 5174: 5171: 5168: 5167: 5164: 5161: 5158: 5157: 5154: 5151: 5148: 5147: 5144: 5141: 5139: 5136: 5133: 5132: 5129: 5126: 5124: 5121: 5119: 5116: 5114: 5111: 5109: 5106: 5104: 5101: 5099: 5096: 5094: 5091: 5089: 5086: 5084: 5083:Ethylestrenol 5081: 5079: 5076: 5074: 5071: 5069: 5066: 5064: 5061: 5058: 5057: 5054: 5051: 5049: 5046: 5044: 5041: 5039: 5036: 5034: 5031: 5029: 5026: 5024: 5021: 5017: 5014: 5012: 5009: 5008: 5007: 5004: 5002: 4999: 4997: 4994: 4992: 4989: 4987: 4984: 4982: 4979: 4976: 4975: 4972: 4969: 4967: 4964: 4962: 4959: 4955: 4952: 4951: 4949: 4945: 4942: 4940: 4937: 4933: 4930: 4928: 4925: 4923: 4920: 4918: 4915: 4914: 4913: 4910: 4908: 4905: 4903: 4900: 4898: 4895: 4893: 4890: 4888: 4885: 4883: 4880: 4878: 4875: 4873: 4870: 4868: 4865: 4863: 4860: 4858: 4855: 4852: 4851: 4848: 4845: 4843: 4840: 4838: 4835: 4832: 4831: 4826: 4823: 4821: 4818: 4817: 4816: 4813: 4811: 4808: 4804: 4801: 4799: 4796: 4794: 4791: 4789: 4786: 4785: 4784: 4781: 4777: 4774: 4773: 4772: 4769: 4767: 4764: 4760: 4757: 4756: 4755: 4752: 4748: 4745: 4744: 4743: 4740: 4738: 4735: 4733: 4731: 4727: 4722: 4718: 4715: 4713: 4710: 4708: 4705: 4704: 4703: 4700: 4698: 4695: 4693: 4690: 4688: 4685: 4683: 4680: 4676: 4673: 4672: 4671: 4668: 4666: 4663: 4661: 4658: 4656: 4653: 4649: 4646: 4645: 4644: 4641: 4639: 4636: 4633: 4632: 4629: 4626: 4622: 4619: 4618: 4617: 4614: 4612: 4609: 4605: 4602: 4601: 4600: 4597: 4595: 4592: 4588: 4585: 4584: 4583: 4580: 4578: 4575: 4573: 4570: 4568: 4565: 4563: 4560: 4556: 4553: 4552: 4551: 4548: 4544: 4541: 4540: 4538: 4534: 4531: 4529: 4526: 4524: 4521: 4519: 4516: 4512: 4509: 4508: 4507: 4504: 4502: 4499: 4497: 4494: 4492: 4489: 4487: 4484: 4482: 4479: 4477: 4474: 4472: 4469: 4467: 4464: 4462: 4459: 4456: 4455: 4450: 4447: 4445: 4442: 4441: 4439: 4435: 4432: 4430: 4427: 4425: 4422: 4420: 4417: 4415: 4412: 4410: 4407: 4403: 4400: 4398: 4395: 4394: 4393: 4390: 4388: 4385: 4381: 4378: 4377: 4376: 4373: 4369: 4366: 4364: 4361: 4359: 4356: 4355: 4354: 4351: 4349: 4346: 4342: 4339: 4338: 4337: 4334: 4332: 4329: 4327: 4324: 4320: 4317: 4315: 4312: 4310: 4307: 4305: 4302: 4301: 4300: 4297: 4295: 4292: 4290: 4287: 4285: 4282: 4280: 4277: 4275: 4272: 4270: 4267: 4265: 4262: 4260: 4257: 4254: 4253: 4251: 4247: 4244: 4239: 4233: 4229: 4226: 4219: 4214: 4212: 4207: 4205: 4200: 4199: 4196: 4184: 4181: 4179: 4176: 4174: 4171: 4169: 4166: 4163: 4162: 4155: 4153: 4150: 4149: 4147: 4144: 4141: 4138: 4136: 4133: 4132: 4128: 4118: 4115: 4113: 4110: 4107: 4106: 4104: 4100: 4093: 4089: 4085: 4081: 4077: 4073: 4069: 4066: 4063: 4059: 4056: 4053: 4049: 4048:GnRH agonists 4046: 4043: 4039: 4035: 4031: 4027: 4023: 4019: 4015: 4012: 4009: 4005: 4001: 3997: 3993: 3989: 3985: 3981: 3978: 3971: 3970: 3968: 3966: 3962: 3952: 3949: 3947: 3944: 3942: 3939: 3937: 3934: 3932: 3929: 3927: 3924: 3922: 3919: 3917: 3914: 3912: 3909: 3906: 3905: 3903: 3899: 3893: 3890: 3888: 3885: 3883: 3880: 3878: 3875: 3873: 3870: 3869: 3867: 3865: 3861: 3858: 3856: 3850: 3844: 3841: 3839: 3836: 3834: 3831: 3829: 3826: 3824: 3821: 3819: 3816: 3814: 3811: 3809: 3806: 3804: 3801: 3799: 3796: 3795:Nonsteroidal: 3793: 3792: 3789: 3786: 3784: 3781: 3779: 3776: 3774: 3771: 3769: 3766: 3764: 3761: 3759: 3756: 3754: 3751: 3749: 3746: 3744: 3741: 3739: 3736: 3734: 3731: 3729: 3726: 3724: 3721: 3718: 3715: 3714: 3712: 3710: 3704: 3698: 3695: 3693: 3692:Antiandrogens 3689: 3675: 3666: 3660: 3659:Gonadotropins 3657: 3654: 3650: 3646: 3645:GnRH agonists 3643: 3640: 3636: 3632: 3631:Antiestrogens 3629: 3628: 3626: 3624: 3620: 3614: 3611: 3608: 3607: 3604: 3601: 3598: 3594: 3590: 3586: 3582: 3578: 3574: 3571: 3569: 3566: 3564: 3561: 3558: 3557: 3554: 3551: 3548: 3547: 3544: 3541: 3539: 3536: 3534: 3531: 3529: 3526: 3524: 3523:Ethylestrenol 3521: 3518: 3517: 3514: 3511: 3509: 3506: 3504: 3501: 3499: 3496: 3494: 3491: 3489: 3486: 3484: 3481: 3478: 3477: 3474: 3471: 3469: 3466: 3464: 3461: 3459: 3456: 3454: 3451: 3449: 3446: 3444: 3441: 3439: 3436: 3434: 3431: 3429: 3426: 3424: 3421: 3419: 3416: 3414: 3411: 3409: 3406: 3404: 3401: 3398: 3397: 3394: 3391: 3389: 3386: 3384: 3381: 3379: 3376: 3374: 3371: 3368: 3364: 3360: 3357: 3355: 3352: 3349: 3348: 3345: 3342: 3340: 3337: 3335: 3332: 3330: 3327: 3325: 3322: 3320: 3317: 3315: 3312: 3310: 3307: 3305: 3302: 3300: 3297: 3294: 3293: 3289: 3285: 3281: 3277: 3273: 3269: 3265: 3261: 3257: 3253: 3250: 3248: 3245: 3243: 3240: 3238: 3235: 3233: 3230: 3228: 3225: 3223: 3220: 3218: 3215: 3213: 3210: 3208: 3205: 3203: 3200: 3198: 3195: 3193: 3190: 3187: 3186: 3184: 3182: 3176: 3170: 3167: 3161: 3154: 3150: 3146: 3145:antiandrogens 3142: 3135: 3130: 3128: 3123: 3121: 3116: 3115: 3112: 3100: 3097: 3095: 3092: 3090: 3083: 3081: 3078: 3076: 3073: 3071: 3068: 3066: 3063: 3061: 3058: 3056: 3053: 3051: 3048: 3046: 3043: 3041: 3038: 3036: 3033: 3031: 3028: 3026: 3023: 3021: 3018: 3016: 3013: 3011: 3008: 3006: 3003: 3001: 2998: 2996: 2993: 2991: 2988: 2986: 2983: 2981: 2978: 2976: 2973: 2971: 2968: 2966: 2963: 2961: 2958: 2956: 2953: 2951: 2948: 2946: 2943: 2941: 2938: 2936: 2929: 2927: 2926:Beta-blockers 2924: 2922: 2921:Antiandrogens 2919: 2917: 2914: 2912: 2909: 2907: 2904: 2903: 2901: 2895: 2885: 2882: 2881: 2880: 2877: 2875: 2872: 2871: 2870: 2867: 2865: 2862: 2860: 2857: 2856: 2854: 2850: 2846: 2839: 2834: 2832: 2827: 2825: 2820: 2819: 2816: 2810: 2807: 2806: 2802: 2784: 2780: 2776: 2772: 2768: 2764: 2760: 2756: 2752: 2745: 2738: 2735: 2730: 2726: 2722: 2718: 2714: 2710: 2707:(9): 807–13. 2706: 2702: 2701:Planta Medica 2695: 2692: 2687: 2683: 2679: 2675: 2671: 2667: 2659: 2656: 2651: 2647: 2643: 2639: 2635: 2631: 2627: 2623: 2615: 2612: 2607: 2603: 2599: 2595: 2591: 2587: 2583: 2579: 2572: 2569: 2564: 2560: 2555: 2550: 2546: 2542: 2538: 2534: 2530: 2523: 2520: 2515: 2511: 2506: 2501: 2497: 2493: 2489: 2485: 2481: 2474: 2471: 2466: 2462: 2457: 2452: 2448: 2444: 2440: 2436: 2432: 2428: 2424: 2417: 2415: 2411: 2406: 2402: 2398: 2394: 2391:(4): 623–39. 2390: 2386: 2378: 2376: 2372: 2367: 2363: 2359: 2355: 2351: 2347: 2343: 2339: 2331: 2328: 2323: 2319: 2314: 2309: 2305: 2301: 2297: 2293: 2289: 2282: 2279: 2274: 2270: 2266: 2262: 2258: 2254: 2246: 2243: 2232:on 2012-04-24 2228: 2224: 2220: 2213: 2206: 2204: 2200: 2195: 2191: 2186: 2181: 2176: 2171: 2167: 2163: 2159: 2155: 2151: 2144: 2141: 2136: 2132: 2129:(1): 149–53. 2128: 2124: 2117: 2115: 2113: 2111: 2107: 2102: 2098: 2094: 2090: 2086: 2082: 2078: 2074: 2066: 2064: 2060: 2045: 2041: 2037: 2032: 2027: 2024:(9): 1492–5. 2023: 2019: 2012: 2005: 2002: 1997: 1993: 1989: 1985: 1981: 1977: 1973: 1969: 1962: 1959: 1954: 1950: 1945: 1940: 1936: 1932: 1929:(1): 211–23. 1928: 1924: 1920: 1913: 1911: 1909: 1905: 1900: 1896: 1892: 1888: 1884: 1880: 1876: 1872: 1865: 1862: 1857: 1853: 1849: 1845: 1841: 1837: 1830: 1827: 1822: 1818: 1813: 1808: 1804: 1800: 1796: 1792: 1788: 1781: 1778: 1773: 1767: 1763: 1756: 1754: 1752: 1750: 1748: 1746: 1744: 1740: 1735: 1731: 1726: 1721: 1717: 1713: 1709: 1705: 1701: 1694: 1692: 1690: 1688: 1686: 1684: 1682: 1680: 1678: 1676: 1672: 1667: 1663: 1659: 1655: 1651: 1647: 1640: 1638: 1636: 1634: 1632: 1630: 1628: 1626: 1624: 1622: 1620: 1618: 1616: 1614: 1610: 1605: 1601: 1597: 1593: 1589: 1585: 1581: 1577: 1570: 1568: 1566: 1564: 1562: 1560: 1558: 1556: 1552: 1547: 1543: 1538: 1533: 1530:(3): 288–90. 1529: 1525: 1521: 1514: 1511: 1506: 1502: 1498: 1494: 1490: 1486: 1482: 1478: 1471: 1468: 1463: 1459: 1455: 1451: 1447: 1443: 1440:(5): 705–13. 1439: 1435: 1427: 1424: 1419: 1415: 1411: 1407: 1404:(2): 211–47. 1403: 1399: 1392: 1390: 1388: 1386: 1384: 1382: 1380: 1378: 1374: 1369: 1365: 1361: 1357: 1353: 1349: 1342: 1340: 1338: 1334: 1329: 1325: 1320: 1315: 1311: 1307: 1304:(5): 389–96. 1303: 1299: 1295: 1288: 1286: 1284: 1282: 1280: 1278: 1276: 1272: 1266: 1262: 1259: 1258: 1254: 1252: 1249: 1245: 1241: 1237: 1230: 1221: 1217: 1213: 1208: 1204: 1200: 1199: 1192: 1189: 1186: 1184: 1181: 1178: 1174: 1172: 1169: 1168: 1164: 1160: 1156: 1153: 1150: 1148: 1145: 1142: 1138: 1136: 1133: 1132: 1128: 1124: 1119: 1116: 1113: 1110: 1106: 1103: 1100: 1099: 1095: 1091: 1087: 1083: 1080: 1077: 1074: 1070: 1067: 1064: 1063: 1059: 1056: 1054: 1051: 1048: 1044: 1042: 1039: 1038: 1034: 1030: 1026: 1022: 1018: 1015: 1013: 1010: 1007: 1003: 1001: 998: 997: 993: 992:antiandrogens 989: 986: 983: 981: 978: 975: 971: 969: 966: 965: 961: 958: 955: 952: 949: 948: 942: 936: 931: 928: 925: 924: 923: 920: 918: 914: 909: 907: 903: 895: 893: 891: 890:sintokamide A 886: 884: 880: 871: 867:Sintokamide A 866: 862: 858: 854: 852: 848: 847:phenylalanine 844: 840: 839:phage display 835: 832: 828: 820: 818: 816: 810: 803: 798: 796: 794: 789: 785: 780: 776: 772: 768: 764: 760: 755: 747: 745: 742: 738: 734: 729: 725: 717: 715: 713: 708: 704: 700: 696: 690: 688: 676: 675: 670: 666: 661: 657: 655: 654:meta position 651: 647: 643: 639: 634: 626: 619: 607: 595: 583: 574: 572: 568: 559: 554: 552: 550: 546: 542: 538: 537:para position 534: 529: 526: 519: 515: 508: 506: 504: 500: 496: 491: 487: 484: 480: 472: 468: 461: 459: 457: 453: 449: 445: 441: 437: 436: 431: 427: 423: 419: 411: 407: 400: 398: 396: 392: 386: 383: 379: 375: 370: 364: 362: 358: 354: 350: 341: 339: 337: 333: 329: 328:transcription 325: 321: 317: 313: 309: 305: 301: 297: 293: 289: 281: 279: 277: 273: 265: 262: 259: 256: 253: 250: 249: 248: 246: 242: 238: 233: 231: 227: 223: 219: 215: 211: 207: 199: 195: 190: 182: 180: 178: 174: 170: 166: 162: 158: 154: 150: 146: 141: 139: 135: 130: 126: 122: 118: 114: 110: 106: 98: 96: 94: 90: 86: 82: 79:depending on 78: 74: 70: 65: 63: 59: 55: 51: 47: 43: 39: 35: 31: 27: 23: 19: 6428:Testosterone 6214:Pyrilutamide 6166: 6158: 6150: 6115:Lavender oil 6105:Ketoconazole 6070:Enzalutamide 6040:Darolutamide 5974:Bicalutamide 5949:Atraric acid 5921: 5916: 5900:Trimegestone 5855:Promegestone 5820:Mifepristone 5795:Medrogestone 5740:Drospirenone 5695:Clascoterone 5626: 5592: 5536:JNJ-37654032 5531:JNJ-28330835 5526:JNJ-26146900 5422: 5366: 5346: 5331: 5313:Quingestanol 5230:Etonogestrel 5216: 5196: 5169: 5159: 5149: 5134: 5118:Propetandrol 5059: 5048:Oxymetholone 5023:Methasterone 4977: 4971:Tiomesterone 4961:Oxymesterone 4853: 4833: 4754:Norclostebol 4729: 4725: 4634: 4572:Mepitiostane 4567:Epitiostanol 4550:Drostanolone 4501:Androsterone 4457: 4438:+dutasteride 4434:Testosterone 4402:DHEA sulfate 4255: 4108: 4068:Progestogens 3936:Ketoconazole 3864:5α-Reductase 3828:Ketoconazole 3818:Enzalutamide 3813:Darolutamide 3803:Bicalutamide 3794: 3758:Medrogestone 3753:Drospirenone 3716: 3609: 3559: 3549: 3519: 3508:Oxymetholone 3479: 3463:Oxymesterone 3399: 3373:Norclostebol 3350: 3324:Mepitiostane 3319:Epitiostanol 3295: 3247:Testosterone 3188: 2920: 2790:. Retrieved 2757:(1–2): 1–8. 2754: 2750: 2737: 2704: 2700: 2694: 2669: 2665: 2658: 2625: 2622:The Prostate 2621: 2614: 2584:(5): 480–8. 2581: 2578:The Prostate 2577: 2571: 2539:(4): 880–7. 2536: 2532: 2522: 2487: 2483: 2473: 2430: 2426: 2388: 2384: 2341: 2337: 2330: 2295: 2291: 2281: 2256: 2252: 2245: 2234:. Retrieved 2227:the original 2222: 2218: 2157: 2153: 2143: 2126: 2122: 2079:(3): 153–8. 2076: 2073:The Prostate 2072: 2051:. Retrieved 2021: 2017: 2004: 1971: 1967: 1961: 1926: 1922: 1877:(3): 283–8. 1874: 1870: 1864: 1839: 1835: 1829: 1794: 1790: 1780: 1761: 1707: 1703: 1649: 1645: 1579: 1575: 1527: 1523: 1513: 1480: 1476: 1470: 1437: 1433: 1426: 1401: 1397: 1351: 1347: 1301: 1297: 1247: 1236:Atraric acid 1234: 1219: 1206: 1125:and has not 1102:Enzalutamide 1094:coactivators 1086:bicalutamide 1033:testosterone 1021:antagonistic 940: 921: 910: 899: 887: 875: 864: 855: 836: 824: 814: 811: 807: 751: 721: 711: 707:butylalcohol 697:atom with a 691: 672: 662: 658: 630: 617: 599:Bicalutamide 571:methyl group 563: 530: 525:Bicalutamide 523: 520:Bicalutamide 517: 509:Bicalutamide 476: 470: 433: 415: 409: 387: 382:side effects 369:gonadotropin 365: 349:hypothalamus 345: 336:coregulators 316:translocates 308:dimerisation 285: 269: 245:chromosome X 234: 203: 197: 173:bicalutamide 142: 102: 77:nonsteroidal 66: 30:testosterone 18:antiandrogen 15: 6413:Osteocalcin 6294:Vinclozolin 6279:Thalidomide 6274:Seviteronel 6204:Procymidone 6140:Masofaniten 6095:Inocoterone 5999:bisphenol S 5995:bisphenol F 5991:bisphenol A 5969:BAY-1024767 5944:Apalutamide 5890:Spiroxasone 5885:Spirorenone 5865:Rosterolone 5805:Mespirenone 5750:Edogestrone 5720:Delanterone 5710:Cyproterone 5700:Clometerone 5670:Benorterone 5655:Abiraterone 5620:Antagonists 5551:PF-06260414 5456:BMS-564,929 5380:Alternariol 5272:Lynestrenol 5225:Desogestrel 5108:Norboletone 5098:Metribolone 5043:Oxandrolone 5001:Mestanolone 4966:Penmesterol 4897:Formebolone 4862:Calusterone 4857:Bolasterone 4611:Prostanozol 4582:Mesterolone 4142:from market 4052:leuprorelin 4000:haloperidol 3996:risperidone 3988:domperidone 3980:antagonists 3946:Seviteronel 3887:Finasteride 3882:Epristeride 3877:Dutasteride 3872:Alfatradiol 3838:Seviteronel 3798:Apalutamide 3709:antagonists 3653:leuprorelin 3593:lynestrenol 3503:Oxandrolone 3498:Mestanolone 3468:Penmesterol 3423:Formebolone 3408:Calusterone 3403:Bolasterone 3329:Mesterolone 3276:Deposterona 3089:antagonists 2874:Preclinical 2864:Hit to lead 2845:Drug design 1974:(1): 3–12. 1483:(1): 62–5. 1209:Ataric acid 1187:Preclinical 1066:Apalutamide 1057:Preclinical 1016:Preclinical 985:Preclinical 917:finasteride 879:biochemical 533:cyano group 503:pneumonitis 486:nitro group 378:hyperplasia 361:stimulation 241:amino acids 153:cyproterone 6483:Categories 6407:-ornithine 6350:gadolinium 6199:Prochloraz 6194:Phenothrin 6174:Nilutamide 6145:Methiocarb 6065:Endosulfan 6030:Cioteronel 6025:Cimetidine 6015:BMS-641988 6010:BMS-570511 6005:BMS-501949 5979:Bisphenols 5934:Antarlides 5910:Zanoterone 5845:Oxendolone 5790:Ludaterone 5780:Galeterone 5730:Dicirenone 5627:Steroidal: 5593:Steroidal: 5586:Vosilasarm 5481:GSK2881078 5436:AC-262,536 5395:Trilostane 5303:Norgestrel 5252:Gestrinone 5220:Δ-Tibolone 5103:Mibolerone 5053:Stanozolol 5006:Metenolone 4783:Trenbolone 4742:Nandrolone 4692:Dienedione 4616:Stenbolone 4577:Mesabolone 4429:Silandrone 4424:Quinbolone 4419:Plomestane 4414:Formestane 4409:Exemestane 4331:Atamestane 4228:modulators 4062:cetrorelix 4018:bifluranol 3941:Nilutamide 3921:Bifluranol 3911:+niraparib 3855:inhibitors 3833:Nilutamide 3808:Cimetidine 3778:Oxendolone 3723:+niraparib 3717:Steroidal: 3585:norgestrel 3573:Progestins 3568:Gestrinone 3528:Mibolerone 3513:Stanozolol 3242:Quinbolone 2980:Gliflozins 2792:2019-10-01 2236:2011-09-27 2053:2019-09-02 1267:References 1135:BMS-641988 1129:activity. 1114:Medivation 1078:Medivation 611:Nilutamide 549:enantiomer 473:Nilutamide 462:Nilutamide 452:metabolite 444:amide bond 430:hydrolysis 276:C-terminal 230:Endogenous 177:nilutamide 134:metastatic 121:castration 22:antagonise 16:The first 6393:-arginine 6378:Estradiol 6358:strontium 6354:magnesium 6342:aluminium 6309:YM-175735 6244:Ro 5-2537 6239:Ro 2-7239 6189:PF-998425 6184:Pentomone 6125:LG-120907 6085:Flutamide 6080:Fenarimol 6020:CH5137291 5959:Bakuchiol 5895:Topterone 5860:Prorenone 5835:Osaterone 5830:Nordinone 5815:Mexrenone 5735:Dienogest 5685:Canrenone 5606:TFM-4AS-1 5546:ORM-11984 5486:GSK-4336A 5476:GLPG-0492 5400:ZM-182345 5247:Gestodene 5235:Etynodiol 4991:Furazabol 4882:Enestebol 4810:Trendione 4771:Oxabolone 4697:Dienolone 4670:Bolandiol 4599:Nisterime 4353:Clostebol 4336:Boldenone 4152:Phase III 4140:Withdrawn 4026:estradiol 4014:Estrogens 4008:sulpiride 3986:) (e.g., 3931:Flutamide 3823:Flutamide 3748:Dienogest 3728:Canrenone 3639:clomifene 3635:tamoxifen 3488:Furazabol 3202:Clostebol 3153:Androgens 3141:Androgens 2729:260278595 1220:Figure 10 1171:CH5137291 1123:apoptosis 1068:(Erleada) 953:Structure 827:cofactors 779:cell line 754:mutations 703:imidazole 618:Figure 7: 479:hydantoin 440:half-life 412:Flutamide 401:Flutamide 300:cytosolic 288:cytoplasm 165:flutamide 140:in 1966. 105:pituitary 73:steroidal 54:hirsutism 50:seborrhea 6444:See also 6331:Agonists 6304:YM-92088 6269:RU-58841 6264:RU-58642 6259:RU-57073 6254:RU-56187 6249:RU-22930 6179:ONC1-13B 6130:LGD-1331 6055:Dieldrin 6049:p,p’-DDE 5954:AZD-3514 5939:Arabilin 5870:RU-15328 5810:Metogest 5745:DU-41165 5581:S-101479 5561:RU-59063 5516:LGD-4033 5511:LGD-3303 5501:LGD-2226 5491:GSK-8698 5390:Drupanol 5385:Cl-4AS-1 5325:Tibolone 4506:Bolazine 4249:Agonists 4164:See also 4070:(incl., 3977:receptor 3603:Tibolone 3284:Sustanon 3280:Omnadren 3181:agonists 3050:Triptans 2935:agonists 2879:Clinical 2783:Archived 2779:26865620 2771:20965230 2721:16783690 2686:21050768 2650:42009977 2642:21308717 2606:24620044 2598:20878947 2563:21131556 2514:20398925 2465:19359544 2322:17331889 2273:18834139 2194:15833816 2135:12517791 2101:22806905 2044:Archived 2040:20581083 1988:14689576 1953:12488554 1899:24746807 1856:12089231 1821:19079612 1797:: e010. 1734:16841196 1666:20030610 1604:36184991 1596:21704118 1546:25736005 1497:20164692 1462:24737257 1454:25871467 1418:10637363 1368:20708648 1328:12044015 1255:See also 1248:In vitro 1207:Figure 9 1117:Approved 1104:(Xtandi) 1090:androgen 1081:Approved 1025:prostate 1000:LG120907 945:Table 1 865:Figure 8 831:peptides 759:biopsies 752:AR gene 728:ablation 674:in vitro 567:chlorine 545:racemate 518:Figure 6 490:carbonyl 483:aromatic 471:Figure 5 410:Figure 4 380:. These 320:promoter 296:agonists 222:receptor 198:Figure 1 125:estrogen 93:clinical 6400:-lysine 6388:(incl. 6346:calcium 6340:(incl. 6338:Cations 6135:Linuron 6075:EPI-001 5981:(e.g., 5770:EM-6537 5765:EM-5855 5760:EM-5854 5755:EM-4350 5601:MK-0773 5596:EM-9017 5576:S-40503 5431:ACP-105 5426:198RL26 5291:(e.g., 5264:(e.g., 5173:Danazol 5123:RU-2309 5063:Bolenol 4060:(e.g., 4050:(e.g., 4016:(e.g., 3661:(e.g., 3647:(e.g., 3633:(e.g., 3575:(e.g., 3563:Danazol 3361:(e.g., 3254:(e.g., 3156:(incl. 3040:Statins 2554:3070382 2505:2948179 2456:2981508 2435:Bibcode 2427:Science 2405:9484511 2358:9569015 2313:2072879 2185:1087923 2162:Bibcode 2093:8827083 1996:5773128 1944:2040236 1891:3930312 1812:2602589 1725:2072875 1505:6922842 1319:4124639 1127:agonist 968:RU58642 956:Company 851:leucine 815:in vivo 712:in vivo 669:sulfone 665:sulfide 650:aniline 633:anilide 535:at the 495:radical 435:in vivo 235:The AR 226:protein 220:of the 214:binding 157:acetate 129:atrophy 99:History 44:(BHP), 6323:GPRC6A 6299:YM-580 6229:RD-162 6120:LG-105 5471:FTBU-1 4135:WHO-EM 4102:Others 3901:Others 2884:Phases 2777: 2769: 2727: 2719: 2684: 2648: 2640: 2604: 2596: 2561: 2551: 2512: 2502: 2484:Lancet 2463: 2453: 2403: 2366:290926 2364: 2356: 2320: 2310: 2271: 2192: 2182: 2133: 2099: 2091: 2038: 1994: 1986: 1951: 1941: 1897: 1889: 1854: 1819: 1809: 1768: 1732: 1722: 1664: 1602: 1594: 1544: 1503: 1495: 1460: 1452: 1416: 1366: 1326: 1316: 849:, L = 788:indole 784:phenyl 761:. The 699:sulfur 695:oxygen 687:acetyl 638:alkene 541:chiral 456:potent 418:analog 374:libido 109:testes 81:ligand 5987:BFDGE 5983:BADGE 5929:AA560 5611:YK-11 5521:LY305 5411:SARMs 2786:(PDF) 2775:S2CID 2747:(PDF) 2725:S2CID 2646:S2CID 2602:S2CID 2362:S2CID 2230:(PDF) 2215:(PDF) 2097:S2CID 2047:(PDF) 2014:(PDF) 1992:S2CID 1895:S2CID 1600:S2CID 1501:S2CID 1458:S2CID 1041:LG105 775:LNCaP 771:W741C 767:W741L 763:T877A 733:tumor 155:. An 6419:SHBG 6362:zinc 6060:DIMP 5675:BOMT 5571:S-23 5461:DTIB 3143:and 3085:5-HT 2931:Beta 2767:PMID 2717:PMID 2682:PMID 2638:PMID 2594:PMID 2559:PMID 2510:PMID 2461:PMID 2401:PMID 2354:PMID 2318:PMID 2269:PMID 2190:PMID 2131:PMID 2089:PMID 2036:PMID 1984:PMID 1949:PMID 1887:PMID 1852:PMID 1817:PMID 1766:ISBN 1730:PMID 1662:PMID 1592:PMID 1542:PMID 1493:PMID 1450:PMID 1414:PMID 1364:PMID 1324:PMID 1238:and 1031:and 881:and 769:and 667:and 565:the 314:and 237:gene 111:and 56:and 46:acne 32:and 24:the 6045:DDT 5566:S-1 5556:R-1 3673:hCG 3159:AAS 2759:doi 2755:332 2709:doi 2674:doi 2630:doi 2586:doi 2549:PMC 2541:doi 2500:PMC 2492:doi 2488:375 2451:PMC 2443:doi 2431:324 2393:doi 2346:doi 2308:PMC 2300:doi 2261:doi 2180:PMC 2170:doi 2158:102 2081:doi 2026:doi 1976:doi 1939:PMC 1931:doi 1879:doi 1844:doi 1807:PMC 1799:doi 1720:PMC 1712:doi 1654:doi 1584:doi 1580:352 1532:doi 1485:doi 1442:doi 1406:doi 1356:doi 1314:PMC 1306:doi 123:or 75:or 6485:: 6402:, 6395:, 6360:, 6356:, 6352:, 6348:, 6344:, 5997:, 5993:, 5989:, 5985:, 5295:, 4950:) 4539:) 4440:) 4237:AR 4148:: 4090:, 4086:, 4082:, 4078:, 4074:, 4040:, 4036:, 4032:, 4028:, 4024:, 4020:, 4006:, 4002:, 3998:, 3994:, 3990:, 3702:AR 3670:, 3664:LH 3651:, 3637:, 3595:, 3591:, 3587:, 3583:, 3579:, 3365:, 3290:)) 3286:, 3282:, 3278:, 3270:, 3266:, 3262:, 3258:, 3174:AR 2781:. 2773:. 2765:. 2753:. 2749:. 2723:. 2715:. 2705:72 2703:. 2680:. 2670:18 2668:. 2644:. 2636:. 2626:71 2624:. 2600:. 2592:. 2582:71 2580:. 2557:. 2547:. 2537:17 2535:. 2531:. 2508:. 2498:. 2486:. 2482:. 2459:. 2449:. 2441:. 2429:. 2425:. 2413:^ 2399:. 2389:41 2387:. 2374:^ 2360:. 2352:. 2342:64 2340:. 2316:. 2306:. 2296:12 2294:. 2290:. 2267:. 2257:10 2255:. 2221:. 2217:. 2202:^ 2188:. 2178:. 2168:. 2156:. 2152:. 2127:63 2125:. 2109:^ 2095:. 2087:. 2077:29 2075:. 2062:^ 2042:. 2034:. 2022:56 2020:. 2016:. 1990:. 1982:. 1972:91 1970:. 1947:. 1937:. 1927:63 1925:. 1921:. 1907:^ 1893:. 1885:. 1875:42 1873:. 1850:. 1840:20 1838:. 1815:. 1805:. 1793:. 1789:. 1742:^ 1728:. 1718:. 1708:23 1706:. 1702:. 1674:^ 1660:. 1650:16 1648:. 1612:^ 1598:. 1590:. 1578:. 1554:^ 1540:. 1528:13 1526:. 1522:. 1499:. 1491:. 1481:16 1479:. 1456:. 1448:. 1438:39 1436:. 1412:. 1400:. 1376:^ 1362:. 1352:62 1350:. 1336:^ 1322:. 1312:. 1300:. 1296:. 1274:^ 1165:. 1096:. 1035:. 1029:LH 994:. 765:, 681:CH 363:. 310:, 107:, 52:, 48:, 40:, 6409:) 6405:L 6398:L 6391:L 6384:L 6364:) 6167:N 6159:N 6151:N 6051:) 6001:) 5922:N 5920:5 5299:) 5268:) 4946:( 4730:N 4726:N 4535:( 4436:( 4217:e 4210:t 4203:v 4094:) 4064:) 4054:) 4044:) 4010:) 3982:( 3975:2 3973:D 3679:) 3655:) 3641:) 3599:) 3369:) 3274:( 3165:) 3133:e 3126:t 3119:v 3087:3 2933:2 2837:e 2830:t 2823:v 2795:. 2761:: 2731:. 2711:: 2688:. 2676:: 2652:. 2632:: 2608:. 2588:: 2565:. 2543:: 2516:. 2494:: 2467:. 2445:: 2437:: 2407:. 2395:: 2368:. 2348:: 2324:. 2302:: 2275:. 2263:: 2239:. 2223:6 2196:. 2172:: 2164:: 2137:. 2103:. 2083:: 2056:. 2028:: 1998:. 1978:: 1955:. 1933:: 1901:. 1881:: 1858:. 1846:: 1823:. 1801:: 1795:6 1774:. 1736:. 1714:: 1668:. 1656:: 1606:. 1586:: 1548:. 1534:: 1507:. 1487:: 1464:. 1444:: 1420:. 1408:: 1402:7 1370:. 1358:: 1330:. 1308:: 1302:2 683:3 679:2

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Knowledge (XXG)

Discovery and development of antiandrogens

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