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29:
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Auci D, Kaler L, Subramanian S, Huang Y, Frincke J, Reading C, Offner H (September 2007). "A new orally bioavailable synthetic androstene inhibits collagen-induced arthritis in the mouse: androstene hormones as regulators of regulatory T cells".
271:
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Brown AP, Kirchner DL, Morrissey RL, Das SR, Fitzgerald RL, Crowell JA, Levine BS (2003). "Endocrine effects of dehydroepiandrosterone and its fluorinated analog, fluasterone, in rats".
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formulation of fluasterone was selected for clinical development. However, the development of fluasterone was nonetheless stopped reportedly due to its low potency and low oral
458:
activities of DHEA, much but not all of which it is thought may possibly be mediated via G6PDH inhibition (with some experimental evidence to support this notion available).
514:
785:"Chemoprevention of rat prostate carcinogenesis by dietary 16alpha-fluoro-5-androsten-17-one (fluasterone), a minimally androgenic analog of dehydroepiandrosterone"
285:
1039:
313:
InChI=1S/C19H27FO/c1-18-9-4-3-5-12(18)6-7-13-14(18)8-10-19(2)15(13)11-16(20)17(19)21/h6,13-16H,3-5,7-11H2,1-2H3/t13-,14+,15+,16-,18+,19+/m1/s1
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Ciolino HP, MacDonald CJ, Yeh GC (July 2002). "Inhibition of carcinogen-activating enzymes by 16alpha-fluoro-5-androsten-17-one".
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44:
3β-Dehydroxy-16α-fluoro-DHEA; Fl-DHEA; DHEF; DHEA 8354; DHEA analogue 8354; HE-2500; 16α-Fluoroandrost-5-en-17-one
671:
Schwartz AG, Pashko LL (April 2004). "Dehydroepiandrosterone, glucose-6-phosphate dehydrogenase, and longevity".
482:
1049:
1014:
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356:(DHEA) which was under investigation by Aeson Therapeutics for a variety of therapeutic indications including
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Schwartz AG, Pashko LL (2001). "Potential therapeutic use of dehydroepiandrosterone and structural analogs".
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377:
921:"A novel dehydroepiandrosterone analog improves functional recovery in a rat traumatic brain injury model"
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534:. It is for these reasons that fluasterone was developed and was considered to be advantageous to DHEA.
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metabolism, very high doses of DHEA and fluasterone are necessary for effectiveness. In animals, the
443:
970:"DHEA and Its Metabolites and Analogs: A Role in Immune Modulation and Arthritis TreatmentWatson RS"
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of DHEA and fluasterone is unknown. However, similarly to DHEA but more strongly, fluasterone is a
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346:
600:"Neuroprotective and Neurogenic Properties of Dehydroepiandrosterone and its Synthetic Analogs"
89:)-16-Fluoro-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopentaphenanthren-17-one
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McCormick DL, Johnson WD, Kozub NM, Rao KV, Lubet RA, Steele VE, Bosland MC (February 2007).
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Malik AS, Narayan RK, Wendling WW, Cole RW, Pashko LL, Schwartz AG, Strauss KI (May 2003).
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activity, and due to the presence of the fluorine atom at the C16α position, its
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Fluorine and Health: Molecular
Imaging, Biomedical Materials and Pharmaceuticals
629:"Biological Impactes of Fluorination: Pharmaceuticals Based on Natural Products"
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509:. In addition, unlike DHEA, fluasterone has reduced or no effects as a
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564:, which are said to have rendered it unsuitable for clinical use.
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430:= 0.5 μM versus 17 μM for DHEA). The drug retains the
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Auci DL, Ahlem CN, Reading CL, Frincke JM (22 July 2011).
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in animals and hence is not thought to interact with the
493:. Also in contrast to DHEA, fluasterone does not produce
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Tooltip peroxisome proliferator-activated receptor alpha
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among others but was ultimately never marketed. It is a
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Conversely, unlike DHEA, fluasterone has minimal or no
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of fluasterone is increased 40-fold when administered
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403:prior to the discontinuation of its development.
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396:atom at the C16α position. Fluasterone reached
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627:Bégué JP, Bonnet-Delpon D (6 June 2008).
424:Tooltip glucose-6-phosphate dehydrogenase
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606:. John Wiley & Sons. pp. 170–.
598:Gravanis AG, Mellon SH (24 June 2011).
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477:and thus it cannot be metabolized into
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716:Diabetes Technology & Therapeutics
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522:), and hence does not pose a risk of
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587:. S pringer Nature Switzerland AG.
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631:. In Tressaud A, Haufe G (eds.).
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1040:Experimental anti-obesity drugs
318:Key:VHZXNQKVFDBFIK-NBBHSKLNSA-N
974:DHEA in Human Health and Aging
240:
225:
1:
556:, and for this reason, a non-
513:(i.e., lacks activity at the
340:16α-fluoroandrost-5-en-17-one
293:C12CCCCC1=CC32CC4(3C(C4=O)F)C
976:. CRC Press. pp. 212–.
1025:Experimental diabetes drugs
635:. Elsevier. pp. 603–.
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937:10.1089/089771503765355531
728:10.1089/152091501300209589
215:Chemical and physical data
1000:Fluasterone - AdisInsight
878:Drug Development Research
685:10.1016/j.arr.2003.05.001
380:of DHEA in which the C3β
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53:
26:
1030:Anti-inflammatory agents
532:hepatocellular carcinoma
473:at the C17α position is
333:3β-dehydroxy-16α-fluoro-
847:10.1196/annals.1423.066
673:Ageing Research Reviews
511:peroxisome proliferator
415:uncompetitive inhibitor
384:has been removed and a
362:cardiovascular diseases
1060:Immunomodulating drugs
1045:Chemopreventive agents
925:Journal of Neurotrauma
374:traumatic brain injury
354:dehydroepiandrosterone
802:10.1093/carcin/bgl141
454:, as well as certain
1055:Hypolipidemic agents
1035:Antineoplastic drugs
839:2007NYASA1110..630A
475:sterically hindered
408:mechanism of action
23:
444:antihyperlipidemic
983:978-1-4398-3884-6
890:10.1002/ddr.10156
764:(13): 3685–3690.
642:978-0-08-055811-0
613:978-3-527-63397-5
537:Due to extensive
440:chemopreventative
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272:Interactive image
184:CompTox Dashboard
16:Chemical compound
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1020:Androstanes
585:AdisInsight
390:substituted
344:fluorinated
329:Fluasterone
255: g·mol
108:112859-71-9
49:Identifiers
41:Other names
21:Fluasterone
1009:Categories
568:References
539:first-pass
471:metabolism
467:estrogenic
463:androgenic
452:antiobesic
260:3D model (
248:Molar mass
173:R7M5UGD04G
144:ChemSpider
99:CAS Number
58:IUPAC name
898:0272-4391
491:estradiol
487:estrogens
479:androgens
347:synthetic
955:12803978
906:98206458
863:32258529
855:17911478
811:16952912
770:12097275
736:11478328
701:11871872
693:15177053
550:efficacy
526:such as
507:receptor
499:seizures
495:sedation
398:phase II
394:fluorine
386:hydrogen
382:hydroxyl
366:diabetes
350:analogue
1065:Ketones
946:1456324
835:Bibcode
544:and/or
542:hepatic
392:with a
370:obesity
342:, is a
253:290.422
221:Formula
119:PubChem
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450:, and
412:potent
372:, and
358:cancer
286:SMILES
153:118130
133:133967
902:S2CID
859:S2CID
697:S2CID
516:PPARα
489:like
481:like
420:G6PDH
306:InChI
262:JSmol
978:ISBN
951:PMID
894:ISSN
851:PMID
831:1110
807:PMID
766:PMID
732:PMID
689:PMID
637:ISBN
608:ISBN
558:oral
503:GABA
406:The
335:DHEA
164:UNII
941:PMC
933:doi
886:doi
843:doi
797:doi
724:doi
681:doi
530:or
497:or
485:or
465:or
417:of
352:of
338:or
189:EPA
123:CID
85:,16
81:,14
77:,13
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