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Fluconazole

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efficacy. These viruses are integral components of diverse ecosystems, including the human microbiome. Their unique attributes, such as specificity, potency, compatibility with biological systems, and ability to kill fungi, make them attractive candidates for therapeutic interventions. However, challenges remain in terms of their production scalability, formulation, stability, and the emergence of fungal resistance, which hinders their widespread adoption. Prior to clinical use, phages intended for therapy require thorough purification, characterization, and validation of their virulence. While further research is needed, phage therapy holds promise in the fight against antifungal resistance that other therapies struggle to address.
1098:, are potent against candidiasis, which has grown resistant to fluconazole because of the differences in their action mechanism. However, resistance to echinocandins can still develop through point mutations within highly conserved regions of the FKS1 and FKS2 genes through the exposure of members of this class. These genes encode for an enzyme called β-1,3-glucan synthase, responsible for building the yeast’s cell wall. Mutations in this enzyme reduce resistance to antifungal medications that target this enzyme and affect the yeast’s ability to construct its cell wall. 614: 591: 40: 31: 1073: 3555: 1304:
Powder for oral suspension contains sucrose and should not be used in patients with hereditary fructose, glucose/galactose malabsorption or sucrase-isomaltase deficiency. Capsules contain lactose and should not be given to patients with rare hereditary problems of galactose intolerance, Lapp lactase
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is not significantly affected by the absence of stomach acid. Concentrations measured in the urine, tears, and skin are approximately 10 times the plasma concentration, whereas saliva, sputum, and vaginal fluid concentrations are approximately equal to the plasma concentration, following a standard
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While combination therapy offers the benefits of faster and more extensive fungal eradication, including a reduced risk of resistance or tolerance, it also presents challenges. These include potential increases in toxicity, costs, and the need for standardized practices to test the efficacy of the
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The rising fungal resistance to fluconazole and related azole drugs spurs the need to find effective combative solutions swiftly. Rising resistance raises concerns since fluconazole is commonly used due to its inexpensiveness and ease of administration, according to the World Health Organization.
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Another promising avenue is the integration of phage therapy, which has shown successive results in functional therapies. Phages, viruses that infect microbes including fungi, exhibit potent antimicrobial effects against various resistant fungal strains, demonstrating remarkable specificity and
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One possible solution to counter the increasing prevalence of Candida infections–fungal infections caused by the yeast Candida–is combination antifungal therapy, combining natural components with commercial antifungal drugs to combat resistance. Research shows that natural substances can have
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infections in people with healthy immune systems, including infections of the bloodstream, kidney, or joints. Other antifungals are usually preferred when the infection is in the heart or central nervous system, and for the treatment of active infections in people with weak immune
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Some people are allergic to azoles, so those allergic to other azole drugs might be allergic to fluconazole. That is, some azole drugs have adverse side-effects. Some azole drugs may disrupt estrogen production in pregnancy, affecting pregnancy outcome.
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ring. While the imidazole antifungals are mainly used topically, fluconazole and certain other triazole antifungals are preferred when systemic treatment is required because of their improved safety and predictable absorption when administered orally.
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Xu Y, Wang Y, Yan L, Liang RM, Dai BD, Tang RJ, et al. (November 2009). "Proteomic analysis reveals a synergistic mechanism of fluconazole and berberine against fluconazole-resistant Candida albicans: endogenous ROS augmentation".
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In 2011, the US FDA reports that treatment with chronic, high doses of fluconazole during the first trimester of pregnancy may be associated with a rare and distinct set of birth defects in infants.
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Surov AO, Voronin AP, Vasilev NA, Churakov AV, Perlovich GL (20 December 2019). "Cocrystals of Fluconazole with Aromatic Carboxylic Acids: Competition between Anhydrous and Hydrated Solid Forms".
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Mølgaard-Nielsen D, Svanström H, Melbye M, Hviid A, Pasternak B (January 2016). "Association Between Use of Oral Fluconazole During Pregnancy and Risk of Spontaneous Abortion and Stillbirth".
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to lesser extent) In theory, therefore, fluconazole decreases the metabolism and increases the concentration of any drug metabolised by these enzymes. In addition, its potential effect on
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infections in people with weak immune systems, such as those neutropenic due to cancer chemotherapy, those with advanced HIV infections, transplant patients, and premature infants.
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Kragie L, Turner SD, Patten CJ, Crespi CL, Stresser DM (August 2002). "Assessing pregnancy risks of azole antifungals using a high throughput aromatase inhibition assay".
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specified interactions with cell components, increasing the intracellular concentration of associated antifungal drugs and their effectiveness. For example, Brazilian red
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Fuentefria AM, Pippi B, Dalla Lana DF, Donato KK, de Andrade SF (January 2018). "Antifungals discovery: an insight into new strategies to combat antifungal resistance".
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class tends to occur gradually over the course of prolonged drug therapy, resulting in clinical failure in immunocompromised patients (e.g., patients with advanced
1520: 62: 710: 3620: 1021: 997:. Development of resistance to one azole in this way will confer resistance to all drugs in the class. Another resistance mechanism employed by both 1086:, recommended as the first method of treatment against invasive candidiasis. The three echinocandins currently licensed for medical use, namely 2497: 2123:"FDA Alert: Diflucan (fluconazole): Drug Safety Communication - Long-term, High-dose Use During Pregnancy May be Associated with Birth Defects" 3509: 2793: 2647: 2614: 2444: 2225: 1684: 855: 2468: 1851: 1821: 2189: 1374:. Mammalian demethylase activity is much less sensitive to fluconazole than fungal demethylase. This inhibition prevents the conversion of 1648: 1690: 3595: 2671: 1940: 1910: 1020:
The full spectrum of fungal susceptibility and resistance to fluconazole can be found in the product data sheet. According to the US
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In a bulk powder form, it appears as a white crystalline powder, and it is very slightly soluble in water and soluble in alcohol.
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and major facilitator superfamily transporters. Other gene mutations are also known to contribute to development of resistance.
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As a second-line agent for the treatment of cryptococcal meningoencephalitis, a fungal infection of the central nervous system.
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Common (≥1% of patients): rash, headache, dizziness, nausea, vomiting, abdominal pain, diarrhea, and/or elevated liver enzymes
3276: 2159: 1740: 2730:"Evolution of Fluconazole-Resistant Candida albicans Strains by Drug-Induced Mating Competence and Parasexual Recombination" 3610: 3575: 2843: 2701: 1886: 3545: 1196: 3600: 1642: 483: 993:. These mutations prevent the azole drug from binding, while still allowing binding of the enzyme's natural substrate, 113: 3526: 2554:
Pfizer Australia Pty Ltd. Diflucan (Australian Approved Product Information). West Ryde (NSW): Pfizer Australia; 2004.
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in 1981 in the United Kingdom and came into commercial use in 1988. Patent expirations occurred in 2004 and 2005.
3344: 3314: 2786: 2566:"Dose response effect of high-dose fluconazole for HIV-associated cryptococcal meningitis in southwestern Uganda" 1704: 3209: 957: 1386:, and subsequent accumulation of 14α-methyl sterols. Fluconazole is primarily fungistatic; however, it may be 1082:
An alternative to combination therapy for those who had prior exposure to Azoles is antifungal drugs of class
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it may result in harm. These cases of harm, however, were only in women who took large doses for most of the
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infections. Fluconazole may increase the serum concentration of Erythromycin (Risk X: avoid combination).
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InChI=1S/C13H12F2N6O/c14-10-1-2-11(12(15)3-10)13(22,4-20-8-16-6-18-20)5-21-9-17-7-19-21/h1-3,6-9,22H,4-5H2
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is still low. Women using fluconazole during pregnancy have a 50% higher risk of spontaneous abortion.
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Whalen K, Feild C, Radhakrishnan R (21 September 2018). Whalen K, Feild C, Radhakrishnan R (eds.).
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Longley N, Muzoora C, Taseera K, Mwesigye J, Rwebembera J, Chakera A, et al. (December 2008).
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combination. Therefore, it is crucial to critically evaluate the role of combination therapy.
1045:, an organic bee liquid, synergizes with fluconazole to combat common yeast infections such as 30: 3295: 2759: 2653: 2643: 2620: 2610: 2587: 2537: 2450: 2440: 2417: 2382: 2333: 2283: 2231: 2221: 2104: 2053: 2018: 1890: 1680: 1674: 879: 848: 773: 539: 279: 266: 249: 52: 2073:"Bacteriophages and the One Health Approach to Combat Multidrug Resistance: Is This the Way?" 3439: 3389: 2749: 2741: 2577: 2529: 2409: 2372: 2325: 2273: 2265: 2094: 2084: 2045: 2008: 1998: 1712: 1565: 1200: 981: 908: 896: 844: 801: 626: 298: 2679: 1918: 492: 407: 3559: 3021: 3011: 1403: 1367: 1314: 1242: 828: 797: 472: 326: 306: 1795: 804:. It is also used to prevent candidiasis in those who are at high risk such as following 1964: 613: 590: 3520: 3451: 3394: 3364: 3349: 3117: 3006: 2754: 2729: 2278: 2099: 2072: 2013: 1986: 1208: 1115: 902: 824: 793: 789: 3569: 3354: 3250: 3224: 3031: 2983: 2949: 2904: 2874: 2469:"Diflucan (Fluconazole) dosing, indications, interactions, adverse effects, and more" 1577: 1456: 1412: 1287: 1212: 1087: 919: 840: 781: 697: 602: 86: 2728:
Popp C, Ramírez-Zavala B, Schwanfelder S, Krüger I, Morschhäuser J (February 2019).
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has been shown to exert synergistic effects with fluconazole even in drug-resistant
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is mediated by reduced sensitivity of the target enzyme to inhibition by the agent.
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Fluconazole was patented in 1981 and came into commercial use in 1988. It is on the
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Following oral dosing, fluconazole is almost completely absorbed within two hours.
1275: 1188: 1184: 1121: 1083: 1076: 883: 205: 200: 195: 190: 185: 180: 72: 2694:"Pfizer to Expand Fluconazole Donation Program to More than 50 Developing Nations" 1732: 432: 3495: 3456: 3414: 3384: 3285: 3229: 3165: 3153: 2993: 2959: 2954: 2944: 2939: 2914: 2889: 1330: 1298: 1252: 1222: 1216: 1128: 1091: 969: 836: 813: 809: 777: 80: 2693: 2089: 3485: 3466: 3429: 3424: 3409: 3379: 3359: 3324: 3244: 3239: 3234: 3195: 3174: 3139: 3092: 2929: 2879: 2864: 2828: 2802: 2657: 2624: 2235: 1416: 1387: 1379: 1375: 1279: 1150: 1146: 1095: 1062: 994: 662: 463: 2454: 3471: 3419: 3148: 3107: 3073: 2899: 2855: 2771: 2413: 1569: 1491:"Diflucan- fluconazole tablet; Diflucan- fluconazole powder, for suspension" 1359: 1338: 1294: 1260: 1238: 1204: 1135: 887: 352: 66: 22: 2763: 2591: 2541: 2421: 2386: 2337: 2287: 2108: 2057: 2022: 1709:
World Health Organization model list of essential medicines: 21st list 2019
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Fluconazole is secreted in human milk at concentrations similar to plasma.
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Oral fluconazole is not associated with a significantly increased risk of
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is increasing the rate of efflux of the azole drug from the cell, by both
3369: 3112: 3064: 2974: 2269: 1363: 1264: 1192: 1180: 1042: 875: 832: 443: 108: 2361:"Use of oral fluconazole during pregnancy and the risk of birth defects" 2251:"Lack of allergic cross-reactivity between fluconazole and voriconazole" 2003: 1717: 1061:, a tree species native to wet tropical biomes, plays a similar role in 452: 3490: 3102: 2218:
Goodman & Gilman's : the Pharmacological Basis of Therapeutics
1987:"Antifungal resistance: current trends and future strategies to combat" 1318: 1072: 418: 2533: 2049: 1431: 1326: 1322: 847:
family of medication. It is believed to work by affecting the fungal
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if used concurrently with other drugs that prolong the QT interval.
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against certain organisms in a dose-dependent manner, specifically
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develops resistance by up regulating CDR genes, and resistance in
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infections of the vagina ("yeast infections"), throat, and mouth.
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Goodman & Gilman's The Pharmacological Basis of Therapeutics
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dose range of between 100 mg and 400 mg per day. The
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have known hypersensitivity to other azole medicines such as
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Common side effects include vomiting, diarrhea, rash, and
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Mølgaard-Nielsen D, Pasternak B, Hviid A (August 2013).
1965:"Antifungal Resistance | Fungal Disease | CDC" 1721:. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO. 244: 2216:
Brunton LL, Knollmann BC, Hilal-Dandan R, eds. (2018).
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World Health Organization's List of Essential Medicines
755: 3543: 2158:. The American Society of Health-System Pharmacists. 1889:
2006. Adelaide: Australian Medicines Handbook; 2006.
1613:. The American Society of Health-System Pharmacists. 1485: 1483: 1481: 1479: 1477: 1475: 1366:-class antifungals, fluconazole inhibits the fungal 3337: 3313: 3294: 3270: 3263: 3208: 3187: 3164: 3138: 3127: 3086: 3063: 2973: 2854: 2838: 2827: 2818: 696: 674: 661: 625: 620: 601: 569: 549: 529: 502: 482: 462: 442: 417: 397: 364: 351: 338: 325: 315: 305: 297: 221: 216: 171: 149: 123: 93: 79: 61: 51: 46: 2488: 2486: 1980: 1978: 1913:. In Brunton LL, Chabner BA, Knollmann BC (eds.). 894:Fluconazole's spectrum of activity includes most 1790: 1788: 1528:List of nationally authorised medicinal products 1305:deficiency, or glucose-galactose malabsorption 1110:Fluconazole is contraindicated in patients who: 878:antifungal medication. It differs from earlier 431: 2211: 2209: 2207: 1530:. European Medicines Agency. 12 November 2020. 985:, resistance occurs by way of mutations in the 835:. During pregnancy it may increase the risk of 406: 1134:concomitant administration of fluconazole and 3616:World Health Organization essential medicines 2787: 2182:"Prescribing medicines in pregnancy database" 1251:Fluconazole therapy has been associated with 1165:associated with fluconazole therapy include: 8: 2220:(13th ed.). McGraw-Hill Education LLC. 112: 21: 2640:Lippincott Illustrated Reviews Pharmacology 2146: 2144: 3267: 3135: 2851: 2835: 2824: 2794: 2780: 2772: 1904: 1902: 1881: 1879: 1877: 1605: 1603: 1601: 1599: 1597: 1595: 1593: 1591: 1589: 1587: 1022:Centers for Disease Control and Prevention 808:, low birth weight babies, and those with 612: 589: 471: 2753: 2581: 2376: 2277: 2098: 2088: 2012: 2002: 1716: 1313:Fluconazole is an inhibitor of the human 491: 1668: 1666: 1452:"Product monograph brand safety updates" 1415:, and only 10% of elimination is due to 1255:prolongation, which may lead to serious 3550: 1693:from the original on 10 September 2017. 1443: 1382:, an essential component of the fungal 1278:overall, although it does increase the 735: 715: 585: 451: 378: 85: 2162:from the original on 27 September 2014 2129:from the original on 28 September 2011 1679:. John Wiley & Sons. p. 503. 603: 20: 3591:Lanosterol 14α-demethylase inhibitors 2500:from the original on 21 December 2016 2258:Antimicrobial Agents and Chemotherapy 1802:from the original on 10 February 2015 1763:"Fluconazole - Drug Usage Statistics" 1711:. Geneva: World Health Organization. 1617:from the original on 20 December 2016 1537:from the original on 24 February 2024 1501:from the original on 22 February 2024 1293:Fluconazole should not be taken with 922:, among others. Common uses include: 558: 538: 71: 7: 2704:from the original on 30 October 2020 1743:from the original on 15 January 2024 1217:anaphylactic/anaphylactoid reactions 812:. It is given either by mouth or by 204: 194: 184: 2365:The New England Journal of Medicine 823:. Serious side effects may include 518: 511: 422: 3621:General cytochrome P450 inhibitors 874:Fluconazole is a first-generation 718:OC(Cn1cncn1)(Cn1cncn1)c1ccc(F)cc1F 14: 2607:Basic & clinical pharmacology 2297:from the original on 11 June 2011 2192:from the original on 8 April 2014 1971:from the original on 19 May 2017. 1317:system, particularly the isozyme 1172:Infrequent (0.1–1% of patients): 3553: 1985:Wiederhold NP (29 August 2017). 1773:from the original on 8 July 2020 858:. Fluconazole is available as a 649: 643: 637: 240:(Pharmacist only) / S4 38: 29: 3277:thymidylate synthase inhibitors 2605:Katzung BG (30 November 2017). 2249:Pinto A, Chan RC (April 2009). 2038:Letters in Applied Microbiology 1917:(12th ed.). Archived from 1911:"Chapter 57: Antifungal Agents" 1673:Fischer J, Ganellin CR (2006). 1647:. 26 April 2016. Archived from 1521:"Active substance: Fluconazole" 1028:strains in the US is about 7%. 1024:, fluconazole resistance among 743:Key:RFHAOTPXVQNOHP-UHFFFAOYSA-N 389:-1,2,4-triazol-1-yl)propan-2-ol 2437:Rang & Dale's pharmacology 926:The treatment of non-systemic 655: 631: 1: 1991:Infection and Drug Resistance 1887:Australian Medicines Handbook 1676:Analogue-based Drug Discovery 1179:Rare (<0.1% of patients): 1065:, another common antifungal. 2570:Clinical Infectious Diseases 2522:Journal of Proteome Research 2439:. Elsevier Health Sciences. 1643:Food and Drug Administration 1430:Fluconazole was patented by 918:, some dimorphic fungi, and 839:while large doses may cause 347:30 hours (range 20–50 hours) 2435:Rang HP (21 January 2015). 1558:Crystal Growth & Design 810:low blood neutrophil counts 381:2-(2,4-Difluorophenyl)-1,3- 3637: 2090:10.3390/antibiotics9070414 621:Chemical and physical data 3596:Drugs developed by Pfizer 3504: 3345:bromochlorosalicylanilide 3315:Aminoacyl tRNA synthetase 2609:. McGraw-Hill Education. 1705:World Health Organization 1055:. The essential oil from 751: 726: 706: 702:139 Â°C (282 Â°F) 369: 37: 28: 1197:Stevens–Johnson syndrome 968:receiving treatment for 843:. Fluconazole is in the 2414:10.1001/jama.2015.17844 1854:Cryptococcal Infections 1570:10.1021/acs.cgd.9b01490 1411:of fluconazole follows 1176:, fatigue, constipation 915:Cryptococcus neoformans 866:million prescriptions. 821:increased liver enzymes 3129:Squalene monooxygenase 2966:Systemic: ketoconazole 2473:reference.medscape.com 2071:Garvey M (July 2020). 1333:increases the risk of 1163:Adverse drug reactions 1079: 989:gene, which codes for 3157:Systemic: terbinafine 2746:10.1128/mBio.02740-18 2378:10.1056/NEJMoa1301066 2330:10.1081/ERC-120015045 2186:Australian Government 1733:"The Top 300 of 2021" 1497:. 21 September 2023. 1409:elimination half-life 1221:Very rare: prolonged 1075: 958:Antifungal resistance 814:injection into a vein 806:organ transplantation 772:used for a number of 770:antifungal medication 16:Antifungal medication 3611:Triazole antifungals 3576:Antiprotozoal agents 3445:Whitfield's ointment 3272:Pyrimidine analogues 3088:Polyene antimycotics 2270:10.1128/AAC.01500-08 1384:cytoplasmic membrane 1058:Nectandra lanceolata 1032:Combating Resistance 1007:ATP-binding cassette 3601:Phenylethanolamines 2682:on 16 January 2009. 2004:10.2147/IDR.S124918 1967:. 25 January 2019. 1921:on 31 December 2013 1909:Bennett JE (2011). 1284:tetralogy of Fallot 1257:cardiac arrhythmias 1228:torsades de pointes 269:(Prescription only) 25: 3531:Never to phase III 3435:tribromometacresol 3405:sodium thiosulfate 3400:selenium disulfide 3296:Mitotic inhibitors 2698:Kaiser Health News 2642:. Wolters Kluwer. 2318:Endocrine Research 1862:on 3 February 2015 1852:"IDSA Guidelines: 1832:on 3 February 2015 1824:Candida Infections 1822:"IDSA Guidelines: 1335:cardiac arrhythmia 1080: 941:The prevention of 860:generic medication 786:coccidioidomycosis 3606:Tertiary alcohols 3581:CYP3A4 inhibitors 3541: 3540: 3333: 3332: 3259: 3258: 3210:β-glucan synthase 3204: 3203: 3183: 3182: 3082: 3081: 2649:978-1-4963-8413-3 2616:978-1-259-64115-2 2576:(12): 1556–1561. 2534:10.1021/pr9005074 2528:(11): 5296–5304. 2479:on 23 April 2014. 2446:978-0-7020-5362-7 2227:978-1-259-58473-2 2050:10.1111/lam.12820 1953:on 14 March 2016. 1885:Rossi S, editor. 1686:978-3-527-60749-5 1106:Contraindications 933:Certain systemic 900:species (but not 880:azole antifungals 849:cellular membrane 774:fungal infections 763: 762: 687:Interactive image 571:CompTox Dashboard 289: 277: 264: 247: 235: 139: 106: 3628: 3558: 3557: 3556: 3549: 3440:undecylenic acid 3390:potassium iodide 3268: 3136: 2852: 2836: 2825: 2796: 2789: 2782: 2773: 2767: 2757: 2714: 2713: 2711: 2709: 2690: 2684: 2683: 2678:. 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Archived from 1818: 1812: 1811: 1809: 1807: 1792: 1783: 1782: 1780: 1778: 1759: 1753: 1752: 1750: 1748: 1729: 1723: 1722: 1720: 1701: 1695: 1694: 1670: 1661: 1660: 1658: 1656: 1651:on 29 April 2016 1633: 1627: 1626: 1624: 1622: 1607: 1582: 1581: 1564:(2): 1218–1228. 1553: 1547: 1546: 1544: 1542: 1536: 1525: 1517: 1511: 1510: 1508: 1506: 1487: 1470: 1469: 1467: 1465: 1448: 1398:Pharmacokinetics 1354:Pharmacodynamics 1343:Candida albicans 1237:If taken during 1201:thrombocytopenia 960:to drugs in the 909:Candida glabrata 865: 845:azole antifungal 802:tinea versicolor 776:. This includes 759: 758: 689: 669: 657: 651: 645: 639: 633: 616: 605: 594: 593: 579: 577: 562: 542: 522: 515: 495: 475: 455: 435: 425: 424: 410: 343: 287: 284: 275: 272: 262: 259: 255: 246: 243: 233: 230: 208: 198: 188: 137: 134: 116: 105: 102: 89: 75: 57:Diflucan, others 42: 33: 26: 24: 3636: 3635: 3631: 3630: 3629: 3627: 3626: 3625: 3566: 3565: 3564: 3554: 3552: 3544: 3542: 3537: 3536: 3521:Clinical trials 3500: 3329: 3309: 3290: 3275: 3255: 3212: 3200: 3179: 3160: 3156: 3131: 3123: 3115: 3090: 3078: 3059: 3012:fosravuconazole 2969: 2845: 2844:lanosterol 14α- 2831: 2820: 2814: 2800: 2770: 2727: 2723: 2721:Further reading 2718: 2717: 2707: 2705: 2700:. 7 June 2001. 2692: 2691: 2687: 2670: 2669: 2665: 2650: 2637: 2636: 2632: 2617: 2604: 2603: 2599: 2563: 2562: 2558: 2553: 2549: 2518: 2517: 2513: 2503: 2501: 2492: 2491: 2484: 2467: 2466: 2462: 2447: 2434: 2433: 2429: 2399: 2398: 2394: 2358: 2357: 2353: 2315: 2314: 2310: 2300: 2298: 2294: 2253: 2248: 2247: 2243: 2228: 2215: 2214: 2205: 2195: 2193: 2180: 2179: 2175: 2165: 2163: 2150: 2149: 2142: 2132: 2130: 2121: 2120: 2116: 2070: 2069: 2065: 2035: 2034: 2030: 1984: 1983: 1976: 1963: 1962: 1958: 1950: 1943: 1939: 1938: 1934: 1924: 1922: 1908: 1907: 1900: 1884: 1875: 1865: 1863: 1850: 1849: 1845: 1835: 1833: 1820: 1819: 1815: 1805: 1803: 1796:"US Pharmacist" 1794: 1793: 1786: 1776: 1774: 1761: 1760: 1756: 1746: 1744: 1731: 1730: 1726: 1703: 1702: 1698: 1687: 1672: 1671: 1664: 1654: 1652: 1635: 1634: 1630: 1620: 1618: 1609: 1608: 1585: 1555: 1554: 1550: 1540: 1538: 1534: 1523: 1519: 1518: 1514: 1504: 1502: 1489: 1488: 1473: 1463: 1461: 1450: 1449: 1445: 1440: 1428: 1404:Bioavailability 1400: 1372:14α-demethylase 1368:cytochrome P450 1356: 1351: 1315:cytochrome P450 1311: 1243:first trimester 1160: 1108: 1048:C. parapsilosis 1034: 991:14α-demethylase 955: 872: 863: 829:QT prolongation 798:dermatophytosis 754: 752: 747: 744: 739: 734: 733: 722: 719: 714: 713: 692: 667: 654: 648: 642: 636: 597: 573: 565: 545: 525: 498: 478: 458: 438: 421: 413: 393: 390: 377: 376: 341: 317:Protein binding 307:Bioavailability 299:Pharmacokinetic 293: 253: 212: 152: 145: 126: 119: 17: 12: 11: 5: 3634: 3632: 3624: 3623: 3618: 3613: 3608: 3603: 3598: 3593: 3588: 3583: 3578: 3568: 3567: 3563: 3562: 3539: 3538: 3535: 3534: 3533: 3532: 3529: 3518: 3512: 3506: 3505: 3502: 3501: 3499: 3498: 3493: 3488: 3479: 3474: 3469: 3464: 3459: 3454: 3452:citronella oil 3448: 3447: 3442: 3437: 3432: 3427: 3422: 3417: 3412: 3407: 3402: 3397: 3395:salicylic acid 3392: 3387: 3382: 3377: 3372: 3367: 3365:crystal violet 3362: 3357: 3352: 3350:chlorophetanol 3347: 3341: 3339: 3335: 3334: 3331: 3330: 3328: 3327: 3320: 3318: 3311: 3310: 3308: 3307: 3300: 3298: 3292: 3291: 3289: 3288: 3281: 3279: 3265: 3261: 3260: 3257: 3256: 3254: 3253: 3248: 3242: 3237: 3232: 3227: 3216: 3214: 3206: 3205: 3202: 3201: 3199: 3198: 3191: 3189: 3185: 3184: 3181: 3180: 3178: 3177: 3170: 3168: 3162: 3161: 3159: 3158: 3151: 3144: 3142: 3133: 3125: 3124: 3122: 3121: 3118:amphotericin B 3110: 3105: 3098: 3096: 3084: 3083: 3080: 3079: 3077: 3076: 3069: 3067: 3061: 3060: 3058: 3057: 3052: 3045: 3044: 3039: 3034: 3029: 3024: 3019: 3014: 3009: 3007:fosfluconazole 3004: 2997: 2996: 2991: 2986: 2979: 2977: 2971: 2970: 2968: 2967: 2963: 2962: 2957: 2952: 2947: 2942: 2937: 2932: 2927: 2922: 2917: 2912: 2907: 2902: 2897: 2892: 2887: 2882: 2877: 2872: 2867: 2860: 2858: 2849: 2833: 2822: 2816: 2815: 2801: 2799: 2798: 2791: 2784: 2776: 2769: 2768: 2724: 2722: 2719: 2716: 2715: 2685: 2676:MP Biomedicals 2663: 2648: 2630: 2615: 2597: 2583:10.1086/593194 2556: 2547: 2511: 2482: 2460: 2445: 2427: 2392: 2371:(9): 830–839. 2351: 2324:(3): 129–140. 2308: 2241: 2226: 2203: 2173: 2140: 2114: 2063: 2028: 1974: 1956: 1932: 1898: 1873: 1843: 1813: 1784: 1754: 1724: 1696: 1685: 1662: 1628: 1583: 1548: 1512: 1471: 1442: 1441: 1439: 1436: 1427: 1424: 1399: 1396: 1355: 1352: 1350: 1347: 1310: 1307: 1235: 1234: 1231: 1219: 1209:hepatotoxicity 1203:, other blood 1177: 1170: 1159: 1156: 1155: 1154: 1139: 1132: 1125: 1118: 1107: 1104: 1033: 1030: 972:or esophageal 954: 951: 950: 949: 946: 939: 931: 903:Candida krusei 871: 868: 825:liver problems 794:histoplasmosis 790:cryptococcosis 761: 760: 749: 748: 746: 745: 742: 740: 737: 729: 728: 727: 724: 723: 721: 720: 717: 709: 708: 707: 704: 703: 700: 694: 693: 691: 690: 682: 680: 672: 671: 665: 659: 658: 652: 646: 640: 634: 629: 623: 622: 618: 617: 607: 599: 598: 596: 595: 582: 580: 567: 566: 564: 563: 555: 553: 547: 546: 544: 543: 535: 533: 527: 526: 524: 523: 516: 508: 506: 500: 499: 497: 496: 488: 486: 480: 479: 477: 476: 468: 466: 460: 459: 457: 456: 448: 446: 440: 439: 437: 436: 428: 426: 415: 414: 412: 411: 403: 401: 395: 394: 392: 391: 380: 372: 371: 370: 367: 366: 362: 361: 355: 349: 348: 345: 336: 335: 329: 323: 322: 319: 313: 312: 311:>90% (oral) 309: 303: 302: 295: 294: 292: 291: 282: 270: 257: 241: 227: 225: 219: 218: 214: 213: 211: 210: 177: 175: 169: 168: 155: 153:administration 147: 146: 144: 143: 141: 131: 129: 121: 120: 118: 117: 99: 97: 91: 90: 83: 77: 76: 69: 59: 58: 55: 49: 48: 44: 43: 35: 34: 15: 13: 10: 9: 6: 4: 3: 2: 3633: 3622: 3619: 3617: 3614: 3612: 3609: 3607: 3604: 3602: 3599: 3597: 3594: 3592: 3589: 3587: 3584: 3582: 3579: 3577: 3574: 3573: 3571: 3561: 3551: 3547: 3530: 3528: 3525: 3524: 3522: 3519: 3516: 3513: 3511: 3508: 3507: 3503: 3497: 3494: 3492: 3489: 3487: 3483: 3480: 3478: 3475: 3473: 3470: 3468: 3465: 3463: 3460: 3458: 3455: 3453: 3450: 3449: 3446: 3443: 3441: 3438: 3436: 3433: 3431: 3428: 3426: 3423: 3421: 3418: 3416: 3413: 3411: 3408: 3406: 3403: 3401: 3398: 3396: 3393: 3391: 3388: 3386: 3383: 3381: 3378: 3376: 3373: 3371: 3368: 3366: 3363: 3361: 3358: 3356: 3355:chlorphenesin 3353: 3351: 3348: 3346: 3343: 3342: 3340: 3336: 3326: 3322: 3321: 3319: 3316: 3312: 3306: 3302: 3301: 3299: 3297: 3293: 3287: 3283: 3282: 3280: 3278: 3273: 3269: 3266: 3264:Intracellular 3262: 3252: 3251:ibrexafungerp 3249: 3246: 3243: 3241: 3238: 3236: 3233: 3231: 3228: 3226: 3225:anidulafungin 3222: 3221:echinocandins 3218: 3217: 3215: 3211: 3207: 3197: 3193: 3192: 3190: 3186: 3176: 3172: 3171: 3169: 3167: 3163: 3155: 3152: 3150: 3146: 3145: 3143: 3141: 3137: 3134: 3130: 3126: 3119: 3114: 3111: 3109: 3106: 3104: 3100: 3099: 3097: 3094: 3089: 3085: 3075: 3071: 3070: 3068: 3066: 3062: 3056: 3053: 3051: 3047: 3046: 3043: 3040: 3038: 3035: 3033: 3032:oteseconazole 3030: 3028: 3025: 3023: 3022:isavuconazole 3020: 3018: 3015: 3013: 3010: 3008: 3005: 3003: 2999: 2998: 2995: 2992: 2990: 2987: 2985: 2984:efinaconazole 2981: 2980: 2978: 2976: 2972: 2965: 2964: 2961: 2958: 2956: 2953: 2951: 2950:sertaconazole 2948: 2946: 2943: 2941: 2938: 2936: 2933: 2931: 2928: 2926: 2923: 2921: 2918: 2916: 2913: 2911: 2908: 2906: 2905:fenticonazole 2903: 2901: 2898: 2896: 2893: 2891: 2888: 2886: 2883: 2881: 2878: 2876: 2875:chlormidazole 2873: 2871: 2868: 2866: 2862: 2861: 2859: 2857: 2853: 2850: 2847: 2841: 2837: 2834: 2830: 2826: 2823: 2817: 2812: 2808: 2804: 2797: 2792: 2790: 2785: 2783: 2778: 2777: 2774: 2765: 2761: 2756: 2751: 2747: 2743: 2739: 2735: 2731: 2726: 2725: 2720: 2703: 2699: 2695: 2689: 2686: 2681: 2677: 2673: 2672:"Fluconazole" 2667: 2664: 2659: 2655: 2651: 2645: 2641: 2634: 2631: 2626: 2622: 2618: 2612: 2608: 2601: 2598: 2593: 2589: 2584: 2579: 2575: 2571: 2567: 2560: 2557: 2551: 2548: 2543: 2539: 2535: 2531: 2527: 2523: 2515: 2512: 2499: 2495: 2489: 2487: 2483: 2478: 2474: 2470: 2464: 2461: 2456: 2452: 2448: 2442: 2438: 2431: 2428: 2423: 2419: 2415: 2411: 2407: 2403: 2396: 2393: 2388: 2384: 2379: 2374: 2370: 2366: 2362: 2355: 2352: 2347: 2343: 2339: 2335: 2331: 2327: 2323: 2319: 2312: 2309: 2293: 2289: 2285: 2280: 2275: 2271: 2267: 2263: 2259: 2252: 2245: 2242: 2237: 2233: 2229: 2223: 2219: 2212: 2210: 2208: 2204: 2191: 2187: 2183: 2177: 2174: 2161: 2157: 2153: 2152:"Fluconazole" 2147: 2145: 2141: 2128: 2124: 2118: 2115: 2110: 2106: 2101: 2096: 2091: 2086: 2082: 2078: 2074: 2067: 2064: 2059: 2055: 2051: 2047: 2043: 2039: 2032: 2029: 2024: 2020: 2015: 2010: 2005: 2000: 1996: 1992: 1988: 1981: 1979: 1975: 1970: 1966: 1960: 1957: 1949: 1942: 1936: 1933: 1920: 1916: 1912: 1905: 1903: 1899: 1896: 1895:0-9757919-2-3 1892: 1888: 1882: 1880: 1878: 1874: 1861: 1857: 1855: 1847: 1844: 1831: 1827: 1825: 1817: 1814: 1801: 1797: 1791: 1789: 1785: 1772: 1768: 1764: 1758: 1755: 1742: 1738: 1734: 1728: 1725: 1719: 1714: 1710: 1706: 1700: 1697: 1692: 1688: 1682: 1678: 1677: 1669: 1667: 1663: 1650: 1646: 1644: 1638: 1632: 1629: 1616: 1612: 1611:"Fluconazole" 1606: 1604: 1602: 1600: 1598: 1596: 1594: 1592: 1590: 1588: 1584: 1579: 1575: 1571: 1567: 1563: 1559: 1552: 1549: 1533: 1529: 1522: 1516: 1513: 1500: 1496: 1492: 1486: 1484: 1482: 1480: 1478: 1476: 1472: 1460:. 7 July 2016 1459: 1458: 1457:Health Canada 1453: 1447: 1444: 1437: 1435: 1433: 1425: 1423: 1420: 1418: 1414: 1410: 1405: 1397: 1395: 1393: 1389: 1385: 1381: 1377: 1373: 1369: 1365: 1361: 1353: 1348: 1346: 1344: 1340: 1336: 1332: 1328: 1324: 1320: 1316: 1308: 1306: 1302: 1300: 1296: 1291: 1289: 1288:absolute risk 1285: 1281: 1277: 1276:birth defects 1272: 1268: 1266: 1262: 1258: 1254: 1249: 1246: 1244: 1240: 1232: 1230: 1229: 1224: 1220: 1218: 1214: 1213:liver failure 1210: 1206: 1202: 1198: 1194: 1190: 1186: 1182: 1178: 1175: 1171: 1168: 1167: 1166: 1164: 1157: 1152: 1148: 1144: 1140: 1137: 1133: 1130: 1126: 1123: 1119: 1117: 1113: 1112: 1111: 1105: 1103: 1099: 1097: 1093: 1089: 1088:anidulafungin 1085: 1084:echinocandins 1078: 1074: 1070: 1066: 1064: 1060: 1059: 1054: 1050: 1049: 1044: 1038: 1031: 1029: 1027: 1023: 1018: 1016: 1012: 1008: 1004: 1000: 996: 992: 988: 984: 983: 977: 975: 971: 967: 963: 959: 952: 947: 944: 940: 936: 932: 929: 925: 924: 923: 921: 920:dermatophytes 917: 916: 911: 910: 905: 904: 899: 898: 892: 889: 885: 881: 877: 869: 867: 861: 857: 852: 850: 846: 842: 841:birth defects 838: 834: 830: 826: 822: 817: 815: 811: 807: 803: 799: 795: 791: 787: 783: 782:blastomycosis 779: 775: 771: 767: 757: 750: 741: 736: 732: 725: 716: 712: 705: 701: 699: 698:Melting point 695: 688: 684: 683: 681: 678: 673: 666: 664: 660: 630: 628: 624: 619: 615: 611: 608: 606: 604:ECHA InfoCard 600: 592: 588: 587:DTXSID3020627 584: 583: 581: 572: 568: 561: 557: 556: 554: 552: 548: 541: 537: 536: 534: 532: 528: 521: 517: 514: 510: 509: 507: 505: 501: 494: 490: 489: 487: 485: 481: 474: 470: 469: 467: 465: 461: 454: 450: 449: 447: 445: 441: 434: 430: 429: 427: 420: 416: 409: 405: 404: 402: 400: 396: 388: 384: 379: 375: 368: 363: 359: 356: 354: 350: 346: 344: 337: 333: 330: 328: 324: 320: 318: 314: 310: 308: 304: 300: 296: 290: Rx-only 283: 281: 271: 268: 258: 251: 242: 239: 229: 228: 226: 224: 220: 215: 207: 202: 197: 192: 187: 182: 179: 178: 176: 174: 170: 167: 163: 159: 156: 154: 148: 142: 133: 132: 130: 128: 122: 115: 110: 101: 100: 98: 96: 92: 88: 84: 82: 78: 74: 70: 68: 64: 60: 56: 54: 50: 47:Clinical data 45: 41: 36: 32: 27: 19: 3586:Fluoroarenes 3477:tea tree oil 3462:lemon myrtle 3375:ethylparaben 3305:griseofulvin 3166:Benzylamines 3055:ravuconazole 3050:albaconazole 3042:voriconazole 3037:posaconazole 3027:itraconazole 3017:hexaconazole 3001: 2988: 2935:neticonazole 2925:luliconazole 2920:ketoconazole 2910:flutrimazole 2895:eberconazole 2885:clotrimazole 2870:butoconazole 2737: 2733: 2706:. Retrieved 2697: 2688: 2680:the original 2675: 2666: 2639: 2633: 2606: 2600: 2573: 2569: 2559: 2550: 2525: 2521: 2514: 2502:. Retrieved 2477:the original 2472: 2463: 2436: 2430: 2408:(1): 58–67. 2405: 2401: 2395: 2368: 2364: 2354: 2321: 2317: 2311: 2299:. Retrieved 2261: 2257: 2244: 2217: 2194:. Retrieved 2185: 2176: 2166:27 September 2164:. Retrieved 2155: 2131:. Retrieved 2117: 2080: 2076: 2066: 2041: 2037: 2031: 1994: 1990: 1959: 1948:the original 1935: 1923:. Retrieved 1919:the original 1914: 1864:. Retrieved 1860:the original 1853: 1846: 1834:. Retrieved 1830:the original 1823: 1816: 1804:. Retrieved 1775:. Retrieved 1766: 1757: 1745:. Retrieved 1736: 1727: 1718:10665/325771 1708: 1699: 1675: 1653:. Retrieved 1649:the original 1640: 1631: 1619:. Retrieved 1561: 1557: 1551: 1539:. Retrieved 1527: 1515: 1503:. Retrieved 1494: 1462:. Retrieved 1455: 1446: 1429: 1421: 1401: 1392:Cryptococcus 1391: 1357: 1349:Pharmacology 1342: 1312: 1309:Interactions 1303: 1292: 1273: 1269: 1250: 1247: 1236: 1226: 1191:, seizures, 1189:paraesthesia 1185:hypokalaemia 1161: 1158:Side effects 1122:ketoconazole 1109: 1100: 1081: 1077:Echinocandin 1067: 1057: 1052: 1046: 1039: 1035: 1025: 1019: 1014: 1010: 1002: 998: 986: 980: 978: 976:infection). 973: 956: 942: 934: 927: 913: 907: 901: 895: 893: 884:ketoconazole 873: 870:Medical uses 853: 818: 765: 764: 753:   386: 382: 340:Elimination 223:Legal status 217:Legal status 95:License data 18: 3517:from market 3496:pentamidine 3457:lemon grass 3415:taurolidine 3385:polynoxylin 3286:flucytosine 3230:caspofungin 3154:terbinafine 3140:Allylamines 3002:fluconazole 2994:terconazole 2989:fluconazole 2960:tioconazole 2955:sulconazole 2945:oxiconazole 2940:omoconazole 2915:isoconazole 2890:croconazole 2848:inhibitors) 2846:demethylase 2803:Antifungals 2504:21 December 2077:Antibiotics 2044:(1): 2–13. 1997:: 249–259. 1541:22 December 1505:22 February 1358:Like other 1331:QT interval 1301:may occur. 1299:anaphylaxis 1253:QT interval 1223:QT interval 1129:terfenadine 1127:are taking 1092:caspofungin 1053:C. glabrata 1011:C. glabrata 1003:C. glabrata 999:C. albicans 982:C. albicans 837:miscarriage 778:candidiasis 766:Fluconazole 670: g·mol 610:100.156.133 540:CHEBI:46081 365:Identifiers 162:intravenous 114:Fluconazole 81:MedlinePlus 53:Trade names 23:Fluconazole 3570:Categories 3486:atovaquone 3467:orange oil 3430:tolnaftate 3425:tolciclate 3410:sulbentine 3380:haloprogin 3360:ciclopirox 3325:tavaborole 3317:inhibitors 3303:Systemic: 3284:Systemic: 3245:rezafungin 3240:micafungin 3235:cilofungin 3219:Systemic: 3213:inhibitors 3196:amorolfine 3175:butenafine 3132:inhibitors 3116:Systemic: 3093:ergosterol 3000:Systemic: 2930:miconazole 2880:climbazole 2865:bifonazole 2856:Imidazoles 2832:inhibitors 2829:Ergosterol 2658:1114483879 2625:1035129378 2301:20 October 2236:1075550900 2083:(7): 414. 1866:28 January 1836:28 January 1806:28 January 1777:14 January 1747:14 January 1621:8 December 1438:References 1417:metabolism 1413:zero order 1388:fungicidal 1380:ergosterol 1376:lanosterol 1286:, but the 1280:odds ratio 1211:including 1207:, serious 1205:dyscrasias 1151:sertraline 1147:fluoxetine 1096:micafungin 1063:ciclopirox 995:lanosterol 953:Resistance 675:3D model ( 663:Molar mass 493:8VZV102JFY 464:ChemSpider 408:86386-73-4 399:CAS Number 374:IUPAC name 327:Metabolism 3527:Phase III 3515:Withdrawn 3472:patchouli 3420:ticlatone 3323:Topical: 3194:Topical: 3173:Topical: 3149:naftifine 3147:Topical: 3120:, hamycin 3108:natamycin 3101:Topical: 3074:abafungin 3072:Topical: 3065:Thiazoles 3048:Unknown: 2982:Topical: 2975:Triazoles 2900:econazole 2863:Topical: 2455:942814866 2156:Monograph 1578:213008181 1360:imidazole 1339:Berberine 1295:cisapride 1261:cisapride 1239:pregnancy 1136:quinidine 1015:C. krusei 888:imidazole 882:(such as 560:ChEMBL106 353:Excretion 342:half-life 151:Routes of 125:Pregnancy 73:Monograph 67:Drugs.com 3560:Medicine 3370:dimazole 3113:nystatin 3095:binding) 2821:membrane 2764:30723130 2702:Archived 2592:18990067 2542:19754040 2498:Archived 2422:26746458 2387:23984730 2338:12489563 2292:Archived 2288:19164151 2196:22 April 2190:Archived 2160:Archived 2133:4 August 2127:Archived 2109:32708627 2058:29112282 2023:28919789 1969:Archived 1800:Archived 1771:Archived 1767:ClinCalc 1741:Archived 1737:ClinCalc 1707:(2019). 1691:Archived 1655:29 April 1615:Archived 1532:Archived 1499:Archived 1495:DailyMed 1364:triazole 1265:pimozide 1193:alopecia 1181:oliguria 1174:anorexia 1145:such as 1043:propolis 938:systems. 876:triazole 833:seizures 756:(verify) 444:DrugBank 173:ATC code 158:By mouth 127:category 109:DailyMed 3491:dapsone 3103:hamycin 2755:6428756 2708:18 June 2494:"Login" 2346:8282678 2279:2663085 2100:7400126 2014:5587015 1464:3 April 1426:History 1370:enzyme 1319:CYP2C19 1116:alcohol 1026:Candida 974:Candida 943:Candida 935:Candida 928:Candida 897:Candida 668:306.277 627:Formula 453:DB00196 419:PubChem 252: / 248:: 203: ( 201:J01RA07 193: ( 191:J02AC01 189:) 183: ( 181:D01AC15 166:topical 140: D 111::  87:a690002 3546:Portal 3510:WHO-EM 3338:Others 3188:Others 2840:Azoles 2762:  2752:  2656:  2646:  2623:  2613:  2590:  2540:  2453:  2443:  2420:  2385:  2344:  2336:  2286:  2276:  2234:  2224:  2107:  2097:  2056:  2021:  2011:  1925:22 May 1893:  1683:  1576:  1432:Pfizer 1362:- and 1327:CYP2C9 1323:CYP3A4 1114:Drink 1094:, and 970:thrush 864:  831:, and 800:, and 768:is an 711:SMILES 551:ChEMBL 520:C07002 513:D00322 360:61–88% 358:Kidney 321:11–12% 280:â„ž-only 278: 265: 254:  250:â„ž-only 236: 107:  2819:Wall/ 2740:(1). 2342:S2CID 2295:(PDF) 2254:(PDF) 1951:(PDF) 1944:(PDF) 1645:(FDA) 1641:U.S. 1574:S2CID 1535:(PDF) 1524:(PDF) 1143:SSRIs 1141:take 987:ERG11 962:azole 731:InChI 677:JSmol 531:ChEBI 332:Liver 2809:and 2760:PMID 2734:mBio 2710:2019 2654:OCLC 2644:ISBN 2621:OCLC 2611:ISBN 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Index



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a690002
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Pharmacokinetic
Bioavailability

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