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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.
1109:, 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. 625: 602: 51: 42: 1084: 3566: 1315:
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
1531: 73: 721: 3631: 1032: 1008:. Development of resistance to one azole in this way will confer resistance to all drugs in the class. Another resistance mechanism employed by both 1097:, recommended as the first method of treatment against invasive candidiasis. The three echinocandins currently licensed for medical use, namely 2508: 2134:"FDA Alert: Diflucan (fluconazole): Drug Safety Communication - Long-term, High-dose Use During Pregnancy May be Associated with Birth Defects" 3520: 2804: 2658: 2625: 2455: 2236: 1695: 866: 2479: 1862: 1832: 2200: 1385:. Mammalian demethylase activity is much less sensitive to fluconazole than fungal demethylase. This inhibition prevents the conversion of 1659: 1701: 3606: 2682: 1951: 1921: 1031:
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.
2302: 1308:(Propulsid) due to the possibility of serious, even fatal, heart problems. In rare cases, severe allergic reactions including 959:
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
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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.
3355: 3325: 2797: 2577:"Dose response effect of high-dose fluconazole for HIV-associated cryptococcal meningitis in southwestern Uganda" 1715: 3220: 968: 1397:, and subsequent accumulation of 14α-methyl sterols. Fluconazole is primarily fungistatic; however, it may be 1093:
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.
1056:, an organic bee liquid, synergizes with fluconazole to combat common yeast infections such as 41: 3306: 2770: 2664: 2654: 2631: 2621: 2598: 2548: 2461: 2451: 2428: 2393: 2344: 2294: 2242: 2232: 2115: 2064: 2029: 1901: 1691: 1685: 890: 859: 784: 550: 290: 277: 260: 63: 2084:"Bacteriophages and the One Health Approach to Combat Multidrug Resistance: Is This the Way?" 3450: 3400: 2760: 2752: 2588: 2540: 2420: 2383: 2336: 2284: 2276: 2105: 2095: 2056: 2019: 2009: 1723: 1576: 1211: 992: 919: 907: 855: 812: 637: 309: 2690: 1929: 503: 418: 3570: 3032: 3022: 1414: 1378: 1325: 1253: 839: 808: 483: 337: 317: 1806: 815:. It is also used to prevent candidiasis in those who are at high risk such as following 1975: 624: 601: 3531: 3462: 3405: 3375: 3360: 3128: 3017: 2765: 2740: 2289: 2110: 2083: 2024: 1997: 1219: 1126: 913: 835: 804: 800: 3580: 3365: 3261: 3235: 3042: 2994: 2960: 2915: 2885: 2480:"Diflucan (Fluconazole) dosing, indications, interactions, adverse effects, and more" 1588: 1467: 1423: 1298: 1223: 1098: 930: 851: 792: 708: 613: 97: 2739:
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.
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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
3380: 3123: 3075: 2985: 2280: 1374: 1275: 1203: 1191: 1053: 886: 843: 454: 119: 2372:"Use of oral fluconazole during pregnancy and the risk of birth defects" 2262:"Lack of allergic cross-reactivity between fluconazole and voriconazole" 2014: 1728: 1072:, a tree species native to wet tropical biomes, plays a similar role in 463: 17: 3501: 3113: 2229:
Goodman & Gilman's : the Pharmacological Basis of Therapeutics
1998:"Antifungal resistance: current trends and future strategies to combat" 1329: 1083: 429: 2544: 2060: 1442: 1337: 1333: 858:
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).
1976:"Antifungal Resistance | Fungal Disease | CDC" 1732:. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO. 255: 2227:
Brunton LL, Knollmann BC, Hilal-Dandan R, eds. (2018).
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World Health Organization's List of Essential Medicines
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2006. Adelaide: Australian Medicines Handbook; 2006.
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During pregnancy it may increase the risk of 417: 1145:concomitant administration of fluconazole and 3627:World Health Organization essential medicines 2798: 2193:"Prescribing medicines in pregnancy database" 1262:Fluconazole therapy has been associated with 1176:associated with fluconazole therapy include: 8: 2231:(13th ed.). McGraw-Hill Education LLC. 123: 32: 2651:Lippincott Illustrated Reviews Pharmacology 2157: 2155: 3278: 3146: 2862: 2846: 2835: 2805: 2791: 2783: 1915: 1913: 1892: 1890: 1888: 1616: 1614: 1612: 1610: 1608: 1606: 1604: 1602: 1600: 1598: 1033:Centers for Disease Control and Prevention 819:, low birth weight babies, and those with 623: 600: 482: 2764: 2592: 2387: 2288: 2109: 2099: 2023: 2013: 1727: 1324:Fluconazole is an inhibitor of the human 502: 1679: 1677: 1463:"Product monograph brand safety updates" 1426:, and only 10% of elimination is due to 1266:prolongation, which may lead to serious 3561: 1704:from the original on 10 September 2017. 1454: 1393:, an essential component of the fungal 1289:overall, although it does increase the 746: 726: 596: 462: 389: 96: 2173:from the original on 27 September 2014 2140:from the original on 28 September 2011 1690:. John Wiley & Sons. p. 503. 614: 31: 3602:Lanosterol 14α-demethylase inhibitors 2511:from the original on 21 December 2016 2269:Antimicrobial Agents and Chemotherapy 1813:from the original on 10 February 2015 1774:"Fluconazole - Drug Usage Statistics" 1722:. Geneva: World Health Organization. 1628:from the original on 20 December 2016 1548:from the original on 24 February 2024 1512:from the original on 22 February 2024 1304:Fluconazole should not be taken with 933:, among others. Common uses include: 569: 549: 82: 7: 2715:from the original on 30 October 2020 1754:from the original on 15 January 2024 1228:anaphylactic/anaphylactoid reactions 823:. It is given either by mouth or by 215: 205: 195: 2376:The New England Journal of Medicine 834:. Serious side effects may include 529: 522: 433: 3632:General cytochrome P450 inhibitors 885:Fluconazole is a first-generation 729:OC(Cn1cncn1)(Cn1cncn1)c1ccc(F)cc1F 25: 2618:Basic & clinical pharmacology 2308:from the original on 11 June 2011 2203:from the original on 8 April 2014 1982:from the original on 19 May 2017. 1328:system, particularly the isozyme 1183:Infrequent (0.1–1% of patients): 3564: 1996:Wiederhold NP (29 August 2017). 1784:from the original on 8 July 2020 869:. Fluconazole is available as a 660: 654: 648: 251:(Pharmacist only) / S4 49: 40: 3288:thymidylate synthase inhibitors 2616:Katzung BG (30 November 2017). 2260:Pinto A, Chan RC (April 2009). 2049:Letters in Applied Microbiology 1928:(12th ed.). Archived from 1922:"Chapter 57: Antifungal Agents" 1684:Fischer J, Ganellin CR (2006). 1658:. 26 April 2016. Archived from 1532:"Active substance: Fluconazole" 1039:strains in the US is about 7%. 1035:, fluconazole resistance among 754:Key:RFHAOTPXVQNOHP-UHFFFAOYSA-N 400:-1,2,4-triazol-1-yl)propan-2-ol 2448:Rang & Dale's pharmacology 937:The treatment of non-systemic 666: 642: 1: 2002:Infection and Drug Resistance 1898:Australian Medicines Handbook 1687:Analogue-based Drug Discovery 1190:Rare (<0.1% of patients): 1076:, another common antifungal. 2581:Clinical Infectious Diseases 2533:Journal of Proteome Research 2450:. Elsevier Health Sciences. 1654:Food and Drug Administration 1441:Fluconazole was patented by 929:, some dimorphic fungi, and 850:while large doses may cause 358:30 hours (range 20–50 hours) 2446:Rang HP (21 January 2015). 1569:Crystal Growth & Design 821:low blood neutrophil counts 392:2-(2,4-Difluorophenyl)-1,3- 3648: 2101:10.3390/antibiotics9070414 632:Chemical and physical data 3607:Drugs developed by Pfizer 3515: 3356:bromochlorosalicylanilide 3326:Aminoacyl tRNA synthetase 2620:. McGraw-Hill Education. 1716:World Health Organization 1066:. The essential oil from 762: 737: 717: 713:139 Â°C (282 Â°F) 380: 48: 39: 1208:Stevens–Johnson syndrome 979:receiving treatment for 854:. Fluconazole is in the 2425:10.1001/jama.2015.17844 1865:Cryptococcal Infections 1581:10.1021/acs.cgd.9b01490 1422:of fluconazole follows 1187:, fatigue, constipation 926:Cryptococcus neoformans 877:million prescriptions. 832:increased liver enzymes 3140:Squalene monooxygenase 2977:Systemic: ketoconazole 2484:reference.medscape.com 2082:Garvey M (July 2020). 1344:increases the risk of 1174:Adverse drug reactions 1090: 1000:gene, which codes for 3168:Systemic: terbinafine 2757:10.1128/mBio.02740-18 2389:10.1056/NEJMoa1301066 2341:10.1081/ERC-120015045 2197:Australian Government 1744:"The Top 300 of 2021" 1508:. 21 September 2023. 1420:elimination half-life 1232:Very rare: prolonged 1086: 969:Antifungal resistance 825:injection into a vein 817:organ transplantation 783:used for a number of 781:antifungal medication 27:Antifungal medication 3622:Triazole antifungals 3587:Antiprotozoal agents 3456:Whitfield's ointment 3283:Pyrimidine analogues 3099:Polyene antimycotics 2281:10.1128/AAC.01500-08 1395:cytoplasmic membrane 1069:Nectandra lanceolata 1043:Combating Resistance 1018:ATP-binding cassette 3612:Phenylethanolamines 2693:on 16 January 2009. 2015:10.2147/IDR.S124918 1978:. 25 January 2019. 1932:on 31 December 2013 1920:Bennett JE (2011). 1295:tetralogy of Fallot 1268:cardiac arrhythmias 1239:torsades de pointes 280:(Prescription only) 36: 3542:Never to phase III 3446:tribromometacresol 3416:sodium thiosulfate 3411:selenium disulfide 3307:Mitotic inhibitors 2709:Kaiser Health News 2653:. Wolters Kluwer. 2329:Endocrine Research 1873:on 3 February 2015 1863:"IDSA Guidelines: 1843:on 3 February 2015 1835:Candida Infections 1833:"IDSA Guidelines: 1346:cardiac arrhythmia 1091: 952:The prevention of 871:generic medication 797:coccidioidomycosis 3617:Tertiary alcohols 3592:CYP3A4 inhibitors 3552: 3551: 3344: 3343: 3270: 3269: 3221:β-glucan synthase 3215: 3214: 3194: 3193: 3093: 3092: 2660:978-1-4963-8413-3 2627:978-1-259-64115-2 2587:(12): 1556–1561. 2545:10.1021/pr9005074 2539:(11): 5296–5304. 2490:on 23 April 2014. 2457:978-0-7020-5362-7 2238:978-1-259-58473-2 2061:10.1111/lam.12820 1964:on 14 March 2016. 1896:Rossi S, editor. 1697:978-3-527-60749-5 1117:Contraindications 944:Certain systemic 911:species (but not 891:azole antifungals 860:cellular membrane 785:fungal infections 774: 773: 698:Interactive image 582:CompTox Dashboard 300: 288: 275: 258: 246: 150: 117: 16:(Redirected from 3639: 3569: 3568: 3567: 3560: 3451:undecylenic acid 3401:potassium iodide 3279: 3147: 2863: 2847: 2836: 2807: 2800: 2793: 2784: 2778: 2768: 2725: 2724: 2722: 2720: 2701: 2695: 2694: 2689:. 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Archived from 1829: 1823: 1822: 1820: 1818: 1803: 1794: 1793: 1791: 1789: 1770: 1764: 1763: 1761: 1759: 1740: 1734: 1733: 1731: 1712: 1706: 1705: 1681: 1672: 1671: 1669: 1667: 1662:on 29 April 2016 1644: 1638: 1637: 1635: 1633: 1618: 1593: 1592: 1575:(2): 1218–1228. 1564: 1558: 1557: 1555: 1553: 1547: 1536: 1528: 1522: 1521: 1519: 1517: 1498: 1481: 1480: 1478: 1476: 1459: 1409:Pharmacokinetics 1365:Pharmacodynamics 1354:Candida albicans 1248:If taken during 1212:thrombocytopenia 971:to drugs in the 920:Candida glabrata 876: 856:azole antifungal 813:tinea versicolor 787:. This includes 770: 769: 700: 680: 668: 662: 656: 650: 644: 627: 616: 605: 604: 590: 588: 573: 553: 533: 526: 506: 486: 466: 446: 436: 435: 421: 354: 298: 295: 286: 283: 273: 270: 266: 257: 254: 244: 241: 219: 209: 199: 148: 145: 127: 116: 113: 100: 86: 68:Diflucan, others 53: 44: 37: 35: 21: 3647: 3646: 3642: 3641: 3640: 3638: 3637: 3636: 3577: 3576: 3575: 3565: 3563: 3555: 3553: 3548: 3547: 3532:Clinical trials 3511: 3340: 3320: 3301: 3286: 3266: 3223: 3211: 3190: 3171: 3167: 3142: 3134: 3126: 3101: 3089: 3070: 3023:fosravuconazole 2980: 2856: 2855:lanosterol 14α- 2842: 2831: 2825: 2811: 2781: 2738: 2734: 2732:Further reading 2729: 2728: 2718: 2716: 2711:. 7 June 2001. 2703: 2702: 2698: 2681: 2680: 2676: 2661: 2648: 2647: 2643: 2628: 2615: 2614: 2610: 2574: 2573: 2569: 2564: 2560: 2529: 2528: 2524: 2514: 2512: 2503: 2502: 2495: 2478: 2477: 2473: 2458: 2445: 2444: 2440: 2410: 2409: 2405: 2369: 2368: 2364: 2326: 2325: 2321: 2311: 2309: 2305: 2264: 2259: 2258: 2254: 2239: 2226: 2225: 2216: 2206: 2204: 2191: 2190: 2186: 2176: 2174: 2161: 2160: 2153: 2143: 2141: 2132: 2131: 2127: 2081: 2080: 2076: 2046: 2045: 2041: 1995: 1994: 1987: 1974: 1973: 1969: 1961: 1954: 1950: 1949: 1945: 1935: 1933: 1919: 1918: 1911: 1895: 1886: 1876: 1874: 1861: 1860: 1856: 1846: 1844: 1831: 1830: 1826: 1816: 1814: 1807:"US Pharmacist" 1805: 1804: 1797: 1787: 1785: 1772: 1771: 1767: 1757: 1755: 1742: 1741: 1737: 1714: 1713: 1709: 1698: 1683: 1682: 1675: 1665: 1663: 1646: 1645: 1641: 1631: 1629: 1620: 1619: 1596: 1566: 1565: 1561: 1551: 1549: 1545: 1534: 1530: 1529: 1525: 1515: 1513: 1500: 1499: 1484: 1474: 1472: 1461: 1460: 1456: 1451: 1439: 1415:Bioavailability 1411: 1383:14α-demethylase 1379:cytochrome P450 1367: 1362: 1326:cytochrome P450 1322: 1254:first trimester 1171: 1119: 1059:C. parapsilosis 1045: 1002:14α-demethylase 966: 883: 874: 840:QT prolongation 809:dermatophytosis 765: 763: 758: 755: 750: 745: 744: 733: 730: 725: 724: 703: 678: 665: 659: 653: 647: 608: 584: 576: 556: 536: 509: 489: 469: 449: 432: 424: 404: 401: 388: 387: 352: 328:Protein binding 318:Bioavailability 310:Pharmacokinetic 304: 264: 223: 163: 156: 137: 130: 28: 23: 22: 15: 12: 11: 5: 3645: 3643: 3635: 3634: 3629: 3624: 3619: 3614: 3609: 3604: 3599: 3594: 3589: 3579: 3578: 3574: 3573: 3550: 3549: 3546: 3545: 3544: 3543: 3540: 3529: 3523: 3517: 3516: 3513: 3512: 3510: 3509: 3504: 3499: 3490: 3485: 3480: 3475: 3470: 3465: 3463:citronella oil 3459: 3458: 3453: 3448: 3443: 3438: 3433: 3428: 3423: 3418: 3413: 3408: 3406:salicylic acid 3403: 3398: 3393: 3388: 3383: 3378: 3376:crystal violet 3373: 3368: 3363: 3361:chlorophetanol 3358: 3352: 3350: 3346: 3345: 3342: 3341: 3339: 3338: 3331: 3329: 3322: 3321: 3319: 3318: 3311: 3309: 3303: 3302: 3300: 3299: 3292: 3290: 3276: 3272: 3271: 3268: 3267: 3265: 3264: 3259: 3253: 3248: 3243: 3238: 3227: 3225: 3217: 3216: 3213: 3212: 3210: 3209: 3202: 3200: 3196: 3195: 3192: 3191: 3189: 3188: 3181: 3179: 3173: 3172: 3170: 3169: 3162: 3155: 3153: 3144: 3136: 3135: 3133: 3132: 3129:amphotericin B 3121: 3116: 3109: 3107: 3095: 3094: 3091: 3090: 3088: 3087: 3080: 3078: 3072: 3071: 3069: 3068: 3063: 3056: 3055: 3050: 3045: 3040: 3035: 3030: 3025: 3020: 3018:fosfluconazole 3015: 3008: 3007: 3002: 2997: 2990: 2988: 2982: 2981: 2979: 2978: 2974: 2973: 2968: 2963: 2958: 2953: 2948: 2943: 2938: 2933: 2928: 2923: 2918: 2913: 2908: 2903: 2898: 2893: 2888: 2883: 2878: 2871: 2869: 2860: 2844: 2833: 2827: 2826: 2812: 2810: 2809: 2802: 2795: 2787: 2780: 2779: 2735: 2733: 2730: 2727: 2726: 2696: 2687:MP Biomedicals 2674: 2659: 2641: 2626: 2608: 2594:10.1086/593194 2567: 2558: 2522: 2493: 2471: 2456: 2438: 2403: 2382:(9): 830–839. 2362: 2335:(3): 129–140. 2319: 2252: 2237: 2214: 2184: 2151: 2125: 2074: 2039: 1985: 1967: 1943: 1909: 1884: 1854: 1824: 1795: 1765: 1735: 1707: 1696: 1673: 1639: 1594: 1559: 1523: 1482: 1453: 1452: 1450: 1447: 1438: 1435: 1410: 1407: 1366: 1363: 1361: 1358: 1321: 1318: 1246: 1245: 1242: 1230: 1220:hepatotoxicity 1214:, other blood 1188: 1181: 1170: 1167: 1166: 1165: 1150: 1143: 1136: 1129: 1118: 1115: 1044: 1041: 983:or esophageal 965: 962: 961: 960: 957: 950: 942: 914:Candida krusei 882: 879: 836:liver problems 805:histoplasmosis 801:cryptococcosis 772: 771: 760: 759: 757: 756: 753: 751: 748: 740: 739: 738: 735: 734: 732: 731: 728: 720: 719: 718: 715: 714: 711: 705: 704: 702: 701: 693: 691: 683: 682: 676: 670: 669: 663: 657: 651: 645: 640: 634: 633: 629: 628: 618: 610: 609: 607: 606: 593: 591: 578: 577: 575: 574: 566: 564: 558: 557: 555: 554: 546: 544: 538: 537: 535: 534: 527: 519: 517: 511: 510: 508: 507: 499: 497: 491: 490: 488: 487: 479: 477: 471: 470: 468: 467: 459: 457: 451: 450: 448: 447: 439: 437: 426: 425: 423: 422: 414: 412: 406: 405: 403: 402: 391: 383: 382: 381: 378: 377: 373: 372: 366: 360: 359: 356: 347: 346: 340: 334: 333: 330: 324: 323: 322:>90% (oral) 320: 314: 313: 306: 305: 303: 302: 293: 281: 268: 252: 238: 236: 230: 229: 225: 224: 222: 221: 188: 186: 180: 179: 166: 164:administration 158: 157: 155: 154: 152: 142: 140: 132: 131: 129: 128: 110: 108: 102: 101: 94: 88: 87: 80: 70: 69: 66: 60: 59: 55: 54: 46: 45: 26: 24: 14: 13: 10: 9: 6: 4: 3: 2: 3644: 3633: 3630: 3628: 3625: 3623: 3620: 3618: 3615: 3613: 3610: 3608: 3605: 3603: 3600: 3598: 3595: 3593: 3590: 3588: 3585: 3584: 3582: 3572: 3562: 3558: 3541: 3539: 3536: 3535: 3533: 3530: 3527: 3524: 3522: 3519: 3518: 3514: 3508: 3505: 3503: 3500: 3498: 3494: 3491: 3489: 3486: 3484: 3481: 3479: 3476: 3474: 3471: 3469: 3466: 3464: 3461: 3460: 3457: 3454: 3452: 3449: 3447: 3444: 3442: 3439: 3437: 3434: 3432: 3429: 3427: 3424: 3422: 3419: 3417: 3414: 3412: 3409: 3407: 3404: 3402: 3399: 3397: 3394: 3392: 3389: 3387: 3384: 3382: 3379: 3377: 3374: 3372: 3369: 3367: 3366:chlorphenesin 3364: 3362: 3359: 3357: 3354: 3353: 3351: 3347: 3337: 3333: 3332: 3330: 3327: 3323: 3317: 3313: 3312: 3310: 3308: 3304: 3298: 3294: 3293: 3291: 3289: 3284: 3280: 3277: 3275:Intracellular 3273: 3263: 3262:ibrexafungerp 3260: 3257: 3254: 3252: 3249: 3247: 3244: 3242: 3239: 3237: 3236:anidulafungin 3233: 3232:echinocandins 3229: 3228: 3226: 3222: 3218: 3208: 3204: 3203: 3201: 3197: 3187: 3183: 3182: 3180: 3178: 3174: 3166: 3163: 3161: 3157: 3156: 3154: 3152: 3148: 3145: 3141: 3137: 3130: 3125: 3122: 3120: 3117: 3115: 3111: 3110: 3108: 3105: 3100: 3096: 3086: 3082: 3081: 3079: 3077: 3073: 3067: 3064: 3062: 3058: 3057: 3054: 3051: 3049: 3046: 3044: 3043:oteseconazole 3041: 3039: 3036: 3034: 3033:isavuconazole 3031: 3029: 3026: 3024: 3021: 3019: 3016: 3014: 3010: 3009: 3006: 3003: 3001: 2998: 2996: 2995:efinaconazole 2992: 2991: 2989: 2987: 2983: 2976: 2975: 2972: 2969: 2967: 2964: 2962: 2961:sertaconazole 2959: 2957: 2954: 2952: 2949: 2947: 2944: 2942: 2939: 2937: 2934: 2932: 2929: 2927: 2924: 2922: 2919: 2917: 2916:fenticonazole 2914: 2912: 2909: 2907: 2904: 2902: 2899: 2897: 2894: 2892: 2889: 2887: 2886:chlormidazole 2884: 2882: 2879: 2877: 2873: 2872: 2870: 2868: 2864: 2861: 2858: 2852: 2848: 2845: 2841: 2837: 2834: 2828: 2823: 2819: 2815: 2808: 2803: 2801: 2796: 2794: 2789: 2788: 2785: 2776: 2772: 2767: 2762: 2758: 2754: 2750: 2746: 2742: 2737: 2736: 2731: 2714: 2710: 2706: 2700: 2697: 2692: 2688: 2684: 2683:"Fluconazole" 2678: 2675: 2670: 2666: 2662: 2656: 2652: 2645: 2642: 2637: 2633: 2629: 2623: 2619: 2612: 2609: 2604: 2600: 2595: 2590: 2586: 2582: 2578: 2571: 2568: 2562: 2559: 2554: 2550: 2546: 2542: 2538: 2534: 2526: 2523: 2510: 2506: 2500: 2498: 2494: 2489: 2485: 2481: 2475: 2472: 2467: 2463: 2459: 2453: 2449: 2442: 2439: 2434: 2430: 2426: 2422: 2418: 2414: 2407: 2404: 2399: 2395: 2390: 2385: 2381: 2377: 2373: 2366: 2363: 2358: 2354: 2350: 2346: 2342: 2338: 2334: 2330: 2323: 2320: 2304: 2300: 2296: 2291: 2286: 2282: 2278: 2274: 2270: 2263: 2256: 2253: 2248: 2244: 2240: 2234: 2230: 2223: 2221: 2219: 2215: 2202: 2198: 2194: 2188: 2185: 2172: 2168: 2164: 2163:"Fluconazole" 2158: 2156: 2152: 2139: 2135: 2129: 2126: 2121: 2117: 2112: 2107: 2102: 2097: 2093: 2089: 2085: 2078: 2075: 2070: 2066: 2062: 2058: 2054: 2050: 2043: 2040: 2035: 2031: 2026: 2021: 2016: 2011: 2007: 2003: 1999: 1992: 1990: 1986: 1981: 1977: 1971: 1968: 1960: 1953: 1947: 1944: 1931: 1927: 1923: 1916: 1914: 1910: 1907: 1906:0-9757919-2-3 1903: 1899: 1893: 1891: 1889: 1885: 1872: 1868: 1866: 1858: 1855: 1842: 1838: 1836: 1828: 1825: 1812: 1808: 1802: 1800: 1796: 1783: 1779: 1775: 1769: 1766: 1753: 1749: 1745: 1739: 1736: 1730: 1725: 1721: 1717: 1711: 1708: 1703: 1699: 1693: 1689: 1688: 1680: 1678: 1674: 1661: 1657: 1655: 1649: 1643: 1640: 1627: 1623: 1622:"Fluconazole" 1617: 1615: 1613: 1611: 1609: 1607: 1605: 1603: 1601: 1599: 1595: 1590: 1586: 1582: 1578: 1574: 1570: 1563: 1560: 1544: 1540: 1533: 1527: 1524: 1511: 1507: 1503: 1497: 1495: 1493: 1491: 1489: 1487: 1483: 1471:. 7 July 2016 1470: 1469: 1468:Health Canada 1464: 1458: 1455: 1448: 1446: 1444: 1436: 1434: 1431: 1429: 1425: 1421: 1416: 1408: 1406: 1404: 1400: 1396: 1392: 1388: 1384: 1380: 1376: 1372: 1364: 1359: 1357: 1355: 1351: 1347: 1343: 1339: 1335: 1331: 1327: 1319: 1317: 1313: 1311: 1307: 1302: 1300: 1299:absolute risk 1296: 1292: 1288: 1287:birth defects 1283: 1279: 1277: 1273: 1269: 1265: 1260: 1257: 1255: 1251: 1243: 1241: 1240: 1235: 1231: 1229: 1225: 1224:liver failure 1221: 1217: 1213: 1209: 1205: 1201: 1197: 1193: 1189: 1186: 1182: 1179: 1178: 1177: 1175: 1168: 1163: 1159: 1155: 1151: 1148: 1144: 1141: 1137: 1134: 1130: 1128: 1124: 1123: 1122: 1116: 1114: 1110: 1108: 1104: 1100: 1099:anidulafungin 1096: 1095:echinocandins 1089: 1085: 1081: 1077: 1075: 1071: 1070: 1065: 1061: 1060: 1055: 1049: 1042: 1040: 1038: 1034: 1029: 1027: 1023: 1019: 1015: 1011: 1007: 1003: 999: 995: 994: 988: 986: 982: 978: 974: 970: 963: 958: 955: 951: 947: 943: 940: 936: 935: 934: 932: 931:dermatophytes 928: 927: 922: 921: 916: 915: 910: 909: 903: 900: 896: 892: 888: 880: 878: 872: 868: 863: 861: 857: 853: 852:birth defects 849: 845: 841: 837: 833: 828: 826: 822: 818: 814: 810: 806: 802: 798: 794: 793:blastomycosis 790: 786: 782: 778: 768: 761: 752: 747: 743: 736: 727: 723: 716: 712: 710: 709:Melting point 706: 699: 695: 694: 692: 689: 684: 677: 675: 671: 641: 639: 635: 630: 626: 622: 619: 617: 615:ECHA InfoCard 611: 603: 599: 598:DTXSID3020627 595: 594: 592: 583: 579: 572: 568: 567: 565: 563: 559: 552: 548: 547: 545: 543: 539: 532: 528: 525: 521: 520: 518: 516: 512: 505: 501: 500: 498: 496: 492: 485: 481: 480: 478: 476: 472: 465: 461: 460: 458: 456: 452: 445: 441: 440: 438: 431: 427: 420: 416: 415: 413: 411: 407: 399: 395: 390: 386: 379: 374: 370: 367: 365: 361: 357: 355: 348: 344: 341: 339: 335: 331: 329: 325: 321: 319: 315: 311: 307: 301: Rx-only 294: 292: 282: 279: 269: 262: 253: 250: 240: 239: 237: 235: 231: 226: 218: 213: 208: 203: 198: 193: 190: 189: 187: 185: 181: 178: 174: 170: 167: 165: 159: 153: 144: 143: 141: 139: 133: 126: 121: 112: 111: 109: 107: 103: 99: 95: 93: 89: 85: 81: 79: 75: 71: 67: 65: 61: 58:Clinical data 56: 52: 47: 43: 38: 30: 19: 3597:Fluoroarenes 3488:tea tree oil 3473:lemon myrtle 3386:ethylparaben 3316:griseofulvin 3177:Benzylamines 3066:ravuconazole 3061:albaconazole 3053:voriconazole 3048:posaconazole 3038:itraconazole 3028:hexaconazole 3012: 2999: 2946:neticonazole 2936:luliconazole 2931:ketoconazole 2921:flutrimazole 2906:eberconazole 2896:clotrimazole 2881:butoconazole 2748: 2744: 2717:. Retrieved 2708: 2699: 2691:the original 2686: 2677: 2650: 2644: 2617: 2611: 2584: 2580: 2570: 2561: 2536: 2532: 2525: 2513:. Retrieved 2488:the original 2483: 2474: 2447: 2441: 2419:(1): 58–67. 2416: 2412: 2406: 2379: 2375: 2365: 2332: 2328: 2322: 2310:. Retrieved 2272: 2268: 2255: 2228: 2205:. Retrieved 2196: 2187: 2177:27 September 2175:. Retrieved 2166: 2142:. Retrieved 2128: 2091: 2087: 2077: 2052: 2048: 2042: 2005: 2001: 1970: 1959:the original 1946: 1934:. Retrieved 1930:the original 1925: 1875:. Retrieved 1871:the original 1864: 1857: 1845:. Retrieved 1841:the original 1834: 1827: 1815:. Retrieved 1786:. Retrieved 1777: 1768: 1756:. Retrieved 1747: 1738: 1729:10665/325771 1719: 1710: 1686: 1664:. Retrieved 1660:the original 1651: 1642: 1630:. Retrieved 1572: 1568: 1562: 1550:. Retrieved 1538: 1526: 1514:. Retrieved 1505: 1473:. Retrieved 1466: 1457: 1440: 1432: 1412: 1403:Cryptococcus 1402: 1368: 1360:Pharmacology 1353: 1323: 1320:Interactions 1314: 1303: 1284: 1280: 1261: 1258: 1247: 1237: 1202:, seizures, 1200:paraesthesia 1196:hypokalaemia 1172: 1169:Side effects 1133:ketoconazole 1120: 1111: 1092: 1088:Echinocandin 1078: 1068: 1063: 1057: 1050: 1046: 1036: 1030: 1025: 1021: 1013: 1009: 997: 991: 989: 987:infection). 984: 967: 953: 945: 938: 924: 918: 912: 906: 904: 895:ketoconazole 884: 881:Medical uses 864: 829: 776: 775: 764:   397: 393: 351:Elimination 234:Legal status 228:Legal status 106:License data 29: 3528:from market 3507:pentamidine 3468:lemon grass 3426:taurolidine 3396:polynoxylin 3297:flucytosine 3241:caspofungin 3165:terbinafine 3151:Allylamines 3013:fluconazole 3005:terconazole 3000:fluconazole 2971:tioconazole 2966:sulconazole 2956:oxiconazole 2951:omoconazole 2926:isoconazole 2901:croconazole 2859:inhibitors) 2857:demethylase 2814:Antifungals 2515:21 December 2088:Antibiotics 2055:(1): 2–13. 2008:: 249–259. 1552:22 December 1516:22 February 1369:Like other 1342:QT interval 1312:may occur. 1310:anaphylaxis 1264:QT interval 1234:QT interval 1140:terfenadine 1138:are taking 1103:caspofungin 1064:C. glabrata 1022:C. glabrata 1014:C. glabrata 1010:C. albicans 993:C. albicans 848:miscarriage 789:candidiasis 777:Fluconazole 681: g·mol 621:100.156.133 551:CHEBI:46081 376:Identifiers 173:intravenous 125:Fluconazole 92:MedlinePlus 64:Trade names 34:Fluconazole 3581:Categories 3497:atovaquone 3478:orange oil 3441:tolnaftate 3436:tolciclate 3421:sulbentine 3391:haloprogin 3371:ciclopirox 3336:tavaborole 3328:inhibitors 3314:Systemic: 3295:Systemic: 3256:rezafungin 3251:micafungin 3246:cilofungin 3230:Systemic: 3224:inhibitors 3207:amorolfine 3186:butenafine 3143:inhibitors 3127:Systemic: 3104:ergosterol 3011:Systemic: 2941:miconazole 2891:climbazole 2876:bifonazole 2867:Imidazoles 2843:inhibitors 2840:Ergosterol 2669:1114483879 2636:1035129378 2312:20 October 2247:1075550900 2094:(7): 414. 1877:28 January 1847:28 January 1817:28 January 1788:14 January 1758:14 January 1632:8 December 1449:References 1428:metabolism 1424:zero order 1399:fungicidal 1391:ergosterol 1387:lanosterol 1297:, but the 1291:odds ratio 1222:including 1218:, serious 1216:dyscrasias 1162:sertraline 1158:fluoxetine 1107:micafungin 1074:ciclopirox 1006:lanosterol 964:Resistance 686:3D model ( 674:Molar mass 504:8VZV102JFY 475:ChemSpider 419:86386-73-4 410:CAS Number 385:IUPAC name 338:Metabolism 3538:Phase III 3526:Withdrawn 3483:patchouli 3431:ticlatone 3334:Topical: 3205:Topical: 3184:Topical: 3160:naftifine 3158:Topical: 3131:, hamycin 3119:natamycin 3112:Topical: 3085:abafungin 3083:Topical: 3076:Thiazoles 3059:Unknown: 2993:Topical: 2986:Triazoles 2911:econazole 2874:Topical: 2466:942814866 2167:Monograph 1589:213008181 1371:imidazole 1350:Berberine 1306:cisapride 1272:cisapride 1250:pregnancy 1147:quinidine 1026:C. krusei 899:imidazole 893:(such as 571:ChEMBL106 364:Excretion 353:half-life 162:Routes of 136:Pregnancy 84:Monograph 78:Drugs.com 3571:Medicine 3381:dimazole 3124:nystatin 3106:binding) 2832:membrane 2775:30723130 2713:Archived 2603:18990067 2553:19754040 2509:Archived 2433:26746458 2398:23984730 2349:12489563 2303:Archived 2299:19164151 2207:22 April 2201:Archived 2171:Archived 2144:4 August 2138:Archived 2120:32708627 2069:29112282 2034:28919789 1980:Archived 1811:Archived 1782:Archived 1778:ClinCalc 1752:Archived 1748:ClinCalc 1718:(2019). 1702:Archived 1666:29 April 1626:Archived 1543:Archived 1510:Archived 1506:DailyMed 1375:triazole 1276:pimozide 1204:alopecia 1192:oliguria 1185:anorexia 1156:such as 1054:propolis 949:systems. 887:triazole 844:seizures 767:(verify) 455:DrugBank 184:ATC code 169:By mouth 138:category 120:DailyMed 18:Diflucan 3502:dapsone 3114:hamycin 2766:6428756 2719:18 June 2505:"Login" 2357:8282678 2290:2663085 2111:7400126 2025:5587015 1475:3 April 1437:History 1381:enzyme 1330:CYP2C19 1127:alcohol 1037:Candida 985:Candida 954:Candida 946:Candida 939:Candida 908:Candida 679:306.277 638:Formula 464:DB00196 430:PubChem 263: / 259:: 214: ( 212:J01RA07 204: ( 202:J02AC01 200:) 194: ( 192:D01AC15 177:topical 151: D 122::  98:a690002 3557:Portal 3521:WHO-EM 3349:Others 3199:Others 2851:Azoles 2773:  2763:  2667:  2657:  2634:  2624:  2601:  2551:  2464:  2454:  2431:  2396:  2355:  2347:  2297:  2287:  2245:  2235:  2118:  2108:  2067:  2032:  2022:  1936:22 May 1904:  1694:  1587:  1443:Pfizer 1373:- and 1338:CYP2C9 1334:CYP3A4 1125:Drink 1105:, and 981:thrush 875:  842:, and 811:, and 779:is an 722:SMILES 562:ChEMBL 531:C07002 524:D00322 371:61–88% 369:Kidney 332:11–12% 291:â„ž-only 289: 276: 265:  261:â„ž-only 247: 118:  2830:Wall/ 2751:(1). 2353:S2CID 2306:(PDF) 2265:(PDF) 1962:(PDF) 1955:(PDF) 1656:(FDA) 1652:U.S. 1585:S2CID 1546:(PDF) 1535:(PDF) 1154:SSRIs 1152:take 998:ERG11 973:azole 742:InChI 688:JSmol 542:ChEBI 343:Liver 2820:and 2771:PMID 2745:mBio 2721:2019 2665:OCLC 2655:ISBN 2632:OCLC 2622:ISBN 2599:PMID 2549:PMID 2517:2016 2462:OCLC 2452:ISBN 2429:PMID 2413:JAMA 2394:PMID 2345:PMID 2314:2009 2295:PMID 2243:OCLC 2233:ISBN 2209:2014 2179:2014 2146:2011 2116:PMID 2065:PMID 2030:PMID 1938:2012 1902:ISBN 1879:2015 1849:2015 1819:2015 1790:2024 1760:2024 1692:ISBN 1668:2016 1634:2016 1554:2020 1518:2024 1477:2024 1336:and 1274:and 1062:and 1012:and 515:KEGG 495:UNII 484:3248 444:3365 312:data 74:AHFS 3493:PCP 2822:J02 2818:D01 2761:PMC 2753:doi 2589:doi 2541:doi 2421:doi 2417:315 2384:doi 2380:369 2337:doi 2285:PMC 2277:doi 2106:PMC 2096:doi 2057:doi 2020:PMC 2010:doi 1724:hdl 1577:doi 1389:to 1293:of 1278:). 1160:or 990:In 977:HIV 923:), 917:or 587:EPA 434:CID 394:bis 345:11% 278:POM 267:OTC 217:WHO 210:), 207:WHO 197:WHO 3583:: 3534:: 3495:: 2769:. 2759:. 2749:10 2747:. 2743:. 2707:. 2685:. 2663:. 2630:. 2597:. 2585:47 2583:. 2579:. 2547:. 2535:. 2507:. 2496:^ 2482:. 2460:. 2427:. 2415:. 2392:. 2378:. 2374:. 2351:. 2343:. 2333:28 2331:. 2301:. 2293:. 2283:. 2273:53 2271:. 2267:. 2241:. 2217:^ 2195:. 2165:. 2154:^ 2136:. 2114:. 2104:. 2090:. 2086:. 2063:. 2053:66 2051:. 2028:. 2018:. 2006:10 2004:. 2000:. 1988:^ 1912:^ 1887:^ 1809:. 1798:^ 1780:. 1776:. 1750:. 1746:. 1700:. 1676:^ 1650:. 1597:^ 1583:. 1573:20 1571:. 1537:. 1504:. 1485:^ 1465:. 1405:. 1256:. 1236:, 1226:, 1210:, 1206:, 1198:, 1194:, 1101:, 862:. 838:, 827:. 807:, 803:, 799:, 795:, 791:, 652:12 646:13 396:(1 297:EU 285:US 272:UK 256:CA 249:S3 243:AU 175:, 171:, 147:AU 115:US 3559:: 3285:/ 3258:) 3234:( 3102:( 2853:( 2824:) 2816:( 2806:e 2799:t 2792:v 2777:. 2755:: 2723:. 2671:. 2638:. 2605:. 2591:: 2555:. 2543:: 2537:8 2519:. 2468:. 2435:. 2423:: 2400:. 2386:: 2359:. 2339:: 2316:. 2279:: 2249:. 2211:. 2181:. 2148:. 2122:. 2098:: 2092:9 2071:. 2059:: 2036:. 2012:: 1940:. 1881:. 1867:" 1851:. 1837:" 1821:. 1792:. 1762:. 1726:: 1670:. 1636:. 1591:. 1579:: 1556:. 1520:. 1479:. 1332:( 1164:. 1135:; 690:) 667:O 664:6 661:N 658:2 655:F 649:H 643:C 589:) 585:( 398:H 299:: 287:: 274:: 245:: 220:) 149:: 76:/ 20:)

Index

Diflucan


Trade names
AHFS
Drugs.com
Monograph
MedlinePlus
a690002
License data
DailyMed
Fluconazole
Pregnancy
category

Routes of
administration

By mouth
intravenous
topical
ATC code
D01AC15
WHO
J02AC01
WHO
J01RA07
WHO
Legal status
S3
â„ž-only
POM
â„ž-only
Pharmacokinetic

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