Identification
- Summary
Fluconazole is a triazole antifungal used to treat various fungal infections including candidiasis.
- Brand Names
- Diflucan
- Generic Name
- Fluconazole
- DrugBank Accession Number
- DB00196
- Background
Fluconazole, commonly known as Diflucan, is an antifungal drug used for the treatment of both systemic and superficial fungal infections in a variety of tissues. It was initially approved by the FDA in 1990. This drug is an azole antifungal, in the same drug family as ketoconazole and itraconazole. Fluconazole has many advantages over the other antifungal drugs including the option of oral administration. The side effect profile of this drug is minimal. It has been demonstrated as an efficacious treatment for vaginal yeast infections in one single dose.2
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Fluconazole (DB00196)
- Weight
- Average: 306.2708
Monoisotopic: 306.104065446 - Chemical Formula
- C13H12F2N6O
- Synonyms
- Diflucan
- Difluconazole
- Fluconazol
- Fluconazole
- Fluconazolum
- Triflucan
- External IDs
- UK-49,858
- UK-49858
Pharmacology
- Indication
Fluconazole can be administered in the treatment of the following fungal infections27:
1) Vaginal yeast infections caused by Candida 2) Systemic Candida infections 3) Both esophageal and oropharyngeal candidiasis 4) Cryptococcal meningitis 5) UTI (urinary tract infection) by Candida 6) Peritonitis (inflammation of the peritoneum) caused by Candida
A note on fungal infection prophylaxis
Patients receiving bone marrow transplantation who are treated with cytotoxic chemotherapy and/or radiation therapy may be predisposed to candida infections, and may receive fluconazole as prophylactic therapy.27
A note on laboratory testing
Obtaining specimens for fungal culture and other important laboratory studies such as serology or pathology is advised before starting fluconazole therapy in order to isolate the organisms to be eliminated through treatment. It is permissible to start therapy before the results are available, however, adjusting the therapy once laboratory results confirm the causative organism may be necessary.27
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Candida intertrigo ••• ••••• Treatment of Candida pneumonia •••••••••••• Treatment of Candidemia •••••••••••• Prophylaxis of Candidiasis •••••••••••• Prophylaxis of Candidiasis •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Fluconazole has been demonstrated to show fungistatic activity against the majority of strains of the following microorganisms, curing fungal infections27:
Candida albicans, Candida glabrata (Many strains are intermediately susceptible), Candida parapsilosis, Candida tropicalis, Cryptococcus neoformans
This is achieved through steroidal inhibition in fungal cells, interfering with cell wall synthesis and growth as well as cell adhesion, thereby treating fungal infections and their symptoms.27,2,5
The fungistatic activity of fluconazole has also been shown in normal and immunocompromised animal models with both systemic and intracranial fungal infections caused by Cryptococcus neoformans and for systemic infections caused by Candida albicans.27 It is important to note that resistant organisms have been found against various strains of organisms treated with fluconazole.11,12,13 This further substantiates the need to perform susceptibility testing when fluconazole is considered as an antifungal therapy.14,20
A note on steroidal effects of fluconazole
There has been some concern that fluconazole may interfere with and inactivate human steroids/hormones due to the inhibition of hepatic cytochrome enzymes.26 Fluconazole has demonstrated to be more selective for fungal cytochrome P-450 enzymes than for a variety of mammalian cytochrome P-450 enzymes. Fluconazole 50 mg administered daily for up to 28 days in individuals of reproductive age has been show to have no effect on testosterone plasma concentrations of males and plasma concentrations of steroids in females. A 200-400 mg dose of fluconazole showed no clinically relevant effect on steroid levels or on ACTH-stimulated steroid response in healthy males, in one clinical study mentioned on the European Medicines Agency label.26 Other studies have shown no significant effects of fluconazole on steroid levels, further confirming these data.10,18
- Mechanism of action
Fluconazole is a very selective inhibitor of fungal cytochrome P450 dependent enzyme lanosterol 14-α-demethylase. This enzyme normally works to convert lanosterol to ergosterol, which is necessary for fungal cell wall synthesis. The free nitrogen atom located on the azole ring of fluconazole binds with a single iron atom located in the heme group of lanosterol 14-α-demethylase.16 This prevents oxygen activation and, as a result, inhibits the demethylation of lanosterol, halting the process of ergosterol biosynthesis.17 Methylated sterols are then found to accumulate in the fungal cellular membrane, leading to an arrest of fungal growth.16 These accumulated sterols negatively affect the structure and function of the fungal cell plasma membrane.8
Fluconazole resistance may arise from an alteration in the amount or function of the target enzyme (lanosterol 14-α-demethylase), altered access to this enzyme, or a combination of the above.8 Other mechanisms may also be implicated, and studies are ongoing.19
Target Actions Organism ACytochrome P450 51 inhibitorYeast - Absorption
The pharmacokinetic properties of fluconazole are comparable after administration by the intravenous (IV) and oral (PO) routes. In healthy volunteers, the bioavailability of orally administered fluconazole is measured to be above 90%.27 It is extensively absorbed in the gastrointestinal tract when an oral dose is taken.23 Oral absorption is not affected by food intake with fluconazole but may increase the time until the maximum concentration is reached.26,21
Tmax (or the time taken to achieve the maximum concentration) in one clinical study of healthy patients receiving 50 mg/kg of fluconazole was 3 hours.21
Peak plasma concentrations (Cmax) in fasting and healthy volunteers occur between 1-2 hours post-dose.27 Steady-state concentrations are achieved within 5 to 10 days after oral doses of 50-400 mg administered once daily. Administration of a loading dose on the first day of fluconazole treatment, or twice the usual daily dose, leads to plasma concentrations close to steady-state by the second day.27 Mean AUC (area under the curve) was 20.3 in healthy volunteers receiving 25 mg of fluconazole.21
A note on the capsule and powder form and malabsorption syndromes
The capsule forms of fluconazole often contain lactose and should not be administered with hereditary galactose intolerance, Lapp lactase enzyme deficiency, or malabsorption of glucose/galactose.27 The powder form, used for the oral suspension, lists sucrose as an ingredient and should not be used in patients who have been diagnosed with fructose, glucose/galactose malabsorption, and sucrase-isomaltase enzyme deficiency.27
- Volume of distribution
The apparent volume of distribution is said to be similar to the volume of distribution of total body water.27 One clinical study of healthy volunteers administered 50 mg/kg of fluconazole was 39L, based on a body weight of 60kg.21
Fluconazole shows substantial penetration in many body fluids, which is a property that renders it an ideal treatment for systemic fungal infections, especially when administered over a longer time.21,27 Fluconazole is found in high concentrations in the stratum corneum and dermis-epidermis of skin, in addition to eccrine sweat. Fluconazole is found to accumulate especially well in the stratum corneum, which is beneficial in superficial fungal infections.26 Saliva and sputum concentrations of fluconazole are found to be similar to the plasma concentrations.25 In patients diagnosed with fungal meningitis, fluconazole CSF (cerebrospinal fluid) levels are measured to be about 80% of the corresponding plasma levels. Therefore, fluconazole crosses the blood-brain barrier.26 The meninges are increasingly permeable to fluconazole in states of inflammation, facilitating treatment in meningitis.22
- Protein binding
The protein binding of fluconazole is low and estimated to be 11 to 12%.27,21
- Metabolism
Fluconazole is metabolized minimally in the liver. Fluconazole is an inhibitor of CYP2C9, CYP3A4 and CYP2C19.26,27 Two metabolites were detected in the urine of healthy volunteers taking a 50 mg radiolabeled dose of fluconazole; a glucuronidated metabolite on the hydroxyl moiety (6.5%) and a fluconazole N-oxide metabolite (2%).23 The same study indicated that no signs of metabolic cleavage of fluconazole were observed, suggesting a difference in metabolism when compared to other agents in the same drug class, which are heavily metabolized in the liver.23,24
Hover over products below to view reaction partners
- Route of elimination
In normal volunteers, fluconazole is cleared primarily by renal excretion, with approximately 80% of the administered dose measured in the urine as unchanged drug.27 About 11% of the dose is excreted in the urine as metabolites.27. A study of a 50mg radiolabeled dose of fluconazole revealed that 93.3% of the dose was found excreted in the urine.23
A note on renal failure
The pharmacokinetics of fluconazole are significantly affected by renal dysfunction. The dose of fluconazole may need to be reduced in patients with decreased renal function. A 3-hour hemodialysis treatment lowers plasma fluconazole concentrations by about 50%.27
- Half-life
The terminal elimination half-life in the plasma is approximately 30 hours (range: 20-50 hours) after oral administration.27 The long plasma elimination half-life supports a single-dose therapy for vaginal candidiasis, once daily and once weekly dosing for other indications.26 Patients with renal failure may require dosage adjustment, and half-life can be significantly increased in these patients.21
- Clearance
This drug is mainly eliminated by the kidneys and the mean body clearance in adults is reported to be 0.23 mL/min/kg.27 One clinical study of healthy subjects showed total clearance of 19.5 ± 4.7 mL/min and renal clearance of 14.7 ± 3.7 mL/min (1.17 ± 0.28 and 0.88 ± 0.22 L/h).21
Clearance in the pediatric population varies according to age, as does clearance in patients with renal failure.27
- Adverse Effects
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Acute oral toxicity (LD50): 1271 mg/kg (rat) MSDS
Overdose information
Fluconazole overdoses have been associated with hallucination and paranoia, sometimes in combination.27 In cases of overdose, employ supportive treatment. Gastric lavage may be necessary.27 Other modalities such as forced diuresis or hemodialysis may also be used.27
A note on liver toxicity
The FDA label warns that this drug carries a risk of hepatotoxicity. Rare but serious cases of serious hepatic toxicity have been reported, especially in patients with serious underlying medical conditions using fluconazole. This group of patients has an increased risk of fatality when using fluconazole.27 In patients with existing liver dysfunction, use caution during fluconazole therapy. Those who are found to have abnormal liver function tests during therapy should be carefully monitored for the development of increasingly severe injury to the liver. Fluconazole should be stopped if its use is likely to be the underlying cause of liver injury, and medical attention should be sought.27,25 Fluconazole induced hepatotoxicity is usually reversible.27
Carcinogenesis, mutagenesis, and impairment of fertility
Fluconazole demonstrated no evidence of carcinogenic risk in mice and rats treated orally for 24 months at doses equivalent to approximately 2-7 time the recommended human dose). Male rats given fluconazole at doses equivalent to supratherapeutic human doses showed an increased incidence of hepatocellular adenomas. Cytogenetic studies in vivo and in vitro demonstrated no sign of chromosomal mutation. The significance of these findings for humans is unknown.27
Use in pregnancy
There are no sufficient and well-controlled studies of fluconazole use in pregnant women. Available human data do not show an increased risk of congenital anomalies after pregnant women were treated with standard doses (<200 mg/day) of fluconazole, either in a single dose or multiple doses in the first trimester did not appear to impact the fetus negatively.27 Several case reports describe rare but striking congenital anomalies observed in infants who were exposed to fluconazole at high doses reaching 400-800 mg/day, primarily in the first trimester of pregnancy. Similar findings were observed in animal studies. If this drug is administered during pregnancy, or if the patient becomes pregnant while taking fluconazole, the risk should be discussed thoroughly.27
Use in nursing
Fluconazole is secreted in breastmilk at high concentrations. Exercise caution if this drug is used during nursing.27
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The metabolism of 1,2-Benzodiazepine can be decreased when combined with Fluconazole. Abacavir Fluconazole may decrease the excretion rate of Abacavir which could result in a higher serum level. Abemaciclib The serum concentration of Abemaciclib can be increased when it is combined with Fluconazole. Abiraterone The metabolism of Abiraterone can be decreased when combined with Fluconazole. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Fluconazole. - Food Interactions
- Take with or without food. The absorption is unaffected by food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Images
- International/Other Brands
- Elazor / Flucazol / Flucostat / Flunizol / Pritenzol / Trican / Triflucan
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Act Fluconazole Tablet 50 mg Oral TEVA Canada Limited 2007-12-03 Not applicable Canada 
Act Fluconazole Tablet 100 mg Oral TEVA Canada Limited 2007-12-03 Not applicable Canada Diflucan Solution 2 mg/1mL Intravenous Roerig 2006-06-08 2006-06-08 US 
Diflucan Tablet 50 mg Oral Pfizer Canada Ulc 1990-12-31 Not applicable Canada Diflucan Tablet 150 mg/1 Oral A-S Medication Solutions 1990-01-29 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-fluconazole Tablet 100 mg Oral Apotex Corporation 1998-10-13 Not applicable Canada Apo-fluconazole Tablet 50 mg Oral Apotex Corporation 1998-10-13 Not applicable Canada Apo-fluconazole Tablet 200 mg Oral Apotex Corporation Not applicable Not applicable Canada Direct Rx Tablet 200 mg/1 Oral Direct Rx 2015-01-01 2015-08-03 US Dom-fluconazole Tablet 50 mg Oral Dominion Pharmacal 2002-07-09 Not applicable Canada - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-fluconazole-150 Capsule 150 mg Oral Apotex Corporation 2000-03-20 Not applicable Canada Bio-fluconazole Capsule 150 mg Oral Biomed Pharma 2019-09-20 Not applicable Canada Canesoral Capsule 150 mg Oral Bayer 2010-03-10 Not applicable Canada Co Fluconazole-150 Capsule 150 mg Oral Cobalt Laboratories 2009-07-21 2019-03-26 Canada Diflucan One Capsule 150 mg Oral Pfizer Canada Ulc 1995-12-31 Not applicable Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Canesoral Combi Fluconazole (150 mg / cap) + Clotrimazole (1 %) Capsule; Cream Oral; Topical; Vaginal Bayer 2010-03-10 2020-12-21 Canada Canesoral Combi 1 Day Fluconazole (150 mg) + Clotrimazole (2 % w/w) Capsule; Cream Oral; Topical Bayer 2020-02-14 Not applicable Canada Clotrimaderm-fluconazole Combi-pack Fluconazole (150 mg / cap) + Clotrimazole (1 % w/w) Capsule; Cream; Kit Oral; Topical Taro Pharmaceuticals, Inc. 2017-02-14 2022-08-29 Canada Clotrimazole-fluconazole Combi Fluconazole (150 mg / cap) + Clotrimazole (1 % w/w) Capsule; Cream; Kit Oral; Topical Taro Pharmaceuticals, Inc. 2017-02-03 Not applicable Canada Extra Strength Clotrimazole Extra Fort -fluconazole Combi Fluconazole (150 mg) + Clotrimazole (2 %) Capsule; Cream Oral; Topical Taro Pharmaceuticals, Inc. 2022-05-03 Not applicable Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Ciclopirox 8% / Fluconazole 1% / Terbinafine HCl 1% Fluconazole (1 g/100g) + Ciclopirox (8 g/100g) + Terbinafine (1 g/100g) Solution Topical Sincerus Florida, LLC 2019-05-01 Not applicable US Fluconazole 4% / Ibuprofen 2% / Itraconazole 1% / Terbinafine HCl 4% Fluconazole (4 g/100g) + Ibuprofen (2 g/100g) + Itraconazole (1 g/100g) + Terbinafine (4 g/100g) Solution Topical Sincerus Florida, LLC 2019-05-01 Not applicable US
Categories
- ATC Codes
- J01RA07 — Azithromycin, fluconazole and secnidazole
- J01RA — Combinations of antibacterials
- J01R — COMBINATIONS OF ANTIBACTERIALS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- J02AC — Triazole and tetrazole derivatives
- J02A — ANTIMYCOTICS FOR SYSTEMIC USE
- J02 — ANTIMYCOTICS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- Drug Categories
- 14-alpha Demethylase Inhibitors
- Agents causing hyperkalemia
- Anti-Infective Agents
- Antifungal Agents
- Antifungals for Dermatological Use
- Antifungals for Topical Use
- Antiinfectives for Systemic Use
- Antimycotics for Systemic Use
- Azole Antifungals
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 inhibitors (strength unknown)
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (strong)
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (moderate)
- Cytochrome P-450 CYP3A5 Inhibitors
- Cytochrome P-450 CYP3A5 Inhibitors (weak)
- Cytochrome P-450 Enzyme Inhibitors
- Dermatologicals
- Drugs that are Mainly Renally Excreted
- Enzyme Inhibitors
- Hormone Antagonists
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Imidazole and Triazole Derivatives
- P-glycoprotein inhibitors
- Potential QTc-Prolonging Agents
- QTc Prolonging Agents
- Steroid Synthesis Inhibitors
- Triazole and tetrazole derivatives
- Triazole Derivatives
- Triazoles
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as fluorobenzenes. These are compounds containing one or more fluorine atoms attached to a benzene ring.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Halobenzenes
- Direct Parent
- Fluorobenzenes
- Alternative Parents
- Aryl fluorides / Triazoles / Tertiary alcohols / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organofluorides / Hydrocarbon derivatives / Aromatic alcohols
- Substituents
- 1,2,4-triazole / Alcohol / Aromatic alcohol / Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Azacycle / Azole / Fluorobenzene / Heteroaromatic compound
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- tertiary alcohol, triazole antifungal drug, conazole antifungal drug, difluorobenzene (CHEBI:46081)
- Affected organisms
- Fungi
Chemical Identifiers
- UNII
- 8VZV102JFY
- CAS number
- 86386-73-4
- InChI Key
- RFHAOTPXVQNOHP-UHFFFAOYSA-N
- InChI
- 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
- IUPAC Name
- 2-(2,4-difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol
- SMILES
- OC(CN1C=NC=N1)(CN1C=NC=N1)C1=C(F)C=C(F)C=C1
References
- Synthesis Reference
- US4404216
- General References
- Bongomin F, Oladele RO, Gago S, Moore CB, Richardson MD: A systematic review of fluconazole resistance in clinical isolates of Cryptococcus species. Mycoses. 2018 May;61(5):290-297. doi: 10.1111/myc.12747. Epub 2018 Feb 14. [Article]
- Hollier LM, Cox SM: Fluconazole (Diflucan). Infect Dis Obstet Gynecol. 1995;3(6):222-5. doi: 10.1155/S1064744995000676. [Article]
- Allen D, Wilson D, Drew R, Perfect J: Azole antifungals: 35 years of invasive fungal infection management. Expert Rev Anti Infect Ther. 2015 Jun;13(6):787-98. doi: 10.1586/14787210.2015.1032939. Epub 2015 Apr 5. [Article]
- Zonios DI, Bennett JE: Update on azole antifungals. Semin Respir Crit Care Med. 2008 Apr;29(2):198-210. doi: 10.1055/s-2008-1063858. [Article]
- Lewis RE: Current concepts in antifungal pharmacology. Mayo Clin Proc. 2011 Aug;86(8):805-17. doi: 10.4065/mcp.2011.0247. [Article]
- Thamban Chandrika N, Shrestha SK, Ngo HX, Howard KC, Garneau-Tsodikova S: Novel fluconazole derivatives with promising antifungal activity. Bioorg Med Chem. 2018 Feb 1;26(3):573-580. doi: 10.1016/j.bmc.2017.12.018. Epub 2017 Dec 17. [Article]
- Berkow EL, Lockhart SR: Fluconazole resistance in Candida species: a current perspective. Infect Drug Resist. 2017 Jul 31;10:237-245. doi: 10.2147/IDR.S118892. eCollection 2017. [Article]
- Ghannoum MA, Rice LB: Antifungal agents: mode of action, mechanisms of resistance, and correlation of these mechanisms with bacterial resistance. Clin Microbiol Rev. 1999 Oct;12(4):501-17. [Article]
- Trosken ER, Adamska M, Arand M, Zarn JA, Patten C, Volkel W, Lutz WK: Comparison of lanosterol-14 alpha-demethylase (CYP51) of human and Candida albicans for inhibition by different antifungal azoles. Toxicology. 2006 Nov 10;228(1):24-32. doi: 10.1016/j.tox.2006.08.007. Epub 2006 Aug 12. [Article]
- Magill SS, Puthanakit T, Swoboda SM, Carson KA, Salvatori R, Lipsett PA, Hendrix CW: Impact of fluconazole prophylaxis on cortisol levels in critically ill surgical patients. Antimicrob Agents Chemother. 2004 Jul;48(7):2471-6. doi: 10.1128/AAC.48.7.2471-2476.2004. [Article]
- de Carvalho Santana R, Schiave LA, Dos Santos Quaglio AS, de Gaitani CM, Martinez R: Fluconazole Non-susceptible Cryptococcus neoformans, Relapsing/Refractory Cryptococcosis and Long-term Use of Liposomal Amphotericin B in an AIDS Patient. Mycopathologia. 2017 Oct;182(9-10):855-861. doi: 10.1007/s11046-017-0165-1. Epub 2017 Jun 27. [Article]
- Jessup CJ, Pfaller MA, Messer SA, Zhang J, Tumberland M, Mbidde EK, Ghannoum MA: Fluconazole susceptibility testing of Cryptococcus neoformans: comparison of two broth microdilution methods and clinical correlates among isolates from Ugandan AIDS patients. J Clin Microbiol. 1998 Oct;36(10):2874-6. [Article]
- Garnacho-Montero J, Diaz-Martin A, Garcia-Cabrera E, Ruiz Perez de Pipaon M, Hernandez-Caballero C, Aznar-Martin J, Cisneros JM, Ortiz-Leyba C: Risk factors for fluconazole-resistant candidemia. Antimicrob Agents Chemother. 2010 Aug;54(8):3149-54. doi: 10.1128/AAC.00479-10. Epub 2010 May 24. [Article]
- Alastruey-Izquierdo A, Melhem MS, Bonfietti LX, Rodriguez-Tudela JL: SUSCEPTIBILITY TEST FOR FUNGI: CLINICAL AND LABORATORIAL CORRELATIONS IN MEDICAL MYCOLOGY. Rev Inst Med Trop Sao Paulo. 2015 Sep;57 Suppl 19:57-64. doi: 10.1590/S0036-46652015000700011. [Article]
- Sun G, Thai SF, Lambert GR, Wolf DC, Tully DB, Goetz AK, George MH, Grindstaff RD, Dix DJ, Nesnow S: Fluconazole-induced hepatic cytochrome P450 gene expression and enzymatic activities in rats and mice. Toxicol Lett. 2006 Jun 20;164(1):44-53. doi: 10.1016/j.toxlet.2005.11.015. Epub 2006 Jan 6. [Article]
- Joseph-Horne T, Hollomon DW: Molecular mechanisms of azole resistance in fungi. FEMS Microbiol Lett. 1997 Apr 15;149(2):141-9. doi: 10.1111/j.1574-6968.1997.tb10321.x. [Article]
- Sheng C, Miao Z, Ji H, Yao J, Wang W, Che X, Dong G, Lu J, Guo W, Zhang W: Three-dimensional model of lanosterol 14 alpha-demethylase from Cryptococcus neoformans: active-site characterization and insights into azole binding. Antimicrob Agents Chemother. 2009 Aug;53(8):3487-95. doi: 10.1128/AAC.01630-08. Epub 2009 May 26. [Article]
- Devenport MH, Crook D, Wynn V, Lees LJ: Metabolic effects of low-dose fluconazole in healthy female users and non-users of oral contraceptives. Br J Clin Pharmacol. 1989 Jun;27(6):851-9. doi: 10.1111/j.1365-2125.1989.tb03449.x. [Article]
- Grossman NT, Pham CD, Cleveland AA, Lockhart SR: Molecular mechanisms of fluconazole resistance in Candida parapsilosis isolates from a U.S. surveillance system. Antimicrob Agents Chemother. 2015 Feb;59(2):1030-7. doi: 10.1128/AAC.04613-14. Epub 2014 Dec 1. [Article]
- Nasrollahi Z, Yadegari MH, Roudbar Mohammadi S, Roudbary M, Hosseini Poor M, Nikoomanesh F, Rajabi Bazl M: Fluconazole Resistance Candida albicans in Females With Recurrent Vaginitis and Pir1 Overexpression. Jundishapur J Microbiol. 2015 Sep 23;8(9):e21468. doi: 10.5812/jjm.21468. eCollection 2015 Sep. [Article]
- Debruyne D, Ryckelynck JP: Clinical pharmacokinetics of fluconazole. Clin Pharmacokinet. 1993 Jan;24(1):10-27. doi: 10.2165/00003088-199324010-00002. [Article]
- Manosuthi W, Chetchotisakd P, Nolen TL, Wallace D, Sungkanuparph S, Anekthananon T, Supparatpinyo K, Pappas PG, Larsen RA, Filler SG, Andes D: Monitoring and impact of fluconazole serum and cerebrospinal fluid concentration in HIV-associated cryptococcal meningitis-infected patients. HIV Med. 2010 Apr;11(4):276-81. doi: 10.1111/j.1468-1293.2009.00778.x. Epub 2009 Dec 8. [Article]
- Brammer KW, Coakley AJ, Jezequel SG, Tarbit MH: The disposition and metabolism of [14C]fluconazole in humans. Drug Metab Dispos. 1991 Jul-Aug;19(4):764-7. [Article]
- Elewski B, Tavakkol A: Safety and tolerability of oral antifungal agents in the treatment of fungal nail disease: a proven reality. Ther Clin Risk Manag. 2005 Dec;1(4):299-306. [Article]
- Fluconazole, Medsafe NZ data sheet [Link]
- EMA Summary of Product Characteristics: Diflucan (fluconazole) oral capsules [Link]
- FDA Approved Drug Products: Diflucan (fluconazole) [Link]
- External Links
- Human Metabolome Database
- HMDB0014342
- KEGG Drug
- D00322
- PubChem Compound
- 3365
- PubChem Substance
- 46505735
- ChemSpider
- 3248
- BindingDB
- 25817
- 4450
- ChEBI
- 46081
- ChEMBL
- CHEMBL106
- ZINC
- ZINC000000004009
- Therapeutic Targets Database
- DAP000628
- PharmGKB
- PA449653
- PDBe Ligand
- TPF
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Fluconazole
- PDB Entries
- 1ea1 / 2ij7 / 2wuz / 2wv2 / 2wx2 / 3l4d / 4wmz / 4zdz / 4ze3 / 5ese … show 6 more
- FDA label
- Download (468 KB)
- MSDS
- Download (73.9 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Prevention Candidiasis 1 4 Completed Prevention Central Nervous System Fungal Infections / Fungaemia / Fungal Infections / Lung Diseases, Fungal 1 4 Completed Prevention Cryptococcosis / Cryptococcus Neoformans / Meningitis, Cryptococcal 1 4 Completed Supportive Care Bacterial Infections and Mycoses / Ductus Arteriosis, Patent 1 4 Completed Treatment Acquired Immune Deficiency Syndrome (AIDS) / Candidiasis / Oral Candidiasis 1
Pharmacoeconomics
- Manufacturers
- Pfizer chemicals div pfizer inc
- Aurobindo pharma usa inc
- Ivax pharmaceuticals inc sub teva pharmaceuticals usa
- Ranbaxy laboratories ltd
- Roxane laboratories inc
- Taro pharmaceutical industries ltd
- Pfizer inc
- Acs dobfar info sa
- Apotex inc richmond hill
- Hospira inc
- App pharmaceuticals llc
- Bedford laboratories div ben venue laboratories inc
- Claris lifesciences ltd
- Hikma farmaceutica portugal lda
- Teva parenteral medicines inc
- Baxter healthcare corp
- Bedford laboratories
- Pfizer central research
- Apotex inc
- Aurobindo pharma ltd
- Dr reddys laboratories inc
- Gedeon richter usa inc
- Genpharm inc
- Glenmark generics ltd
- Mylan pharmaceuticals inc
- Pliva inc
- Sandoz inc
- Teva pharmaceuticals usa inc
- Unique pharmaceutical laboratories
- Packagers
- Advanced Pharmaceutical Services Inc.
- Amerisource Health Services Corp.
- Apotex Inc.
- Apotheca Inc.
- APP Pharmaceuticals
- AQ Pharmaceuticals Inc.
- A-S Medication Solutions LLC
- Atlantic Biologicals Corporation
- Aurobindo Pharma Ltd.
- Baxter International Inc.
- Bedford Labs
- Ben Venue Laboratories Inc.
- Bryant Ranch Prepack
- Cardinal Health
- Cipla Ltd.
- Claris Lifesciences Inc.
- Comprehensive Consultant Services Inc.
- Direct Pharmaceuticals Inc.
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- Doctor Reddys Laboratories Ltd.
- Glenmark Generics Ltd.
- Greenstone LLC
- H.J. Harkins Co. Inc.
- Haemonetics Corp.
- Hikma Pharmaceuticals
- Hospira Inc.
- Ivax Pharmaceuticals
- J.B. Chemicals & Pharmaceuticals
- Lake Erie Medical and Surgical Supply
- Medisca Inc.
- Murfreesboro Pharmaceutical Nursing Supply
- Mylan
- Northstar Rx LLC
- Novopharm Ltd.
- Nucare Pharmaceuticals Inc.
- Palmetto Pharmaceuticals Inc.
- Par Pharmaceuticals
- PCA LLC
- PD-Rx Pharmaceuticals Inc.
- Pfizer Inc.
- Pharmaceutical Utilization Management Program VA Inc.
- Physicians Total Care Inc.
- Preferred Pharmaceuticals Inc.
- Prepackage Specialists
- Prepak Systems Inc.
- Ranbaxy Laboratories
- Rebel Distributors Corp.
- Redpharm Drug
- Remedy Repack
- Resource Optimization and Innovation LLC
- Roxane Labs
- Sagent Pharmaceuticals
- Sandhills Packaging Inc.
- Shanghai Ziyuan Pharmaceutical Co. Ltd.
- Southwood Pharmaceuticals
- Stat Rx Usa
- Taro Pharmaceuticals USA
- Teva Pharmaceutical Industries Ltd.
- UDL Laboratories
- West-Ward Pharmaceuticals
- Dosage Forms
Form Route Strength Solution Parenteral 100 mg Tablet Oral 200 mg Tablet Oral 37.500 mg Capsule, gelatin coated Oral Solution Intravenous 2 mg Capsule Oral 100.00 mg Injection, solution Intravenous Powder, for suspension Oral Capsule Oral 150 mg Capsule Oral 150.000 mg Injection Intravenous 200 mg/100ml Capsule; cream Oral; Topical; Vaginal Capsule; cream Oral; Topical Solution Intravenous 200.000 mg Capsule, coated Oral 150 mg Tablet Oral Capsule Oral 0.1500 g Injection, solution 2 MG/ML Powder, for solution Oral 50 mg / 5 mL Powder, for suspension Oral 10 MG/ML Solution Intravenous 100.000 mg Solution Intravenous 200 mg Powder, for solution Oral Capsule Oral Solution Parenteral Injection Intravenous 2 mg/ml Suspension Oral 200 mg/5ml Suspension Oral 50 mg/5ml Gel Topical 5 MG/G Powder, for suspension Oral 50 MG/5ML Capsule, coated Oral 15000000 mg Solution Intravenous 0.2 g Capsule, coated Oral 20000000 mg Capsule, coated Oral 50 mg Capsule, coated Oral 200 mg Solution Parenteral 200 mg Solution Intramuscular 2 mg Tablet, film coated Oral Solution Intravenous 20000000 mg Powder, for solution Oral 1 g Injection Intravenous Injection Intravenous 2 mg/1mL Injection, solution Intravenous 2 mg/1mL Injection, solution Intravenous 200 mg/100mL Injection, solution Intravenous 400 mg/200mL Powder Not applicable 1 g/1g Powder, for suspension Oral 10 mg/1mL Powder, for suspension Oral 1400 mg/35mL Powder, for suspension Oral 350 mg/35mL Powder, for suspension Oral 40 mg/1mL Solution Intravenous 2 mg/1mL Solution Oral 10 mg/1mL Solution Oral 40 mg/1mL Tablet Oral 100 mg/1 Tablet Oral 150 mg/1 Tablet Oral 200 mg/1 Tablet Oral 50 mg/1 Solution Topical Solution Intravenous 200 mg/100ml Solution Intravenous 2 mg / mL Injection, solution Intravenous 2 mg/ml Solution 2 mg/ml Solution Intravenous 2 mg/ml Injection, solution Parenteral 100 MG/50ML Injection, solution Parenteral 200 MG/100ML Injection, solution Parenteral 400 MG/200ML Injection, solution Parenteral 2 MG/ML Injection, solution Injection, solution Parenteral 2 MG/MG Injection, solution Intravenous 100 mg/50ml Solution / drops Ophthalmic 0.3 % Syrup Oral 500 mg Capsule, coated Oral 100 mg Capsule Oral 100 mg Capsule Oral 50 mg Capsule Oral 50.000 MG Powder, for suspension Oral 4 g Powder, for suspension Oral 1 g Syrup Oral Syrup Oral 25 mg/5ml Tablet Oral Capsule; cream; kit Oral; Topical Injection, solution 100 MG/50ML Injection, solution 200 MG/100ML Injection, solution 400 MG/200ML Tablet Oral 100 mg Tablet Oral 50 mg Injection Parenteral 200 mg Tablet Oral 150 mg Tablet Vaginal 150.00 mg Tablet, coated Oral Capsule Oral 100.000 mg Syrup Oral 5 mg/ml Solution 2 mg/1ml Capsule Oral 200 mg - Prices
Unit description Cost Unit Diflucan 40 mg/ml Suspension 35ml Bottle 203.65USD bottle Fluconazole 40 mg/ml Suspension 35ml Bottle 135.99USD bottle Diflucan 10 mg/ml Suspension 35ml Bottle 56.06USD bottle Fluconazole 10 mg/ml Suspension 35ml Bottle 35.94USD bottle Diflucan 150 mg tablet 24.71USD tablet Diflucan 200 mg tablet 20.82USD tablet Diflucan 150 mg Capsule 16.44USD capsule Fluconazole 200 mg tablet 14.26USD tablet Fluconazole powder 14.08USD g Fluconazole 150 mg tablet 13.93USD tablet Diflucan 100 mg tablet 12.61USD tablet Apo-Fluconazole-150 150 mg Capsule 9.18USD capsule Co Fluconazole 150 mg Capsule 9.18USD capsule Mylan-Fluconazole 150 mg Capsule 9.18USD capsule Pms-Fluconazole 150 mg Capsule 9.18USD capsule Fluconazole 100 mg tablet 8.95USD tablet Diflucan 50 mg tablet 8.05USD tablet Apo-Fluconazole 100 mg Tablet 5.81USD tablet Mylan-Fluconazole 100 mg Tablet 5.81USD tablet Fluconazole 50 mg tablet 5.7USD tablet Co Fluconazole 100 mg Tablet 5.42USD tablet Novo-Fluconazole 100 mg Tablet 5.42USD tablet Pms-Fluconazole 100 mg Tablet 5.42USD tablet Apo-Fluconazole 50 mg Tablet 3.28USD tablet Mylan-Fluconazole 50 mg Tablet 3.28USD tablet Co Fluconazole 50 mg Tablet 3.06USD tablet Novo-Fluconazole 50 mg Tablet 3.06USD tablet Pms-Fluconazole 50 mg Tablet 3.06USD tablet Diflucan-dextr 200 mg/100 ml 1.28USD ml Diflucan-saline 200 mg/100 ml 1.28USD ml Diflucan 2 mg/ml 0.6USD ml Fluconazole 2 mg/ml 0.33USD ml Fluconazole Omega 2 mg/ml 0.33USD ml Fluconazole-dext 200 mg/100 ml 0.32USD ml Fluconazole-ns 200 mg/100 ml 0.19USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 138-140 °C http://www.chemspider.com/Chemical-Structure.3248.html boiling point (°C) 579.8 https://www.lookchem.com/Fluconazole/ water solubility slightly soluble in water FDA label logP 0.5 https://www.pfizer.ca/sites/g/files/g10050796/f/201806/Diflucan_PM_E_207077_12June2018.pdf pKa 1.76 https://www.pfizer.ca/sites/g/files/g10017036/f/201410/DIFLUCAN(2).pdf - Predicted Properties
Property Value Source Water Solubility 1.39 mg/mL ALOGPS logP 0.58 ALOGPS logP 0.56 Chemaxon logS -2.3 ALOGPS pKa (Strongest Acidic) 12.68 Chemaxon pKa (Strongest Basic) 2.3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 81.65 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 97.2 m3·mol-1 Chemaxon Polarizability 26.52 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9894 Blood Brain Barrier + 0.9382 Caco-2 permeable + 0.8867 P-glycoprotein substrate Non-substrate 0.6008 P-glycoprotein inhibitor I Non-inhibitor 0.8782 P-glycoprotein inhibitor II Non-inhibitor 0.9004 Renal organic cation transporter Non-inhibitor 0.6461 CYP450 2C9 substrate Non-substrate 0.7898 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.565 CYP450 1A2 substrate Non-inhibitor 0.6312 CYP450 2C9 inhibitor Non-inhibitor 0.5497 CYP450 2D6 inhibitor Non-inhibitor 0.809 CYP450 2C19 inhibitor Inhibitor 0.532 CYP450 3A4 inhibitor Non-inhibitor 0.8196 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.524 Ames test Non AMES toxic 0.548 Carcinogenicity Non-carcinogens 0.7298 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.4136 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8229 hERG inhibition (predictor II) Non-inhibitor 0.6614
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 168.8356435 predictedDarkChem Lite v0.1.0 [M-H]- 169.1223435 predictedDarkChem Lite v0.1.0 [M-H]- 164.52318 predictedDeepCCS 1.0 (2019) [M+H]+ 168.9887435 predictedDarkChem Lite v0.1.0 [M+H]+ 169.4990435 predictedDarkChem Lite v0.1.0 [M+H]+ 166.88118 predictedDeepCCS 1.0 (2019) [M+Na]+ 169.0752435 predictedDarkChem Lite v0.1.0 [M+Na]+ 169.0680435 predictedDarkChem Lite v0.1.0 [M+Na]+ 172.97432 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Yeast
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Sterol 14-demethylase activity
- Specific Function
- Catalyzes C14-demethylation of lanosterol which is critical for ergosterol biosynthesis. It transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
- Gene Name
- ERG11
- Uniprot ID
- P10613
- Uniprot Name
- Lanosterol 14-alpha demethylase
- Molecular Weight
- 60674.965 Da
References
- Bellamine A, Lepesheva GI, Waterman MR: Fluconazole binding and sterol demethylation in three CYP51 isoforms indicate differences in active site topology. J Lipid Res. 2004 Nov;45(11):2000-7. Epub 2004 Aug 16. [Article]
- Guinea J, Sanchez-Somolinos M, Cuevas O, Pelaez T, Bouza E: Fluconazole resistance mechanisms in Candida krusei: the contribution of efflux-pumps. Med Mycol. 2006 Sep;44(6):575-8. [Article]
- Chau AS, Chen G, McNicholas PM, Mann PA: Molecular basis for enhanced activity of posaconazole against Absidia corymbifera and Rhizopus oryzae. Antimicrob Agents Chemother. 2006 Nov;50(11):3917-9. Epub 2006 Sep 11. [Article]
- Hollier LM, Cox SM: Fluconazole (Diflucan). Infect Dis Obstet Gynecol. 1995;3(6):222-5. doi: 10.1155/S1064744995000676. [Article]
- Ghannoum MA, Rice LB: Antifungal agents: mode of action, mechanisms of resistance, and correlation of these mechanisms with bacterial resistance. Clin Microbiol Rev. 1999 Oct;12(4):501-17. [Article]
- Fluconazole, Medsafe NZ data sheet [Link]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Niwa T, Imagawa Y, Yamazaki H: Drug interactions between nine antifungal agents and drugs metabolized by human cytochromes P450. Curr Drug Metab. 2014;15(7):651-79. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Niwa T, Shiraga T, Takagi A: Effect of antifungal drugs on cytochrome P450 (CYP) 2C9, CYP2C19, and CYP3A4 activities in human liver microsomes. Biol Pharm Bull. 2005 Sep;28(9):1805-8. [Article]
- Kunze KL, Wienkers LC, Thummel KE, Trager WF: Warfarin-fluconazole. I. Inhibition of the human cytochrome P450-dependent metabolism of warfarin by fluconazole: in vitro studies. Drug Metab Dispos. 1996 Apr;24(4):414-21. [Article]
- Sakaeda T, Iwaki K, Kakumoto M, Nishikawa M, Niwa T, Jin JS, Nakamura T, Nishiguchi K, Okamura N, Okumura K: Effect of micafungin on cytochrome P450 3A4 and multidrug resistance protein 1 activities, and its comparison with azole antifungal drugs. J Pharm Pharmacol. 2005 Jun;57(6):759-64. [Article]
- Clin-Info. (2006). In Compendium of Pharmaceuticals and Specialties: The Canadian Drug Reference for Health Professionals (pp. L55). Canadian Pharmacists Association. [ISBN:1-894402-22-7]
- Flockhart Table of Drug Interactions [Link]
- Drug Interactions & Labeling - FDA [Link]
- Fluconazole, Medsafe NZ data sheet [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Niwa T, Shiraga T, Takagi A: Effect of antifungal drugs on cytochrome P450 (CYP) 2C9, CYP2C19, and CYP3A4 activities in human liver microsomes. Biol Pharm Bull. 2005 Sep;28(9):1805-8. [Article]
- Kunze KL, Wienkers LC, Thummel KE, Trager WF: Warfarin-fluconazole. I. Inhibition of the human cytochrome P450-dependent metabolism of warfarin by fluconazole: in vitro studies. Drug Metab Dispos. 1996 Apr;24(4):414-21. [Article]
- Kantola T, Backman JT, Niemi M, Kivisto KT, Neuvonen PJ: Effect of fluconazole on plasma fluvastatin and pravastatin concentrations. Eur J Clin Pharmacol. 2000 Jun;56(3):225-9. [Article]
- Debruyne D, Coquerel A: Pharmacokinetics of antifungal agents in onychomycoses. Clin Pharmacokinet. 2001;40(6):441-72. [Article]
- Venkatakrishnan K, von Moltke LL, Greenblatt DJ: Effects of the antifungal agents on oxidative drug metabolism: clinical relevance. Clin Pharmacokinet. 2000 Feb;38(2):111-80. doi: 10.2165/00003088-200038020-00002. [Article]
- `Clin-Info. (2006). In Compendium of Pharmaceuticals and Specialties: The Canadian Drug Reference for Health Professionals (pp. L55). Canadian Pharmacists Association. [ISBN:1-894402-22-7]
- Flockhart Table of Drug Interactions [Link]
- Fluconazole, Medsafe NZ data sheet [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- Fluconazole has been shown to be a CYP2C19 inhibitor in in vitro, however, the clinical significance of this is unknown. The EMA label notes that fluconazole is an inhibitor of CYP2C19.
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- Niwa T, Shiraga T, Takagi A: Effect of antifungal drugs on cytochrome P450 (CYP) 2C9, CYP2C19, and CYP3A4 activities in human liver microsomes. Biol Pharm Bull. 2005 Sep;28(9):1805-8. [Article]
- Venkatakrishnan K, von Moltke LL, Greenblatt DJ: Effects of the antifungal agents on oxidative drug metabolism: clinical relevance. Clin Pharmacokinet. 2000 Feb;38(2):111-80. doi: 10.2165/00003088-200038020-00002. [Article]
- Fluconazole, Medsafe NZ data sheet [Link]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Nwaroh E, Jupp J, Jadusingh E, Guilcher G: Clinical impact and management of fluconazole discontinuation on sirolimus levels in bone marrow transplant patients. J Oncol Pharm Pract. 2018 Apr;24(3):235-238. doi: 10.1177/1078155217701293. Epub 2017 Mar 29. [Article]
- FDA Approved Drug Products: Diflucan (fluconazole) [Link]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54