Identification

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Name
Fluconazole
Accession Number
DB00196  (APRD00327)
Type
Small Molecule
Groups
Approved, Investigational
Description

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

Structure
Thumb
Synonyms
  • Diflucan
  • Difluconazole
  • Fluconazol
  • Fluconazole
  • Fluconazolum
  • Triflucan
External IDs
UK-49,858 / UK-49858
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act FluconazoleTabletOralActavis Pharma Company2007-12-03Not applicableCanada
Act FluconazoleTabletOralActavis Pharma Company2007-12-03Not applicableCanada
DiflucanSolution2 mg/1mLIntravenousRoerig2006-06-082006-06-08Us
DiflucanTablet150 mg/1OralA-S Medication Solutions1990-01-29Not applicableUs
DiflucanPowder, for suspension350 mg/35mLOralRoerig1993-12-23Not applicableUs
DiflucanSolution2 mg/1mLIntravenousRoerig2006-06-082006-06-08Us
DiflucanSolution2 mg/1mLIntravenousRoerig2006-06-082006-06-08Us
DiflucanPowder, for solution50 mgOralPfizer Canada Ulc1995-12-31Not applicableCanada
DiflucanTablet200 mg/1OralPhysicians Total Care, Inc.1990-01-292012-06-30Us
DiflucanTablet200 mg/1OralRoerig1990-01-29Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-fluconazoleTabletOralApotex Corporation1998-10-13Not applicableCanada
Apo-fluconazoleTabletOralApotex CorporationNot applicableNot applicableCanada
Apo-fluconazoleTabletOralApotex Corporation1998-10-13Not applicableCanada
Direct RxTablet200 mg/1OralDirect Rx2015-01-012015-08-03Us
Dom-fluconazoleTabletOralDominion Pharmacal2002-07-09Not applicableCanada
Dom-fluconazoleTabletOralDominion Pharmacal2002-07-09Not applicableCanada
FluconazoleInjection2 mg/1mLIntravenousBaxter Laboratories2010-06-092019-12-31Us
FluconazoleTablet100 mg/1OralNucare Pharmaceuticals,inc.2017-04-06Not applicableUs
FluconazoleInjection2 mg/1mLIntravenousWest-Ward Pharmaceuticals Corp2005-08-23Not applicableUs
FluconazoleTablet100 mg/1OralPhysicians Total Care, Inc.2005-07-06Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-fluconazole-150CapsuleOralApotex Corporation2000-03-20Not applicableCanada
Bio-fluconazoleCapsuleOralBiomed Pharma2019-09-20Not applicableCanada
CanesoralCapsuleOralBayer2010-03-10Not applicableCanada
Co Fluconazole-150CapsuleOralCobalt Laboratories2009-07-212019-03-26Canada
Diflucan OneCapsuleOralPfizer Canada Ulc1995-12-31Not applicableCanada
Dom-fluconazoleCapsuleOralDominion PharmacalNot applicableNot applicableCanada
FluconazoleCapsule150 mgOralSorres Pharma Inc2009-06-172014-06-20Canada
FluconazoleCapsule150 mgOralPendopharm Division Of Pharmascience IncNot applicableNot applicableCanada
FluconazoleCapsule150 mgOralPharmel IncNot applicableNot applicableCanada
Fluconazole 150CapsuleOralTaro Pharmaceuticals, Inc.Not applicableNot applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Canesoral CombiFluconazole (150 mg) + Clotrimazole (1 %)Capsule; CreamOral; Topical; VaginalBayer2010-03-10Not applicableCanada
Canesoral Combi 1 DayFluconazole (150 mg) + Clotrimazole (2 %)Capsule; CreamOral; TopicalBayerNot applicableNot applicableCanada
Clotrimaderm-fluconazole Combi-packFluconazole (150 mg) + Clotrimazole (1 %)Capsule; Cream; KitOral; TopicalTaro Pharmaceuticals, Inc.2017-02-14Not applicableCanada
Clotrimazole-fluconazole Combi-packFluconazole (150 mg) + Clotrimazole (1 %)Capsule; Cream; KitOral; TopicalTaro Pharmaceuticals, Inc.2017-02-03Not applicableCanada
Monicure ComboFluconazole (150 mg) + Miconazole nitrate (2 %)Capsule; Cream; KitOral; TopicalInsight Pharmaceuticals LLC2012-10-25Not applicableCanada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Ciclopirox 8% / Fluconazole 1% / Terbinafine HCl 1%Fluconazole (1 g/100g) + Ciclopirox (8 g/100g) + Terbinafine (1 g/100g)SolutionTopicalSincerus Florida, LLC2019-05-01Not applicableUs
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)SolutionTopicalSincerus Florida, LLC2019-05-01Not applicableUs
International/Other Brands
Elazor / Flucazol / Flucostat / Flunizol / Pritenzol / Trican / Triflucan
Categories
UNII
8VZV102JFY
CAS number
86386-73-4
Weight
Average: 306.2708
Monoisotopic: 306.104065446
Chemical Formula
C13H12F2N6O
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

Pharmacology

Indication

Fluconazole can be administered in the treatment of the following fungal infectionsLabel:

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.Label

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.Label

Associated Conditions
Pharmacodynamics

Fluconazole has been demonstrated to show fungistatic activity against the majority of strains of the following microorganisms, curing fungal infectionsLabel:

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.Label,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.Label 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.25 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.25 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

TargetActionsOrganism
ACytochrome P450 51
inhibitor
Yeast
Additional Data Available
Adverse Effects

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Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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%.Label 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.25,21

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.Label 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.Label 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.Label 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.Label

Volume of distribution

The apparent volume of distribution is said to be similar to the volume of distribution of total body water.Label 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,Label 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.25 Saliva and sputum concentrations of fluconazole are found to be similar to the plasma concentrations.26 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 barrier25. 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%.Label,21

Metabolism

Fluconazole is metabolized minimally in the liver. Fluconazole is an inhibitor of CYP2C9, CYP3A4 and CYP2C19.25,Label 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

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.Label About 11% of the dose is excreted in the urine as metabolites.Label. 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%.Label

Half life

The terminal elimination half-life in the plasma is approximately 30 hours (range: 20-50 hours) after oral administration.Label The long plasma elimination half-life supports a single dose therapy for vaginal candidiasis, once daily and once weekly dosing for other indications.25. 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.Label 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.Label

Toxicity

Acute oral toxicity (LD50): 1271 mg/kg (rat) MSDS

Overdose information

Fluconazole overdoses have been associated with hallucination and paranoia, sometimes in combination.Label In cases of overdose, employ supportive treatment. Gastric lavage may be necessary.Label Other modalities such as forced diuresis or hemodialysis may also be used.Label

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.Label 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.Label,26 Fluconazole induced hepatotoxicity is usually reversible.Label

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.Label

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.Label 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.Label

Use in nursing

Fluconazole is secreted in breastmilk at high concentrations. Exercise caution if this drug is used during nursing.Label

Affected organisms
  • Fungi
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
(R)-warfarinThe serum concentration of (R)-warfarin can be increased when it is combined with Fluconazole.
(S)-WarfarinThe serum concentration of (S)-Warfarin can be increased when it is combined with Fluconazole.
2,4-thiazolidinedioneThe risk or severity of hypoglycemia can be increased when 2,4-thiazolidinedione is combined with Fluconazole.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Fluconazole.
4-hydroxycoumarinThe therapeutic efficacy of 4-hydroxycoumarin can be increased when used in combination with Fluconazole.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Fluconazole.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Fluconazole.
7-ethyl-10-hydroxycamptothecinThe metabolism of 7-ethyl-10-hydroxycamptothecin can be decreased when combined with Fluconazole.
9-aminocamptothecinThe metabolism of 9-aminocamptothecin can be decreased when combined with Fluconazole.
AbacavirFluconazole may decrease the excretion rate of Abacavir which could result in a higher serum level.
Additional Data Available
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    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

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  • Action
    Action

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Food Interactions
  • Take without regard to meals.

References

Synthesis Reference
US4404216
General References
  1. 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. [PubMed:29377368]
  2. Hollier LM, Cox SM: Fluconazole (Diflucan). Infect Dis Obstet Gynecol. 1995;3(6):222-5. doi: 10.1155/S1064744995000676. [PubMed:18476045]
  3. 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. [PubMed:25843556]
  4. 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. [PubMed:18366001]
  5. Lewis RE: Current concepts in antifungal pharmacology. Mayo Clin Proc. 2011 Aug;86(8):805-17. doi: 10.4065/mcp.2011.0247. [PubMed:21803962]
  6. 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. [PubMed:29279242]
  7. 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. [PubMed:28814889]
  8. 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. [PubMed:10515900]
  9. 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. [PubMed:16989930]
  10. 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. [PubMed:15215096]
  11. 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. [PubMed:28656554]
  12. 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. [PubMed:9738036]
  13. 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. [PubMed:20498325]
  14. 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. [PubMed:26465371]
  15. 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. [PubMed:16406388]
  16. 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. [PubMed:9141655]
  17. 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. [PubMed:19470512]
  18. 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. [PubMed:2547410]
  19. 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. [PubMed:25451046]
  20. 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. [PubMed:26495107]
  21. Debruyne D, Ryckelynck JP: Clinical pharmacokinetics of fluconazole. Clin Pharmacokinet. 1993 Jan;24(1):10-27. doi: 10.2165/00003088-199324010-00002. [PubMed:8448970]
  22. 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. [PubMed:20002501]
  23. 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. [PubMed:1680653]
  24. 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. [PubMed:18360572]
  25. EMA label, Fluconazole [Link]
  26. Fluconazole, Medsafe NZ data sheet [Link]
External Links
Human Metabolome Database
HMDB0014342
KEGG Drug
D00322
PubChem Compound
3365
PubChem Substance
46505735
ChemSpider
3248
BindingDB
25817
ChEBI
46081
ChEMBL
CHEMBL106
Therapeutic Targets Database
DAP000628
PharmGKB
PA449653
HET
TPF
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Fluconazole
ATC Codes
J01RA07 — Azithromycin, fluconazole and secnidazoleJ02AC01 — FluconazoleD01AC15 — Fluconazole
AHFS Codes
  • 08:14.08 — Azoles
PDB Entries
1ea1 / 2ij7 / 2wuz / 2wv2 / 2wx2 / 3khm / 3l4d / 4wmz / 4zdz / 4ze3
show 7 more
FDA label
Download (468 KB)
MSDS
Download (73.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentVaginal Inflammation1
1Active Not RecruitingTreatmentAdvanced Solid Tumors / Lymphoma, Large B-Cell, Diffuse (DLBCL) / Mantle Cell Lymphoma (MCL) / Marginal Zone Lymphoma / Primary Mediastinal Lymphoma1
1Active Not RecruitingTreatmentNeoplasms1
1CompletedNot AvailableHealthy Volunteers2
1CompletedNot AvailableMetabolic Detoxication, Phase I1
1CompletedBasic ScienceAlzheimer's Disease (AD)1
1CompletedBasic ScienceAtopic Dermatitis (AD)1
1CompletedBasic ScienceBioequivalence2
1CompletedBasic ScienceDrug Drug Interaction (DDI)1
1CompletedBasic ScienceHealthy Volunteers3
1CompletedBasic ScienceNASH - Nonalcoholic Steatohepatitis1
1CompletedBasic ScienceTumors, Solid1
1CompletedOtherHealthy Volunteers1
1CompletedOtherPharmacology, Clinical1
1CompletedTreatmentAdvanced Solid Tumors1
1CompletedTreatmentBacterial Infections / Human Immunodeficiency Virus (HIV) Infections / Mycoses1
1CompletedTreatmentCardio Respiratory Arrest / Infections, Fungal1
1CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD) / Healthy Volunteers1
1CompletedTreatmentEndometriosis / Prostate Cancer1
1CompletedTreatmentGraft Versus Host Disease (GVHD) / Transplantation, Stem Cell1
1CompletedTreatmentHealthy Participants1
1CompletedTreatmentHealthy Volunteers3
1CompletedTreatmentCandidiasis infection / Human Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentInvasive Aspergillosis1
1CompletedTreatmentOveractive Bladder With Symptoms of Frequency, Urgency, and Urge Urinary Incontinence1
1CompletedTreatmentCandidiasis infection1
1Not Yet RecruitingOtherBioequivalence1
1RecruitingBasic ScienceHealthy Volunteers1
1WithdrawnBasic ScienceHealthy Volunteers1
1WithdrawnTreatmentMalignant Lymphomas1
1, 2CompletedDiagnosticHealthy Volunteers1
1, 2CompletedTreatmentHIV Associated Neurocognitive Disorders (HAND)1
1, 2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Meningitis, Cryptococcal1
1, 2WithdrawnTreatmentLeukemia Acute Myeloid Leukemia (AML)1
2CompletedBasic ScienceVery Low Birth Weight Infant1
2CompletedPreventionIntra-abdominal Perforation1
2CompletedTreatmentBlastomycosis / Histoplasmosis / Sporotrichosis1
2CompletedTreatmentCandida Vulvovaginitis1
2CompletedTreatmentCandidemia / Candidiasis, Invasive / Fungaemia / Infections, Fungal / Mycoses1
2CompletedTreatmentCandidemia / Candidiasis, Invasive / Mycoses1
2CompletedTreatmentCrohn's Disease (CD)1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Meningitis, Cryptococcal2
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Oral Candidiasis1
2CompletedTreatmentMeningitis, Cryptococcal1
2CompletedTreatmentMoniliasis, Vulvovaginal / Mycoses / Vaginitis, Monilial / Vulvovaginal Candidiasis / Yeast Infections1
2CompletedTreatmentSporotrichosis1
2CompletedTreatmentVulvovaginal Candidiasis3
2CompletedTreatmentVulvovaginal Candidiasis / Vulvovaginitis / Yeast Infection Vaginal / Yeast Infections1
2RecruitingTreatmentCrohn's Disease (CD)1
2RecruitingTreatmentHuman Immunodeficiency Virus (HIV) / Meningitis / Meningitis streptococcal / Meningoencephalitis1
2SuspendedSupportive CareStem Cell Transplant Complications1
2TerminatedDiagnosticHyperlipidemias1
2TerminatedTreatmentCrohn's Disease Aggravated1
2TerminatedTreatmentCryptococcal Infection Disseminated1
2, 3Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) / Meningitis, Cryptococcal1
2, 3CompletedTreatmentHead and Neck Carcinoma / Infection NOS / Oral Complications1
2, 3CompletedTreatmentMinor burns1
2, 3Not Yet RecruitingPreventionMeningitis, Cryptococcal1
2, 3Not Yet RecruitingTreatmentCandidiasis infection1
2, 3RecruitingTreatmentMinor burns1
3Active Not RecruitingSupportive CareAdult Acute Megakaryoblastic Leukemia / Adult Acute Megakaryoblastic Leukemia (M7) / Adult Acute Minimally Differentiated Myeloid Leukemia (M0) / Adult Acute Monoblastic Leukemia / Adult Acute Monoblastic Leukemia (M5a) / Adult Acute Monocytic Leukemia / Adult Acute Monocytic Leukemia (M5b) / Adult Acute Myeloblastic Leukemia With Maturation (M2) / Adult Acute Myeloblastic Leukemia Without Maturation (M1) / Adult Acute Myeloid Leukemia in Remission / Adult Acute Myeloid Leukemia With 11q23 (MLL) Abnormalities / Adult Acute Myeloid Leukemia With Del(5q) / Adult Acute Myeloid Leukemia With Inv(16)(p13.1q22); CBFB-MYH11 / Adult Acute Myeloid Leukemia With Inv(16)(p13;q22) / Adult Acute Myeloid Leukemia With Maturation / Adult Acute Myeloid Leukemia With Minimal Differentiation / Adult Acute Myeloid Leukemia With t(16;16)(p13.1;q22); CBFB-MYH11 / Adult Acute Myeloid Leukemia With T(16;16)(p13;q22) / Adult Acute Myeloid Leukemia With T(8;21)(q22;q22) / Adult Acute Myeloid Leukemia With t(8;21); (q22; q22.1); RUNX1-RUNX1T1 / Adult Acute Myeloid Leukemia With t(9;11)(p22.3;q23.3); MLLT3-KMT2A / Adult Acute Myeloid Leukemia Without Maturation / Adult Acute Myelomonocytic Leukemia / Adult Acute Myelomonocytic Leukemia (M4) / Adult Erythroleukemia / Adult Erythroleukemia (M6a) / Adult Pure Erythroid Leukemia / Adult Pure Erythroid Leukemia (M6b) / Alkylating Agent-Related Acute Myeloid Leukemia / Childhood Acute Erythroid Leukemia / Childhood Acute Erythroleukemia (M6) / Childhood Acute Megakaryoblastic Leukemia / Childhood Acute Megakaryocytic Leukemia (M7) / Childhood Acute Minimally Differentiated Myeloid Leukemia (M0) / Childhood Acute Monoblastic Leukemia / Childhood Acute Monoblastic Leukemia (M5a) / Childhood Acute Monocytic Leukemia / Childhood Acute Monocytic Leukemia (M5b) / Childhood Acute Myeloblastic Leukemia With Maturation (M2) / Childhood Acute Myeloblastic Leukemia Without Maturation (M1) / Childhood Acute Myeloid Leukemia in Remission / Childhood Acute Myeloid Leukemia With Maturation / Childhood Acute Myeloid Leukemia With Minimal Differentiation / Childhood Acute Myeloid Leukemia Without Maturation / Childhood Acute Myelomonocytic Leukemia / Childhood Acute Myelomonocytic Leukemia (M4) / Infections, Fungal / Leukemia Acute Myeloid Leukemia (AML) / Myeloid Neoplasm / Neutropenias / Recurrent Adult Acute Myeloid Leukemia / Recurrent Childhood Acute Myeloid Leukemia / Secondary Acute Myeloid Leukemia (Secondary AML, sAML) / Untreated Adult Acute Myeloid Leukemia / Untreated Childhood Acute Myeloid Leukemia and Other Myeloid Malignancies / Untreated Childhood Myeloid Neoplasm1
3Active Not RecruitingSupportive CareHematopoietic and Lymphoid Cell Neoplasm / Hematopoietic/Lymphoid Cancer / Infections, Fungal1
3CompletedPreventionAppendicitis Acute / Perforated Gastroduodenal Ulcer / Small intestinal obstruction1
3CompletedPreventionBacterial Diseases / Other Mycoses / Sexually Transmitted Infections (STIs)1
3CompletedPreventionCandidiasis infection / Human Immunodeficiency Virus (HIV) Infections / Mycoses1
3CompletedPreventionLeukopenia1
3CompletedPreventionMycoses / Transplantation, Liver1
3CompletedPreventionCandidiasis infection1
3CompletedSupportive CareMalignancies1
3CompletedTreatmentAspergillosis / Candidiasis infection / Fungaemia / Mycoses1
3CompletedTreatmentBacterial Vaginosis (BV) / Candidiasis infection / Vaginal Inflammation1
3CompletedTreatmentCandidemia1
3CompletedTreatmentCandidemia / Candidiasis, Invasive1
3CompletedTreatmentCandidiasis, Invasive1
3CompletedTreatmentCoccidioidomycosis1
3CompletedTreatmentDiabetes Mellitus (DM) / Vulvovaginal Candidiasis1
3CompletedTreatmentEsophageal Candidiasis / Human Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV)1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare / Mycoses1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Meningitis, Cryptococcal1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Mycoses1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Oral Candidiasis1
3CompletedTreatmentInfection NOS / Leukemias / Malignant Lymphomas1
3CompletedTreatmentOral Candidiasis1
3CompletedTreatmentTinea Capitis1
3CompletedTreatmentVaginal Discharge1
3CompletedTreatmentVulvovaginal Candidiasis1
3CompletedTreatmentCandidiasis infection2
3Not Yet RecruitingTreatmentAntifungal Drugs in Onychomycosis1
3RecruitingPreventionRecurrent Vulvovaginal Candidiasis1
3RecruitingTreatmentCandidemia / Infections, Fungal / Invasive Candidiases / Mycoses1
3RecruitingTreatmentRecurrent Vulvovaginal Candidiasis1
3TerminatedNot AvailableCandidemia1
3TerminatedTreatmentAIDS-Related Opportunistic Infections / Cryptococcal infections / Cryptococcus Neoformans1
3TerminatedTreatmentLeishmaniasis, Cutaneous1
3Unknown StatusPreventionLiver Transplanted Patients1
4CompletedPreventionCentral Nervous System Fungal Infections / Fungaemia / Lung Diseases, Fungal / Mycoses1
4CompletedPreventionCryptococcus Neoformans / Meningitis, Cryptococcal1
4CompletedPreventionCandidiasis infection1
4CompletedSupportive CareBacterial Infections and Mycoses / Ductus Arteriosis, Patent1
4CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Candidiasis infection / Oral Candidiasis1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Oral Candidiasis1
4CompletedTreatmentOropharyngeal Candidiasis1
4CompletedTreatmentVulvovaginal Candidiasis2
4CompletedTreatmentCandidiasis infection1
4TerminatedTreatmentCoccidioidomycosis1
4TerminatedTreatmentMinor burns1
4Unknown StatusDiagnosticPulmonary Candidiasis1
4WithdrawnTreatmentCandidiasis infection / Sepsis1
Not AvailableActive Not RecruitingNot AvailableCentral Nervous System Fungal Infections / Central Nervous System Infections / Meningitis, Cryptococcal / Meningitis, Fungal1
Not AvailableActive Not RecruitingScreeningMeningitis, Cryptococcal1
Not AvailableCompletedNot AvailableDeep Mycosis1
Not AvailableCompletedNot AvailableDelirium / Prolongation of QT interval1
Not AvailableCompletedNot AvailableFungal Infection by Site1
Not AvailableCompletedNot AvailableHealthy Volunteers3
Not AvailableCompletedNot AvailableSystemic Fungal Infections1
Not AvailableCompletedNot AvailableCandidiasis infection1
Not AvailableCompletedBasic ScienceDrug Drug Interaction (DDI) / Healthy Volunteers / Warfarin1
Not AvailableCompletedBasic ScienceHeart Diseases / Vascular Diseases1
Not AvailableCompletedPreventionBlood Diseases / Graft Versus Host Disease (GVHD) / Hematopoietic Stem Cell Transplantation (HSCT) / Leukemias / Multiple Myeloma (MM) / Myelodysplastic Syndromes / Transplantation, Bone Marrow1
Not AvailableCompletedTreatmentCoccidioidomycosis / Human Immunodeficiency Virus (HIV) Infections / Mycoses1
Not AvailableCompletedTreatmentEsophageal Candidiasis / Human Immunodeficiency Virus (HIV) Infections2
Not AvailableCompletedTreatmentCandidiasis infection / Esophageal Candidiasis / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentHistoplasmosis / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Meningitis1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Meningitis, Cryptococcal13
Not AvailableCompletedTreatmentCandidiasis infection / Human Immunodeficiency Virus (HIV) Infections / Mycoses1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Oral Candidiasis2
Not AvailableNot Yet RecruitingTreatmentCoronary Artery Disease / Extracorporeal Circulation; Complications / Postoperative Shock / Systemic Inflammatory Response Syndrome (SIRS)1
Not AvailableRecruitingNot AvailableMyelodysplastic Syndrome1
Not AvailableRecruitingBasic ScienceCold / Hyperemia / Raynaud's Disease1
Not AvailableRecruitingPreventionAspergillosis / Candidiasis infection / Genetic Predisposition / Infections, Fungal / Leukemia Acute Myeloid Leukemia (AML)1
Not AvailableUnknown StatusTreatmentAutism Spectrum Conditions/Disorders1

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
FormRouteStrength
Capsule; creamOral; Topical; Vaginal
Capsule; creamOral; Topical
Powder, for solutionOral50 mg
SolutionIntravenous2 mg
CapsuleOral
CapsuleOral150 mg
InjectionIntravenous2 mg/1mL
Injection, solutionIntravenous2 mg/1mL
Injection, solutionIntravenous200 mg/100mL
Injection, solutionIntravenous400 mg/200mL
PowderNot applicable1 g/1g
Powder, for suspensionOral10 mg/1mL
Powder, for suspensionOral1400 mg/35mL
Powder, for suspensionOral350 mg/35mL
Powder, for suspensionOral40 mg/1mL
SolutionIntravenous2 mg/1mL
SolutionOral10 mg/1mL
SolutionOral40 mg/1mL
TabletOral100 mg/1
TabletOral100 mg
TabletOral150 mg/1
TabletOral200 mg/1
TabletOral50 mg
TabletOral50 mg/1
SolutionTopical
SolutionIntravenous
Capsule; cream; kitOral; Topical
TabletOral
Prices
Unit descriptionCostUnit
Diflucan 40 mg/ml Suspension 35ml Bottle203.65USD bottle
Fluconazole 40 mg/ml Suspension 35ml Bottle135.99USD bottle
Diflucan 10 mg/ml Suspension 35ml Bottle56.06USD bottle
Fluconazole 10 mg/ml Suspension 35ml Bottle35.94USD bottle
Diflucan 150 mg tablet24.71USD tablet
Diflucan 200 mg tablet20.82USD tablet
Diflucan 150 mg Capsule16.44USD capsule
Fluconazole 200 mg tablet14.26USD tablet
Fluconazole powder14.08USD g
Fluconazole 150 mg tablet13.93USD tablet
Diflucan 100 mg tablet12.61USD tablet
Apo-Fluconazole-150 150 mg Capsule9.18USD capsule
Co Fluconazole 150 mg Capsule9.18USD capsule
Mylan-Fluconazole 150 mg Capsule9.18USD capsule
Pms-Fluconazole 150 mg Capsule9.18USD capsule
Fluconazole 100 mg tablet8.95USD tablet
Diflucan 50 mg tablet8.05USD tablet
Apo-Fluconazole 100 mg Tablet5.81USD tablet
Mylan-Fluconazole 100 mg Tablet5.81USD tablet
Fluconazole 50 mg tablet5.7USD tablet
Co Fluconazole 100 mg Tablet5.42USD tablet
Novo-Fluconazole 100 mg Tablet5.42USD tablet
Pms-Fluconazole 100 mg Tablet5.42USD tablet
Apo-Fluconazole 50 mg Tablet3.28USD tablet
Mylan-Fluconazole 50 mg Tablet3.28USD tablet
Co Fluconazole 50 mg Tablet3.06USD tablet
Novo-Fluconazole 50 mg Tablet3.06USD tablet
Pms-Fluconazole 50 mg Tablet3.06USD tablet
Diflucan-dextr 200 mg/100 ml1.28USD ml
Diflucan-saline 200 mg/100 ml1.28USD ml
Diflucan 2 mg/ml0.6USD ml
Fluconazole 2 mg/ml0.33USD ml
Fluconazole Omega 2 mg/ml0.33USD ml
Fluconazole-dext 200 mg/100 ml0.32USD ml
Fluconazole-ns 200 mg/100 ml0.19USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)138-140 °Chttp://www.chemspider.com/Chemical-Structure.3248.html
boiling point (°C)579.8https://www.lookchem.com/Fluconazole/
water solubilityslightly soluble in waterFDA label
logP0.5https://www.pfizer.ca/sites/g/files/g10050796/f/201806/Diflucan_PM_E_207077_12June2018.pdf
pKa1.76https://www.pfizer.ca/sites/g/files/g10017036/f/201410/DIFLUCAN(2).pdf
Predicted Properties
PropertyValueSource
Water Solubility1.39 mg/mLALOGPS
logP0.58ALOGPS
logP0.56ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)12.71ChemAxon
pKa (Strongest Basic)2.56ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area81.65 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.2 m3·mol-1ChemAxon
Polarizability26.52 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9894
Blood Brain Barrier+0.9382
Caco-2 permeable+0.8867
P-glycoprotein substrateNon-substrate0.6008
P-glycoprotein inhibitor INon-inhibitor0.8782
P-glycoprotein inhibitor IINon-inhibitor0.9004
Renal organic cation transporterNon-inhibitor0.6461
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.565
CYP450 1A2 substrateNon-inhibitor0.6312
CYP450 2C9 inhibitorNon-inhibitor0.5497
CYP450 2D6 inhibitorNon-inhibitor0.809
CYP450 2C19 inhibitorInhibitor0.532
CYP450 3A4 inhibitorNon-inhibitor0.8196
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.524
Ames testNon AMES toxic0.548
CarcinogenicityNon-carcinogens0.7298
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4136 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8229
hERG inhibition (predictor II)Non-inhibitor0.6614
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0900000000-339ec0708a6a6299e4d1
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0900000000-ea278fc262275613a1fe
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0900000000-bbdadb624a7360b26fa3
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-00kf-6900000000-0316b801589bae74a3f9
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-9100000000-d7b76913f55978a00d10
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-9000000000-45cd8f87d45358745d5b
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-9000000000-2f3230e2968762340fb0
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0900000000-ea0bdd0dd4905f7ca2a7
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0900000000-643df112c60eecdd6f26
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-00kf-6900000000-636d53fe2393f25b4cc4
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-9100000000-2d05579f16a7ce194afb
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-9000000000-bb834fc848ba7398b278
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-9000000000-e3f46745a82b72dc28b0
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0900000000-565636d9f9e684b11429
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0006-0900000000-224c620bb2943c3558aa
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0090000000-d00a2d66aa1d04145279
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0019000000-9ddd55ba2decdc6d3007
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0079-0091000000-5501d6ab39e3fb2e3676
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00y0-1690000000-fb006053901bf08be9c9
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00y0-1920000000-a0f9f745307937304b45
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00g0-1900000000-f3d3042120b194b579d4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00bi-1900000000-8d82f395b99e530cb46e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0019000000-cf2933c2544adb816b0b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0079-0091000000-066891bc3d77fcb69c5d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00y0-1590000000-5d278aae398bb4d6c6b6
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00y0-1920000000-3dcfbc3d71451cc9331c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00g0-1900000000-c4af46372e623cdeb3dd
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0fi9-1900000000-c15061f8dd5425cdede4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0090000000-af8c5257ccffbdd94e82
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4r-0696000000-6b076061ba56c532c132
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0abi-2795000000-c36fbab24191f149ce46
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0g70-2920000000-a8a6188f5a32495c6efa
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-05g0-1795000000-7cf5f5c74fd37b2b188f
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00dr-0390000000-5ae132600e3f7f3b30a1

Taxonomy

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
Fluorobenzene / Aryl fluoride / Aryl halide / Azole / Tertiary alcohol / 1,2,4-triazole / Heteroaromatic compound / Organoheterocyclic compound / Azacycle / Aromatic alcohol
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
tertiary alcohol, triazole antifungal drug, conazole antifungal drug, difluorobenzene (CHEBI:46081)

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
  1. 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. [PubMed:15314102]
  2. 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. [PubMed:16966178]
  3. 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. [PubMed:16966400]
  4. Hollier LM, Cox SM: Fluconazole (Diflucan). Infect Dis Obstet Gynecol. 1995;3(6):222-5. doi: 10.1155/S1064744995000676. [PubMed:18476045]
  5. 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. [PubMed:10515900]
  6. Fluconazole, Medsafe NZ data sheet [Link]
  7. EMA label, Fluconazole [Link]

Enzymes

Details
1. Cytochrome P450 3A4
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
  1. 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. [PubMed:16141567]
  2. 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. [PubMed:8801056]
  3. 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. [PubMed:15969931]
  4. 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]
  5. Flockhart Table of Drug Interactions [Link]
  6. Drug Interactions & Labeling - FDA [Link]
  7. 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
  1. 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. [PubMed:16141567]
  2. 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. [PubMed:8801056]
  3. 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. [PubMed:10952477]
  4. Debruyne D, Coquerel A: Pharmacokinetics of antifungal agents in onychomycoses. Clin Pharmacokinet. 2001;40(6):441-72. [PubMed:11475469]
  5. 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. [PubMed:10709776]
  6. `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]
  7. Flockhart Table of Drug Interactions [Link]
  8. 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
  1. 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. [PubMed:16141567]
  2. 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. [PubMed:10709776]
  3. Fluconazole, Medsafe NZ data sheet [Link]
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
  1. 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. [PubMed:25429674]

Transporters

Details
1. P-glycoprotein 1
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
  1. 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. [PubMed:28355970]
  2. Fluconazole FDA label [Link]

Drug created on June 13, 2005 07:24 / Updated on October 12, 2019 09:54