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Systematic (IUPAC) name
Clinical data
Routes of
Oral, IV, topical
Legal status
Legal status
  • S3/S4 (Au), POM (UK), ℞-only (U.S.)
Pharmacokinetic data
Bioavailability >90%
Protein binding 11–12%
Metabolism Hepatic 11%
Biological half-life 30 hours (range 20-50 hours)
Excretion Renal 61–88%
CAS Number 86386-73-4
ATC code D01AC15 (WHO) J02AC01
PubChem CID 3365
DrugBank APRD00327
ChemSpider 3248
Chemical data
Formula C13H12F2N6O
Molar mass 306.271 g/mol[[Script error: No such module "String".]]
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Fluconazole (pronounced /fluːˈkɒnəzoʊl/) is a triazole antifungal drug used in the treatment and prevention of superficial and systemic fungal infections. In a bulk powder form, it appears as a white crystalline powder, and it is very slightly soluble in water and soluble in alcohol.[1] It is commonly marketed under the trade name Diflucan or Trican (Pfizer). In Mexico it is sold over the counter as Alfumet. It is marketed under the brand name "candivast" in the Persian Gulf area.


Mode of action

Like other imidazole- and triazole-class antifungals, fluconazole inhibits the fungal cytochrome P450 enzyme 14α-demethylase. Mammalian demethylase activity is much less sensitive to fluconazole than fungal demethylase. This inhibition prevents the conversion of lanosterol to ergosterol, an essential component of the fungal cytoplasmic membrane, and subsequent accumulation of 14α-methyl sterols.[2] Fluconazole is primarily fungistatic, however may be fungicidal against certain organisms in a dose-dependent manner.[citation needed] It is interesting to note that, when fluconazole was in development at Pfizer, it was decided early in the process to avoid producing any chiral centers in the drug so that subsequent synthesis and purification would not encounter difficulties with enantiomer separation and associated variations in biological effect.[citation needed] A number of related compounds were found to be extremely potent teratogens, and were subsequently discarded.[citation needed]


Fluconazole is active against the following microorganisms:[3]


Following oral dosing, fluconazole is almost completely absorbed within two hours.[citation needed] Bioavailability is not significantly affected by the absence of stomach acid. Concentrations measured in the urine, tears, and skin are approximately 10 times the plasma concentration, whereas saliva, sputum, and vaginal fluid concentrations are approximately equal to the plasma concentration, following a standard dose range of between 100 mg and 400 mg per day.[citation needed] The elimination half-life of fluconazole follows zero order kinetics, and only 10% of elimination is due to metabolism, the remainder is excreted in urine and sweat. Patients with impaired renal function will be at risk of overdose as well as patients taking drugs such as warfarin.[citation needed]

Clinical use


Fluconazole is a prescription drug indicated for the treatment and prophylaxis of fungal infections where other antifungals have failed or are not tolerated (e.g., due to adverse effects), including:[4]

Fluconazole can be used first-line for the following indications:[4]


Dosage varies with indication and between patient groups, ranging from: a two-week course of 150 mg/day for vulvovaginal candidiasis, to 150–300 mg once weekly for resistant skin infections or some prophylactic indications. A dosage of 500–600 mg/day may be used for systemic or severe infections, and, in urgent infections such as meningitis caused by yeast, 800 mg/day have been used. Pediatric doses are measured at 6–12 mg/kg/d. A loading dose will be indicated when entering a daily dosage schedule; for example, a loading dose of 200 mg on the first day is commonly used with 150 mg/day following that.[4]


Fluconazole is contraindicated in patients that:[4]

  • Have known hypersensitivity to other azole medicine
  • Are taking Terfenadine, if 400 mg per day multidose of Fluconazole is administered
  • Are in concomitant use of cisapride, due to risk of serious cardiac arrhythmias (relative contraindication)
  • Are pregnant.


Fluconazole is secreted in human milk at concentrations similar to plasma. Therefore, the use of fluconazole in nursing mothers is not recommended.[5]

Fluconazole therapy has been associated with QT interval prolongation, which may lead to serious cardiac arrhythmias. Thus, it is used with caution in patients with risk factors for prolonged QT interval such as electrolyte imbalance or use of other drugs that may prolong the QT interval (particularly cisapride).[citation needed]

Fluconazole has also rarely been associated with severe or lethal hepatotoxicity and liver function tests are usually performed regularly during prolonged fluconazole therapy. In addition, it is used with caution in patients with pre-existing liver disease.[2]

High concentrations of fluconazole have been detected in human breast milk from patients receiving fluconazole therapy, thus its use is not recommended in breastfeeding mothers.[2]

Some people are allergic to azole(s). People allergic to other azole drugs might be allergic to fluconazole.[6] That is, some azole drugs have adverse side-effects. Some azole drugs may disrupt estrogen production in pregnancy, affecting pregnancy outcome.[7]

Fluconazole/Diflucan is in the FDA pregnancy category C.
This means that it is not known whether it will be harmful to an unborn baby. Do not take Fluconazole/Diflucan without first talking to your doctor if you are pregnant or could become pregnant during treatment.
Do not take Fluconazole/Diflucan if you are taking cisapride (Propulsid).
Combined with cisapride (Propulsid), Diflucan could cause serious, even fatal, heart problems.
In rare cases, Fluconazole/Diflucan has caused severe liver damage, sometimes resulting in death.
Notify your doctor immediately if you develop nausea, vomiting, abdominal pain, unusual fatigue, loss of appetite, yellow skin or eyes, itching, dark urine, or clay-colored stools.
These symptoms may be early signs of liver damage.[citation needed]
Severe allergic reaction like anaphylaxis has been reported (as listed in the data sheet of pfizer Diflucan). In rare cases, Fluconazole/Diflucan has also caused anaphylaxis, sometimes resulting in death. Notify your doctor immediately if you develop a rash while taking Fluconazole/Diflucan.[8][unreliable source?]

Adverse effects

Adverse drug reactions associated with fluconazole therapy include:[4]

Drug interactions

Fluconazole is an inhibitor of the human cytochrome P450 system, particularly the isozymes CYP2C9 and CYP3A4. In theory, therefore, fluconazole decreases the metabolism and increases the concentration of any drug metabolised by these enzymes. In addition, its potential effect on QT interval increases the risk of cardiac arrhythmia if used concurrently with other drugs that prolong the QT interval. Berberine has been shown to exert synergistic effects with fluconazole even in drug-resistant Candida albicans infections.[9]


800px Richardson, R. K.; 1983, U.S. Patent 4,404,216.

See also


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es:Fluconazol fr:Fluconazole it:Fluconazolo hu:Flukonazol nl:Fluconazol ja:フルコナゾール pl:Flukonazol pt:Fluconazol ru:Флуконазол fi:Flukonatsoli

  1. MP Biomedicals
  2. 2.0 2.1 2.2 Pfizer Australia Pty Ltd. Diflucan (Australian Approved Product Information). West Ryde (NSW): Pfizer Australia; 2004.
  3. Sweetman S, editor. Martindale: The complete drug reference. 34th ed. London: Pharmaceutical Press; 2004. ISBN 0-85369-550-4
  4. 4.0 4.1 4.2 4.3 4.4 Rossi S, editor. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006. ISBN 0-9757919-2-3
  5. Product information from Pfizer Inc
  6. http://aac.asm.org/cgi/reprint/AAC.01500-08v1.pdf
  7. Kragie, Laura; Turner, Stephanie D.; Patten, Christopher J.; Crespi, Charles L.; Stresser, David M. (2002). "Assessing Pregnancy Risks of Azole Antifungals Using a High Throughput Aromatase Inhibition Assay". Endocrine Research. 28 (3): 129. doi:10.1081/ERC-120015045. PMID 12489563. 
  8. http://www.med-store.info/fluconazole.html
  9. Xu Y, Wang Y, Yan L, et al. (September 14, 2009) Proteomic Analysis Reveals a Synergistic Mechanism of Fluconazole and Berberine against Fluconazole-Resistant Candida albicans: Endogenous ROS Augmentation. Journal of Proteome Research. Publication Date (Web)Free Full Text