pharmacopeia
GET
/api/v1/drug/fluconazole
2D structure
2-(2,4-difluorophenyl)-1,3-bis(1,2,4-triazol-1-yl)propan-2-ol
SMILES C1=CC(=C(C=C1F)F)C(CN2C=NC=N2)(CN3C=NC=N3)O
InChIKey RFHAOTPXVQNOHP-UHFFFAOYSA-N

Mechanism of action

Sourced from openFDA

Mechanism-of-action classes: 14-alpha Demethylase Inhibitors; Cytochrome P450 2C19 Inhibitors; Cytochrome P450 2C9 Inhibitors; Cytochrome P450 3A4 Inhibitors.

14-alpha DemethylaseCytochrome P450 2C19Cytochrome P450 2C9Cytochrome P450 3A4

Indications

Sourced from openFDA
  • Fluconazole tablets are indicated for the treatment of: Vaginal candidiasis (vaginal yeast infections due to Candida ). Oropharyngeal and esophageal candidiasis.ICD-10: B37.9

Contraindications

Sourced from openFDA
  • Fluconazole tablets are contraindicated in patients who have shown hypersensitivity to fluconazole or to any of its excipients. There is no information regarding cross-hypersensitivity between fluconazole and other azole antifungal agents.contraindicated

Dosage & administration

Sourced from openFDA

Dosage and Administration in Adults: Single Dose Vaginal candidiasis: The recommended dosage of fluconazole for vaginal candidiasis is 150 mg as a single oral dose. Multiple Dose SINCE ORAL ABSORPTION IS RAPID AND ALMOST COMPLETE, THE DAILY DOSE OF FLUCONAZOLE IS THE SAME FOR ORAL AND INTRAVENOUS ADMINISTRATION. In general, a loading dose of twice the daily dose is recommended on the first day of therapy to result in plasma concentrations close to steady-state by the second day of therapy. The daily dose of fluconazole for the treatment of infections other than vaginal candidiasis should be based on the infecting organism and the patient’s response to therapy. Treatment should be continued until clinical parameters or laboratory tests indicate that active fungal infection has subsided. An inadequate period of treatment may lead to recurrence of active infection. Patients with AIDS and cryptococcal meningitis or recurrent oropharyngeal candidiasis usually require maintenance therapy to prevent relapse. Oropharyngeal candidiasis: The recommended dosage of fluconazole for oropharyngeal candidiasis is 200 mg on the first day, followed by 100 mg once daily. Clinical evidence of oropharyngeal candidiasis generally resolves within several days, but treatment should be continued for at least 2 weeks to decrease the likelihood of relapse. Esophageal candidiasis: The recommended dosage of fluconazole for esophageal candidiasis is 200 mg on the first day, followed by 100 mg once daily. Doses up to 400 mg/day may be used, based on medical judgment of the patient’s response to therapy.

Warnings & precautions

Sourced from openFDA

(1) Hepatic injury: Fluconazole should be administered with caution to patients with liver dysfunction. Fluconazole has been associated with rare cases of serious hepatic toxicity, including fatalities primarily in patients with serious underlying medical conditions. In cases of fluconazole-associated hepatotoxicity, no obvious relationship to total daily dose, duration of therapy, sex, or age of the patient has been observed. Fluconazole hepatotoxicity has usually, but not always, been reversible on discontinuation of therapy. Patients who develop abnormal liver function tests during fluconazole therapy should be monitored for the development of more severe hepatic injury. Fluconazole should be discontinued if clinical signs and symptoms consistent with liver disease develop that may be attributable to fluconazole. (2) Anaphylaxis: In rare cases, anaphylaxis has been reported. (3) Dermatologic: Exfoliative skin disorders during treatment with fluconazole have been reported. Fatal outcomes have been reported in patients with serious underlying diseases. Patients with deep seated fungal infections who develop rashes during treatment with fluconazole should be monitored closely and the drug discontinued if lesions progress. Fluconazole should be discontinued in patients treated for superficial fungal infection who develop a rash that may be attributed to fluconazole. (4) Potential for fetal harm: There are no adequate and well-controlled clinical trials of fluconazole in pregnant women.

Adverse reactions

Sourced from openFDA

Fluconazole is generally well tolerated. In some patients, particularly those with serious underlying diseases such as AIDS and cancer, changes in renal and hematological function test results and hepatic abnormalities have been observed during treatment with fluconazole and comparative agents, but the clinical significance and relationship to treatment is uncertain. In Patients Receiving a Single Dose for Vaginal Candidiasis: During comparative clinical studies conducted in the United States, 448 patients with vaginal candidiasis were treated with fluconazole, 150 mg single dose. The overall incidence of side effects possibly related to fluconazole was 26%. In 422 patients receiving active comparative agents, the incidence was 16%. The most common treatment-related adverse events reported in the patients who received 150 mg single dose fluconazole for vaginitis were headache (13%), nausea (7%), and abdominal pain (6%). Other side effects reported with an incidence equal to or greater than 1% included diarrhea (3%), dyspepsia (1%), dizziness (1%), and taste perversion (1%). Most of the reported side effects were mild to moderate in severity. Rarely, angioedema and anaphylactic reaction have been reported in marketing experience. In Patients Receiving Multiple Doses for Other Infections: Sixteen percent of over 4000 patients treated with fluconazole in clinical trials of 7 days or more experienced adverse events. Treatment was discontinued in 1.5% of patients due to adverse clinical events and in 1.3% of patients due to laboratory test abnormalities.

Use in specific populations

Sourced from openFDA

Pregnancy Teratogenic Effects Potential for Fetal Harm: Use in pregnancy should be avoided except in patients with severe or potentially life-threatening fungal infections in whom fluconazole may be used if the anticipated benefit outweighs the possible risk to the fetus. A few published case reports describe a pattern of distinct congenital anomalies in infants exposed in utero to high dose maternal fluconazole (400 to 800 mg/day) during most or all of the first trimester. These reported anomalies are similar to those seen in animal studies. Effective contraceptive measures should be considered in women of child-bearing potential who are being treated with fluconazole 400 to 800 mg/day and should continue throughout the treatment period and for approximately 1 week (5 to 6 half-lives) after the final dose. If fluconazole is used during pregnancy, or if the patient becomes pregnant while taking the drug, the patient should be informed of the potential hazard to the fetus. Spontaneous abortions and congenital abnormalities have been suggested as potential risks associated with 150 mg of fluconazole as a single or repeated dose in the first trimester of pregnancy based on retrospective epidemiological studies. There are no adequate and well-controlled studies of fluconazole in pregnant women. (See WARNINGS: Potential for Fetal Harm .

Overdosage

Sourced from openFDA

There have been reports of overdose with fluconazole accompanied by hallucination and paranoid behavior. In the event of overdose, symptomatic treatment (with supportive measures and gastric lavage if clinically indicated) should be instituted. Fluconazole is largely excreted in urine. A 3-hour hemodialysis session decreases plasma levels by approximately 50%. In mice and rats receiving very high doses of fluconazole, clinical effects in both species included decreased motility and respiration, ptosis, lacrimation, salivation, urinary incontinence, loss of righting reflex, and cyanosis; death was sometimes preceded by clonic convulsions.

Approval history

Sourced from openFDA
  • Dec 23, 1993NDANDA020090Pfizer
  • Jul 29, 2004ANDAANDA076766Baxter Hlthcare
  • Jul 29, 2004ANDAANDA076658Dr Reddys Labs Inc
  • Jul 29, 2004ANDAANDA076665Chartwell
  • Aug 23, 2005ANDAANDA076736Hikma Farmaceutica
  • Jan 25, 2006ANDAANDA077253Glenmark Pharms Ltd
  • Oct 7, 2008ANDAANDA077731Aurobindo Pharma
  • Jul 30, 2009ANDAANDA079104Inforlife

FAERS reports

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Reference statistics only. FAERS reports are voluntarily submitted and are not incidence rates, safety signals, or causal evidence. Counts reflect reporting volume — how often a reaction was reported, not how often it occurs. For decision-grade use, consult openFDA and the FAERS Public Dashboard directly.
68,733 total reports matchedLatest report Share = reports listing the reaction ÷ total matched reports. Rows can sum to >100% because a single report often lists multiple reactions.
  1. 1Drug Ineffective5,0727.4%
  2. 2Off Label Use4,4426.5%
  3. 3Pyrexia4,1766.1%
  4. 4Nausea3,7635.5%
  5. 5Diarrhoea3,5755.2%
  6. 6Fatigue3,2134.7%
  7. 7Pain3,1484.6%
  8. 8Drug Interaction2,9864.3%
  9. 9Pneumonia2,8744.2%
  10. 10Headache2,8594.2%
  11. 11Febrile Neutropenia2,6893.9%
  12. 12Rash2,4383.5%
  13. 13Dyspnoea2,4343.5%
  14. 14Vomiting2,3713.4%
  15. 15Death2,1713.2%

Literature

View JSON

Recent PubMed references pinned to Fluconazole as a MeSH major topic. Citations link to pubmed.ncbi.nlm.nih.gov.

Clinical trials

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The 10 most recently updated of 303 ClinicalTrials.gov registrations naming Fluconazole as an intervention. Registration is not evidence of efficacy or safety — reference crosswalk only.

Frequently asked questions

How does Fluconazole work?
Mechanism-of-action classes: 14-alpha Demethylase Inhibitors; Cytochrome P450 2C19 Inhibitors; Cytochrome P450 2C9 Inhibitors; Cytochrome P450 3A4 Inhibitors.
What is Fluconazole used for?
According to FDA labeling, Fluconazole carries indications including: Fluconazole tablets are indicated for the treatment of: Vaginal candidiasis (vaginal yeast infections due to Candida ). Oropharyngeal and esophageal candidiasis.. This is a reference summary of labeled uses, not medical advice or a treatment recommendation.
What class of drug is Fluconazole?
Fluconazole is classified as Imidazole and triazole derivatives, Triazole and tetrazole derivatives, Azole Antifungal, 14-alpha Demethylase Inhibitors, Cytochrome P450 2C19 Inhibitors, Cytochrome P450 2C9 Inhibitors, Cytochrome P450 3A4 Inhibitors, Cardiac Rate Alteration, Decreased Cell Wall Integrity.
What are the brand names for Fluconazole?
Fluconazole is marketed under brand names including Diflucan.
What are the contraindications for Fluconazole?
Fluconazole labeling lists contraindications including: Fluconazole tablets are contraindicated in patients who have shown hypersensitivity to fluconazole or to any of its excipients. There is no information regarding cross-hypersensitivity between fluconazole and other azole antifungal agents.. Always consult the full prescribing information and a clinician.
Note. Data for fluconazole is illustrative MVP content compiled from public sources. pharmacopeia is for educational and informational use only and is not a substitute for professional medical advice.

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