pharmacopeia
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/api/v1/drug/ketoconazole
2D structure
1-[4-[4-[[(2S,4R)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone
SMILES CC(=O)N1CCN(CC1)C2=CC=C(C=C2)OC[C@@H]3CO[C@@](O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl
InChIKey XMAYWYJOQHXEEK-ZEQKJWHPSA-N

Mechanism of action

Sourced from openFDA

Mechanism-of-action classes: 14-alpha Demethylase Inhibitors; Cytochrome P450 3A4 Inhibitors; Cytochrome P450 3A5 Inhibitors; Ergosterol Synthesis Inhibitors; P-Glycoprotein Inhibitors.

14-alpha DemethylaseCytochrome P450 3A4Cytochrome P450 3A5Ergosterol SynthesisP-Glycoprotein

Indications

Sourced from openFDA
  • & USAGE Ketoconazole shampoo, 2% is indicated for the treatment of tinea (pityriasis) versicolor caused by or presumed to be caused by Pityrosporum orbiculare (also known as Malassezia furfur or M. orbiculare ) .

Contraindications

Sourced from openFDA
  • Ketoconazole shampoo, 2% is contraindicated in persons who have known hypersensitivity to the active ingredient or excipients of this formulation.contraindicated

Dosage & administration

Sourced from openFDA

DOSAGE & ADMINISTRATION Apply the shampoo to the damp skin of the affected area and a wide margin surrounding this area. Lather, leave in place for 5 minutes, and then rinse off with water. One application of the shampoo should be sufficient.

Adverse reactions

Sourced from openFDA

Clinical Trials Experience In 11 double-blind trials in 264 patients using ketoconazole shampoo, 2% for the treatment of dandruff or seborrheic dermatitis, an increase in normal hair loss and irritation occurred in less than 1% of patients. In three open label safety trials in which 41 patients shampooed 4-10 times weekly for six months, the following adverse experiences each occurred once: abnormal hair texture, scalp pustules, mild dryness of the skin, and itching. As with other shampoos, oiliness and dryness of hair and scalp have been reported. In a double-blind, placebo-controlled trial in which patients with tinea versicolor were treated with either a single application of ketoconazole shampoo, 2% (n=106), a daily application for three consecutive days (n=107), or placebo (n=105), drug-related adverse events occurred in 5 (5%), 7 (7%) and 4 (4%) of patients, respectively. The only events that occurred in more than one patient in any one of the three treatment groups were pruritus, application site reaction, and dry skin; none of these events occurred in more than 3% of the patients in any one of the three groups. Post-marketing Experience Because these reactions are reported voluntarily from a population of uncertain size, it is not possible to reliably estimate their frequency.

Use in specific populations

Sourced from openFDA

PREGNANCY Teratogenic effects: Pregnancy Category C: There are no adequate and well-controlled studies in pregnant women. Ketoconazole should be used during pregnancy only if the potential benefit justifies the potential risk to the fetus. In humans, ketoconazole is not detected in plasma after chronic shampooing on the scalp. Ketoconazole has been shown to be teratogenic (syndactylia and oligodactylia) in the rat when given orally in the diet at 80 mg/kg/day (a dose 10 times the maximum recommended human oral dose). However, these effects may be related to maternal toxicity, which was seen at this and higher dose levels.

Overdosage

Sourced from openFDA

Ketoconazole shampoo, 2% is intended for external use only. In the event of accidental ingestion, supportive and symptomatic measures should be employed. Induced emesis and gastric lavage should not be performed to avoid aspiration.

Approval history

Sourced from openFDA
  • Oct 10, 1997NDANDA020310Kramer
  • Jun 15, 1999ANDAANDA075319Taro
  • Apr 25, 2000ANDAANDA075581Teva
  • Jan 10, 2002ANDAANDA075912Senores Pharms
  • Dec 18, 2002ANDAANDA075638Sun Pharma Canada
  • Jan 7, 2004ANDAANDA076419Padagis Israel
  • Apr 28, 2004ANDAANDA076294Fougera Pharms
  • Apr 11, 2005ANDAANDA076942Cosette

FAERS reports

View JSON
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.
16,862 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 Ineffective1,72910%
  2. 2Off Label Use1,2137.2%
  3. 3Fatigue9495.6%
  4. 4Pruritus9425.6%
  5. 5Nausea8615.1%
  6. 6Rash8304.9%
  7. 7Diarrhoea7884.7%
  8. 8Pain7414.4%
  9. 9Headache7284.3%
  10. 10Psoriasis6493.8%
  11. 11Dyspnoea6223.7%
  12. 12Dizziness6043.6%
  13. 13Product Use In Unapproved Indication5663.4%
  14. 14Arthralgia5523.3%
  15. 15Chronic Kidney Disease5213.1%

Literature

View JSON

Recent PubMed references pinned to Ketoconazole 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 213 ClinicalTrials.gov registrations naming Ketoconazole as an intervention. Registration is not evidence of efficacy or safety — reference crosswalk only.

Structural analogs

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Ranked by 2D fingerprint (Tanimoto) similarity over PubChem structures. Structural proximity only — not a claim of therapeutic equivalence.

Frequently asked questions

How does Ketoconazole work?
Mechanism-of-action classes: 14-alpha Demethylase Inhibitors; Cytochrome P450 3A4 Inhibitors; Cytochrome P450 3A5 Inhibitors; Ergosterol Synthesis Inhibitors; P-Glycoprotein Inhibitors.
What is Ketoconazole used for?
According to FDA labeling, Ketoconazole carries indications including: & USAGE Ketoconazole shampoo, 2% is indicated for the treatment of tinea (pityriasis) versicolor caused by or presumed to be caused by Pityrosporum orbiculare (also known as Malassezia furfur or M. orbiculare ) .. This is a reference summary of labeled uses, not medical advice or a treatment recommendation.
What class of drug is Ketoconazole?
Ketoconazole is classified as Anticorticosteroids, Imidazole and triazole derivatives, Imidazole derivatives, Azole Antifungal, 14-alpha Demethylase Inhibitors, Cytochrome P450 3A4 Inhibitors, Cytochrome P450 3A5 Inhibitors, Ergosterol Synthesis Inhibitors, P-Glycoprotein Inhibitors, Decreased Cell Membrane Integrity, Decreased Cell Wall Integrity.
What are the brand names for Ketoconazole?
Ketoconazole is marketed under brand names including Extina, Keto-C, Ketochlor, Ketodan, Kuric, Mal-A-Ket, Mal-A-Ket Wipes, Malacetic.
What are the contraindications for Ketoconazole?
Ketoconazole labeling lists contraindications including: Ketoconazole shampoo, 2% is contraindicated in persons who have known hypersensitivity to the active ingredient or excipients of this formulation.. Always consult the full prescribing information and a clinician.
Note. Data for ketoconazole 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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