Ketoconazole
keh-toh-KOH-nuh-zohl
Category
Compound type
Phase / Status
FDA approved for fungal infections
Standard Dose
As directed
Half-life
Plasma elimination
Route(s)
Oral, Injectable or Topical
Research Stage
Regulatory approval granted; post-market monitoring ongoing.
Overview
Oral ketoconazole can inhibit steroid synthesis, which is why it's sometimes used under medical supervision for conditions involving excess cortisol. The catch is safety: oral ketoconazole carries a meaningful risk of hepatotoxicity (liver injury). Using it outside an approved indication - or self-medicating for hormone changes - is not something to take lightly. Topical ketoconazole is generally associated with far less systemic exposure, but it still isn't risk-free.
Plain-language summary
Oral ketoconazole can inhibit steroid synthesis, which is why it's sometimes used under medical supervision for conditions involving excess cortisol. The catch is safety: oral ketoconazole carries a meaningful risk of hepatotoxicity (liver injury). Using it outside an approved indication - or self-medicating for hormone changes - is not something to take lightly. Topical ketoconazole is generally associated with far less systemic exposure, but it still isn't risk-free.
Administration Routes
- Oral
- Injectable
- Topical
Also known as
Mechanisms
CYP17 and CYP11A1 inhibitor - blocks steroid synthesis
Detailed mechanism
Ketoconazole is an imidazole-class antifungal that inhibits fungal CYP51 (lanosterol 14-alpha-demethylase), disrupting ergosterol biosynthesis and compromising membrane integrity in fungi. At systemic concentrations achievable in humans, it also potently inhibits mammalian CYP17A1 (17-alpha-hydroxylase/17,20-lyase) and CYP11A1 (cholesterol side-chain cleavage enzyme), effectively blocking adrenal and gonadal steroid synthesis and lowering cortisol and testosterone. This dual antifungal and steroidogenesis-blocking activity underlies both its medical applications in hypercortisolism and its significant risk profile, particularly drug-induced liver injury via reactive metabolite formation and CYP3A4-mediated drug interactions.
Safety
Side effects
- Severe liver toxicity
- Adrenal insufficiency
- Gynecomastia
Reported benefits
- Lowers cortisol
- Reduces testosterone
- Antifungal
Safety profile
Consult medical professional before use
Clinical trials
See research status
Structure
Verified structure
Ketoconazole
Exact 2D structure can be rendered from a PubChem-backed canonical SMILES string.
- Chemical Formula
- C26H28Cl2N4O4
- Molecular Weight
- 531.4 g/mol
- CAS Number
- 65277-42-1
- InChIKey
- XMAYWYJOQHXEEK-ZEQKJWHPSA-N
Stack Context
No stack data available.
References
- 1View source
Ketoconazole-associated hepatotoxicity: a systematic review and meta-analysis (PubMed)
2013
- 2View source
Ketoconazole - LiverTox: Clinical and Research Information on Drug-Induced Liver Injury (NCBI Bookshelf)
2019
- 3View source
FDA Drug Safety Communication: FDA limits usage of Nizoral (ketoconazole) oral tablets due to potentially fatal liver injury and risk of drug interactions (FDA.gov)
2013
This profile summarizes research literature for education only. It is not medical advice, and it does not diagnose, treat, or recommend a dose. Consult a qualified professional before changing a protocol.