ketoconazole

Also known as Nizoral A-D, Ketozole, Nizoral, Extina, SID456469, Xolegel, Ketoconazol, NSC 317629

thumb|150px|Stada Ketoconazole, sold under the brand name Nizoral, among others, is an antiandrogen, antifungal, and antiglucocorticoid medication used to treat a number of fungal infections. Applied to the skin it is used for fungal skin infections such as tinea, cutaneous candidiasis, pityriasis versicolor, dandruff, and seborrheic dermatitis. Taken by mouth it is a less preferred option and recommended for only severe infections when other agents cannot be used. Other uses include treatment of excessive male-patterned hair growth in women and Cushing's syndrome.

Key facts

Drug.IUPAC_name: 1-[4-[4-[[2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone | C=26 | H=28 | Cl=2 | N=4 | O=4 | SMILES = O=C(N5CCN(c4ccc(OC[C@@H]1O[C@](OC1)(c2ccc(Cl)cc2Cl)Cn3ccnc3)cc4)CC5)C | StdInChI_Ref = | StdInChI = 1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3/t23-,26-/m0/s1 | StdInChI_comment = | StdInChIKey_Ref = | StdInChIKey = XMAYWYJOQHXEEK-OZXSUGGESA-N | density = | density_notes = | melting_point = | melting_high = | melting_notes = | boiling_point = | boiling_notes = | solubility = | sol_units = | specific_rotation =
Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 457114462
Drug.image: Ketoconazole enantiomers.svg
Drug.image_class: skin-invert-image
Drug.width: 250
Drug.caption: (2R,4S)-(+)-ketoconazole (top)(2S,4R)-(−)-ketoconazole (bottom)
Drug.image2: (2R,4S)-(+)-ketoconazole-from-xtal-3D-bs-17.png
Drug.image_class2: bg-transparent
Drug.caption2: Ball-and-stick model of (2R,4S)-(+)-ketoconazole
Drug.chirality: Racemic mixture
Drug.tradename: Nizoral, others
Drug.MedlinePlus: a682816
Drug.DailyMedID: Ketoconazole
Drug.pregnancy_AU: B3
Drug.routes_of_administration: By mouth (tablets), topical (cream, shampoo, solution)
Drug.ATC_prefix: J02

via Wikipedia infobox

Chemical data

Formula: C26H28Cl2N4O4
Molecular weight: 531.4 g/mol
IUPAC name: 1-[4-[4-[[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)OCC3COC(O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl
InChIKey: XMAYWYJOQHXEEK-UHFFFAOYSA-N
XLogP: 4.3
Polar surface area: 69.1 Å²
H-bond donors: 0
H-bond acceptors: 6
Formal charge: 0

via PubChem

Research

10,393 papers

Ketoconazole.Drug intelligence & clinical pharmacy · 1983
Ketoconazole in the treatment of coccidioidomycosis.Drugs · 1983
Evaluation of ketoconazole.Clinical pharmacy · 1982
Ketoconazole.Connecticut medicine · 1984
Ketoconazole and fluconazole drug interactions.Archives of internal medicine · 1993

via PubMed

Wikidata facts

Mass: 530.148761

Show 6 more facts

chemical formula: C₂₆H₂₈Cl₂N₄O₄
Commons category: Ketoconazole
canonical SMILES: CC(=O)N1CCN(CC1)C2=CC=C(C=C2)OCC3COC(O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl
defined daily dose: 0.4
MCN code: 2934.99.31
World Health Organisation international non-proprietary name: ketoconazole

Sources (7)

via Wikidata · CC0

~18 min read

Article

31 sections

Contents

Medical uses
Topical antifungal
Systemic antifungal
Off-label uses
Hair loss
Hormonal
Contraindications
Side effects
Gastrointestinal
Endocrine
Liver
Hypersensitivity
Topical formulations
Pregnancy
Overdose
Interactions
Pharmacology
Pharmacodynamics
Antifungal activity
Antihormonal activity
Other activities
Pharmacokinetics
Chemistry
History
Society and culture
Generic names
Brand names
Availability
Research
Veterinary use
References

thumb|150px|Stada

Ketoconazole, sold under the brand name Nizoral, among others, is an antiandrogen, antifungal, and antiglucocorticoid medication used to treat a number of fungal infections. Applied to the skin it is used for fungal skin infections such as tinea, cutaneous candidiasis, pityriasis versicolor, dandruff, and seborrheic dermatitis. Taken by mouth it is a less preferred option and recommended for only severe infections when other agents cannot be used. Other uses include treatment of excessive male-patterned hair growth in women and Cushing's syndrome.