clotrimazole

Also known as Canesten®, Lotrimin®, 1-(alpha-(2-Chlorophenyl)benzhydryl)imidazole, 1-(o-Chloro-alpha,alpha-diphenylbenzyl)imidazole, 1-((2-Chlorophenyl)diphenylmethyl)-1H-imidazole, 1-(o-Chlorotrityl)imidazole, Mycelex (TN), Lotrimin (TN)

Clotrimazole, sold under the brand name Lotrimin, among others, is an antifungal medication. It is used to treat vaginal yeast infections, oral thrush, diaper rash, tinea versicolor, and types of ringworm including athlete's foot and jock itch. It is in the azole class of medications and works by disrupting the fungal cell membrane. It can be taken by mouth or applied as a cream to the skin or in the vagina.

Key facts

Drug.image: Clotrimazole.svg
Drug.image_class: skin-invert-image
Drug.width: 200
Drug.image2: Clotrimazole-xtal-3D-balls.png
Drug.image_class2: bg-transparent
Drug.width2: 200
Drug.tradename: Lotrimin, others
Drug.MedlinePlus: a682753
Drug.DailyMedID: Clotrimazole
Drug.pregnancy_AU: A
Drug.routes_of_administration: Topical, throat lozenge
Drug.ATC_prefix: A01
Drug.ATC_suffix: AB18
Drug.legal_CA: OTC
Drug.legal_US: OTC
Drug.legal_US_comment: (topical), Rx-only (by mouth)
Drug.bioavailability: Poor absorption by mouth (lozenge), negligible absorption through intact skin (topical)
Drug.protein_bound: 90%

via Wikipedia infobox

Chemical data

Formula: C22H17ClN2
Molecular weight: 344.8 g/mol
IUPAC name: 1-[(2-chlorophenyl)-diphenylmethyl]imidazole
SMILES: C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3Cl)N4C=CN=C4
InChIKey: VNFPBHJOKIVQEB-UHFFFAOYSA-N
XLogP: 5
Polar surface area: 17.8 Å²
H-bond donors: 0
H-bond acceptors: 1
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1975
Admin. routes: oral, topical
Indications: infection, HIV infection, vulvovaginal candidiasis, tinea pedis

via ChEMBL · EBI

Wikidata facts

Subclass of: azole
Has part: carbon
Mass: 344.108
Has use: medication

Show 7 more facts

chemical formula: C₂₂H₁₇ClN₂
World Health Organisation international non-proprietary name: clotrimazole
Commons category: Clotrimazole
canonical SMILES: C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3Cl)N4C=CN=C4
defined daily dose: 0.1
subject has role: aromatase inhibitors
MCN code: 2933.29.25

Sources (5)

via Wikidata · CC0

~5 min read

Encyclopedic overview

9 sections

Contents

Medical uses
Pregnancy
Side effects
Interactions
Pharmacology
Pharmacodynamics
Society and culture
Economics
References

Common side effects of clotrimazole taken by mouth include nausea and itchiness. When it is applied to the skin, common side effects include redness and a burning sensation. In pregnancy, topical use, even in the vagina, is believed to be safe, nor is there evidence of harm by oral use, but the latter has been less well studied.

Excerpted from Wikipedia’s “clotrimazole” article, available under the CC BY-SA 4.0 licence.