Clotrimazole

Clotrimazole

Systematic (IUPAC) name
1-[(2-chlorophenyl)(diphenyl)methyl]-1H-imidazole
Clinical data
Trade names	Lotriminaf, Mycelex
AHFS/Drugs.com	monograph
MedlinePlus	a682753
Pregnancy cat.	A(AU) C (oral) & B (topical) (US)
Legal status	P (UK)
Routes	topical
Pharmacokinetic data
Bioavailability	Poorly and erratically absorbed orally
Protein binding	90%
Metabolism	hepatic
Half-life	2 hours
Identifiers
CAS number	23593-75-1 Y
ATC code	A01AB18 D01AC01 G01AF02 QJ02AB90
PubChem	CID 2812
DrugBank	APRD00244
ChemSpider	2710 Y
UNII	G07GZ97H65 Y
KEGG	D00282 Y
ChEBI	CHEBI:3764 Y
ChEMBL	CHEMBL104 Y
Chemical data
Formula	C22H17ClN2
Mol. mass	344.837 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C22H17ClN2/c23-21-14-8-7-13-20(21)22(25-16-15-24-17-25,18-9-3-1-4-10-18)19-11-5-2-6-12-19/h1-17H Y Key:VNFPBHJOKIVQEB-UHFFFAOYSA-N Y
Y(what is this?)  (verify)

Clotrimazole (brand name Canesten or Lotrimin) is an antifungal medication commonly used in the treatment of fungal infections (of both humans and other animals) such as vaginal yeast infections, oral thrush, and ringworm. It is also used to treat athlete's foot and jock itch.

Medical uses

It is commonly available as an over-the-counter substance in various dosage forms, such as a cream, and also (especially in the case of ear infection) as a combination medicine. It is also available as a troche (prescription only). For ear infection, it is often applied in liquid form, as ear drops. Fungal infections can be slow to clear up, so the usual course for an anti-fungal agent is, in general, longer than the typical 3–7 days of an antibiotic. Clotrimazole is also commonly found in conjunction with Betamethasone, known as Lotriderm, to add steroid properties.^[1]

Method of action

Clotrimazole alters the permeability of the fungal cell wall and inhibits the activity of enzymes within the cell. This leads eventually to the cell's death. It does not appreciably spread through the user's body but remains at the point of application. ^[2]

Drug interactions

Potential for drug interactions with clotrimazole oral exists, as it is a potent, specific inhibitor of cytochrome P450 oxidase and may alter the metabolism of other drugs.

Side-effects

Side effects include skin rash, hives, blistering, burning, itching, peeling, redness, stinging, swelling, or other sign of skin irritation.^[3]

Production

This compound (3) is produced by alkylating imidazole (1) with o-chlorotrityl chloride (2) in acetone, with triethylamine as the base.^[4]

Environmental impact

Some research suggests that, in combination with other commonly used chemicals, clotrimazole has negative effects on the ocean environment, in particular microalgae.^[5]

References

1. ^ http://www.rxmed.com/b.main/b2.pharmaceutical/b2.1.monographs/CPS-%20Monographs/CPS-%20%28General%20Monographs-%20L%29/LOTRIDERM.html
2. ^ "Clotrimazole". Fungal Guide .ca. Vancouver , B.C. Canada. http://www.fungalguide.ca/treatments/clotrimazole.html. Retrieved 15 February 2011. 
3. ^ Canesten Topical consumer information from Drugs.com
4. ^ OSPAR Commission: Hazardous Substances Series: OSPAR background document on clotrimazole. OSPAR Publication 2005/199, 2005, ISBN 1-904426-38-7 (pdf, engl.)
5. ^ Drug used to treat skin conditions is a marine pollutant

External links

Canesten (clotrimazole) antifungal cream

• Clotrimazole | MedlinePlus

This antiinfective drug article is a stub. You can help Wikipedia by expanding it.v · Categories: Antifungals Imidazoles World Health Organization essential medicines Organochlorides Antiinfective agent stubs Wikimedia Foundation. 2010. Игры ⚽ Нужен реферат? Janice Hadlow Mama Rock Look at other dictionaries: Clotrimazole — КЛОТРИМАЗОЛ ( Clotrimazole ). Дифенил (2 хлорфенил) 1 имидазолилметан. Синонимы: Канестен, Candid, Canesten, Empecid, Imidil, Lotrimin, Mycosporin, Panmicol и др. Клотримазол является одним из представителей группы имидазольных противогрибковых… …   Словарь медицинских препаратов clotrimazole — noun Etymology: probably from International Scientific Vocabulary chlor + tri + imidazole Date: 1970 an antifungal agent C22H17ClN2 …   New Collegiate Dictionary clotrimazole — clo·trim·a·zole (klō trĭmʹə zōl ) n. A broad spectrum antifungal drug used topically to treat a variety of superficial fungal infections, including candidiasis and tinea.   [chloro + tri (from its three phenyl groups) + imidazole.] * * * …   Universalium clotrimazole — noun An antifungal medication used to treat humans and animals …   Wiktionary clotrimazole — An antifungal agent used topically to treat a variety of fungal and yeast infections. * * * clo·tri·ma·zole klō trī mə .zōl, .zȯl n an antifungal agent C22H17ClN2 used to treat candida infections, tinea, and ringworm see LOTRIMIN …   Medical dictionary clotrimazole — clo·tri·ma·zole …   English syllables clotrimazole — n. an antifungal drug used to treat all types of fungal skin infections (including ringworm) and vaginal candidosis (thrush). It is applied to the infected part as a cream or solution or as vaginal pessaries and occasionally causes mild burning… …   The new mediacal dictionary clotrimazole — klōˈtrīməˌzōl, ȯl noun ( s) Etymology: probably from International Scientific Vocabulary chlor + trityl + imidazole : an antifungal agent C22H17ClN2 used to treat candidiasis, tinea, and ringworm …   Useful english dictionary Miconazole — Systematic (IUPAC) name (RS) 1 (2 (2,4 Dichlorobenzyloxy) 2 (2,4 dichlorophenyl)ethyl) 1H imidazole Clinical data Trade names …   Wikipedia Tea tree oil — (Melaleuca Oil) Tea tree oil, or melaleuca oil, is a pale yellow colour to nearly clear essential oil with a fresh camphoraceous odor.[1] It is taken from the leaves of the …   Wikipedia 18+ © Academic, 2000-2024 Contact us: Technical Support, Advertising Dictionaries export, created on PHP, Joomla, Drupal, WordPress, MODx. Mark and share Search through all dictionaries Translate… Search Internet Share the article and excerpts Direct link … Do a right-click on the link above and select “Copy Link”