Clotrimazole

Clotrimazole

Drug Nomenclature

Date of monograph revision: 15-Oct-1997; 10-Aug-2001; 07-Aug-2002; 06-Sep-2005; 14-Jul-2006
Synonyms: Bay-5097; Clotrimazol; Clotrimazolum; FB-5097; Klotrimatsoli; Klotrimazol; Klotrimazolas
BAN: Clotrimazole
USAN: Clotrimazole
INN: Clotrimazole [rINN (en)]
INN: Clotrimazol [rINN (es)]
INN: Clotrimazole [rINN (fr)]
INN: Clotrimazolum [rINN (la)]
INN: Клотримазол [rINN (ru)]
Chemical name: 1-(α-2-Chlorotrityl)imidazole
Molecular formula: C22H17ClN2 =344.8
CAS: 23593-75-1
ATC code: A01AB18; D01AC01; G01AF02
Read code: y00o9 [Ear]; y08EL [Skin]; y03Dg
Chemical Structure of Clotrimazole

Chemical Structure of Clotrimazole

NOTE:

Compounded preparations of clotrimazole may be represented by the following names:

Co-climasone (PEN)—clotrimazole and betamethasone dipropionate.

Pharmacopoeias:

In Chin., Eur. (see Go to European Pharmacopoeia Convention Signatories), Jpn, Pol., and US.

Ph. Eur. 5.5 (Clotrimazole). A white or pale yellow crystalline powder. Practically insoluble in water; soluble in alcohol and in dichloromethane. Protect from light.

USP 29 (Clotrimazole). A white to pale yellow, crystalline powder. Practically insoluble in water; freely soluble in alcohol, in acetone, in chloroform, and in methyl alcohol. Store in airtight containers.

Adverse Effects and Precautions

Nausea, vomiting, unpleasant mouth sensations, and pruritus have been reported after the use of oral clotrimazole lozenges. Elevation of liver enzyme values has also occurred. Local reactions including irritation and a burning sensation may occur in patients treated topically; contact allergic dermatitis has been reported.

Intravaginal preparations of clotrimazole may damage latex contraceptives and additional contraceptive measures are therefore necessary during local administration.

Gastrointestinal disturbance, elevation of liver enzymes, dysuria, and mental depression have been reported after clotrimazole by mouth (although this route is no longer used). For a discussion of the caution needed when using azole antifungals during pregnancy, see under Pregnancy in Precautions of Fluconazole, Go to Pregnancy..

Antimicrobial Action

Clotrimazole is an imidazole antifungal with antimicrobial activity similar to that of ketoconazole (Go to Antimicrobial Action).

Pharmacokinetics

When applied topically clotrimazole penetrates the epidermis but there is little if any systemic absorption. Absorption of 3 to 10% of a dose has been reported following vaginal administration. Clotrimazole is metabolised in the liver to inactive compounds and excreted in the faeces and urine.

Uses and Administration

Clotrimazole is an imidazole antifungal used topically in superficial candidiasis (Go to Candidiasis), and in the skin infections pityriasis versicolor and dermatophytosis (see Skin Infections, Go to Skin infections). Clotrimazole may also be used occasionally for symptomatic relief of the protozoal infection trichomoniasis when other drugs are contra-indicated (see Go to Trichomoniasis).

Clotrimazole is applied topically two or three times daily for 2 to 4 weeks as a 1% cream, lotion, spray, or solution in the treatment of fungal skin infections; a 1% powder may be used with the cream or solution and has been applied to prevent re-infection. The 1% solution is also used topically for fungal otitis externa. Clotrimazole is given as pessaries in dosage regimens of 100 mg for 6 days, 200 mg for 3 days, or a single dose of 500 mg in the treatment of vulvovaginal candidiasis; similar doses are given as a 1, 2, or 10% vaginal cream. It may be necessary to treat balanitis in male partners concurrently.

For the treatment of oropharyngeal candidiasis one 10-mg lozenge of clotrimazole is dissolved in the mouth five times daily for 14 days. For the prophylaxis of oropharyngeal candidiasis in patients receiving immunosuppressant therapy the dose is one 10-mg lozenge three times daily for the duration of the immunosuppressant treatment. Clotrimazole has also been given by mouth but has now been largely superseded by other azole drugs.

Sickle-cell disease.

Oral clotrimazole is under investigation for the treatment of sickle-cell disease (Go to Sickle-cell disease).

  1. 1. Brugnara C, et al. Therapy with oral clotrimazole induces inhibition of the Gardos channel and reduction of erythrocyte dehydration in patients with sickle cell disease. J Clin Invest 1996; 97: 1227–34. PubMed

Preparations

Single-ingredient Preparations

The symbol ¤ denotes a preparation which is discontinued or no longer actively marketed.

Argentina: Aflorix; Empecid; Eximius; Ikolan; Klomazole; Livomonil; Medifungol; Micoclin; Micomax; Micomazol Deo; Micomazol; Micosep B; Micosep; Micotrim; Mycanden; Panmicol; Trimazol; Australia: Canesten; Chemists Own Clozole¤; Clofeme; Clonea; Clotreme¤; Clozole¤; Femizol; Gyne-Lotrimin¤; Hiderm¤; Lotremin¤; Tinaderm Extra; Topizol; Austria: Candibene; Canesten; Mycofug¤; Myko Cordes; Pedikurol; Belgium: Canestene; Gyno-Canestene; Brazil: Antimicotico Martel; Canesten; Clogen¤; Clomazen; Clomazol; Clonasten¤; Clotigen; Clotren; Clotriderm; Clotrimix; Clotrizan; Dermobene; Gino Clotrimix¤; Gino-Canesten; Kinasten; Miclonazol; Micosten; Micotrat; Micotrizol; Neo Clotrimazyl; Tricosten¤; Canada: Canesten; Clotrimaderm; Myclo-Derm¤; Myclo-Gyne¤; Neo-Zol; Chile: Arnela; Axasol; Canesten; Cestop; Clotrimin; Cotrisan; Creminem; Funzal; Gynocanesten; Konifungil; Laboterol¤; Novacetol; Telugren; Czech Republic: Aknecolor; Baycuten; Candibene; Canesten; Canifug; Imazol; Jenamazol; Plimycol; Denmark: Canazol¤; Canesten; Finland: Canesten; Klotricid¤; France: Trimysten¤; Germany: Antifungol; Antimyk¤; Apocanda¤; Aru C¤; Azutrimazol¤; Benzoderm Myco; Candazol¤; Canesten; Canifug; Cloderm; Clotri OPT¤; Clotrifug¤; Clotrigalen; Contrafungin¤; cutistad; Dignotrimazol¤; durafungol; Fungiderm; Fungizid; Gilt; Gyno-Canesten¤; Holfungin; Jenamazol¤; KadeFungin; Logomed Hautpilz-Salbe¤; Lokalicid¤; Mono Baycuten¤; Mycofug; Mycohaug C¤; Myko Cordes; Mykofungin; Mykohaug; Onymyken¤; Ovis Neu¤; Pedisafe¤; Radikal¤; SD-Hermal; Stiemazol¤; Uromykol; Greece: Canesten; Factodin; Hong Kong: Canesten; Clocreme; Clotri-Denk; Clozole; Cotren¤; Fungizid; Gyne-Lotremin; Kamicin; Lotremin; Mycoril; Tricloderm; Warimazol¤; Hungary: Candibene; Canesten; Canifug; India: Candid; Clocip; Clozol; Imidil; Mycocid; Mycoderm-C; Surfaz; Ireland: Canesten; Israel: Agisten; Baby Agisten; Clotrimaderm; Myco-Hermal; Oralten Troche; Italy: Antimicotico; Canesten; Gyno-Canesten; Malaysia: Candazole; Candid; Canesten; Cotren; Gyne-Lotremin; Gynostatum; Loriderm¤; Lotremin; Micoter; Trimazol¤; Mexico: Baycuten¤; Candimon; Candiphen; Canesten; Cinabel; Clocan; Dermasten; Euroderm; Liferzol; Lomecan V; Lonestin¤; Lotrimin¤; Tenescan; Netherlands: Canesten; Parvemaxol; Norway: Canesten; Fungisten¤; New Zealand: Canesten; Clocreme; Clomazol; Clotrihexal; Clotrimaderm; Fungizid¤; Portugal: Candid; Canesten; Diomicete; Gino-Canesten; Gino-Lotremine; Lotremine¤; Pan-Fungex; Russia: Amyclon (Амиклон); Antifungol (Антифунгол); Candibene (Кандибене); Candid (Кандид); Candid V6 (Кандид В6); South Africa: A-Por; Canalba; Candaspor; Candizole; Canesten; Canex; Clomaderm¤; Closcript; Covospor; Dynaspor¤; Fungispor; Gynezol¤; Gyno-Trimaze; Medaspor; Micomisan; Mycoban; Mycohexal; Normospor; Stiemazol; Trimaze; Xeraspor; Singapore: Candazole; Canesten; Clozole¤; Cotren; Cristan; Gyne-Lotremin; Lotremin; Myco-Hermal; Mycoril; Sastid Anti-Fungal; Vanesten¤; Spain: Canesten; Fungidermo; Gine Canesten; Ictan¤; Micomisan¤; Micoter¤; Sweden: Canesten; Clotriferm¤; Switzerland: Acnecolor; Canestene; Clocim¤; clot-basan¤; Corisol; cutistad¤; Eurosan¤; Fungotox; Gromazol; Gyno-Canestene; Imazol; Undex; Thailand: Caginal¤; Canadine; Canazol; Candid; Candinox; Canesten; Chingazol; Clotri; Clotricin; Comat; Cotren; CST; Defungo; Dermaten; Fungicon; Fungiderm; Gynebo; Kanezin; Klamacin; Manomazole; Mycozole; Nestic; Taraten; Vamazole; Vanesten; United Kingdom: Abtrim; Athletes Foot Cream¤; Candiden¤; Canesten Combi; Canesten; Fungederm; Masnoderm¤; Medisport Athlete's Foot¤; Mycil Gold¤; Privacom¤; United States: Femcare¤; Fungoid¤; Gyne-Lotrimin; Lotrimin AF; Lotrimin; Mycelex-7; Mycelex-G¤; Mycelex; Prescription Strength Desenex¤; Venezuela: Canesten; Clortilen; Clotrizol; Fugolin; Ginolotricomb; Gyno Canesten; Imazol; Ipalat; Lecibis; Oxisol; Polik;

Multi-ingredient Preparations

The symbol ¤ denotes a preparation which is discontinued or no longer actively marketed.

Argentina: Becortin; Calmurid; Cortispec; Dermovit¤; Empecid Cort; Lotricomb; Micomazol B; Quadriderm CD; Quiacort G Plus; Vagarne¤; Vagisan Compuesto; Vitacortil; Australia: Hydrozole; Austria: Myko Cordes; Belgium: Lotriderm; Brazil: Baycuten; Floregin Composto¤; Canada: Lotriderm; Chile: B-Laboterol; Baycuten; Cestop B; Clotrimin-B; Creminem-B; Cutanil; Donomix; Locrim; Lotriderm; Novadrel; Novarnela; Telugren Plus; Tribesona; Czech Republic: Imacort; Imazol Plus; Lotriderm; Denmark: Clotrason; France: Triazol; Germany: Antifungol; Baycuten HC; Baycuten SD¤; Baycuten¤; Canesten HC¤; Fungidexan; Imazol comp; Imazol; Imazol; Lotricomb; Myko Cordes Plus; Hong Kong: Becogem; Canesten HC; Clobeta-G; Clotrinolon; Derzid-C; Lozopin; Synco-CFN; Triderm; India: Candibiotic; Candid B; Candid Ear Drops; Candid-TV; Candiderma +; Candiderma; Cloben-G; Clocip B; Clocip NB; Clomycin; Cutinorm; Fourderm AF; NC-Derm; Neocip FC; Otek-AC+; Sofradex-F; Surfaz-SN; Surfaz; Translipo-Triple; Ireland: Canesten HC; Lotriderm; Israel: Hydroagisten; Polycutan; Tevacutan; Triderm; Italy: Desamix Effe; Meclon; Malaysia: Baycuten N; Betamethasone Clo; Candacort; Triderm-C; Mexico: Baycuten N; Betrigen; Gelmicin; Miclobet; Prubagen; Quadriderm NF; Triderm; New Zealand: Lotricomb¤; Portugal: Baycuten; Beta-Micoter; Flotiran; Quadriderme; Russia: Akriderm GK (Акридерм ГК); Candibiotic (Кандибиотик); Candid B (Кандид Б); Triderm (Тридерм); South Africa: Lotriderm; Singapore: Candacort; Canesten HC; Clotrasone; Combiderm; Gentrisone; Neoderm; Triderm; Spain: Beta Micoter; Clotrasone; Switzerland: Imacort; Imazol; Triderm; Thailand: Bacda-B; Canasone; Canazol-BE; Clotrasone; Derzid-C; Fungiderm-B; Gynesten-B; Gynestin; Myda-B; Twina; United Kingdom: Canesten HC; Lotriderm¤; United States: Lotrisone; Venezuela: Baycuten N; Lotricomb; Lotrisone; Triderm;



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