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QuickView for Clotrimazole (compound)

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PubChem

PubChem Compound 2812

PubChem Compound 2812

Name:	Clotrimazole
PubChem Compound ID:	2812
Description:	An imidazole derivative with a broad spectrum of antimycotic activity. It inhibits biosynthesis of the sterol ergostol, an important component of fungal CELL MEMBRANES. Its action leads to increased membrane permeability and apparent disruption of enzyme systems bound to the membrane.
Molecular formula:	C₂₂H₁₇ClN₂
Molecular weight:	344.837 g/mol
Synonyms:	1-[(2-Chlorophenyl)diphenylmethyl]-1H-imidazole; C06922; (Chlorotrityl)imidazole; Rimazole; Mycelex (TN); NCGC00015251-02; Spectrum3_000359; NCGC00015251-01; Clotrimazole [USAN:BAN:INN:JAN]; Spectrum_001343. show more » 1-[(2-Chlorophenyl)diphenylmethyl]-1H-imidazole; C06922; (Chlorotrityl)imidazole; Rimazole; Mycelex (TN); NCGC00015251-02; Spectrum3_000359; NCGC00015251-01; Clotrimazole [USAN:BAN:INN:JAN]; Spectrum_001343; 1H-Imidazole, 1-[(2-chlorophenyl)-diphenylmethyl]; 1H-Imidazole, 1-[ (2-chlorophenyl)diphenylmethyl]-; Lotrimin AF Cream; Lotrimin AF Jock-Itch Cream; (2-Chlorophenyl)diphenyl-1-imidazolylmethane; Desamix F; Bis-phenyl-(2-chlorophenyl)-1-imidazoyl)methane; Mycelex: MycosporinRimazole; CCRIS 6245; Bisphenyl-(2-chlorphenyl)-1-imidazolyl-methan [German]; KBio1_000665; Lotrimax; Spectrum2_000128; D00282; Prestwick_120; Clotrimazolum [INN-Latin]; Pedisafe; 1-((2-Chlorophenyl)diphenylmethyl)-1H-imidazole; 117829-71-7; SPBio_000176; 23593-75-1; Mono-Baycuten; 1-(o-Chloro-alpha,alpha-diphenylbenzyl)imidazole; Lotrimin; Clotrimazole; 1-(o-Chloro-.alpha., .alpha.-diphenylbenzyl)imidazole; BAY b5097; Lopac-C-6019; 1-((o-Chloro-phenyl)diphenylmethyl)imidazole; AIDS-007336; Canestine; 1H-Imidazole, 1-((2-chlorophenyl)diphenylmethyl)-; 5-23-04-00291 (Beilstein Handbook Reference); KBioSS_001823; Imidazole, 1- (o-chloro-.alpha.,.alpha.-diphenylbenzyl)-; BRN 0622318; Gyne lotrimin; Mycelex Troches; KBioGR_000850; Prestwick0_000267; Canesten; 1-(alpha-(2-Chlorophenyl)benzhydryl)imidazole; BAY 5097; B 5097; 1-(o-Chlorotrityl)imidazole; Mycelex; 1-((2-Chlorophenyl)diphenylmethyl)-1H-imidazole (9CI); NCIMech_000609; 1-[(2-chlorophenyl)(diphenyl)methyl]-1H-imidazole; Bay-B 5097; Mycelex OTC; Methane, bis-phenyl-(2-chlorophenyl)-1-imidazolyl-; SPBio_002333; BAYb 5097; Gyne-Lotrimin; Clotrimazole (JP15/USP); EU-0100315; Empecid; Diphenyl-(2-chlorophenyl)-1-imidazolylmethane; Mycelex 7; Clotrimazol; Imidazole, 1-(o-chloro-alpha,alpha-diphenylbenzyl)-; NINDS_000665; KBio2_004391; Mycelex G; Mykosporin; NSC257473; Diphenyl(2-chlorophenyl)(1-imidazolyl)methane; CHEBI:3764; Spectrum4_000295; BAY b 5097; Mycosporin; Bis-phenyl-(2-chlorophenyl)(1-imidazoyl)methane; SMR000058306; FB 5097; Chlotrimazole; HSDB 3266; Otomax (Veterinary); KBio3_001277; nchembio790-comp30; Clotrimazol [INN-Spanish]; DivK1c_000665; MLS000028502; Prestwick1_000267; Veltrim; KBio2_001823; Trimysten; CAS-23593-75-1; Tibatin; KBio2_006959; 1H-Imidazole, 1-[(2-chlorophenyl)diphenylmethyl]-; Lotrimin (TN); 1-(o-Chlorophenyldiphenylmethyl)imidazole; ZINC03807804; Lotrimin AF Solution; NSC 257473; DRG-0072; Bis-fenil-(2-clorofenil)-1-imidazolil-metano [Italian]; Fem Care; Monobaycuten; AIDS007336; Bay b 9057; Lotrisone; EINECS 245-764-8 show less «

DrugBank

Identification

Name:	Clotrimazole
Name (isomeric):	DB00257
Drug Type:	small molecule
Description:	An imidazole derivative with a broad spectrum of antimycotic activity. It inhibits biosynthesis of the sterol ergostol, an important component of fungal CELL MEMBRANES. Its action leads to increased membrane permeability and apparent disruption of enzyme systems bound to the membrane.
Synonyms:	Clotrimazol; Chlotrimazole
Brand:	Mycelex Solution, Clotrimaderm, Mycelex Cream, Neo-Zol Cream, Veltrim, Mycelex-7 Combination Pack, Mykosporin, Gyne-Lotrimin 3, Canesten Cream, Canesten 1-Day Cream Combi-Pak, Mycelex Twin Pack, Gynix, Gyne lotrimin, Mycelax, Lotrimin AF Lotion, Gyne-Lotrimin Combination Pack, FemCare, Myclo Solution, Empecid, Lotrimin Af, Canesten, Canesten 3-Day Therapy, Trivagizole 3, Trimysten, Canesten 6-Day Therapy, Mycelex, Mycelex-G, Mycelex Troches, Canifug, Lotrimin, Lotrimin AF Jock-Itch Cream, Lotrimin Solution, Mycosporin, Gyne-Lotrimin 3 Combination Pack, Lotrimin Cream, Lotrimin AF Solution, Myclo Cream, Myclo-Gyne, Myclo Spray Solution, Cimitidine, Canesten Solution, Lotrimin Lotion, Mycelex G, Canesten Combi-Pak 3-Day Therapy, Gyne-lotrimin, Canesten Combi-Pak 1-Day Therapy, Lotrimin AF Cream, Canesten 1-Day Therapy, Mycelex 7, Mono-baycuten, Canestine, Mycelex-7
Brand name mixture:	Lotrisone(clotrimazole + betamethasone)
Category:	Anti-Infective Agents, Local, Antifungal Agents, Growth Inhibitors
CAS number:	23593-75-1

Pharmacology

Indication:	For the local treatment of oropharyngeal candidiasis and vaginal yeast infections, also used in fungal infections of the skin such as ringworm, athlete's foot, and jock itch.
Pharmacology:	Clotrimazole, an imidazole derivative with a broad spectrum of antimycotic activity, inhibits biosynthesis of the sterol ergostol, an important component of fungal cell membranes. Its action leads to increased membrane permeability and apparent disruption of enzyme systems bound to the membrane. Betamethasone and clotrimazole are used together to t... show more » Clotrimazole, an imidazole derivative with a broad spectrum of antimycotic activity, inhibits biosynthesis of the sterol ergostol, an important component of fungal cell membranes. Its action leads to increased membrane permeability and apparent disruption of enzyme systems bound to the membrane. Betamethasone and clotrimazole are used together to treat cutaneous tinea infections. In studies in fungal cultures, the minimum fungicidal concentration of clotrimazole caused leakage of intracellular phosphorous compounds into the ambient medium with concomitant breakdown of cellular nucleic acids, and accelerated potassium etflux. Both of these events began rapidly and extensively after addition of the drug to the cultures. The primary action of clotrimazole is against dividing and growing organisms. show less «
Mechanism of Action:	Clotrimazole interacts with yeast 14-α demethylase, a cytochrome P-450 enzyme that converts lanosterol to ergosterol, an essential component of the membrane. In this way, clotrimazole inhibits ergosterol synthesis, resulting in increased cellular permeability. Clotrimazole may also inhibit endogenous respiration, interact with membrane phosph... show more » Clotrimazole interacts with yeast 14-α demethylase, a cytochrome P-450 enzyme that converts lanosterol to ergosterol, an essential component of the membrane. In this way, clotrimazole inhibits ergosterol synthesis, resulting in increased cellular permeability. Clotrimazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms and the uptake of purine, impair triglyceride and/or phospholipid biosynthesis, and inhibit the movement of calcium and potassium ions across the cell membrane by blocking the ion transport pathway known as the Gardos channel. show less «
Absorption:	Poorly and erratically absorbed orally, minimal vaginal or topical absorption.
Protein binding:	90%
Biotransformation:	Hepatic (metabolized to inactive metabolites)
Half Life:	2 hours
Toxicity:	Symptoms of overdose include erythema, stinging, blistering, peeling, edema, pruritus, urticaria, burning, and general irritation of the skin, and cramps.
Affected organisms:	Yeast and other fungi

Interactions

Drug interaction:

Tolterodine	Clotrimazole may decrease the metabolism and clearance of Tolterodine. Adjust Tolterodine dose and monitor for efficacy and toxicity.
Tacrolimus	The antifungal, Clotrimazole, may increase serum concentrations of Tacrolimus. Monitor for changes in the therapeutic/toxic effects of Tacrolimus if Clotrimazole therapy is initiated, discontinued or altered.
Trazodone	The CYP3A4 inhibitor, Clotrimazole, may increase Trazodone efficacy/toxicity by decreasing Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Clotrimazole is initiated, discontinued or dose changed.
Halofantrine	CYP3A4 Inhibitors (Moderate) such as clotrmazole may increase the serum concentration of halofantrine. Extreme caution, with possibly increased monitoring of cardiac status (e.g., ECG), should be used with concurrent use of halofantrine with any moderate CYP3A4 inhibitor(s).
Tolvaptan	CYP3A4 Inhibitors (Moderate) may increase the serum concentration of tolvaptan. Coadministration of a strong CYP3A4 inhibitor with tolvaptan is contraindicated.

Tolterodine	Clotrimazole may decrease the metabolism and clearance of Tolterodine. Adjust Tolterodine dose and monitor for efficacy and toxicity.
Tacrolimus	The antifungal, Clotrimazole, may increase serum concentrations of Tacrolimus. Monitor for changes in the therapeutic/toxic effects of Tacrolimus if Clotrimazole therapy is initiated, discontinued or altered.
Trazodone	The CYP3A4 inhibitor, Clotrimazole, may increase Trazodone efficacy/toxicity by decreasing Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Clotrimazole is initiated, discontinued or dose changed.
Halofantrine	CYP3A4 Inhibitors (Moderate) such as clotrmazole may increase the serum concentration of halofantrine. Extreme caution, with possibly increased monitoring of cardiac status (e.g., ECG), should be used with concurrent use of halofantrine with any moderate CYP3A4 inhibitor(s).
Tolvaptan	CYP3A4 Inhibitors (Moderate) may increase the serum concentration of tolvaptan. Coadministration of a strong CYP3A4 inhibitor with tolvaptan is contraindicated.
Everolimus	CYP3A4 Inhibitors (Moderate)such as clotrimazole may increase the serum concentration of everolimus. The prescribing information for the Afinitor branded everolimus product lists indication-specific recommendations for managing this interaction.
Tramadol	Clotrimazole may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance.
Fentanyl	CYP3A4 Inhibitors (Moderate) such as clotrimazole may increase the serum concentration of fentanyl. Concurrent use of fentanyl with any CYP3A4 inhibitor may result in increased fentanyl concentrations and could increase or prolong adverse effects, including potentially fatal respiratory depression. Patients receiving fentanyl and any CYP3A4 inhibitor should be closely monitored for several days following initiation of the combination, and fentanyl dosage reductions should be made as appropriate.
Ranolazine	CYP3A4 Inhibitors (Moderate) such as clotrimazole may increase the serum concentration of ranolazine. Limit the ranolazine dose to a maximum of 500mg twice daily in patients concurrently receiving moderate CYP3A4 inhibitors (e.g., diltiazem, verapamil, erythromycin, etc.). Monitor for increased effects/toxicity of ranolazine during concomitant use.
Colchicine	CYP3A4 Inhibitors (Moderate) such as clotrimazole may increase the serum concentration of colchicine. Reduce colchicine dose (for gout flares: to 1.2 mg x 1 dose, with next dose no sooner than 3 days later; for Familial Mediterranean Fever: to no more than 1.2 mg/day) when using in combination with a moderate CYP3A4 inhibitor such as erythromycin or verapamil. Increase monitoring for colchicine-related toxicity when using such combinations. Use extra caution in patients with impaired renal and/or hepatic function.
Lurasidone	CYP3A4 Inhibitors (Moderate) such as clotrimazole may increase the serum concentration of lurasidone. Limit adult lurasidone dose to 40 mg/day in patients receiving a moderate CYP3A4 inhibitor.
Tamsulosin	Clotrimazole, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Clotrimazole is initiated, discontinued, or dose changed.
Budesonide	CYP3A4 Inhibitors (Moderate) such as clotrimazole may increase the serum concentration of Budesonide (Systemic, Oral Inhalation). Consider reducing the oral budesonide dose when used together with a CYP3A4 inhibitor. This interaction is likely less severe with orally inhaled budesonide. Any patient receiving both budesonide and a moderate CYP3A4 inhibitor should be monitored closely for signs/symptoms of corticosteroid excess.

Targets

Cytochrome P450 51

Intermediate conductance calcium-activated potassium channel protein 4

Enzymes

Cytochrome P450 2C8

Cytochrome P450 3A4

Cytochrome P450 2B6

Cholesterol side-chain cleavage enzyme, mitochondrial

Cytochrome P450 1A2

Cytochrome P450 2D6

Cytochrome P450 11B1, mitochondrial

Cytochrome P450 19A1

Cytochrome P450 2A6

Cytochrome P450 2C19

Cytochrome P450 2C9

Cytochrome P450 2E1

Cytochrome P450 3A7

Transporters

Canalicular multispecific organic anion transporter 2

Multidrug resistance protein 1

Canalicular multispecific organic anion transporter 1