CLOTRIMAZOLE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H17ClN2
Molecular Weight	344.837
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

ClC1=CC=CC=C1C(N2C=CN=C2)(C3=CC=CC=C3)C4=CC=CC=C4

InChI

InChIKey=VNFPBHJOKIVQEB-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C22H17ClN2
Molecular Weight	344.837
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

Clotrimazole is an anti-fungal medicine indicated for the treatment of vaginal yeast infections and tinea. It can be used either in combination with other drugs (betamethasone dipropionate) or alone, in form of topical or vaginal cream. The drug exerts its action by inhibiting lanosterol demethylase thereby affecting the growth of fungi.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 51 28	Inhibitor 8,504		19.7 nM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Vaginal yeast infections 1	Curative	Approved 8,583	GYNE-LOTRIMIN
Tinea pedis 28	Curative	Approved 8,583	LOTRISONE
Tinea cruris 11	Curative	Approved 8,583	LOTRISONE
Tinea corporis 19	Curative	Approved 8,583	LOTRISONE

C_max

Value	Dose	Co-administered	Analyte	Population
2.4 μM	1 g single, oral		CLOTRIMAZOLE plasma	Homo sapiens
4.98 ng/mL	10 mg single, buccal		CLOTRIMAZOLE serum	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
12.59 μM × h	1 g single, oral		CLOTRIMAZOLE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.99 h	1 g single, oral		CLOTRIMAZOLE plasma	Homo sapiens
4.25 h	500 mg single, vaginal		CLOTRIMAZOLE plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
10 mg 5 times / day multiple, oral Recommended	unhealthy, 33 years (range: 22 - 43 years)	Disc. AE: Nausea, Taste abnormality...
500 mg single, vaginal Highest studied dose	unhealthy, adult	Disc. AE: Vulvovaginal pruritus...
500 mg single, vaginal Highest studied dose	unhealthy, adult	Disc. AE: Vulvovaginal burning sensation...
50 mg 1 times / day multiple, vaginal	unhealthy, adult	Disc. AE: Vaginal irritation, Spotting vaginal...

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AEs

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AE	Significance	Dose	Population
Nausea	2 patients Disc. AE	10 mg 5 times / day multiple, oral Recommended	unhealthy, 33 years (range: 22 - 43 years)
Taste abnormality	2 patients Disc. AE	10 mg 5 times / day multiple, oral Recommended	unhealthy, 33 years (range: 22 - 43 years)
Vulvovaginal pruritus	1 patient Disc. AE	500 mg single, vaginal Highest studied dose	unhealthy, adult
Vulvovaginal burning sensation	1 patient Disc. AE	500 mg single, vaginal Highest studied dose	unhealthy, adult
Spotting vaginal	1 patient Disc. AE	50 mg 1 times / day multiple, vaginal	unhealthy, adult

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 2,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP3A1 1 CYP3A2 10 CYP2C11 4 CYP2B1/2 3 CYP1A 70 CYP2E1 1,060 UGT1A1 246 UGT1A3 89 UGT1A4 98 UGT1A6 136 UGT1A9 148 UGT2B7 197 UGT2B15 84 MRP1 116		CYP1A 59 P-gp 301

Drug as perpetrator

Show entries

Target	Modality	Activity
CYP2E1 1,146	inhibitor 4,027	no
CYP3A2 13	inhibitor 4,027	yes [IC50 0.00315 uM]
CYP3A1 5	inhibitor 4,027	yes [IC50 0.00822 uM]
CYP2B1/2 4	inhibitor 4,027	yes [IC50 0.1 uM]
CYP2C11 15	inhibitor 4,027	yes [IC50 0.745 uM]

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2,263	inhibitor 2,237

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3764	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3764
ChemicalBook	CB7404063	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7404063
eMolecules	499093	https://www.emolecules.com/cgi-bin/more?vid=499093
MolPort	MolPort-002-557-756	https://www.molport.com/shop/molecule-link/MolPort-002-557-756
Selleck Chemicals	Clotrimazole(Canesten)	http://www.selleckchem.com/products/Clotrimazole(Canesten).html

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PubMed

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Title	Date	PubMed
Bactericidal and inhibitory effects of azole antifungal compounds on Mycobacterium smegmatis.	2000 Nov 15	11064188
Swelling-induced K(+) fluxes in vascular smooth muscle cells are mediated by charybdotoxin-sensitive K(+) channels.	2001	11832655
K+ channels and the microglial respiratory burst.	2001 Apr	11245596
A novel drug-regulated gene expression system based on the nuclear receptor constitutive androstane receptor (CAR).	2001 Feb	11405283
In vitro metabolism of 14C-moxidectin by hepatic microsomes from various species.	2001 Jul	11469506

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Patents

Sample Use Guides

In Vivo Use Guide

Vaginal 1% cream: insert an applicator full of cream into the vagina at bedtime for 7 days. External 1% cream for vaginal yeast infections: apply to the skin outside the vagina 2 times daily for up to 7 days. Topical 1% cream: apply a thin layer to the affected area twice daily for 2 weeks (tinea pedis) or 1 week (tinea cruris and tinea corporis).

Route of Administration: Topical

In Vitro Use Guide

In vitro antifungal activity indicated Clotrimazole (MIC 16 and 8 microg/ml) effective against 68 (70%) of Candida SPP.