CROCONAZOLE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H15ClN2O
Molecular Weight	310.778
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

ClC1=CC=CC(COC2=C(C=CC=C2)C(=C)N3C=CN=C3)=C1

InChI

InChIKey=WHPAGCJNPTUGGD-UHFFFAOYSA-N

InChI=1S/C18H15ClN2O/c1-14(21-10-9-20-13-21)17-7-2-3-8-18(17)22-12-15-5-4-6-16(19)11-15/h2-11,13H,1,12H2

HIDE SMILES / InChI

Molecular Formula	C18H15ClN2O
Molecular Weight	310.778
Charge	0
Count

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

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/3069196

Croconazole is a antifungal drug developed for the treatment of dermatomycoses and candidiasis. It has a broad spectrum activity against many microorganisms such as T. mentagrophytes, T. rubrum, M. canis, Microsporum gypseum, and Epidermophyton floccosum. The drug was used as a topical 1% cream under the name Pilzcin. According to the information on the manufacturer (Merz pharma) website, Pilzcin is no longer marketed.

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Dermatomycosis 20 Sources: http://www.ncbi.nlm.nih.gov/pubmed/3069196	Curative		Approved 8429	PILZCIN Approved Use The topical treatment of dermatomycoses and candidiasis.
Candida infections 20 Sources: http://www.ncbi.nlm.nih.gov/pubmed/3069196	Curative		Approved 8429	PILZCIN Approved Use The topical treatment of dermatomycoses and candidiasis.

PubMed

Title	Date	PubMed
1-[1-[2-[(3-Chlorobenzyl)oxy]phenyl]vinyl]-1H-imidazole hydrochloride, a new potent antifungal agent.	1983 May	6842519
Synthesis and antifungal activity of new 1-vinylimidazoles.	1987 Aug	3302257
In vitro activity of cloconazole, sulconazole, butoconazole, isoconazole, fenticonazole, and five other antifungal agents against clinical isolates of Candida albicans and Candida spp.	1992 Apr	1406898
Reptilian chemistry: volatile compounds from paracloacal glands of the American crocodile (Crocodylus acutus).	2002 Apr	12035925
[Contact sensitization to azole antimycotics].	2009 May	19367370
Investigation into UDP-glucuronosyltransferase (UGT) enzyme kinetics of imidazole- and triazole-containing antifungal drugs in human liver microsomes and recombinant UGT enzymes.	2010 Jun	20304965

Patents

Sample Use Guides

In Vivo Use Guide

One topical application per day (1% cream formulation).

Route of Administration: Topical

In Vitro Use Guide

The range of MICs against isolates of T. mentagrophytes, T. rubrum, M. canis, Microsporum gypseum, and Epidermophyton floccosum were 0.16 to 1.25 ug/ml. Five isolates of Aspergillus species and two isolates of Penicillium species were susceptible, with MICs of 0.63 to 5.0 ug/ml. However, this compound was less active (MICs, 10 to 80 ug/ml) against yeast-like fungi, including isolates of C. albicans, Candida species, Torulopsis glabrata, and Cryptococcus neoformans.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:04:01 GMT 2023` Edited by `admin` on `Fri Dec 15 16:04:01 GMT 2023`
Record UNII	446254H55G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CROCONAZOLE

Official Name

English

1-(1-(2-((3-CHLOROPHENYL)METHOXY)PHENYL)ETHENYL)-1H-IMIDAZOLE

Systematic Name

English

1-(1-(O-((M-CHLOROBENZYL)OXY)PHENYL)VINYL)IMIDAZOLE

Common Name

English

croconazole [INN]

Common Name

English

CROCONAZOLE [MI]

Common Name

English

Croconazole [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C514