GENACONAZOLE

Details

Stereochemistry	RACEMIC
Molecular Formula	C13H15F2N3O3S
Molecular Weight	331.338
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H]([C@](O)(CN1C=NC=N1)C2=C(F)C=C(F)C=C2)S(C)(=O)=O

InChI

InChIKey=HFGZFHCWKKQGIS-NOZJJQNGSA-N

InChI=1S/C13H15F2N3O3S/c1-9(22(2,20)21)13(19,6-18-8-16-7-17-18)11-4-3-10(14)5-12(11)15/h3-5,7-9,19H,6H2,1-2H3/t9-,13-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://clinicaltrials.gov/ct2/show/record/NCT00000677 | https://www.ncbi.nlm.nih.gov/pubmed/8360815 | https://www.ncbi.nlm.nih.gov/pubmed/1588494

Sch 39304 is a new broad-spectrum orally active triazole antifungal agent that is active, orally and topically, against a broad range of fungal pathogens, including superficial Trichophyton mentagrophytes and vaginal Candida albicans infections. The mechanism of action of SCH-39304 appears similar to those of ketoconazole and fluconazole, involving inhibition of cell membrane ergosterol synthesis. SCH-39304 has two asymmetrical carbon atoms, and the formulation used in clinical trials has been a racemic mixture of two enantiomers, active SCH-42427 (RR (+)-) and inactive SCH-424264 (SS (–)-). Unfortunately, hepatocarcinomas associated with the use of SCH-39304 in animals have sharply restricted the development and use of this agent.

Approval Year

PubMed

Title	Date	PubMed
SCH-39304 in prevention and treatment of disseminated candidiasis in persistently granulocytopenic rabbits.	1990 Aug	2221866
Treatment of murine cryptococcal meningitis with an SCH 39304-amphotericin B combination.	1991 Sep	1952837
Comparison of SCH 39304 and its isomers, RR 42427 and SS 42426, for treatment of murine cryptococcal and coccidioidal meningitis.	1992 Jan	1590692
Ro 09-1470 is a selective inhibitor of P-450 lanosterol C-14 demethylase of fungi.	1993 Dec	8109933
Pneumocystis carinii is resistant to imidazole antifungal agents.	1994 Aug	7986021
Evaluation of SCH51048 in an experimental model of pulmonary aspergillosis.	1995 Jun	7574528
Synthesis and antifungal activity of alkylthio and alkylsulfonyl derivatives of SM-8668.	1996 Feb	8814884
Stereoselective interaction of the azole antifungal agent SCH39304 with the cytochrome P-450 monooxygenase system isolated from Cryptococcus neoformans.	1997 Jul	9210667

Sample Use Guides

In Vivo Use Guide

200 mg once daily for 12 weeks

Route of Administration: Oral

Name

Type

Language

GENACONAZOLE

Common Name

English

SCH39304

Code

English

SM-8668

Code

English

SM8668

Code

English

1H-1,2,4-TRIAZOLE-1-ETHANOL, .ALPHA.-(2,4-DIFLUOROPHENYL)-.ALPHA.-((1R)-1-(METHYLSULFONYL)ETHYL)-, (.ALPHA.R)-REL-

Systematic Name

English

1H-1,2,4-TRIAZOLE-1-ETHANOL, .ALPHA.-(2,4-DIFLUOROPHENYL)-.ALPHA.-(1-(METHYLSULFONYL)ETHYL)-, (R*,R*)-(±)-

Common Name

English

SCH-39304

Code

English

Code System Code Type Description

FDA UNII

1BFZ5CM687