Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C13H15F2N3O3S |
| Molecular Weight | 331.338 |
| Optical Activity | ( + ) |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@H]([C@](O)(CN1C=NC=N1)C2=CC=C(F)C=C2F)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
| Molecular Formula | C13H15F2N3O3S |
| Molecular Weight | 331.338 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 |
|---|---|---|
| Stereoselective interaction of the azole antifungal agent SCH39304 with the cytochrome P-450 monooxygenase system isolated from Cryptococcus neoformans. | 1997-07 |
|
| Synthesis and antifungal activity of alkylthio and alkylsulfonyl derivatives of SM-8668. | 1996-02 |
|
| Evaluation of SCH51048 in an experimental model of pulmonary aspergillosis. | 1995-06 |
|
| Pneumocystis carinii is resistant to imidazole antifungal agents. | 1994-08 |
|
| Ro 09-1470 is a selective inhibitor of P-450 lanosterol C-14 demethylase of fungi. | 1993-12 |
|
| Comparative study of six antifungal treatments in an experimental model of murine cryptococcosis. | 1992-05 |
|
| Comparison of SCH 39304 and its isomers, RR 42427 and SS 42426, for treatment of murine cryptococcal and coccidioidal meningitis. | 1992-01 |
|
| Treatment of murine cryptococcal meningitis with an SCH 39304-amphotericin B combination. | 1991-09 |
|
| SCH-39304 in prevention and treatment of disseminated candidiasis in persistently granulocytopenic rabbits. | 1990-08 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:03:57 GMT 2025
by
admin
on
Mon Mar 31 18:03:57 GMT 2025
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| Record UNII |
I87RHM3O1J
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| Record Status |
Validated (UNII)
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| Record Version |
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I87RHM3O1J
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452261
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121650-83-7
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DTXSID90923916
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admin on Mon Mar 31 18:03:57 GMT 2025 , Edited by admin on Mon Mar 31 18:03:57 GMT 2025
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RACEMATE -> ENANTIOMER |
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