Details
Stereochemistry | ACHIRAL |
Molecular Formula | C10H8N4O4 |
Molecular Weight | 248.1949 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=NC(=CN1C2=CC=C(C=C2)[N+]([O-])=O)[N+]([O-])=O
InChI
InChIKey=NMTBSNPBIGRZBL-UHFFFAOYSA-N
InChI=1S/C10H8N4O4/c1-7-11-10(14(17)18)6-12(7)8-2-4-9(5-3-8)13(15)16/h2-6H,1H3
Nitrefazole (2-methyl-4-nitro-1-(4-nitro-phenyl)imidazole, Altimol) is a strong and long lasting inhibitor of aldehyde dehydrogenase, an enzyme involved in the metabolism of alcohol. It was used for the treatment of alcoholism as an alcohol-sensitizing agent (alcohol deterrent). Nitrefazole was introduced in the early 1980s. By 1984 its use had been associated with hepatotoxic reactions, some of which were fatal. This lets to its withdrawal. WHO has no information to suggest that preparations containing nitrefazole remain commercially available.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL3542434 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Preventing | ALTIMOL Approved UseNitrefazole (2-methyl-4-nitro-1-(4-nitro-phenyl)imidazole, Altimol) was used for the treatment of alcoholism as an alcohol-sensitizing agent. Launch Date1983 |
PubMed
Title | Date | PubMed |
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[Nitrefazole, a 4-nitroimidazole derivative with a marked inhibitory effect on aldehyde dehydrogenase. Synthesis and structural assignment]. | 1985 |
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Differences in kinetic characteristics and in sensitivity to inhibitors between human and rat liver alcohol dehydrogenase and aldehyde dehydrogenase. | 1990 |
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Differences in the kinetic properties and sensitivity to inhibitors of human placental, erythrocyte, and major hepatic aldehyde dehydrogenase isoenzymes. | 1990 Mar 1 |
Patents
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C471
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ACTIVE MOIETY