NITREFAZOLE

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

Structure Search

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

HIDE SMILES / InChI

Molecular Formula	C10H8N4O4
Molecular Weight	248.1949
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2276587 | https://www.ncbi.nlm.nih.gov/pubmed/2310412 | https://www.ncbi.nlm.nih.gov/pubmed/4074438 | https://www.ncbi.nlm.nih.gov/pubmed/6144620 | https://www.ncbi.nlm.nih.gov/pubmed/6598964 | https://books.google.at/books?id=leVCukUgNlsC&printsec=frontcover&hl=ru#v=onepage&q&f=false

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Aldehyde dehydrogenase 8 Target ID: CHEMBL3542434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2276587 \| https://www.ncbi.nlm.nih.gov/pubmed/2310412 \| https://www.ncbi.nlm.nih.gov/pubmed/4074438	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Alcoholism 19 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6144620 https://www.ncbi.nlm.nih.gov/pubmed/6598964	Preventing		Withdrawn	ALTIMOL Approved Use Nitrefazole (2-methyl-4-nitro-1-(4-nitro-phenyl)imidazole, Altimol) was used for the treatment of alcoholism as an alcohol-sensitizing agent. Launch Date 1983

PubMed

Title	Date	PubMed
[Nitrefazole, a 4-nitroimidazole derivative with a marked inhibitory effect on aldehyde dehydrogenase. Synthesis and structural assignment].	1985	4074438
Differences in kinetic characteristics and in sensitivity to inhibitors between human and rat liver alcohol dehydrogenase and aldehyde dehydrogenase.	1990	2276587
Differences in the kinetic properties and sensitivity to inhibitors of human placental, erythrocyte, and major hepatic aldehyde dehydrogenase isoenzymes.	1990 Mar 1	2310412

Patents

Sample Use Guides

In Vivo Use Guide

800 mg nitrefazole

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:24:40 GMT 2023` Edited by `admin` on `Fri Dec 15 16:24:40 GMT 2023`
Record UNII	VFD629099M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NITREFAZOLE

Official Name

English

nitrefazole [INN]

Common Name

English

EMD-15-700

Code

English

NITREFAZOLE [MI]

Common Name

English

Nitrefazole [WHO-DD]

Common Name

English

EMD 15 700

Code

English

2-METHYL-4-NITRO-1-(4-NITROPHENYL)IMIDAZOLE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C471