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Details

Stereochemistry ACHIRAL
Molecular Formula C2H4N4O2
Molecular Weight 116.0788
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of AZODICARBONAMIDE

SMILES

NC(=O)\N=N\C(N)=O

InChI

InChIKey=XOZUGNYVDXMRKW-AATRIKPKSA-N
InChI=1S/C2H4N4O2/c3-1(7)5-6-2(4)8/h(H2,3,7)(H2,4,8)/b6-5+

HIDE SMILES / InChI

Molecular Formula C2H4N4O2
Molecular Weight 116.0788
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

The principal end-use of azodicarbonamide (ADA) is as a blowing agent in the rubber and plastics industries. It is used in the expansion of a wide range of polymers, including polyvinyl chloride, polyolefins, and natural and synthetic rubbers. Azodicarbonamide has in the past been used in the United Kingdom and Eire (but not other European Union member states) as a flour improver in the bread-making industry, but this use is no longer permitted. In vitro azodicarbonamide decreases the intracellular pool of deoxyribonucleotide and thymidine phosphorylation. Ribonucleotide reductase is a potential target of azodicarbonamide. Azodicarbonamide (ADA) represents a new compound that inhibits HIV-1 and a broad range of retroviruses by targeting the nucleocapsid CCHC domains. Vandevelde et al. also recently disclosed that ADA inhibits HIV-1 infection via an unidentified mechanism and that ADA was introduced into Phase I/II clinical trials in Europe for advanced AIDS. These studies distinguish ADA as the first known nucleocapsid inhibitor to progress to human trials and provide a lead compound for drug optimization. Phase-II development is ongoing in Spain for HIV infections.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
7.6 µM [IC50]
5.3 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Doses

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
The maximal tolerated dosage of azodicarbonamide (ADA) appears to be 2 g (three times daily).
Route of Administration: Oral
In Vitro Use Guide
Two hours exposure of lymphoblastic SUP-T1 cells to 100 uM azodicarbonamide induced a 50% reduction of each deoxyribonucleotide triphosphate.
Substance Class Chemical
Record UNII
56Z28B9C8O
Record Status Validated (UNII)
Record Version