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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
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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.

Approval Year

Doses

Doses

DosePopulationAdverse events​
2 g 3 times / day multiple, oral (unknown)
MTD
Dose: 2 g, 3 times / day
Route: oral
Route: multiple
Dose: 2 g, 3 times / day
Sources:
unhealthy, ADULT
n = 11
Health Status: unhealthy
Condition: AIDS
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Population Size: 11
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
inconclusive [IC50 31.6228 uM]
no [Activation 31.6228 uM]
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Semicarbazide formation in flour and bread.
2008 Mar 26
Comparative studies by IR, Raman, and surface-enhanced Raman spectroscopy of azodicarbonamide, biurea and semicarbazide hydrochloride.
2013 Oct
Application of Visible/Near-Infrared Spectroscopy in the Prediction of Azodicarbonamide in Wheat Flour.
2017 Oct
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Patients with advanced AIDS have been treated compassionately with daily doses of 500 mg tid up to 2 g tid for periods exceeding 12 months. https://www.ncbi.nlm.nih.gov/pubmed/8743081
The maximal tolerated dosage of azodicarbonamide (ADA) appears to be 2 g (three times daily).
Route of Administration: Oral
Two hours exposure of lymphoblastic SUP-T1 cells to 100 uM azodicarbonamide induced a 50% reduction of each deoxyribonucleotide triphosphate.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:55:23 GMT 2023
Edited
by admin
on Fri Dec 15 15:55:23 GMT 2023
Record UNII
56Z28B9C8O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AZODICARBONAMIDE
FCC   MI  
Common Name English
NSC-41038
Code English
AZODICARBOXAMIDE
Common Name English
AZOBISCARBOXAMIDE
Common Name English
AZOBISCARBONAMIDE
Common Name English
1,2-DIAZENEDICARBOXAMIDE
Systematic Name English
1,1'-AZOBIS(FORMAMIDE) [HSDB]
Common Name English
NSC-674447
Code English
DIAZENEDICARBOXAMIDE
Systematic Name English
C,C'-AZODI(FORMAMIDE)
Systematic Name English
FORMAMIDE, 1,1'-AZOBIS-
Systematic Name English
1,1'-AZOBISFORMAMIDE
Systematic Name English
AZODICARBONAMIDE [MI]
Common Name English
1,1'-AZOBISCARBAMIDE
Common Name English
AZODICARBONAMIDE [FCC]
Common Name English
AZODICARBOXYLIC ACID DIAMIDE
Common Name English
Classification Tree Code System Code
CFR 21 CFR 172.806
Created by admin on Fri Dec 15 15:55:23 GMT 2023 , Edited by admin on Fri Dec 15 15:55:23 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
204-650-8
Created by admin on Fri Dec 15 15:55:23 GMT 2023 , Edited by admin on Fri Dec 15 15:55:23 GMT 2023
PRIMARY
EPA CompTox
DTXSID0024553
Created by admin on Fri Dec 15 15:55:23 GMT 2023 , Edited by admin on Fri Dec 15 15:55:23 GMT 2023
PRIMARY
NSC
41038
Created by admin on Fri Dec 15 15:55:23 GMT 2023 , Edited by admin on Fri Dec 15 15:55:23 GMT 2023
PRIMARY
HSDB
1097
Created by admin on Fri Dec 15 15:55:23 GMT 2023 , Edited by admin on Fri Dec 15 15:55:23 GMT 2023
PRIMARY
NSC
674447
Created by admin on Fri Dec 15 15:55:23 GMT 2023 , Edited by admin on Fri Dec 15 15:55:23 GMT 2023
PRIMARY
PUBCHEM
5462814
Created by admin on Fri Dec 15 15:55:23 GMT 2023 , Edited by admin on Fri Dec 15 15:55:23 GMT 2023
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WIKIPEDIA
AZODICARBONAMIDE
Created by admin on Fri Dec 15 15:55:23 GMT 2023 , Edited by admin on Fri Dec 15 15:55:23 GMT 2023
PRIMARY
CAS
123-77-3
Created by admin on Fri Dec 15 15:55:23 GMT 2023 , Edited by admin on Fri Dec 15 15:55:23 GMT 2023
PRIMARY
FDA UNII
56Z28B9C8O
Created by admin on Fri Dec 15 15:55:23 GMT 2023 , Edited by admin on Fri Dec 15 15:55:23 GMT 2023
PRIMARY
SMS_ID
100000177292
Created by admin on Fri Dec 15 15:55:23 GMT 2023 , Edited by admin on Fri Dec 15 15:55:23 GMT 2023
PRIMARY
MERCK INDEX
m2182
Created by admin on Fri Dec 15 15:55:23 GMT 2023 , Edited by admin on Fri Dec 15 15:55:23 GMT 2023
PRIMARY Merck Index
MESH
C004525
Created by admin on Fri Dec 15 15:55:23 GMT 2023 , Edited by admin on Fri Dec 15 15:55:23 GMT 2023
PRIMARY