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
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+
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3301398 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12147296 |
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Target ID: CHEMBL612675 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12672577 |
7.6 µM [IC50] | ||
Target ID: CHEMBL613131 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12672577 |
5.3 µM [IC50] | ||
Target ID: CHEMBL378 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
Doses
Dose | Population | Adverse 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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
inconclusive [IC50 31.6228 uM] | ||||
no [Activation 31.6228 uM] |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Semicarbazide formation in flour and bread. | 2008 Mar 26 |
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Comparative studies by IR, Raman, and surface-enhanced Raman spectroscopy of azodicarbonamide, biurea and semicarbazide hydrochloride. | 2013 Oct |
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Application of Visible/Near-Infrared Spectroscopy in the Prediction of Azodicarbonamide in Wheat Flour. | 2017 Oct |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11192866
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12147296
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
Edited
Fri Dec 15 15:55:23 GMT 2023
by
admin
on
Fri Dec 15 15:55:23 GMT 2023
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Record UNII |
56Z28B9C8O
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Record Status |
Validated (UNII)
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Record Version |
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CFR |
21 CFR 172.806
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