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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H21N7O8.Na.H
Molecular Weight 475.3884
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of AZOTOMYCIN MONOSODIUM

SMILES

[H+].[Na+].N[C@@H](CCC(=O)N[C@@H](CCC(=O)C=[N+]=[N-])C(=O)N[C@@H](CCC(=O)C=[N+]=[N-])C([O-])=O)C([O-])=O

InChI

InChIKey=BLLHCAJGRHAVEL-QKWXXBCPSA-M
InChI=1S/C17H23N7O8.Na/c18-11(16(29)30)3-6-14(27)23-12(4-1-9(25)7-21-19)15(28)24-13(17(31)32)5-2-10(26)8-22-20;/h7-8,11-13H,1-6,18H2,(H,23,27)(H,24,28)(H,29,30)(H,31,32);/q;+1/p-1/t11-,12-,13-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C17H22N7O8
Molecular Weight 452.3987
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 3 / 3
E/Z Centers 2
Optical Activity UNSPECIFIED

Molecular Formula Na
Molecular Weight 22.98976928
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

AZOTOMYCIN, a diazo analog of L-glutamine, is an antineoplastic antibiotic isolated from Streptomyces ambofaciens. It inhibits glutamine-dependent enzymes involved in purine and pyrimidine biosynthesis, resulting in inhibition of DNA synthesis. It was tested in human malignancies in the 1950s.

Approval Year

PubMed

PubMed

TitleDatePubMed
Azaserine, DON, and azotomycin: three diazo analogs of L-glutamine with clinical antitumor activity.
1979-06
Phase II study of azotomycin (NSC-56654).
1968-09
PHASE I STUDY OF AZOTOMYCIN (NSC-56654).
1965-05
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:09:39 GMT 2025
Edited
by admin
on Mon Mar 31 18:09:39 GMT 2025
Record UNII
CGQ6700612
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AZOTOMYCIN MONOSODIUM
Common Name English
L-NORLEUCINE, 6-DIAZO-N-(6-DIAZO-N-L-.GAMMA.-GLUTAMYL-5-OXO-L-NORLEUCYL)-5-OXO-, MONOSODIUM SALT
Preferred Name English
NORLEUCINE, 6-DIAZO-N-(6-DIAZO-N-.GAMMA.-GLUTAMYL-5-OXONORLEUCYL)-5-OXO-, MONOSODIUM SALT
Systematic Name English
Code System Code Type Description
CAS
22204-48-4
Created by admin on Mon Mar 31 18:09:39 GMT 2025 , Edited by admin on Mon Mar 31 18:09:39 GMT 2025
PRIMARY
CAS
55156-24-6
Created by admin on Mon Mar 31 18:09:39 GMT 2025 , Edited by admin on Mon Mar 31 18:09:39 GMT 2025
NON-SPECIFIC STOICHIOMETRY
PUBCHEM
3043141
Created by admin on Mon Mar 31 18:09:39 GMT 2025 , Edited by admin on Mon Mar 31 18:09:39 GMT 2025
PRIMARY
FDA UNII
CGQ6700612
Created by admin on Mon Mar 31 18:09:39 GMT 2025 , Edited by admin on Mon Mar 31 18:09:39 GMT 2025
PRIMARY
Related Record Type Details
ACTIVE MOIETY