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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 H
Molecular Weight 1.0079
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C17H21N7O8
Molecular Weight 451.3907
Charge -2
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 2
Optical Activity UNSPECIFIED

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
PHASE I STUDY OF AZOTOMYCIN (NSC-56654).
1965 May
Phase II study of azotomycin (NSC-56654).
1968 Sep
Azaserine, DON, and azotomycin: three diazo analogs of L-glutamine with clinical antitumor activity.
1979 Jun
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:48:55 GMT 2023
Edited
by admin
on Fri Dec 15 15:48:55 GMT 2023
Record UNII
CGQ6700612
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AZOTOMYCIN MONOSODIUM
Common Name English
NORLEUCINE, 6-DIAZO-N-(6-DIAZO-N-.GAMMA.-GLUTAMYL-5-OXONORLEUCYL)-5-OXO-, MONOSODIUM SALT
Systematic Name English
L-NORLEUCINE, 6-DIAZO-N-(6-DIAZO-N-L-.GAMMA.-GLUTAMYL-5-OXO-L-NORLEUCYL)-5-OXO-, MONOSODIUM SALT
Systematic Name English
Code System Code Type Description
CAS
22204-48-4
Created by admin on Fri Dec 15 15:48:55 GMT 2023 , Edited by admin on Fri Dec 15 15:48:55 GMT 2023
PRIMARY
CAS
55156-24-6
Created by admin on Fri Dec 15 15:48:55 GMT 2023 , Edited by admin on Fri Dec 15 15:48:55 GMT 2023
NON-SPECIFIC STOICHIOMETRY
PUBCHEM
3043141
Created by admin on Fri Dec 15 15:48:55 GMT 2023 , Edited by admin on Fri Dec 15 15:48:55 GMT 2023
PRIMARY
FDA UNII
CGQ6700612
Created by admin on Fri Dec 15 15:48:55 GMT 2023 , Edited by admin on Fri Dec 15 15:48:55 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY