AZOTOMYCIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H23N7O8
Molecular Weight	453.4066
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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=MNHVIVWFCMBFCV-AVGNSLFASA-N

InChI=1S/C17H23N7O8/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)/t11-,12-,13-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C17H23N7O8
Molecular Weight	453.4066
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	2
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/380801 | https://asu.pure.elsevier.com/en/publications/synthesis-of-azotomycin

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

Title	Date	PubMed
Azaserine, DON, and azotomycin: three diazo analogs of L-glutamine with clinical antitumor activity.	1979-06	380801
Phase II study of azotomycin (NSC-56654).	1968-09	5743707
PHASE I STUDY OF AZOTOMYCIN (NSC-56654).	1965-05	14327551

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:55:46 GMT 2025` Edited by `admin` on `Mon Mar 31 17:55:46 GMT 2025`
Record UNII	6TQY580E8M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AZOTOMYCIN

Official Name

English

ANTIBIOTIC-1719

Preferred Name

English

AZOTOMYCIN [USAN]

Common Name

English

azotomycin [INN]

Common Name

English

ANTIBIOTIC PRODUCED BY STREPTOMYCES AMBOFACIENS

Common Name

English

Azotomycin [WHO-DD]

Common Name

English

DUAZOMYCIN B

Common Name

English

NSC-56654

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C259