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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:22:52 GMT 2023` Edited by `admin` on `Fri Dec 15 15:22:52 GMT 2023`
Record UNII	6TQY580E8M
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

AZOTOMYCIN

Official Name

English

AZOTOMYCIN [USAN]

Common Name

English

azotomycin [INN]

Common Name

English

ANTIBIOTIC PRODUCED BY STREPTOMYCES AMBOFACIENS

Common Name

English

ANTIBIOTIC-1719

Code

English

Azotomycin [WHO-DD]

Common Name

English

DUAZOMYCIN B

Common Name

English

NSC-56654

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C259