U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C8H11N3O4
Molecular Weight 213.1906
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of Duazomycin

SMILES

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

InChI

InChIKey=WBSWOKCKZUNHQV-ZETCQYMHSA-N
InChI=1S/C8H11N3O4/c1-5(12)11-7(8(14)15)3-2-6(13)4-10-9/h4,7H,2-3H2,1H3,(H,11,12)(H,14,15)/t7-/m0/s1

HIDE SMILES / InChI
Duazomycin (N-acetyl-DON) is one of the few naturally occurring compounds containing an aliphatic alpha diazoketo group, and is produced by Streptomyces ambofaciens. It is a derivative of 6-diazo-5-oxo-L-norleucine (DON) which was initially isolated from an unidentified Streptomyces species and which is produced together with N-acetyl-DON and duazomycin B (azotomycin) by S. ambofaciens. Duazomycin inhibited purine biosynthesis and caused accumulation of phosphoribosyl-N-formylglycineamide (FGAR) at low levels of inhibitor; higher levels blocked the synthesis of FGAR, indicating that the antibiotic behaved essentially like DON. Duazomycin is readily deacetylated by mammalian acylase to DON. As a glutamine antagonist, duazomycin was used in combination with azathioprine for the treatment of patients with advanced Wegener’s granulomatosis with renal involvement. Prolonged survival, remission of systemic signs and symptoms, roentogenologic improvement of pulmonary lesions, reduction in proteinuria and arrest of progression of renal insufficiency were observed.

Approval Year

PubMed

PubMed

TitleDatePubMed
BIOCHEMICAL EFFECTS OF DUAZOMYCIN A IN THE MOUSE PLASMA CELL NEOPLASM 70429.
1963 Dec
ENHANCED SUPPRESSION OF THE SECONDARY IMMUNE RESPONSE BY COMBINATION OF 6-MERCAPTOPURINE DUAZOMYCIN A'.
1963 Sep 14
Clinical and pharmacologic effects of combinations of 6-thioguanine and duazomycin A in patients with neoplastic disease.
1965 Sep
A pilot study of methotrexate, duazomycin A, and radiation therapy in carcinoma of the lung.
1966 Mar-Apr
Treatment of advanced Wegener's granulomatosis with azathioprine and duazomycin A.
1968 Feb 1
Enhanced suppression of experimental allergic encephalomyelitis by combination chemotherapy with duazomycin-A and 6-mercaptopurine.
1969 May

Sample Use Guides

0.2-0.3 mg/kg
Route of Administration: Intravenous
Name Type Language
Duazomycin
INN   USAN  
USAN   INN  
Official Name English
N-ACETYL-6-DIAZO-5-OXO-L-NORLEUCINE
Systematic Name English
NSC-51097
Code English
DIAZOMYCIN A
Common Name English
DUAZOMYCIN A
Common Name English
A-10270A
Code English
L-NORLEUCINE, N-ACETYL-6-DIAZO-5-OXO-
Systematic Name English
NORLEUCINE, N-ACETYL-6-DIAZO-5-OXO-
Systematic Name English
NORLEUCINE, N-ACETYL-6-DIAZO-5-OXO-, L-
Systematic Name English
N-ACETYL-3-DIAZO-5-OXO-L-NORLEUCINE
Systematic Name English
DUAZOMYCIN [USAN]
Common Name English
duazomycin [INN]
Common Name English
Code System Code Type Description
CAS
2508-89-6
Created by admin on Fri Dec 15 15:42:16 UTC 2023 , Edited by admin on Fri Dec 15 15:42:16 UTC 2023
PRIMARY
PUBCHEM
72622
Created by admin on Fri Dec 15 15:42:16 UTC 2023 , Edited by admin on Fri Dec 15 15:42:16 UTC 2023
PRIMARY
EPA CompTox
DTXSID501318378
Created by admin on Fri Dec 15 15:42:16 UTC 2023 , Edited by admin on Fri Dec 15 15:42:16 UTC 2023
PRIMARY
NSC
51097
Created by admin on Fri Dec 15 15:42:16 UTC 2023 , Edited by admin on Fri Dec 15 15:42:16 UTC 2023
PRIMARY
FDA UNII
W9AO16Q1WX
Created by admin on Fri Dec 15 15:42:16 UTC 2023 , Edited by admin on Fri Dec 15 15:42:16 UTC 2023
PRIMARY
SMS_ID
300000034202
Created by admin on Fri Dec 15 15:42:16 UTC 2023 , Edited by admin on Fri Dec 15 15:42:16 UTC 2023
PRIMARY
NCI_THESAURUS
C169922
Created by admin on Fri Dec 15 15:42:16 UTC 2023 , Edited by admin on Fri Dec 15 15:42:16 UTC 2023
PRIMARY
INN
1383
Created by admin on Fri Dec 15 15:42:16 UTC 2023 , Edited by admin on Fri Dec 15 15:42:16 UTC 2023
PRIMARY
ChEMBL
CHEMBL475736
Created by admin on Fri Dec 15 15:42:16 UTC 2023 , Edited by admin on Fri Dec 15 15:42:16 UTC 2023
PRIMARY