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
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
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
Title | Date | PubMed |
---|---|---|
BIOCHEMICAL EFFECTS OF DUAZOMYCIN A IN THE MOUSE PLASMA CELL NEOPLASM 70429. | 1963 Dec |
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ENHANCED SUPPRESSION OF THE SECONDARY IMMUNE RESPONSE BY COMBINATION OF 6-MERCAPTOPURINE DUAZOMYCIN A'. | 1963 Sep 14 |
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Clinical and pharmacologic effects of combinations of 6-thioguanine and duazomycin A in patients with neoplastic disease. | 1965 Sep |
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A pilot study of methotrexate, duazomycin A, and radiation therapy in carcinoma of the lung. | 1966 Mar-Apr |
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Treatment of advanced Wegener's granulomatosis with azathioprine and duazomycin A. | 1968 Feb 1 |
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Enhanced suppression of experimental allergic encephalomyelitis by combination chemotherapy with duazomycin-A and 6-mercaptopurine. | 1969 May |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/5839715
0.2-0.3 mg/kg
Route of Administration:
Intravenous
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2508-89-6
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72622
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DTXSID501318378
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51097
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W9AO16Q1WX
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300000034202
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C169922
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1383
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CHEMBL475736
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ACTIVE MOIETY