Synonym
Azotomycin, Antibiotic 1719, Duazomycin B, NSC 56654
IUPAC/Chemical Name
L-Norleucine, 6-diazo-N-(6-diazo-N-L-gamma-glutamyl-5-oxo-L-norleucyl)-5-oxo-
InChi Key
MNHVIVWFCMBFCV-AVGNSLFASA-N
InChi Code
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
SMILES Code
O=C(O)[C@H](CCC(C=[N+]=[N-])=O)NC([C@H](CCC(C=[N+]=[N-])=O)NC(CC[C@@H](C(O)=O)N)=O)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
453.41
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Chang P, Wiernik PH. Phase II study of azotomycin in sarcomas. Cancer Treat Rep. 1977 Dec;61(9):1719-20. PubMed PMID: 340036.
2: Cooney DA, Yavelow J, Zlotoff R, Bergenstal R, Burg A, Morrison R, Fleischman R. Azotomycin--toxicologic, biochemical and pharmacologic studies in mice. Biochem Pharmacol. 1974 Dec 15;23(24):3467-89. PubMed PMID: 4155310.
3: Catane R, Von Hoff DD, Glaubiger DL, Muggia FM. Azaserine, DON, and azotomycin: three diazo analogs of L-glutamine with clinical antitumor activity. Cancer Treat Rep. 1979 Jun;63(6):1033-8. Review. PubMed PMID: 380801.
4: Weiss AJ, Mastrangelo MJ. Phase I study of a combination of azotomycin (NSC-56654) and 5-fluorouracil (NSC-19893) in malignant disease. Cancer Chemother Rep. 1970 Apr;54(2):109-11. PubMed PMID: 4946000.
5: Kisner DL, Catane R, Muggia FM. The rediscovery of DON (6-diazo-5-oxo-L-norleucine). Recent Results Cancer Res. 1980;74:258-63. PubMed PMID: 7192426.
6: Pittillo RF, Woolley C, Brockman RW, Ho DH. Azotomycin (NSC-56654): biologic fate in mice and man. Cancer Chemother Rep. 1971 Feb;55(1):47-52. PubMed PMID: 5121650.
7: Carter SK. Azotomycin (NSC-56654)--clinical brochure. Cancer Chemother Rep 3. 1968 Dec;1(1):207-17. PubMed PMID: 4917775.
8: Brockman RW, Pittillo RF, Shaddix S, Hill DL. Mode of action of azotomycin. Antimicrob Agents Chemother (Bethesda). 1969;9:56-62. PubMed PMID: 4919007.
9: Ovejera AA, Houchens DP, Catane R, Sheridan MA, Muggia FM. Efficacy of 6-diazo-5-oxo-L-norleucine and N-[N-gamma-glutamyl-6-diazo-5-oxo-norleucinyl]-6-diazo-5-oxo-norleucine against experimental tumors in conventional and nude mice. Cancer Res. 1979 Aug;39(8):3220-4. PubMed PMID: 572261.
10: Hersh EM, Brown BW. Inhibition of immune responses by glutamine antagonism: effect of azotomycin on lymphocyte blastogenesis. Cancer Res. 1971 Jun;31(6):834-40. PubMed PMID: 5088487.
11: Weiss AJ, Ramirez G, Grage T, Strawitz J, Goldman L, Downing V. Phase II study of azotomycin (NSC-56654). Cancer Chemother Rep. 1968 Sep;52(5):611-4. PubMed PMID: 5743707.
12: Gauze GF. [Search for antibiotic antimetabolites]. Antibiotiki. 1976 Jan;21(1):3-5. Review. Russian. PubMed PMID: 776066.
13: Sava G, Giraldi T, Baldini L. Antitumor activity of N-diazoacetyl derivatives of glycine and phenylalanine against P388 leukemia and B16 melanoma in mice. Cancer Treat Rep. 1982 Jan;66(1):179-81. PubMed PMID: 6796268.
14: ANSFIELD FJ. PHASE I STUDY OF AZOTOMYCIN (NSC-56654). Cancer Chemother Rep. 1965 May;46:37-40. PubMed PMID: 14327551.
