Azaserine
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 206059

CAS#: 115-02-6

Description: Azaserine is a naturally occurring serine derivative diazo compound with antineoplastic properties, Azaserine functions as a purine antagonist and glutamine analogue (glutamine amidotransferase inhibitor) that competitively inhibits pathways in which glutamine is metabolized. An antibiotic and antitumor agent, Azaserine is used in clinical studies as a potential antineoplastic agent.


Chemical Structure

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Azaserine
CAS# 115-02-6

Theoretical Analysis

MedKoo Cat#: 206059
Name: Azaserine
CAS#: 115-02-6
Chemical Formula: C5H7N3O4
Exact Mass: 173.04366
Molecular Weight: 173.12678
Elemental Analysis: C, 34.69; H, 4.08; N, 24.27; O, 36.97

Price and Availability

Size Price Availability Quantity
25.0mg USD 190.0 2 Weeks
50.0mg USD 250.0 2 Weeks
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Synonym: Azaserine; diazoacetate (ester) LSerine; diazoacetylserine; serine diazoacetate. Abbreviations: AZAS; AZS. Code names: CL337; CN15757; P165

IUPAC/Chemical Name: (S)-2-amino-3-(2-diazoacetoxy)propanoic acid

InChi Key: MZZGOOYMKKIOOX-VKHMYHEASA-N

InChi Code: InChI=1S/C5H7N3O4/c6-3(5(10)11)2-12-4(9)1-8-7/h1,3H,2,6H2,(H,10,11)/t3-/m0/s1

SMILES Code: O=C(O)[C@@H](N)COC(C=[N+]=[N-])=O

Appearance: Solid powder

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, not in water

Shelf Life: >5 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 173.12678 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.

Recalculate based on batch purity %
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

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1: Huang JL, Yang SX. Safety of umbilical cord blood-derived mesenchymal stem cells (MSCs) following 5-azaserine induction and inhibition of human cardiac myocyte apoptosis by MSCs. Saudi Med J. 2009 Sep;30(9):1144-9. PubMed PMID: 19750258.

2: Rajapakse AG, Ming XF, Carvas JM, Yang Z. The hexosamine biosynthesis inhibitor azaserine prevents endothelial inflammation and dysfunction under hyperglycemic condition through antioxidant effects. Am J Physiol Heart Circ Physiol. 2009 Mar;296(3):H815-22. doi: 10.1152/ajpheart.00756.2008. Epub 2009 Jan 9. PubMed PMID: 19136606.

3: Wada K, Hiratake J, Irie M, Okada T, Yamada C, Kumagai H, Suzuki H, Fukuyama K. Crystal structures of Escherichia coli gamma-glutamyltranspeptidase in complex with azaserine and acivicin: novel mechanistic implication for inhibition by glutamine antagonists. J Mol Biol. 2008 Jul 4;380(2):361-72. doi: 10.1016/j.jmb.2008.05.007. Epub 2008 May 12. PubMed PMID: 18555071.

4: Hull RL, Zraika S, Udayasankar J, Kisilevsky R, Szarek WA, Wight TN, Kahn SE. Inhibition of glycosaminoglycan synthesis and protein glycosylation with WAS-406 and azaserine result in reduced islet amyloid formation in vitro. Am J Physiol Cell Physiol. 2007 Nov;293(5):C1586-93. Epub 2007 Sep 5. PubMed PMID: 17804609; PubMed Central PMCID: PMC2365901.

5: Koyanagi T, Katayama T, Suzuki H, Kumagai H. The LIV-I/LS system as a determinant of azaserine sensitivity of Escherichia coli K-12. FEMS Microbiol Lett. 2004 Aug 1;237(1):73-7. PubMed PMID: 15268940.

6: Appel MJ, Woutersen RA. Effects of a diet high in fish oil (MaxEPA) on the formation of micronucleated erythrocytes in blood and on the number of atypical acinar cell foci Induced in rat pancreas by azaserine. Nutr Cancer. 2003;47(1):57-61. PubMed PMID: 14769538.

7: Nagy K, Tóth S, Pálfia Z, Réz G. Angiogenesis is continuous with two peaks during azaserine-induced rat pancreatic adenocarcinoma progression: an electron microscopic morphometrical study. Oncol Rep. 2003 Nov-Dec;10(6):1999-2004. PubMed PMID: 14534733.

8: Nagy K, Pálfia Z, Réz G. Characterisation of the progression of azaserine-induced rat pancreatic adenocarcinoma by proliferative cell nuclear antigen, basement membrane laminin and trypsinogen immunohistochemistry. Histochem Cell Biol. 2003 May;119(5):405-13. Epub 2003 May 13. PubMed PMID: 12743826.

9: Tóth S, Nagy K, Pálfia Z, Réz G. Cellular autophagic capacity changes during azaserine-induced tumour progression in the rat pancreas. Up-regulation in all premalignant stages and down-regulation with loss of cycloheximide sensitivity of segregation along with malignant transformation. Cell Tissue Res. 2002 Sep;309(3):409-16. Epub 2002 Jul 10. PubMed PMID: 12195297.

10: Nagy K, Pálfia Z, Réz G. Quantitative microvascular changes during azaserine-initiated pancreatic carcinogenesis. Acta Biol Hung. 2001;52(4):403-9. PubMed PMID: 11693990.



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