Title: Azaserine
CAS Registry Number: 115-02-6
CAS Name: L-Serine diazoacetate (ester)
Additional Names: O-diazoacetyl-L-serine
Manufacturers' Codes: CL-337; CN-15757; P-165
Molecular Formula: C5H7N3O4
Molecular Weight: 173.13
Percent Composition: C 34.69%, H 4.08%, N 24.27%, O 36.97%
Literature References: Antitumor antibiotic produced by Streptomyces sp. Isoln, characterization, and antitumor activity: C. C. Stock et al., Nature 173, 71 (1954); J. Ehrlich et al., ibid. 72; Q. R. Bartz et al., ibid. 72; S. A. Fusari et al., J. Am. Chem. Soc. 76, 2878 (1954). Structural studies: idem et al., ibid. 2881. Synthetic studies: J. A. Moore et al., ibid., 2884; E. D. Nicolaides et al., ibid., 2887; T. J. Curphey, D. S. Daniel, J. Org. Chem. 43, 4666 (1978). Pathology and pharmacology studies: S. S. Sternberg, F. S. Philips, Cancer 10, 889 (1957). Crystal and molecular structure: A. Fitzgerald, L. H. Jensen, Acta Crystallogr. B34, 828 (1978). Review of carcinogenicity studies: IARC Monographs 10, 73-77 (1976). Review: Pettillo, Hunt, Antibiotics vol. 1, D. Gottlieb, P. Shaw, Eds. (Springer-Verlag, New York, 1967) pp 481-493. Use in study of the progression of pancreatic adenocarcinoma in rat models: K. Nagy et al., Histochem. Cell Biol. 119, 405 (2003).
Properties: Light yellow-green needles from aq ethanol, mp 146-162° (dec). [a]D27.5 -0.5° (c = 8.46% in H2O at pH 5.18). uv max (pH 7): 250.5 nm (E1%1cm 1140); in 0.1N NaOH: 252 nm (E1%1cm 1230). Very sol in water; slightly sol in abs methanol, abs ethanol, acetone, but sol in warm aq solns of these solvents. pKa 8.55. LD50 in mice, rats (mg/kg/day): 150, 170 orally (Sternberg, Philips).
Melting point: mp 146-162° (dec)
pKa: pKa 8.55
Optical Rotation: [a]D27.5 -0.5° (c = 8.46% in H2O at pH 5.18)
Absorption maximum: uv max (pH 7): 250.5 nm (E1%1cm 1140)
Toxicity data: LD50 in mice, rats (mg/kg/day): 150, 170 orally (Sternberg, Philips)
Use: Reagent used to induce pancreatic cancer in experimental animal models.
Azasetron Azatadine Azelaic Acid Azelastine Azelnidipine

Systematic (IUPAC) name
Clinical data
Legal status  ?
CAS number 115-02-6 YesY
ATC code None
PubChem CID 5284344
ChemSpider 16735688 YesY
UNII 87299V3Q9W YesY
KEGG D03032 YesY
Chemical data
Formula C5H7N3O4 
Mol. mass 173.127 g/mol
 N (what is this?)  (verify)

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

•Description Azaserine is an inhibitor of the rate limiting step of the hexosamine biosynthethic pathway (HBP) and an irreversible inhibitor of GGT1 (gamma-Glutamyltranspeptidase). Independent of inhibiting the HBP pathway, azarine studies have demonstrated that it can protect against hyperglycemic endothelial damage through its antioxidant effect. Azarine and acivicin (sc-200498), another GGT inhibitor, bind to GGT at its substrate-binding pocket. The compound has been shown to elevate the SOD-2 (manganese-superoxide dismutase (MnSOD)) protein level as well as inhibit the oxidative stress and the expression of VCAM-1 and ICAM-1 in response to TNFα. Research indicates that azaserine has the potential to be used as a probe for identifying the L-(leucine-favoring) system transporter in human T-lymphocytes

•Specifications Purity: ≥98%Physical Appearance: White to yellow to powder•Properties Molecular Weight: 173.127Molecular Formula: C5H7N3O4Form: SolidSolubility: Soluble in water (50 mg/ml), Slightly soluble in methanol, and absolute alcohol.Melting Point: 146-162 °C (dec.)Boling Point: 589.73 °C (Predicted)Vapor Pressure: 1.53 x 10-10 mmHg at 25 °C


1. Segel, G.B., et al. 1989. J. Biol. Chem. 264: 16399-16402. PMID 2789219 2. Hull, R.L., et al. 2007. Am. J. Physiol., Cell Physiol. 293: C1586-C1593. PMID 17804609 3. Wada, K., et al. 2008. J. Mol. Biol. 380: 361-372. PMID 18555071 4. Rajapakse, A.G., et al. 2009. Am. J. Physiol. Heart Circ. Physiol. 296: H815-H822. PMID 19136606 5. Angana Gupta Rajapakse, Xiu-Fen Ming, João M. Carvas, and Zhihong Yang. The hexosamine biosynthesis inhibitor azaserine prevents endothelial inflammation and dysfunction under hyperglycemic condition through antioxidant effects. 6. Lebedeva ZI, Kabanova EA, Berezov TT. 1986 Mar;12(3):413-20. 6-diazo-5-oxo-L-norleucine and azaserine as affinity inhibitors of glutamin(asparagin)ase.