Azaserine | CAS#115-02-6 | glutamine amidotransferase inhibitor

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

Azaserine

CAS# 115-02-6

Instruction

Theoretical Analysis

MedKoo Cat#: 206059
Name: Azaserine
CAS#: 115-02-6
Chemical Formula: C5H7N3O4
Exact Mass: 173.04
Molecular Weight: 173.127
Elemental Analysis: C, 34.69; H, 4.08; N, 24.27; O, 36.97

Price and Availability

Size	Price	Availability
50mg	USD 550	2 Weeks
100mg	USD 950	2 Weeks
200mg	USD 1650	2 Weeks
500mg	USD 2550	2 Weeks
1g	USD 3250	2 Weeks
2g	USD 5850	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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

More Info:

Instruction:

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Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 173.13 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

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Protivinsky R. Azaserine. Antibiot Chemother (1971). 1971;17:95-100. doi: 10.1159/000392366. PMID: 4951003.

2: Azaserine. IARC Monogr Eval Carcinog Risk Chem Man. 1976;10:73-7. PMID: 791808.

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. PMID: 380801.

4: Geisen SM, Aloisi CMN, Huber SM, Sandell ES, Escher NA, Sturla SJ. Direct Alkylation of Deoxyguanosine by Azaserine Leads to O6-Carboxymethyldeoxyguanosine. Chem Res Toxicol. 2021 Jun 21;34(6):1518-1529. doi: 10.1021/acs.chemrestox.0c00471. Epub 2021 Jun 1. PMID: 34061515.

5: COFFEY GL, HILLEGAS AB, KNUDSEN MP, KOEPSELL HJ, OYAAS JE, EHRLICH J. Azaserine: microbiological studies. Antibiot Chemother (Northfield). 1954 Jul;4(7):775-91. PMID: 24543177.

6: Williams-Hill DM, Olesen J, Zucker C, Kubitschek HE. Azaserine: further evidence for DNA damage in Escherichia coli. Mutat Res. 1984 Nov;129(2):153-64. doi: 10.1016/0027-5107(84)90148-9. PMID: 6390189.

7: STERNBERG SS, PHILIPS FS. Azaserine: pathological and pharmacological studies. Cancer. 1957 Sep-Oct;10(5):889-901. doi: 10.1002/1097-0142(195709/10)10:5<889::aid-cncr2820100506>3.0.co;2-t. PMID: 13472634.

8: Morgan RG, Papadimitriou JM, Crass RA. Potentiation of azaserine by cholestyramine in the rat. Int J Exp Pathol. 1990 Aug;71(4):485-91. PMID: 2400737; PMCID: PMC2002277.

9: Wei ZW, Niikura H, Wang M, Ryan KS. Identification of the Azaserine Biosynthetic Gene Cluster Implicates Hydrazine as an Intermediate to the Diazo Moiety. Org Lett. 2023 Jun 9;25(22):4061-4065. doi: 10.1021/acs.orglett.3c01229. Epub 2023 May 26. PMID: 37235858.

10: EHRLICH J, ANDERSON LE, COFFEY GL, HILLEGAS AB, KNUDSEN MP, KOEPSELL HJ, KOHBERGER DL, OYAAS JE. Antibiotic studies of azaserine. Nature. 1954 Jan 9;173(4393):72. doi: 10.1038/173072a0. PMID: 13132876.

11: Mandyam D V, Muthangi S. Survival of silk worm, Bombyx mori in azaserine induced oxidative stress. Comp Biochem Physiol C Toxicol Pharmacol. 2020 Feb;228:108637. doi: 10.1016/j.cbpc.2019.108637. Epub 2019 Oct 23. PMID: 31655299.

12: Kubitschek HE, Sepanski RJ. Azaserine: survival and mutation in Escherichia coli. Mutat Res. 1982 May;94(1):31-8. doi: 10.1016/0027-5107(82)90166-x. PMID: 7048085.

13: Williams MV, Kerr TJ, Lemmon RD, Tritz GJ. Azaserine resistance in Escherichia coli: chromosomal location of multiple genes. J Bacteriol. 1980 Jul;143(1):383-8. doi: 10.1128/jb.143.1.383-388.1980. PMID: 6995438; PMCID: PMC294251.

14: STOCK CC, REILLY HC, BUCKLEY SM, CLARKE DA, RHOADS CP. Azaserine, a new tumour-inhibitory substance; studies with Crocker mouse sarcoma 180. Nature. 1954 Jan 9;173(4393):71-2. doi: 10.1038/173071a0. PMID: 13132875.

15: KAPLAN L, REILLY HC, STOCK CC. Action of azaserine on Escherichia coli. J Bacteriol. 1959 Oct;78(4):511-9. doi: 10.1128/jb.78.4.511-519.1959. PMID: 14404400; PMCID: PMC290578.

16: BARTZ QR, ELDER CC, FROHARDT RP, FUSARI SA, HASKELL TH, JOHANNESSEN DW, RYDER A. Isolation and characterization of azaserine. Nature. 1954 Jan 9;173(4393):72-3. doi: 10.1038/173072b0. PMID: 13132877.

17: Wyngaarden JB. Glutamine phosphoribosylpyrophosphate amidotransferase. Curr Top Cell Regul. 1972;5:135-76. doi: 10.1016/b978-0-12-152805-8.50011-3. PMID: 4358203.

18: Yildiz H, Kalipci E, Oztas H, Yildiz D. Effects of acetylsalicylic acid on rats: An in vivo experimental study in azaserine-rat model. J Cancer Res Ther. 2019 Jan-Mar;15(1):231-236. doi: 10.4103/jcrt.JCRT_1319_16. PMID: 30880783.

19: Fleischman RW, Baker JR, Schaeppi U, Thompson GR, Rosenkrantz H, Cooney DA, Davis RD. Azaserine-induced pathology in dogs. Toxicol Appl Pharmacol. 1972 Aug;22(4):595-606. doi: 10.1016/0041-008x(72)90287-6. PMID: 5045764.

20: Yager JD Jr, Roebuck BD, Zurlo J, Longnecker DS, Weselcouch EO, Wilpone SA. A single-dose protocol for azaserine initiation of pancreatic carcinogenesis in the rat. Int J Cancer. 1981 Nov 15;28(5):601-6. doi: 10.1002/ijc.2910280511. PMID: 6975760.

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