AZASERINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C5H7N3O4
Molecular Weight	173.1268
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=MZZGOOYMKKIOOX-VKHMYHEASA-N

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

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6975044 | https://www.ncbi.nlm.nih.gov/pubmed/23990361 | https://www.ncbi.nlm.nih.gov/pubmed/380801 | https://www.cancer.gov/publications/dictionaries/cancer-drug?cdrid=39156

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 was used in clinical studies as a potential antineoplastic agent. Azaserine is an inhibitor of glutamine: fructose-6-phosphate amidotransferase (GFAT), which is the rate-limiting enzyme in the hexosamine biosynthetic pathway. Azaserine is used to model pancreatic cancer in rodents.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glucosamine--fructose-6-phosphate aminotransferase [isomerizing] 1 1 Target ID: CHEMBL1909481 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23990361	Inhibitor 8504
protein-glutamine gamma-glutamyltransferase activity 1 Target ID: GO:0003810 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2883739	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13172694 https://www.ncbi.nlm.nih.gov/pubmed/380801	Primary		Not Provided 511	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Azaserine, DON, and azotomycin: three diazo analogs of L-glutamine with clinical antitumor activity.	1979-06	380801
Effects of 6-diazo-5-oxol-norleucine and other tumor inhibitors on the biosynthesis of nicotinamide adenine dinucleotide in mice.	1966-02	4285554
Clinical trials of O-diazoacetyl-L-serine (azaserine) in neoplastic disease.	1954-07	13172694
Isolation and characterization of azaserine.	1954-01-09	13132877
Azaserine, a new tumour-inhibitory substance; studies with Crocker mouse sarcoma 180.	1954-01-09	13132875

Sample Use Guides

In Vivo Use Guide

Clinical trials: 8-10 mg/kg/day (p.o. or i.v.). Induction of pancreatic cancer in rats: 10-30 mg/kg daily i.p.

Route of Administration: Other

In Vitro Use Guide

0.1 mg/ml azaserine induces somatic crossing over, point mutation and segmental loss as major effects in a soybean test system.

Name

Type

Language

CL-337

Preferred Name

English

AZASERINE

Official Name

English

CL 337

Code

English

AZASERINE [HSDB]

Common Name

English

CN-15757

Code

English

NSC-742

Code

English

P-165

Code

English

L-SERINE, DIAZOACETATE (ESTER)

Common Name

English

AZASERINE [USAN]

Common Name

English

azaserine [INN]

Common Name

English

AZASERINE [IARC]

Common Name

English

AZASERINE [MI]

Common Name

English

CN-15,757

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C2158