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Alanosine

Names

[ CAS No. ]:
5854-93-3

[ Name ]:
Alanosine

[Synonym ]:
SDX-102
L-Alanine, 3-(hydroxynitrosoamino)-
L-2-Amino-3-[(N-nitroso)hydroxylamino]propionic acid
alanosine
L-2-Amino-3-(hydroxynitrosoamino)propanoic Acid
3-[Hydroxy(nitroso)amino]-L-alanine
SDX 102
L-alanosine
L-Alanine, 3- (hydroxynitrosoamino)-

Biological Activity

[Description]:

L-Alanosine (NSC-153353), an antibiotic from Streptomyces alanosinicus, has antineoplastic activity. L-Alanosine (NSC-153353) inhibits adenylosuccinate synthetase, which converts inosine monophospate (IMP) into adenylosuccinate. L-Alanosine (NSC-153353) blocks the common de novo purine biosynthesis pathway and, thereby, inhibits tumor cells with MTAP deficiency[1][2][3].

[Related Catalog]:

Research Areas >> Cancer
Research Areas >> Infection
Signaling Pathways >> Others >> Others

[References]

[1]. Efferth T, et al. Identification of gene expression profiles predicting tumor cell response to L-alanosine. Biochem Pharmacol. 2003 Aug 15;66(4):613-21.

[2]. Chitnis MP, et al. Antitumor effect of L-alanosine (NSC 153553) on sensitive and resistant sublines of murine leukemias. Tumori. 1984 Aug 31;70(4):317-20.

[3]. Tyagi AK, et al. Identification of the antimetabolite of L-alanosine, L-alanosyl-5-amino-4-imidazolecarboxylic acid ribonucleotide, in tumors and assessment of its inhibition of adenylosuccinate synthetase. Cancer Res. 1980 Dec;40(12):4390-7.

Chemical & Physical Properties

[ Density]:
1.8±0.1 g/cm3

[ Boiling Point ]:
366.9±52.0 °C at 760 mmHg

[ Melting Point ]:
190ºC (dec.)

[ Molecular Formula ]:
C3H7N3O4

[ Molecular Weight ]:
149.105

[ Flash Point ]:
175.7±30.7 °C

[ Exact Mass ]:
149.043655

[ PSA ]:
116.22000

[ LogP ]:
-0.56

[ Vapour Pressure ]:
0.0±1.9 mmHg at 25°C

[ Index of Refraction ]:
1.616

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UE6490000
CHEMICAL NAME :
Propionic acid, 2-amino-3-(hydroxynitrosamino)-, (L)-
CAS REGISTRY NUMBER :
5854-93-3
LAST UPDATED :
199612
DATA ITEMS CITED :
3
MOLECULAR FORMULA :
C3-H7-N3-O4
MOLECULAR WEIGHT :
149.13
WISWESSER LINE NOTATION :
QVYZ1NQNO -L

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
600 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #3676490
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
845 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NCISP* National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. (Bethesda, MD 20205) Volume(issue)/page/year: JAN1986
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
300 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #3676490

Precursor & DownStream

Precursor

DownStream

Related Compounds