ALANOSINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C3H7N3O4
Molecular Weight	149.1054
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

N[C@@H](CN(O)N=O)C(O)=O

InChI

InChIKey=MLFKVJCWGUZWNV-REOHCLBHSA-N

InChI=1S/C3H7N3O4/c4-2(3(7)8)1-6(10)5-9/h2,10H,1,4H2,(H,7,8)/t2-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11763167 | https://www.ncbi.nlm.nih.gov/pubmed/18618081

ALANOSINE is an antiviral and antitumor antibiotic derived from Streptomyces alanosinicus. It inhibits adenylosuccinate synthetase, which converts inosine monophosphate into adenylosuccinate, an intermediate in purine metabolism. ALANOSINE-induced disruption of de novo purine biosynthesis is potentiated by methylthioadenosine phosphorylase (MTAP) deficiency. In cancer cells that lack MTAP, required in the salvage pathway, ALANOSINE should deprive such cells (but not normal cells) of de novo synthesized adenosine. However, in clinical trials, it was ineffective in patients with advanced MTAP-deficient tumors.

Approval Year

PubMed

Title	Date	PubMed
Chemotherapy targeting methylthioadenosine phosphorylase (MTAP) deficiency in adult T cell leukemia (ATL).	2002 Sep	12200696
Identification of gene expression profiles predicting tumor cell response to L-alanosine.	2003 Aug 15	12906926
Status of methylthioadenosine phosphorylase and its impact on cellular response to L-alanosine and methylmercaptopurine riboside in human soft tissue sarcoma cells.	2004	15301428
A phase II multicenter study of L-alanosine, a potent inhibitor of adenine biosynthesis, in patients with MTAP-deficient cancer.	2009 Feb	18618081
Selective killing of tumors deficient in methylthioadenosine phosphorylase: a novel strategy.	2009 May 29	19478948
Gateways to clinical trials.	2009 Sep	19907722
Personalized cancer medicine: from molecular diagnostics to targeted therapy with natural products.	2010 Aug	20486071

Patents

Sample Use Guides

In Vivo Use Guide

80 mg/m2 by continuous intravenous infusion daily for 5 days every 21 days.

Route of Administration: Intravenous

In Vitro Use Guide

Alanosine, at a concentration as low as 2.7 muM, completely inhibits the incorporation of hypoxanthine into adenosine triphosphate by cultured Novikoff rat hepatoma cells.

Name

Type

Language

ALANOSINE

Official Name

English

NSC-153353

Code

English

NSC-529469

Code

English

alanosine [INN]

Common Name

English

(-)-(S)-2-AMINO-3-(HYDROXYNITROSAMINO)PROPIONIC ACID

Common Name

English

L-ALANOSINE [MI]

Common Name

English

ALANOSINE [MART.]

Common Name

English

SDX-102

Common Name

English

L-ALANOSINE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1556