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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 of Alanosine

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

Molecular Formula C3H7N3O4
Molecular Weight 149.1054
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

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.
Substance Class Chemical
Record UNII
2CNI71214Y
Record Status Validated (UNII)
Record Version