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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
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

PubMed

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

Patents

Sample Use Guides

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
INN   MART.  
INN  
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
MI  
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C1556
Created by admin on Fri Dec 15 15:21:45 GMT 2023 , Edited by admin on Fri Dec 15 15:21:45 GMT 2023
NCI_THESAURUS C2168
Created by admin on Fri Dec 15 15:21:45 GMT 2023 , Edited by admin on Fri Dec 15 15:21:45 GMT 2023
Code System Code Type Description
CAS
5854-93-3
Created by admin on Fri Dec 15 15:21:45 GMT 2023 , Edited by admin on Fri Dec 15 15:21:45 GMT 2023
PRIMARY
ChEMBL
CHEMBL452715
Created by admin on Fri Dec 15 15:21:45 GMT 2023 , Edited by admin on Fri Dec 15 15:21:45 GMT 2023
PRIMARY
WIKIPEDIA
ALANOSINE
Created by admin on Fri Dec 15 15:21:45 GMT 2023 , Edited by admin on Fri Dec 15 15:21:45 GMT 2023
PRIMARY
PUBCHEM
90657278
Created by admin on Fri Dec 15 15:21:45 GMT 2023 , Edited by admin on Fri Dec 15 15:21:45 GMT 2023
PRIMARY
EPA CompTox
DTXSID501024175
Created by admin on Fri Dec 15 15:21:45 GMT 2023 , Edited by admin on Fri Dec 15 15:21:45 GMT 2023
PRIMARY
EVMPD
SUB05291MIG
Created by admin on Fri Dec 15 15:21:45 GMT 2023 , Edited by admin on Fri Dec 15 15:21:45 GMT 2023
PRIMARY
MERCK INDEX
m1469
Created by admin on Fri Dec 15 15:21:45 GMT 2023 , Edited by admin on Fri Dec 15 15:21:45 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C994
Created by admin on Fri Dec 15 15:21:45 GMT 2023 , Edited by admin on Fri Dec 15 15:21:45 GMT 2023
PRIMARY
NSC
529469
Created by admin on Fri Dec 15 15:21:45 GMT 2023 , Edited by admin on Fri Dec 15 15:21:45 GMT 2023
PRIMARY
DRUG BANK
DB05540
Created by admin on Fri Dec 15 15:21:45 GMT 2023 , Edited by admin on Fri Dec 15 15:21:45 GMT 2023
PRIMARY
SMS_ID
100000087713
Created by admin on Fri Dec 15 15:21:45 GMT 2023 , Edited by admin on Fri Dec 15 15:21:45 GMT 2023
PRIMARY
INN
5245
Created by admin on Fri Dec 15 15:21:45 GMT 2023 , Edited by admin on Fri Dec 15 15:21:45 GMT 2023
PRIMARY
NSC
153353
Created by admin on Fri Dec 15 15:21:45 GMT 2023 , Edited by admin on Fri Dec 15 15:21:45 GMT 2023
PRIMARY
FDA UNII
2CNI71214Y
Created by admin on Fri Dec 15 15:21:45 GMT 2023 , Edited by admin on Fri Dec 15 15:21:45 GMT 2023
PRIMARY
MESH
C000082
Created by admin on Fri Dec 15 15:21:45 GMT 2023 , Edited by admin on Fri Dec 15 15:21:45 GMT 2023
PRIMARY