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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

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

Unknown
139594
PubMed

PubMed

TitleDatePubMed
Chemotherapy targeting methylthioadenosine phosphorylase (MTAP) deficiency in adult T cell leukemia (ATL).
2002 Sep
Determination of derivatized l-alanosine in plasma by liquid chromatography-tandem mass spectrometry.
2004 Apr 25
Cystine-glutamate transporter SLC7A11 in cancer chemosensitivity and chemoresistance.
2005 Aug 15
Homozygous deletions of methylthioadenosine phosphorylase in human biliary tract cancers.
2005 Dec
MTAP homozygous deletion: an Achilles heel of human cancers ready for clinical use?
2005 Mar
Effects of adenosine monophosphate-activated kinase activators on bovine oocyte nuclear maturation in vitro.
2007 Aug
Gateways to clinical trials.
2007 Dec
MPDA: microarray pooled DNA analyzer.
2008 Apr 15
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
Patents

Patents

20010044451
26

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
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
ACTIVE MOIETY
Structure of ALANOSINE
NIH
NCATS
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DISCLAIMER
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