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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
149124
PubMed

PubMed

TitleDatePubMed
Personalized cancer medicine: from molecular diagnostics to targeted therapy with natural products.
2010-08
Gateways to clinical trials.
2009-09
Selective killing of tumors deficient in methylthioadenosine phosphorylase: a novel strategy.
2009-05-29
A phase II multicenter study of L-alanosine, a potent inhibitor of adenine biosynthesis, in patients with MTAP-deficient cancer.
2009-02
MPDA: microarray pooled DNA analyzer.
2008-04-15
Genome-scale analysis of anti-metabolite directed strain engineering.
2008-03
Gateways to clinical trials.
2007-12
Effects of adenosine monophosphate-activated kinase activators on bovine oocyte nuclear maturation in vitro.
2007-08
EFA (9-beta-D-erythrofuranosyladenine) is an effective salvage agent for methylthioadenosine phosphorylase-selective therapy of T-cell acute lymphoblastic leukemia with L-alanosine.
2006-02-01
Circadian pharmacology of L-alanosine (SDX-102) in mice.
2006-02
T-state active site of aspartate transcarbamylase: crystal structure of the carbamyl phosphate and L-alanosine ligated enzyme.
2006-01-17
Homozygous deletions of methylthioadenosine phosphorylase in human biliary tract cancers.
2005-12
Concordant loss of MTAP and p16/CDKN2A expression in gastroesophageal carcinogenesis: evidence of homozygous deletion in esophageal noninvasive precursor lesions and therapeutic implications.
2005-11
Cystine-glutamate transporter SLC7A11 in cancer chemosensitivity and chemoresistance.
2005-08-15
MTAP homozygous deletion: an Achilles heel of human cancers ready for clinical use?
2005-03
Determination of derivatized l-alanosine in plasma by liquid chromatography-tandem mass spectrometry.
2004-04-25
Status of methylthioadenosine phosphorylase and its impact on cellular response to L-alanosine and methylmercaptopurine riboside in human soft tissue sarcoma cells.
2004
Identification of gene expression profiles predicting tumor cell response to L-alanosine.
2003-08-15
Chemotherapy targeting methylthioadenosine phosphorylase (MTAP) deficiency in adult T cell leukemia (ATL).
2002-09
Methylthioadenosine phosphorylase as target for chemoselective treatment of T-cell acute lymphoblastic leukemic cells.
2002-05-04
Alanosine (UCSD).
2001-11
Patents

Patents

20010044451
27

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
L-ALANOSINE
MI  
Preferred 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
Classification Tree Code System Code
NCI_THESAURUS C1556
Created by admin on Mon Mar 31 17:55:13 GMT 2025 , Edited by admin on Mon Mar 31 17:55:13 GMT 2025
NCI_THESAURUS C2168
Created by admin on Mon Mar 31 17:55:13 GMT 2025 , Edited by admin on Mon Mar 31 17:55:13 GMT 2025
Code System Code Type Description
CAS
5854-93-3
Created by admin on Mon Mar 31 17:55:13 GMT 2025 , Edited by admin on Mon Mar 31 17:55:13 GMT 2025
PRIMARY
ChEMBL
CHEMBL452715
Created by admin on Mon Mar 31 17:55:13 GMT 2025 , Edited by admin on Mon Mar 31 17:55:13 GMT 2025
PRIMARY
WIKIPEDIA
ALANOSINE
Created by admin on Mon Mar 31 17:55:13 GMT 2025 , Edited by admin on Mon Mar 31 17:55:13 GMT 2025
PRIMARY
PUBCHEM
90657278
Created by admin on Mon Mar 31 17:55:13 GMT 2025 , Edited by admin on Mon Mar 31 17:55:13 GMT 2025
PRIMARY
EPA CompTox
DTXSID501024175
Created by admin on Mon Mar 31 17:55:13 GMT 2025 , Edited by admin on Mon Mar 31 17:55:13 GMT 2025
PRIMARY
EVMPD
SUB05291MIG
Created by admin on Mon Mar 31 17:55:13 GMT 2025 , Edited by admin on Mon Mar 31 17:55:13 GMT 2025
PRIMARY
MERCK INDEX
m1469
Created by admin on Mon Mar 31 17:55:13 GMT 2025 , Edited by admin on Mon Mar 31 17:55:13 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C994
Created by admin on Mon Mar 31 17:55:13 GMT 2025 , Edited by admin on Mon Mar 31 17:55:13 GMT 2025
PRIMARY
NSC
529469
Created by admin on Mon Mar 31 17:55:13 GMT 2025 , Edited by admin on Mon Mar 31 17:55:13 GMT 2025
PRIMARY
DRUG BANK
DB05540
Created by admin on Mon Mar 31 17:55:13 GMT 2025 , Edited by admin on Mon Mar 31 17:55:13 GMT 2025
PRIMARY
SMS_ID
100000087713
Created by admin on Mon Mar 31 17:55:13 GMT 2025 , Edited by admin on Mon Mar 31 17:55:13 GMT 2025
PRIMARY
INN
5245
Created by admin on Mon Mar 31 17:55:13 GMT 2025 , Edited by admin on Mon Mar 31 17:55:13 GMT 2025
PRIMARY
NSC
153353
Created by admin on Mon Mar 31 17:55:13 GMT 2025 , Edited by admin on Mon Mar 31 17:55:13 GMT 2025
PRIMARY
FDA UNII
2CNI71214Y
Created by admin on Mon Mar 31 17:55:13 GMT 2025 , Edited by admin on Mon Mar 31 17:55:13 GMT 2025
PRIMARY
MESH
C000082
Created by admin on Mon Mar 31 17:55:13 GMT 2025 , Edited by admin on Mon Mar 31 17:55:13 GMT 2025
PRIMARY
ACTIVE MOIETY
Structure of Alanosine
NIH
NCATS
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