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
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
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 |
|
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
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18618081
80 mg/m2 by continuous intravenous infusion daily for 5 days every 21 days.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/177207
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 | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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