Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C3H7N3O4 |
| Molecular Weight | 149.1054 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(CN(O)N=O)C(O)=O
InChI
InChIKey=MLFKVJCWGUZWNV-UHFFFAOYSA-N
InChI=1S/C3H7N3O4/c4-2(3(7)8)1-6(10)5-9/h2,10H,1,4H2,(H,7,8)
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 |
|---|---|---|
| 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
Sample Use Guides
80 mg/m2 by continuous intravenous infusion daily for 5 days every 21 days.
Route of Administration:
Intravenous
| Name | Type | Language | ||
|---|---|---|---|---|
|
Systematic Name | English | ||
|
Preferred Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
5854-95-5
Created by
admin on Wed Apr 02 12:07:55 GMT 2025 , Edited by admin on Wed Apr 02 12:07:55 GMT 2025
|
PRIMARY | |||
|
DTXSID90863626
Created by
admin on Wed Apr 02 12:07:55 GMT 2025 , Edited by admin on Wed Apr 02 12:07:55 GMT 2025
|
PRIMARY | |||
|
44459810
Created by
admin on Wed Apr 02 12:07:55 GMT 2025 , Edited by admin on Wed Apr 02 12:07:55 GMT 2025
|
PRIMARY | |||
|
Y29Y2ZU8DN
Created by
admin on Wed Apr 02 12:07:55 GMT 2025 , Edited by admin on Wed Apr 02 12:07:55 GMT 2025
|
PRIMARY |
SUBSTANCE RECORD
