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 |
|---|---|---|
| Alanosine (UCSD). | 2001 Nov |
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| Methylthioadenosine phosphorylase as target for chemoselective treatment of T-cell acute lymphoblastic leukemic cells. | 2002 Jan-Feb |
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| Chemotherapy targeting methylthioadenosine phosphorylase (MTAP) deficiency in adult T cell leukemia (ATL). | 2002 Sep |
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| Identification of gene expression profiles predicting tumor cell response to L-alanosine. | 2003 Aug 15 |
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| Status of methylthioadenosine phosphorylase and its impact on cellular response to L-alanosine and methylmercaptopurine riboside in human soft tissue sarcoma cells. | 2004 |
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| Determination of derivatized l-alanosine in plasma by liquid chromatography-tandem mass spectrometry. | 2004 Apr 25 |
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| Cystine-glutamate transporter SLC7A11 in cancer chemosensitivity and chemoresistance. | 2005 Aug 15 |
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| Homozygous deletions of methylthioadenosine phosphorylase in human biliary tract cancers. | 2005 Dec |
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| MTAP homozygous deletion: an Achilles heel of human cancers ready for clinical use? | 2005 Mar |
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| Concordant loss of MTAP and p16/CDKN2A expression in gastroesophageal carcinogenesis: evidence of homozygous deletion in esophageal noninvasive precursor lesions and therapeutic implications. | 2005 Nov |
|
| Circadian pharmacology of L-alanosine (SDX-102) in mice. | 2006 Feb |
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| 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 Feb 1 |
|
| T-state active site of aspartate transcarbamylase: crystal structure of the carbamyl phosphate and L-alanosine ligated enzyme. | 2006 Jan 17 |
|
| Effects of adenosine monophosphate-activated kinase activators on bovine oocyte nuclear maturation in vitro. | 2007 Aug |
|
| Genome-scale analysis of anti-metabolite directed strain engineering. | 2008 Mar |
|
| 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
80 mg/m2 by continuous intravenous infusion daily for 5 days every 21 days.
Route of Administration:
Intravenous
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NCI_THESAURUS |
C1556
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NCI_THESAURUS |
C2168
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5854-93-3
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CHEMBL452715
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ALANOSINE
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90657278
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DTXSID501024175
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SUB05291MIG
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m1469
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C994
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529469
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DB05540
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100000087713
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5245
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153353
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2CNI71214Y
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C000082
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ACTIVE MOIETY
