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
| Molecular Formula | C3H7N3O4 |
| Molecular Weight | 149.1054 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 |
|
| Methylthioadenosine phosphorylase as target for chemoselective treatment of T-cell acute lymphoblastic leukemic cells. | 2002 Jan-Feb |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| MPDA: microarray pooled DNA analyzer. | 2008 Apr 15 |
|
| Genome-scale analysis of anti-metabolite directed strain engineering. | 2008 Mar |
Patents
Sample Use Guides
80 mg/m2 by continuous intravenous infusion daily for 5 days every 21 days.
Route of Administration:
Intravenous
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:21:45 UTC 2023
by
admin
on
Fri Dec 15 15:21:45 UTC 2023
|
| Record UNII |
2CNI71214Y
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| 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 UTC 2023 , Edited by admin on Fri Dec 15 15:21:45 UTC 2023
|
||
|
NCI_THESAURUS |
C2168
Created by
admin on Fri Dec 15 15:21:45 UTC 2023 , Edited by admin on Fri Dec 15 15:21:45 UTC 2023
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
5854-93-3
Created by
admin on Fri Dec 15 15:21:45 UTC 2023 , Edited by admin on Fri Dec 15 15:21:45 UTC 2023
|
PRIMARY | |||
|
CHEMBL452715
Created by
admin on Fri Dec 15 15:21:45 UTC 2023 , Edited by admin on Fri Dec 15 15:21:45 UTC 2023
|
PRIMARY | |||
|
ALANOSINE
Created by
admin on Fri Dec 15 15:21:45 UTC 2023 , Edited by admin on Fri Dec 15 15:21:45 UTC 2023
|
PRIMARY | |||
|
90657278
Created by
admin on Fri Dec 15 15:21:45 UTC 2023 , Edited by admin on Fri Dec 15 15:21:45 UTC 2023
|
PRIMARY | |||
|
DTXSID501024175
Created by
admin on Fri Dec 15 15:21:45 UTC 2023 , Edited by admin on Fri Dec 15 15:21:45 UTC 2023
|
PRIMARY | |||
|
SUB05291MIG
Created by
admin on Fri Dec 15 15:21:45 UTC 2023 , Edited by admin on Fri Dec 15 15:21:45 UTC 2023
|
PRIMARY | |||
|
m1469
Created by
admin on Fri Dec 15 15:21:45 UTC 2023 , Edited by admin on Fri Dec 15 15:21:45 UTC 2023
|
PRIMARY | Merck Index | ||
|
C994
Created by
admin on Fri Dec 15 15:21:45 UTC 2023 , Edited by admin on Fri Dec 15 15:21:45 UTC 2023
|
PRIMARY | |||
|
529469
Created by
admin on Fri Dec 15 15:21:45 UTC 2023 , Edited by admin on Fri Dec 15 15:21:45 UTC 2023
|
PRIMARY | |||
|
DB05540
Created by
admin on Fri Dec 15 15:21:45 UTC 2023 , Edited by admin on Fri Dec 15 15:21:45 UTC 2023
|
PRIMARY | |||
|
100000087713
Created by
admin on Fri Dec 15 15:21:45 UTC 2023 , Edited by admin on Fri Dec 15 15:21:45 UTC 2023
|
PRIMARY | |||
|
5245
Created by
admin on Fri Dec 15 15:21:45 UTC 2023 , Edited by admin on Fri Dec 15 15:21:45 UTC 2023
|
PRIMARY | |||
|
153353
Created by
admin on Fri Dec 15 15:21:45 UTC 2023 , Edited by admin on Fri Dec 15 15:21:45 UTC 2023
|
PRIMARY | |||
|
2CNI71214Y
Created by
admin on Fri Dec 15 15:21:45 UTC 2023 , Edited by admin on Fri Dec 15 15:21:45 UTC 2023
|
PRIMARY | |||
|
C000082
Created by
admin on Fri Dec 15 15:21:45 UTC 2023 , Edited by admin on Fri Dec 15 15:21:45 UTC 2023
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |
