Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C10H13N5O3.H2O |
Molecular Weight | 269.2572 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.NC1=NC=NC2=C1N=CN2[C@H]3C[C@H](O)[C@@H](CO)O3
InChI
InChIKey=WZJWHIMNXWKNTO-VWZUFWLJSA-N
InChI=1S/C10H13N5O3.H2O/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(17)6(2-16)18-7;/h3-7,16-17H,1-2H2,(H2,11,12,13);1H2/t5-,6+,7+;/m0./s1
2′-Deoxyadenosine, a pair of deoxythymidine (T) in double-stranded DNA, is a substrate of adenosine deaminase. In case of absence of this enzyme, 2′-deoxyadenosine accumulates in T lymphocytes and kills these cells resulting in a genetic disorder known as adenosine deaminase severe combined immunodeficiency disease (ADA-SCID).
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P00813 Gene ID: 100.0 Gene Symbol: ADA Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15705418 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Diagnostic | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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S-adenosylhomocysteine catabolism and basis for acquired resistance during treatment of T-cell acute lymphoblastic leukemia with 2'-deoxycoformycin alone and in combination with 9-beta-D-arabinofuranosyladenine. | 1983 Jul |
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Substrate specificity of human deoxycytidine kinase toward antiviral 2',3'-dideoxynucleoside analogs. | 1992 Jan 22 |
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High complete remission rate from 2-chloro-2'-deoxyadenosine in previously treated patients with B-cell chronic lymphocytic leukemia: response predicted by rapid decrease of blood lymphocyte count. | 1993 Apr |
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1H-NMR spectroscopy of body fluids: inborn errors of purine and pyrimidine metabolism. | 1999 Apr |
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Molecular cloning and functional characterization of inhibitor-sensitive (mENT1) and inhibitor-resistant (mENT2) equilibrative nucleoside transporters from mouse brain. | 2000 Dec 1 |
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Phosphorylation of the anti-HIV compound (S,S)-isodideoxyadenosine by human recombinant deoxycytidine kinase. | 2000 Nov 15 |
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5'-Esters of 2'-deoxyadenosine and 2-chloro-2'-deoxyadenosine with cell differentiation-provoking agents. | 2002 |
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Characterization of glycine N-methyltransferase from rabbit liver. | 2004 Jun |
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Inhibition of hepatitis C replicon RNA synthesis by beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine: a specific inhibitor of hepatitis C virus replication. | 2006 |
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Direct detection of 8-oxo-deoxyguanosine using UV resonance Raman spectroscopy. | 2007 May-Jun |
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Investigations into the origin of the molecular recognition of several adenosine deaminase inhibitors. | 2011 Jan 13 |
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F79D3BS9UH
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DTXSID801036040
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16373-93-6
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9549172
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD