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Dideoxyadenosine

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Definition: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is an inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. Its principal side effect is nephrotoxicity. In vivo, dideoxyadenosine is rapidly metabolized to DIDANOSINE (ddI) by enzymatic deamination; ddI is then converted to dideoxyinosine monophosphate and ultimately to dideoxyadenosine triphosphate, the putative active metabolite.  an antiviral; inhibits HIV replication   
Pharmacological Action Antimetabolites; Antiviral Agents 		Other names ddA (Antiviral); 2',3'-Dideoxyadenosine; 2',3' Dideoxyadenosine
 
SubstanceCAS Registry & nameCategoriesSourceDrugs*
3'-azido-2',3'-dideoxyadenosine  0   *Azides Dideoxyadenosine/*analogs & derivatives Reverse Transcriptase Inhibitors HIV Reverse Transcriptase. Antimicrob Agents Chemother. 2011 Aug;55(8):3758-64.
9-(2,3-dideoxy-2,3-difluoro-beta-D-arabinofuranosyl)adenine  0   Dideoxyadenosine/*analogs & derivatives. Nucleosides Nucleotides Nucleic Acids. 2007;26(10-12):1387-9
2',5'-dideoxy-2,5'-difluoroadenosine  0   Dideoxyadenosine/*analogs & derivatives Adenylate Cyclase/antagonists & inhibitors. J Med Chem 2004 Feb 26;47(5):1207-13
2',5'-dideoxy-2-fluoroadenosine  0   Dideoxyadenosine/*analogs & derivatives Adenylate Cyclase/antagonists & inhibitors. J Med Chem 2004 Feb 26;47(5):1207-13
beta-L-2',3'dideoxyadenosine, bis(S-pivaloyl-2-thioethyl) phosphotriester  0   *Dideoxynucleotides Dideoxyadenosine/*analogs & derivatives. Antivir Chem Chemother 2001 Mar;12(2):99-108
9-(5,6-dibromo-5,6-dideoxyhex-5-enofuranosyl)adenine  0   Dideoxyadenosine/*analogs & derivatives. J Med Chem 1998 Jul 30;41(16):3078-83
9-(6,6-dibromo-5,6-dideoxyhex-5-enofuranosyl)adenine  0   Dideoxyadenosine/*analogs & derivatives. J Med Chem 1998 Jul 30;41(16):3078-83
9-(6-bromo-5,6-dideoxy-6-fluorohex-5-enofuranosyl)adenine  0   Dideoxyadenosine/*analogs & derivatives. J Med Chem 1998 Jul 30;41(16):3078-83
3'-((4-azido-3-iodophenyl)butyryl)-2',5'-dideoxyadenosine  0   Dideoxyadenosine/*analogs & derivatives. Biochim Biophys Acta 1995 Aug 17;1245(1):37-42
9-(5,6-dideoxy-6-iodo-ribohex-5-enofuranosyl)adenine  0   Dideoxyadenosine/*analogs & derivatives. J Med Chem 1994 Oct 14;37(21):3579-87
2'3'-didehydro-2'3'-dideoxyadenosine  7057-48-9   Dideoxyadenosine/*analogs & derivatives. J Med Chem 1992 Jul 24;35(15):2728-35
lodenosine  110143-10-7   Dideoxyadenosine/*analogs & derivatives. Nucleic Acids Res 1992 Feb 11;20(3):459-65
9-(5',6'-dideoxy-beta-ribohex-5'-ynofuranosyl)adenine  125296-16-4   Dideoxyadenosine/*analogs & derivatives. Biochemistry 1991;30(41):9988
Ro 24-5098  127682-75-1   Dideoxyadenosine/*analogs & derivatives. Ann N Y Acad Sci 1990;616:408
2',5'-dideoxy-3'-(4-fluorosulfonylbenzoyl)adenosine  121878-15-7   Dideoxyadenosine/*analogs & derivatives. J Biol Chem 1990;265(28):16745
2-chloro-2',3'-didehydro-2',3'-dideoxyadenosine  119530-56-2   Dideoxyadenosine/*analogs & derivatives. J Med Chem 1989;32(5):1135
2-chloro-2',3'-dideoxyadenosine  114849-58-0 Adenosine, 2-chloro-2',3'-dideoxy  Dideoxyadenosine/*analogs & derivatives. J Biol Chem 1988;263(12):5870
2-bromo-2',3'-dideoxyadenosine  114849-57-9 Adenosine, 2-bromo-2',3'-dideoxy  Dideoxyadenosine/*analogs & derivatives. J Biol Chem 1988;263(12):5870
2-fluoro-2',3'-dideoxyadenosine  114849-59-1 Adenosine, 2',3'-dideoxy-2-fluoro  Dideoxyadenosine/*analogs & derivatives. J Biol Chem 1988;263(12):5870
3'-fluoro-2,6-diaminopurine-2',3'-dideoxyriboside  114753-53-6   Dideoxyadenosine/*analogs & derivatives. Mol Pharmacol 1988;33(3):243
3'-azido-2,6-diaminopurine-2',3'-dideoxyriboside  114753-52-5   Dideoxyadenosine/*analogs & derivatives. Mol Pharmacol 1988;33(3):243
2,6-diaminopurine 2',3'-dideoxyriboside  107550-73-2   Dideoxyadenosine/*analogs & derivatives. Biochem Biophys Res Commun 1987;145(1):269
2',5'-dideoxyadenosine  6698-26-6   Dideoxyadenosine/*analogs & derivatives Isomerism. J Cyclic Nucleotide Res 5(3):189;1979
3'-amino-3',5'-dideoxyadenosine  57032-45-8   Dideoxyadenosine/*analogs & derivatives. Helv Chim Acta 58(5):1497;1975

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Sources: NLM Medical Subject Headings, NIH UMLS, Drugs@FDA, FDA AERS original data copyright United States Government. No endorsement implied. Last modified 6/6/2012
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