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Zalcitabine

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Definition: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen.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 a potent inhibitor of HIV replication at low concentrations, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. Its principal toxic side effect is axonal degeneration resulting in peripheral neuropathy.     
Pharmacological Action Anti-HIV Agents; Antimetabolites; Reverse Transcriptase Inhibitors
Examples Lamivudine 		Other names ddC (Antiviral); Dideoxycytidine; 2',3'-Dideoxycytidine; NSC 606170; 2',3' Dideoxycytidine; Roche Brand of Zalcitabine; NSC-606170; HIVID Roche; Hoffman-La Roche Brand of Zalcitabine; NSC606170; HividDrugs* : HIVID
 
SubstanceCAS Registry & nameCategoriesSourceDrugs*
3'-azido-2',3'-dideoxycytidine  0   *Azides Zalcitabine/*analogs & derivatives Reverse Transcriptase Inhibitors HIV Reverse Transcriptase. Antimicrob Agents Chemother. 2011 Aug;55(8):3758-64.
2',3'-didehydro-2',3'-dideoxy-N4-hydroxycytidine  0   Zalcitabine/*analogs & derivatives. Antimicrob Agents Chemother 2010 Jan;54(1):341-5
beta-D-4'-C-ethynyl-2',3'-dideoxycytidine  0   Zalcitabine/*analogs & derivatives. Bioorg Med Chem. 2007 Jan 1;15(1):283-7
3'-fluoro-2',3'-didehydro-2',3'-dideoxycytidine  0   Zalcitabine/*analogs & derivatives. Antimicrob Agents Chemother 2005 Feb;49(2):560-4
6-amino-3-(5-ethynyl-5-(hydroxymethyl)oxolan-2-yl)-3-hydroxypyrimidin-2-one  0   Zalcitabine/*analogs & derivatives. J Med Chem 2004 Oct 7;47(21):5041-8
3'-thio-2',3'-dideoxycytidine  0   Zalcitabine/*analogs & derivatives. Nucleic Acids Res 2004;32(2):495-501
3'-S-(2-Cyanoethyl-N,N-diisopropylphosphorothioamidite)- N4-benzoyl-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidine  0   *Organothiophosphorus Compounds *Dideoxynucleotides Zalcitabine/*analogs & derivatives. Nucleic Acids Res 2004;32(2):495-501
1-(2,3-dideoxy-2,3-didehydro-2-fluoro-4-thioribofuranosyl)cytosine  0   Zalcitabine/*analogs & derivatives. J Med Chem 2002 Oct 24;45(22):4888-98
2',3'-dideoxy-2',3'-dehydro-5-fluorocytidine triphosphate  0   *Dideoxynucleotides Zalcitabine/*analogs & derivatives. Mol Pharmacol 1998 May;53(5):801-7
dexelvucitabine  134379-77-4   Zalcitabine/*analogs & derivatives HIV Reverse Transcriptase. J Med Chem 1996 Apr 26;39(9):1757-9
2',3'-dideoxy-5-fluorocytidine 5'-triphosphate  146369-72-4   *Deoxycytosine Nucleotides *Dideoxynucleotides Zalcitabine/*analogs & derivatives. Antimicrob Agents Chemother 1994 Oct;38(10):2300-5
1,2-dioleoyl-glycero-3-phospho-5'-(2',3')-dideoxycytidine  147556-77-2   Zalcitabine/*analogs & derivatives. Antiviral Res 1994 May;24(1):59-67
2',3'-dideoxy-beta-5-fluorocytidine  147058-39-7   Zalcitabine/*analogs & derivatives. Biochem Pharmacol 1994 Jan 20;47(2):171-4
2',3'-dideoxy-5-fluoro-3'-thiacytidine  143491-54-7   Zalcitabine/*analogs & derivatives.
Pharma Action Antiviral Agents 		Biochem Pharmacol 1992 Jul 22;44(2):199-204
1-(2,3-dideoxy-hexopyranosyl)cytosine  0   Zalcitabine/*analogs & derivatives. Acta Crystallogr B 1992 Feb 1;48 (Pt 1):95-103
1-(2,3-dideoxy-2-fluoropentofuranosyl)-5-fluorocytosine  128496-09-3   Zalcitabine/*analogs & derivatives. J Med Chem 1992 Jun 12;35(12):2195-201
2',3'-dideoxycytidine monophosphate diglyceride  139903-71-2   *Dideoxynucleotides Zalcitabine/*analogs & derivatives. J Chromatogr 1992 Jan 24;590(1):153-61
N4-((diisopropylamino)methylene)-3'-fluoro-2',3'-dideoxycytidine  141018-21-5   Zalcitabine/*analogs & derivatives. J Med Chem 1992 May 29;35(11):1996-2001
N4-((diisopropylamino)methylene)-2',3'-dideoxycytidine  141043-80-3   Zalcitabine/*analogs & derivatives. J Med Chem 1992 May 29;35(11):1996-2001
2',3'-dideoxy-5-methylcytidine  107036-56-6 Cytidine, 2',3'-dideoxy-5-methyl  Zalcitabine/*analogs & derivatives. Biochem Pharmacol 1992 Apr 1;43(7):1571-7
2',3'-dideoxy-2',3'-methanocytidine  131347-68-7   Zalcitabine/*analogs & derivatives. Carbohydr Res 1990;205:87
1-(2,3-dideoxy-2,3-difluoroarabinofuranosyl)cytosine  128496-20-8   Zalcitabine/*analogs & derivatives. J Med Chem 1990;33(8):2137
2',3'-dideoxy-2',3'-didehydro-2'-fluorocytidine  122757-53-3 Cytidine, 2',3'-didehydro-2',3'-dideoxy-2'-fluoro  Zalcitabine/*analogs & derivatives. J Med Chem 1990;33(8):2137
1-(2,3-dideoxy-2-fluoropentofuranosyl)cytosine  119555-47-4   Zalcitabine/*analogs & derivatives. J Med Chem 1990;33(8):2137
N(4)-benzoyl-2',3'-dideoxy-2',3'-didehydrocytidine  123413-57-0   Zalcitabine/*analogs & derivatives. Chem Pharm Bull (Tokyo) 1989;37(9):2547
3'-azido-2',3'-dideoxy-5-methylcytidine  87190-79-2   *Azides Zalcitabine/*analogs & derivatives. Mol Biol (Mosk) 1988;22(3):802
2',3'-dideoxycytidinene  7481-88-1   Zalcitabine/*analogs & derivatives. Biochem Biophys Res Commun 1986;140(2):735
3'-amino-2',3'-dideoxycytidine  84472-90-2   Zalcitabine/*analogs & derivatives. Biochem Pharmacol 1983;32(16):2427
1-(2,5-dideoxy-beta-hexofuranosyl)cytosine  61221-85-0 2(1H)-Pyrimidinone, 4-amino-1-(2,5-dideoxy-beta-D-erythro-hexofuranosyl)  Zalcitabine/*analogs & derivatives. Carbohydr Res 77:79;1979

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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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