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Dideoxynucleosides

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Definition: Nucleosides that have two hydroxy groups removed from the sugar moiety. The majority of these compounds have broad-spectrum antiretroviral activity due to their action as antimetabolites. The nucleosides are phosphorylated intracellularly to their 5'-triphosphates and act as chain-terminating inhibitors of viral reverse transcription.  antivirals & antimetabolites   
Pharmacological Action Antimetabolites; Antiviral Agents; Reverse Transcriptase Inhibitors
Examples Didanosine; Dideoxyadenosine; Stavudine; Zalcitabine; Zidovudine 		Other names Dideoxyribonucleosides; 2',3'-Dideoxynucleosides; 2',3' Dideoxynucleosides; ddNus
 
SubstanceCAS Registry & nameCategoriesSourceDrugs*
2'-methylcarbovir  0   *Dideoxynucleosides. Chemistry 2008;14(22):6722-33
N,N'-dideoxythymidine-3,4,9,10-perylene-tetracarboxylic acid diimide  0   *Dideoxynucleosides Perylene/*analogs & derivatives. Chem Commun (Camb) 2008 Mar 28;(12):1413-5
5-iodo-2',3'-dideoxyuridine  0   *Dideoxynucleosides. J Am Soc Mass Spectrom 2007 Aug;18(8):1477-92
norabacavir  0   *Dideoxynucleosides. Org Biomol Chem 2007 Apr 21;5(8):1164-6
norcarbovir  0   *Dideoxynucleosides. Org Biomol Chem 2007 Apr 21;5(8):1164-6
Kivexa  0   *Dideoxynucleosides *Lamivudine Drug Combinations. AIDS Patient Care STDS 2005 Feb;19(2):127
abacavir, lamivudine drug combination  0   *Dideoxynucleosides *Lamivudine Drug Combinations. Med Health 2004 Aug 9;58(31):3-4EPZICOM; ABACAVIR SULFATE; LAMIVUDINE
3'-thio-3'-deoxythymidine  0   *Dideoxynucleosides Thymidine/*analogs & derivatives. Nucleic Acids Res 2004;32(2):495-501
2',3'-dideoxy-3'-fluoro-2-thiothymidine  0   *Dideoxynucleosides. Nucleosides Nucleotides Nucleic Acids. 2003 May-Aug;22(5-8):805-7
5-o-carboranyl-2',3'-didehydro-2',3'-dideoxyuridine  0   *Dideoxynucleosides. Nucleosides Nucleotides 1998 Apr;17(4):711-27
2',3'-dideoxy-2',3'-didehydroguanine nucleoside  0   *Dideoxynucleosides. Biophys J 1998 Jun;74(6):3131-9
1-(2',3'-dideoxy-3'(hydroxymethyl)erythropentofuranosyl)cytosine  0   *Pyrimidine Nucleosides *Dideoxynucleosides. Bioorg Med Chem 1998;6(5):577-85
6-chloro-2',3'-dideoxyinosine  0   *Dideoxynucleosides. Nucleic Acids Symp Ser 1997;(37):173-4
abacavir  0   *Dideoxynucleosides.
Pharma Action Reverse Transcriptase Inhibitors ; Anti-HIV Agents 		Antimicrob Agents Chemother 1997 May;41(5):1082-93ABACAVIR SULFATE; ZIAGEN; ABACAVIR
1,2-dipalmitoylphosphatidyldideoxyguanosine  0   *Dideoxynucleosides. Hepatology 1996 May;23(5):958-63
5'-amino-2',5'-dideoxyguanosine  0   *Dideoxynucleosides. Chem Res Toxicol 1995 Jul-Aug;8(5):792-9
6-chloro-2',3'-dideoxyguanosine  0   *Dideoxynucleosides. Antimicrob Agents Chemother 1995 Jun;39(6):1259-64
2',3'-dideoxy-6-iodoguanosine  0   *Dideoxynucleosides. Antimicrob Agents Chemother 1995 Jun;39(6):1259-64
5-iodo-6-methoxy-5,6-dihydro-3'-fluoro-3'-deoxythymidine  0   *Dideoxynucleosides. J Med Chem 1994 Oct 14;37(21):3554-60
5-bromo-6-methoxy-5,6-dihydro-3'-fluoro-3'-deoxythymidine  0   *Dideoxynucleosides. J Med Chem 1994 Oct 14;37(21):3554-60
carbovir-5'-O-glucuronide  131956-47-3   *Glucuronates *Dideoxynucleosides. Drug Metab Dispos Biol Fate Chem 1993 Sep-Oct;21(5):902-10
2'-fluoro-2',3'-dideoxyguanosine  125291-17-0   *Dideoxynucleosides. Mol Pharmacol 1993 Sep;44(3):519-23
carbocyclic 3'-oxa-2',3'-dideoxy-7-deazaguanosine  149519-40-4   *Dideoxynucleosides. Antiviral Res 1993 Apr;20(4):333-45
carbocyclic 3'-oxa-2',3'-dideoxyguanosine  133804-87-2   *Dideoxynucleosides. Antiviral Res 1993 Apr;20(4):333-45
1-(2-fluoro-4-iodo-2,4-dideoxyxylopyranosyl)-2-nitroimidazole  147132-90-9   *Nitroimidazoles *Dideoxynucleosides. Radiat Res 1992 Dec;132(3):368-874
3'-C-methylidene-2',3'-dideoxy-5-methyluridine  118744-89-1   *Dideoxynucleosides. J Med Chem 1992 Nov 27;35(24):4567-75
3'-methylamino-2',3'-dideoxyribosylthymine  141039-00-1   *Dideoxynucleosides. Bioorg Khim 1992 Jul;18(7):996-1001
3',3'-difluoro-3'-deoxythymidine  121353-87-5   *Dideoxynucleosides. J Med Chem 1992 Sep 4;35(18):3369-72
3'-amino-2',3'-dideoxyuridine  84472-86-6   *Dideoxynucleosides Deoxyuridine/*analogs & derivatives. Biochem Pharmacol 1992 Sep 1;44(5):973-80
2',3'-dideoxy-3'-O-methylthymidine  108895-42-7   *Dideoxynucleosides. Acta Virol (Praha) 1991 Sep;35(5):430-7
9-(c-4,t-5-bis(hydroxymethyl)cyclopent-2-en-r-1-yl)-9H-adenine  140440-40-0   *Dideoxynucleosides Adenine/*analogs & derivatives. J Med Chem 1992 May 15;35(10):1882-6
5-bromo-2',3'-dideoxyuridine  28616-93-5   *Dideoxynucleosides. Acta Crystallogr C 1991 Sep 15;47( Pt 9):1892-5
6-aminocarbovir  124752-25-6   *Dideoxynucleosides. Drug Metab Dispos 1991;19(2):462
5'-isocyano-5'-deoxythymidine  132101-22-5   *Dideoxynucleosides. J Med Chem 1991;34(4):1426
5'-isocyano-2',5'-dideoxyuridine  132125-31-6   *Dideoxynucleosides. J Med Chem 1991;34(4):1426
3'amino-3'-deoxy-5'-glucopyranuronosylthymidine  133632-85-6   *Dideoxynucleosides. Mol Pharmacol 1991;39(2):258
3'-deoxy-2',3'-didehydro-2'fluorothymidine  122757-54-4   *Dideoxynucleosides. J Med Chem 1990;33(8):2137
3'-isocyano-2',3'-dideoxyuridine  124288-72-8   *Dideoxynucleosides. J Med Chem 1990;33(2):845
2',3'-dideoxyformycin A  40627-17-6 2-Furanmethanol, 5-(7-amino-1H-pyrazolo(4,3-d)pyrimidin-3-yl)tetrahydro-, (2S-cis)  *Dideoxynucleosides. Biochem Biophys Res Commun 1989;161(2):910
3'-fluoro-2',3'-dideoxy-5-iodouridine  119644-23-4   *Dideoxynucleosides. Mol Pharmacol 1989;35(5):571
3'-fluoro-2',3'-dideoxy-5-bromouridine  115249-86-0   *Dideoxynucleosides. Mol Pharmacol 1989;35(5):571
raluridine  119644-22-3   *Dideoxynucleosides. Mol Pharmacol 1989;35(5):571
2',3'-dideoxyuridine  5983-09-5   *Dideoxynucleosides. Appl Environ Microbiol 1989;55(2):419
2',3'-didehydro-2',3'-dideoxyuridine  5974-93-6 2,4(1H,3H)-Pyrimidinedione, 1-(2,5-dihydro-5-(hydroxymethyl)-2-furanyl)-, (2R-cis)  *Dideoxynucleosides. Biochem Pharmacol 1989;38(6):419
3'-fluoro-2',3'-dideoxyuridine  41107-56-6   *Dideoxynucleosides. Biochem Pharmacol 1989;38(6):869
2',3'-dideoxy-N(6)-cyclohexyladenosine  118191-22-3   *Dideoxynucleosides. Eur J Pharmacol 1988;156(1):157
carbovir  118353-05-2   *Dideoxynucleosides.
Pharma Action Anti-HIV Agents 		Biochem Biophys Res Commun 1988;156(2):681
2'-chloro-2',3'-dideoxyuridinene  115259-92-2   *Dideoxynucleosides. Chem Pharm Bull (Tokyo) 1987;35(11):4498
3',5'-dideoxythymidine  29108-89-2   *Dideoxynucleosides. Strahlenther Onkol 1988;164(3):173
3'-fluoro-2',3'-dideoxyguanosine  92562-88-4   *Dideoxynucleosides. Mol Pharmacol 1988;33(3):243
3'-acetamido-2',3'-dideoxythymidine  70465-85-9   *Dideoxynucleosides. Mol Biol (Mosk) 1987;21(3):837
2,6-diaminopurine 2',3'-didehydro-2',3'-dideoxyriboside  109881-25-6   *Dideoxynucleosides. Biochem Biophys Res Commun 1987;145(1):277
3'-azido-2',3'-dideoxyguanosine  66323-46-4   *Dideoxynucleosides. Lancet 1987;1(8523):40
2',3'-dideoxyguanosine  85326-06-3   *Dideoxynucleosides. Biochemistry 1986;25(16):4473
3'-(3-(2-chloroethyl)-3-nitrosoureido)-2',3'-dideoxy-5-fluorouridine  96699-71-7   *Nitrosourea Compounds *Dideoxynucleosides. J Med Chem 1986;29(5):862
3' (3-(2-chloroethyl)-3-nitrosoureido)-2',3'-dideoxyuridine  96699-73-9   *Nitrosourea Compounds *Dideoxynucleosides. J Med Chem 1986;29(5):862
2',5'-dichloro-2',5'-dideoxyuridine  34627-73-1   *Dideoxynucleosides. Nucleic Acids Symp Series 1985;(16):105
5'-deoxy-5'fluorothymidine  17199-43-8   *Dideoxynucleosides. Vopr Virusol 1983;28(5):673
5-fluoro-2',3'-dideoxy-3'-fluorouridine  41107-55-5   *Dideoxynucleosides Thymidine Phosphorylase/antagonists & inhibitors. J Med Chem 1984;27(1):11
2',3'-dideoxy-3'-aminoadenosine  7403-25-0   *Dideoxynucleosides. Biokhimiia 1983;48(10):1747
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