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Zidovudine

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Definition: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. 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, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.     
Pharmacological Action Anti-HIV Agents; Antimetabolites; Reverse Transcriptase Inhibitors
Other names Azidothymidine; AZT (Antiviral); BWA 509U; Antiviral AZT; 3' Azido 3' deoxythymidine; 3' Azido 2',3' Dideoxythymidine; Retrovir; BWA-509U; BW A509U; AZT, Antiviral; AZT Antiviral; 3'-Azido-2',3'-Dideoxythymidine; 3'-Azido-3'-deoxythymidine; BWA509UDrugs* : RETROVIR; ZIDOVUDINE
 
SubstanceCAS Registry & nameCategoriesSourceDrugs*
4'-seleno-AZT  0   *Organoselenium Compounds Zidovudine/*analogs & derivatives. Org Lett. 2010 May 21;12(10):2242-5
cholesteryl-phosphonyl zidovudine  0   *Cholesterol Esters Zidovudine/*analogs & derivatives. Int J Pharm2009 Oct 20;381(1):40-8
bis(4-acetoxybenzyl)zidovudine diphosphate  0   *Thymine Nucleotides Zidovudine/*analogs & derivatives. Nucleic Acids Symp Ser (Oxf) 2008;(52):83-4
3'-azido-3'-deoxythymidine-5'-methoxyalaninyl phosphate  0   *Dideoxynucleotides Zidovudine/*analogs & derivatives. Bioorg Med Chem. 2005 May 2;13(9):3279-88
3'-azido-3'-deoxythymidine 5'-choline phosphate  0   *Dideoxynucleotides Thymidine Monophosphate/*analogs & derivatives Zidovudine/*analogs & derivatives. Nucleosides Nucleotides Nucleic Acids 2007;26(1):23-36
hydroxy tBuSATE phenylphosphotriester AZT derivative  0   *Dideoxynucleotides Zidovudine/*analogs & derivatives. Biomed Chromatogr. 2005 Jul;19(6):415-25
tuftsin-AZT conjugate  0   Tuftsin/*analogs & derivatives Zidovudine/*analogs & derivatives. J Pept Sci 2005 Jan;11(1):37-44
3'-azidothymidine 5'-(p-methoxyphenyl methoxyalaninyl phosphate)  0   *Dideoxynucleotides Zidovudine/*analogs & derivatives. Arzneimittelforschung. 2004;54(11):715-31
3'-azido-2',3'-dideoxyuridine-5'-O-valinate  0   Valine/*analogs & derivatives Zidovudine/*analogs & derivatives. Antivir Chem Chemother 2003 Sep;14(5):263-70
3'-azido-2'-deoxythymidine-5'-methylamino-L-tryptophanylphosphoramidate  0   *Thymine Nucleotides *Dideoxynucleotides Zidovudine/*analogs & derivatives. Pharm Res 2003 Mar;20(3);448-51
trans-(5S,6S)-5-bromo-6, 5'-epoxy-5,6-dihydro-3'-azido-3'-deoxythymidine  0   Zidovudine/*analogs & derivatives. Nucleosides Nucleotides Nucleic Acids. 2003;22(1):45-62
3'-azido-3'-deoxy-5'-O-isonicotinoylthymidine  0   Zidovudine/*analogs & derivatives. Nucleosides Nucleotides Nucleic Acids. 2003;22(1):45-62
5'-O-(1-adamantyl)-3'-azido-3'-deoxythymidine  0   Zidovudine/*analogs & derivatives. Nucleosides Nucleotides Nucleic Acids. 2003;22(1):13-9
AZTp4A  0   *Dideoxynucleotides Zidovudine/*analogs & derivatives. Antiviral Res 2003 May;58(3):227-33
(P(1)-thymidine-3'-azido-2',3'-dideoxyriboside-5')-P(2)-(9-2-(phosphonomethoxypropyl)adenine)  0   *Dideoxynucleotides Adenine/*analogs & derivatives Zidovudine/*analogs & derivatives. Antivir Chem Chemother 2001 May;12(3):151-9
3'-azido-3'-deoxy-5'-(1-hexadecylthio-2-methoxypropyl)phosphothymidine  0   *Dideoxynucleotides Zidovudine/*analogs & derivatives. Antiviral Res 2001 May;50(2):129-37
3'-azido-3'-deoxythymidine 5'-(O-hexadecyl)phosphate  0   *Dideoxynucleotides Zidovudine/*analogs & derivatives. J Med Chem 2001 May 24;44(11):1702-9
3'-azido-3'-deoxythymidine 5'-(3-(1-O-hexadecyl-2-O-methylglycerol)phosphate)  0   Zidovudine/*analogs & derivatives. J Med Chem 2001 May 24;44(11):1702-9
3'-azido-3'-deoxythymidin-5'-yl O-(4-hydroxybutyl)carbonate  0   Zidovudine/*analogs & derivatives. J Med Chem 2001 Mar 1;44(5):777-86
3'-azido-2',3'-dideoxy-N-(1-methylaminocarbonyl-2-(3-indolyl)eth-1-yl)thymidine 5'-phosphoramidate  0   *Dideoxynucleotides Zidovudine/*analogs & derivatives. J Med Chem 2001 Jan 18;44(2):223-31
3'-azido-2',3'-dideoxy-N-(1-methoxycarbonyl-2-(3-indolyl)eth-1-yl)thymidine 5'-phosphoramidate  0   *Dideoxynucleotides Zidovudine/*analogs & derivatives. J Med Chem 2001 Jan 18;44(2):223-31
Trizivir  0   *Zidovudine *Lamivudine Drug Combinations. JAMA. 2001 Jan 3;285(1):34TRIZIVIR; ABACAVIR SULFATE, LAMIVUDINE AND ZIDOVUDINE
bispivaloylthioethyl zidovudine monophosphate  0   *Dideoxynucleotides Zidovudine/*analogs & derivatives Prodrugs. antiviral Chaem Chemother 2000 May;11(3):203-12
KNI 1039  0   *Thiazoles Zidovudine/*analogs & derivatives. Bioorg Med Chem Lett 2000 Jun 5;10(11):1227-31
3'-azido-2',3'-dideoxy-5-(N-15-(6-(3,5-dimethylphenylthio)-5-ethyl-1-(5-oxopentyl)uracil)-4,15-diaza-3-oxopentadecanyl)uridine  0   Zidovudine/*analogs & derivatives. J Med Chem 2000 May 18;43(10):1927-39
3'-azido-2',3'-dideoxy-5-(N-9-(6-(3,5-dimethylphenylthio)-5-ethyl-1-(5-oxopentyl)uracil)-4,9-diaza-3-oxononanyl)uridine  0   Zidovudine/*analogs & derivatives. J Med Chem 2000 May 18;43(10):1927-39
fozivudine tidoxil  141790-23-0   *Lipids Zidovudine/*analogs & derivatives. J Acquir Immune Defic Syndr 2000 Mar 1;23(3):227-35
cyclosaligenyl 3'-azido-2',3'-dideoxythymidine monophosphate  0   *Dideoxynucleotides Zidovudine/*analogs & derivatives. Mol Pharmacol 1999 Dec;56(6):1354-61
5-bromo-6,5'-epoxy-5,6-dihydro-3'-azido-3'-deoxythymidine  0   Zidovudine/*analogs & derivatives. Nucleosides Nucleotides 1999 Mar;18(3):337-51
3'-azido-3'-deoxythymidine-5'-(4-bromophenyl methoxyalaninyl phosphate)  0   *Thymine Nucleotides *Dideoxynucleotides Zidovudine/*analogs & derivatives. Antivir Chem Chemother 1999 Jan;10(1):47-52; Bioorg Med Chem. 2005 May 2;13(9):3279-88
5-bromo-6-methoxy-5,6-dihydro-AZT-5'-(4-bromophenyl methoxyalaninyl phosphate)  0   *Dideoxynucleotides Zidovudine/*analogs & derivatives. Antivir Chem Chemother 1999 Jan;10(1):39-46
5'-O-succinylzidovudine  0   Zidovudine/*analogs & derivatives. J Controlled Release 1998 Aug14;54(3):321-31
5-bromo-6-methoxy-5, 6-dihydro-3'-azidothymidine-5'-(p-bromophenyl) methoxyalaninyl phosphate  0   *Dideoxynucleotides Thymidine Monophosphate/*analogs & derivatives Zidovudine/*analogs & derivatives. Biol Reprod 1998 Sep;59(3):503-15
5-Bromo-6-methoxy-5,6-dihydro-3'-azidothymidine-5'-(p-methoxyphenyl)methoxyalaninyl phosphate  0   *Dideoxynucleotides Thymidine Monophosphate/*analogs & derivatives Zidovudine/*analogs & derivatives. Biol Reprod 1998 Sep;59(3):503-15
phosphoceramide azidothymidine  0   *Ceramides *Dideoxynucleotides Zidovudine/*analogs & derivatives. Bioorg Khim 1997 Jul;23(7):591-6
lamivudine, zidovudine drug combination  0   *Zidovudine *Lamivudine Drug Combinations.
Pharma Action Reverse Transcriptase Inhibitors ; Anti-HIV Agents
Am J Nurs 1997 Nov;97(11):25LAMIVUDINE AND ZIDOVUDINE; COMBIVIR; LAMIVUDINE; ZIDOVUDINE
scriptene  0   *Dideoxynucleotides Zidovudine/*analogs & derivatives Didanosine/*analogs & derivatives. J Clin Pharmacol 1997 Mar;37(3):201-13
O,O'-bis(3'-azido-3'-deoxythymidin-5'-yl)-O''-(2-((phenyloxy)carbonyl)phenyl)phosphate  0   *Dideoxynucleotides Zidovudine/*analogs & derivatives. J Med Chem 1996 Sep 27;39(20):4109-15
azidothymidine homodinucleotide  0   *Thymine Nucleotides *Dideoxynucleotides Zidovudine/*analogs & derivatives. Biochem Biophys Res Commun 1996 Mar 7;220(1):20-5; J Leukoc Biol 1997 Jul;62(1):133-7
2-amino-9-(3-azido-2,3-dideoxy-erythro-pentofuranosyl)-6-(1-pyrrolidinyl)-9H-purine  0   Zidovudine/*analogs & derivatives. Bioorg Med Chem 1995 Apr;3(4):447-58
3'-azido-3'-deoxythymidine-5'-((2-cyanoethyl)(24-ethylcholesta-5,22-dien-3-yl))phosphate  0   *Dideoxynucleotides Zidovudine/*analogs & derivatives. Cell Mol Biol (Noisy-le-grand) 1995;41 Suppl 1:S1-7
3'-azido-3'-deoxythymidine-5'-((cholest-5-en-3-yl)(2-cyanoethyl))phosphate  0   *Dideoxynucleotides Zidovudine/*analogs & derivatives. Cell Mol Biol (Noisy-le-grand) 1995;41 Suppl 1:S1-7
3'-azido-3'-deoxy-5'-O-((16-cyano-11-hydroxy-3-oxo-17-androsta-1,4-dienyl)carbonyl)thymidine  148335-29-9   *Androstadienes Zidovudine/*analogs & derivatives. Cell Mol Biol (Noisy-le-grand) 1995;41 Suppl 1:S1-7
3'-azido-3'-deoxy-5'-O-((11-hydroxy-3-oxo-17-androst-4-enyl)carbonyl)thymidine  148335-28-8   *Androstenols Zidovudine/*analogs & derivatives. Cell Mol Biol (Noisy-le-grand) 1995;41 Suppl 1:S1-7
3',5-diazido-2',3'-dideoxyuridine  136466-27-8   Zidovudine/*analogs & derivatives. J Biol Chem 1995 Jun 9;270(23):13660-4
N(4)-palmitoyl-2'-deoxyribocytidylyl-(3',5')-3'-azido-2',3'-deoxythymidine  0   *Dideoxynucleotides Deoxycytidine Monophosphate/*analogs & derivatives Zidovudine/*analogs & derivatives. Antiviral Res 1994 May;24(1):79-93
N(4)-hexadecyl-2'-deoxyribocytidylyl-(3',5')-3'-azido-2',3'-deoxythymidine  0   *Dideoxynucleotides Deoxycytidine Monophosphate/*analogs & derivatives Zidovudine/*analogs & derivatives. Antiviral Res 1994 May;24(1):79-93
3'-azido-3'-deoxythymidine triphosphate distearoylglycerol  156705-00-9   *Dideoxynucleotides Zidovudine/*analogs & derivatives. Chem Phys Lipids 1994 Apr 19;70(2):213-22
4'-azidothymidine 5'-triphosphate  140158-13-0   *Dideoxynucleotides Zidovudine/*analogs & derivatives. Biochemistry 1993 Jun 15;32(23):6002-10
5'-isoleucyl 3'-azido-3'-deoxythymidine  125780-95-2   Zidovudine/*analogs & derivatives. Antimicrob Agents Chemother 1993 Apr;37(4):818-24
N(3)-methyl-3'-azido-3'-deoxythymidine 5'-triphosphate  142644-39-1   *Thymine Nucleotides *Dideoxynucleotides Zidovudine/*analogs & derivatives. Nucleic Acids Symp Ser 1991;25:27-8
3'-azido-3',5'-dideoxythymidine-5'-methylphosphonic acid diphosphate  142802-35-5   *Dideoxynucleotides Zidovudine/*analogs & derivatives. J Med Chem 1992 Aug 21;35(17):3192-6
3'-azidothymidine-5'-(phenylmethoxyalanyl)phosphate  142629-81-0   *Dideoxynucleotides Zidovudine/*analogs & derivatives. Antiviral Res 1992 Apr;17(4):311-21
3'-azidothymidine-5'-bis(4-nitrophenyl)phosphate  142629-84-3   *Dideoxynucleotides Zidovudine/*analogs & derivatives HIV-1. Antiviral Res 1992 Apr;17(4):311-21
3'-azido-3'-deoxythymidine monophosphate diglyceride  130466-13-6   *Dideoxynucleotides Zidovudine/*analogs & derivatives. J Chromatogr 1992 Jan 24;590(1):153-61
3'-azido-3'-deoxythymidine 5'-(beta,gamma-imido)triphosphate  141171-21-3   *Dideoxynucleotides Zidovudine/*analogs & derivatives HIV-1. J Med Chem 1992 May 29;35(11):1938-41
4'-azidothymidine  130108-72-4 Thymidine, 4'-azido  Zidovudine/*analogs & derivatives. J Biol Chem 1992;267(1):257
2-(mannopyranosidyl)ethyl 3'-azido-3'-deoxy-5'-thymidinyl phosphate  127306-80-3   *Thymine Nucleotides *Dideoxynucleotides Zidovudine/*analogs & derivatives. J Med Chem 1991;34(6):1830
6-mannopyranosyl 3'-azido-3'-deoxy-5'-thymidinyl phosphate  133163-37-8   *Organophosphorus Compounds *Dideoxynucleotides Zidovudine/*analogs & derivatives. J Med Chem 1991;34(6):1830
6-glucopyranosyl 3'-azido-3'-deoxy-5'-thymidinyl phosphate  133101-34-5   *Dideoxynucleotides Zidovudine/*analogs & derivatives. J Med Chem 1991;34(6):1830
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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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