AZZ

3'-azido-3'-deoxythymidine

Created:	2007-11-14
Last modified:	2020-06-05

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Chemical Details
Formal Charge	0
Atom Count	32
Chiral Atom Count	3
Bond Count	33
Aromatic Bond Count	0

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Chemical Component Summary
Name	3'-azido-3'-deoxythymidine
Synonyms	Azidothymidine; Zidovudine
Systematic Name (OpenEye OEToolkits)	1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione
Formula	C₁₀ H₁₃ N₅ O₄
Molecular Weight	267.241
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	O=C1NC(=O)N(C=C1C)C2OC(C(\N=[N+]=[N-])C2)CO
SMILES	CACTVS	3.370	CC1=CN([CH]2C[CH](N=[N+]=[N-])[CH](CO)O2)C(=O)NC1=O
SMILES	OpenEye OEToolkits	1.7.6	CC1=CN(C(=O)NC1=O)C2CC(C(O2)CO)N=[N+]=[N-]
Canonical SMILES	CACTVS	3.370	CC1=CN([C@H]2C[C@H](N=[N+]=[N-])[C@@H](CO)O2)C(=O)NC1=O
Canonical SMILES	OpenEye OEToolkits	1.7.6	CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO)N=[N+]=[N-]
InChI	InChI	1.03	InChI=1S/C10H13N5O4/c1-5-3-15(10(18)12-9(5)17)8-2-6(13-14-11)7(4-16)19-8/h3,6-8,16H,2,4H2,1H3,(H,12,17,18)/t6-,7+,8+/m0/s1
InChIKey	InChI	1.03	HBOMLICNUCNMMY-XLPZGREQSA-N

Drug Info: DrugBank

DrugBank ID	DB00495
Name	Zidovudine
Groups	approved
Description	A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group.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. [PubChem]
Synonyms	Zidovudina AZT Zidovudinum ZDV Zidovudine Azidothymidine
Brand Names	LAMIVUDINE and ZIDOVUDINE Abacavir, Lamivudine and Zidovudine Combivir Auro-lamivudine/zidovudine Apo-zidovudine-lamivudine-nevirapine Apo-lamivudine-zidovudine Lamivudine, Nevirapine, and Zidovudine Zidovudine Oral Solution USP Jamp Lamivudine / Zidovudine Retrovir (azt) 300mg Lamivudine/zidovudine Teva Lamivudine and Zidovudine Apo-abacavir-lamivudine-zidovudine Abacavir Sulfate, Lamivudine and Zidovudine Zidovudine Retrovir (azt) Apo-zidovudine Lamivudine Zidovudine Novo-azt Cap 100mg Trizivir Retrovir Teva-lamivudine/zidovudine
Indication	Used in combination with other antiretroviral agents for the treatment of human immunovirus (HIV) infections.
Categories	Agents Causing Muscle Toxicity Anti-HIV Agents Anti-Infective Agents Anti-Retroviral Agents Antiinfectives for Systemic Use Antimetabolites Antiviral Agents Antivirals for Systemic Use Antivirals used in combination for the treatment of HIV infections BCRP/ABCG2 Substrates Cytochrome P-450 CYP2A6 Substrates Cytochrome P-450 CYP2C8 Substrates Cytochrome P-450 CYP2C9 Substrates Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 Substrates Deoxyribonucleosides Dideoxynucleosides Direct Acting Antivirals Enzyme Inhibitors Human Immunodeficiency Virus Nucleoside Analog Reverse Transcriptase Inhibitor Immunosuppressive Agents Myelosuppressive Agents Noxae Nucleic Acid Synthesis Inhibitors Nucleic Acids, Nucleotides, and Nucleosides Nucleoside and Nucleotide Reverse Transcriptase Inhibitors Nucleoside Reverse Transcriptase Inhibitors Nucleosides OAT1/SLC22A6 Substrates OAT3/SLC22A8 Inhibitors OAT3/SLC22A8 Substrates P-glycoprotein substrates Pyrimidine Nucleosides Pyrimidines Reverse Transcriptase Inhibitors Toxic Actions UGT1A1 Inducers UGT1A1 Substrates UGT2B7 substrates
ATC-Code	J05AR04 J05AF01 J05AR05 J05AR01
CAS number	30516-87-1

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Reverse transcriptase/RNaseH	PISPIETVPVKLKPGMDGPKVKQWPLTEEKIKALVEICTEMEKEGKISKI...	unknown	inhibitor
Telomerase reverse transcriptase	MPRAPRCRAVRSLLRSHYREVLPLATFVRRLGPQGWRLVQRGDPAAFRAL...	unknown	inhibitor
Cytochrome P450 2A6	MLASGMLLVALLVCLTVMVLMSVWQQRKSKGKLPPGPTPLPFIGNYLQLN...	unknown	substrate
Cytochrome P450 2C9	MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...	unknown	substrate
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate
Thymidine kinase, cytosolic	MSCINLPTVLPGSPSKTRGQIQVILGPMFSGKSTELMRRVRRFQIAQYKC...	unknown	substrate
UDP-glucuronosyltransferase 2B7	MSVKWTSVILLIQLSFCFSSGNCGKVLVWAAEYSHWMNIKTILDELIQRG...	unknown	substrate
UDP-glucuronosyltransferase 1-1	MAVESQGGRPLVLGLLLCVLGPVVSHAGKILLIPVDGSHWLSMLGAIQQL...	unknown	substrate,inducer
Serum albumin	MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...	unknown
Solute carrier family 22 member 2	MPTTVDDVLEHGGEFHFFQKQMFFLLALLSATFAPIYVGIVFLGFTPDHR...	unknown
Solute carrier family 22 member 6	MAFNDLLQQVGGVGRFQQIQVTLVVLPLLLMASHNTLQNFTAAIPTHHCR...	unknown	substrate
Solute carrier family 22 member 7	MGFEELLEQVGGFGPFQLRNVALLALPRVLLPLHFLLPIFLAAVPAHRCA...	unknown
Solute carrier family 22 member 8	MTFSEILDRVGSMGHFQFLHVAILGLPILNMANHNLLQIFTAATPVHHCR...	unknown	substrate,inhibitor
Solute carrier family 22 member 11	MAFSKLLEQAGGVGLFQTLQVLTFILPCLMIPSQMLLENFSAAIPGHRCW...	unknown
Sodium/nucleoside cotransporter 1	MENDPSRRRESISLTPVAKGLENMGADFLESLEEGQLPRSDLSPAEIRSS...	unknown
Equilibrative nucleoside transporter 2	MARGDAPRDSYHLVGISFFILGLGTLLPWNFFITAIPYFQARLAGAGNST...	unknown
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate
Multidrug resistance-associated protein 4	MLPVYQEVKPNPLQDANLCSRVFFWWLNPLFKIGHKRRLEEDDMYSVLPE...	unknown	substrate
Multidrug resistance-associated protein 5	MKDIDIGKEYIIPSPGYRSVRERTSTSGTHRDREDSKFRRTRPLECQDAL...	unknown	substrate
ATP-binding cassette sub-family G member 2	MSSSNVEVFIPVSQGNTNGFPATASNDLKAFTEGAVLSFHNICYRVKLKS...	unknown	substrate
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682