Chemical Component Summary

Name3'-azido-3'-deoxythymidine
SynonymsAzidothymidine; Zidovudine
Identifiers1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione
FormulaC10 H13 N5 O4
Molecular Weight267.241
TypeNON-POLYMER
Isomeric SMILESCC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO)N=[N+]=[N-]
InChIInChI=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
InChIKeyHBOMLICNUCNMMY-XLPZGREQSA-N

Chemical Details

Formal Charge0
Atom Count32
Chiral Atom Count3
Bond Count33
Aromatic Bond Count0

Drug Info: DrugBank

DrugBank IDDB00495 
NameZidovudine
Groups approved
DescriptionA dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group.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
  • Azidothymidine
  • ZDV
  • Zidovudina
  • Zidovudinum
  • Zidovudine
Brand Names
  • Apo-zidovudine
  • Trizivir
  • Zidovudine Oral Solution USP
  • Combivir
  • Zidovudine
IndicationUsed 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
ATC-Code
  • J05AR04
  • J05AF01
  • J05AR05
  • J05AR01
CAS number30516-87-1

Drug Targets

NameTarget SequencePharmacological ActionActions
Reverse transcriptase/RNaseHPISPIETVPVKLKPGMDGPKVKQWPLTEEKIKALVEICTEMEKEGKISKI...unknowninhibitor
Telomerase reverse transcriptaseMPRAPRCRAVRSLLRSHYREVLPLATFVRRLGPQGWRLVQRGDPAAFRAL...unknowninhibitor
Cytochrome P450 2A6MLASGMLLVALLVCLTVMVLMSVWQQRKSKGKLPPGPTPLPFIGNYLQLN...unknownsubstrate
Cytochrome P450 2C9MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...unknownsubstrate
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate
View More
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

Related Resource References

Resource NameReference
PubChem 35370
ChEMBL CHEMBL129
ChEBI CHEBI:10110
CCDC/CSD FIXGAU06, FIXGAU01, FIXGAU, FIXGAU03, WOMHEM