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Substance Name: Zidovudine [USAN:USP:INN:BAN:JAN]
RN: 30516-87-1
UNII: 4B9XT59T7S
InChIKey: HBOMLICNUCNMMY-XLPZGREQSA-N

Note

  • A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group.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.

Molecular Formula

  • C10-H13-N5-O4

Molecular Weight

  • 267.2437
 

Classification Codes

Classification Codes

  • Anti-HIV Agents
  • Anti-Infective Agents
  • Anti-Retroviral Agents
  • Antimetabolites
  • Antiretroviral
  • Antiviral
  • Antiviral Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Mutation Data
  • Noxae
  • Nucleic Acid Synthesis Inhibitors
  • Reproductive Effect
  • Reverse Transcriptase Inhibitors
  • Tumor Data

Superlist Classification Code

  • Overall Carcinogenic Evaluation: 2B

Names and Synonyms

Name of Substance

  • Zidovudine
  • Zidovudine [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Zidovudine

Synonyms

  • 1-(3-Azido-2,3-dideoxy-beta-D-ribofuranosyl)-5-methylpyrimidine-2,4-(1H,3H)-dione
  • 3'-Azido-3'-deoxythymidine
  • Azidothymidine
  • AZT
  • BW A509U
  • BW-A 509U
  • CCRIS 105
  • Compound S
  • DRG-0004
  • HSDB 6515
  • NSC 602670
  • Retrovir
  • UNII-4B9XT59T7S
  • ZDV
  • Zidovudina
  • Zidovudina [Spanish]
  • Zidovudine
  • Zidovudinum
  • Zidovudinum [Latin]

Systematic Names

  • Azidothymidine
  • Thymidine, 3'-azido-3'-deoxy-

Superlist Names

  • 3'-Azido-3'-deoxythymidine
  • Zidovudine

Mixture Names

  • Combivir
  • Trizivir

Registry Numbers

CAS Registry Number

  • 30516-87-1

FDA UNII

  • 4B9XT59T7S

Other Registry Number

  • 399024-19-2

System Generated Number

  • 0030516871

Structure Descriptors

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

HBOMLICNUCNMMY-XLPZGREQSA-N

Smiles

Cc1cn(c(=O)[nH]c1=O)[C@H]2C[C@@H]([C@H](O2)CO)N=[N+]=[N-]

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man LDLo oral 86mg/kg/1W-I (86mg/kg) BEHAVIORAL: HEADACHE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Lancet. Vol. 2, Pg. 1392, 1986.
man TDLo oral 434mg/kg/38D- (434mg/kg) BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE

BLOOD: APLASTIC ANEMIA

BLOOD: CHANGES IN CELL COUNT (UNSPECIFIED)
Annals of Internal Medicine. Vol. 107, Pg. 502, 1987.
man TDLo unreported 69mg/kg (69mg/kg) SENSE ORGANS AND SPECIAL SENSES: "RETINAL CHANGES (PIGMENTARY DEPOSITIONS, RETINITIS, OTHER): EYE" Annals of Internal Medicine. Vol. 114, Pg. 297, 1991.
mouse LD50 intravenous > 70mg/kg (70mg/kg)   United States Patent Document. Vol. #4804651,
mouse LD50 oral 3062mg/kg (3062mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Fundamental and Applied Toxicology. Vol. 32, Pg. 129, 1996.
mouse LD50 unreported > 750mg/kg (750mg/kg)   United States Patent Document. Vol. #4857511,
rat LD50 intravenous > 70mg/kg (70mg/kg)   United States Patent Document. Vol. #4804651,
rat LD50 oral 3084mg/kg (3084mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
Fundamental and Applied Toxicology. Vol. 32, Pg. 129, 1996.
rat LD50 unreported > 750mg/kg (750mg/kg)   United States Patent Document. Vol. #4857511,
women TDLo oral 1gm/kg/6W-I (1000mg/kg) SKIN AND APPENDAGES (SKIN): NAILS: OTHER Annals of Internal Medicine. Vol. 107, Pg. 350, 1987.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 113-115 deg C   EXP
log P (octanol-water) 0.05 (none)   EXP
Water Solubility 852 mg/L 25 EST
Vapor Pressure 5.23E-20 mm Hg 25 EST
Henry's Law Constant 2.01E-22 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 7.70E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.