Skip Navigation
ChemIDplus A TOXNET DATABASE LiteBrowseAdvanced

Substance Name: Zalcitabine [USAN:USP:INN:BAN]
RN: 7481-89-2
UNII: 6L3XT8CB3I
InChIKey: WREGKURFCTUGRC-POYBYMJQSA-N

Note

  • A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. 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 at low concentrations, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. Its principal toxic side effect is axonal degeneration resulting in peripheral neuropathy.

Molecular Formula

  • C9-H13-N3-O3

Molecular Weight

  • 211.22
 

Classification Codes

Classification Codes

  • Anti-HIV Agents
  • Anti-Infective Agents
  • Anti-Retroviral Agents
  • Antimetabolites
  • Antiretroviral
  • Antiviral
  • Antiviral Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • 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

  • Zalcitabine
  • Zalcitabine [USAN:USP:INN:BAN]

MeSH Heading

  • Zalcitabine

Synonyms

  • 2',3'-Dideoxycytidine
  • 5-25-14-00313 (Beilstein Handbook Reference)
  • BRN 0654956
  • CCRIS 692
  • DDC
  • ddCyd
  • Dideoxycytidine
  • Hivid
  • HSDB 7156
  • NSC 606170
  • Ro 24-2027/000
  • Ro-24-2027/000
  • UNII-6L3XT8CB3I
  • Zalcitabine

Systematic Names

  • Cytidine, 2',3'-dideoxy-
  • Dideoxycytidine

Superlist Name

  • Zalcitabine

Registry Numbers

CAS Registry Number

  • 7481-89-2

FDA UNII

  • 6L3XT8CB3I

System Generated Number

  • 0007481892

Structure Descriptors

InChI

1S/C9H13N3O3/c10-7-3-4-12(9(14)11-7)8-2-1-6(5-13)15-8/h3-4,6,8,13H,1-2,5H2,(H2,10,11,14)/t6-,8+/m0/s1

InChIKey

WREGKURFCTUGRC-POYBYMJQSA-N

Smiles

n1([C@@H]2O[C@H](CO)CC2)c(nc(N)cc1)=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD intravenous > 500mg/kg (500mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 38, Pg. 2615, 1996.
mouse LD oral > 4gm/kg (4000mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 38, Pg. 2615, 1996.
rat LD oral > 2gm/kg (2000mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 38, Pg. 2615, 1996.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 217-218 deg C   EXP
log P (octanol-water) -1.30E+00 (none)   EXP
Water Solubility 2.42E+04 mg/L 25 EST
Vapor Pressure 5.83E-08 mm Hg 25 EST
Henry's Law Constant 1.17E-16 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.11E-10 cm3/molecule-sec 25 EST

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