Zalcitabine

Zalcitabine
Clinical data
Trade namesHivid (discontinued)
AHFS/Drugs.comMonograph
Pregnancy
category
  • AU: D
Routes of
administration
Oral
ATC code
Legal status
Legal status
  • UK: POM (Prescription only)
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability>80%
Protein binding<4%
MetabolismHepatic
Elimination half-life2 hours
ExcretionRenal (circa 80%)
Identifiers
  • 4-amino-1-((2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard100.149.677 Edit this at Wikidata
Chemical and physical data
FormulaC9H13N3O3
Molar mass211.221 g·mol−1
3D model (JSmol)
  • O=C1/N=C(/N)\C=C/N1[C@@H]2O[C@@H](CC2)CO
  • 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 checkY
  • Key:WREGKURFCTUGRC-POYBYMJQSA-N checkY
  (verify)

Zalcitabine (2′-3′-dideoxycytidine, ddC), also called dideoxycytidine, is a nucleoside analog reverse-transcriptase inhibitor (NRTI) sold under the trade name Hivid. Zalcitabine was the third antiretroviral to be approved by the Food and Drug Administration (FDA) for the treatment of HIV/AIDS. It is used as part of a combination regimen.

Zalcitabine appears less potent than some other nucleoside RTIs, has an inconvenient three-times daily frequency and is associated with serious adverse events. For these reasons it is now rarely used to treat human immunodeficiency virus (HIV), and it has even been removed from pharmacies entirely in some countries.[1]

  1. ^ "zalcitabine (CHEBI:10101)". www.ebi.ac.uk. Retrieved 2021-01-18.