Zalcitabine

Zalcitabine

Clinical data
Trade names	Hivid (discontinued)
AHFS/Drugs.com	Monograph
Pregnancy category	AU: D
Routes of administration	Oral
ATC code	J05AF03 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	>80%
Protein binding	<4%
Metabolism	Hepatic
Elimination half-life	2 hours
Excretion	Renal (circa 80%)
Identifiers
IUPAC name 4-amino-1-((2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one
CAS Number	7481-89-2 Y
PubChem CID	24066
IUPHAR/BPS	4828
DrugBank	DB00943 Y
ChemSpider	22498 Y
UNII	6L3XT8CB3I
KEGG	D00412 Y
ChEBI	CHEBI:10101 Y
ChEMBL	ChEMBL853 Y
NIAID ChemDB	000006
CompTox Dashboard (EPA)	DTXSID0023747
ECHA InfoCard	100.149.677
Chemical and physical data
Formula	C9H13N3O3
Molar mass	211.221 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C1/N=C(/N)\C=C/N1[C@@H]2O[C@@H](CC2)CO
InChI 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 Y Key:WREGKURFCTUGRC-POYBYMJQSA-N Y
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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]