Drug/Small Molecule:
zalcitabine

2D structure

Overview

Generic Names: DDC; DDCYD; Dideoxycytidine
Trade Names: HIVID
PharmGKB Accession Id: PA451950

Description

A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen.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. PubChem (source: Drug Bank)

Indication

For the treatment of Human immunovirus (HIV) infections. (source: Drug Bank)

ATC Therapeutic Category

  • J05AF:Nucleoside and nucleotide reverse transcriptase inhibitors

Pharmacology, Interactions, and Contraindications

Mechanism Of Action

Zalcitabine is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Zalcitabine is phosphorylated to active metabolites that compete for incorporation into viral DNA. They inhibit the HIV reverse transcriptase enzyme competitively and act as a chain terminator of DNA synthesis. The lack of a 3'-OH group in the incorporated nucleoside analogue prevents the formation of the 5' to 3' phosphodiester linkage essential for DNA chain elongation, and therefore, the viral DNA growth is terminated. (source: Drug Bank)

Pharmacology

Zalcitabine inhibits the activity of HIV-1 reverse transcriptase (RT) both by competing with the natural substrate dGTP and by its incorporation into viral DNA. (source: Drug Bank)

Food Interactions

Do not take calcium, aluminium, magnesium or iron supplements within 2 hours of taking this medication.
Take on empty stomach: 1 hour before or 2 hours after meals. (source: Drug Bank)

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Hepatic (source: Drug Bank)

Protein Binding

Less than 4% (source: Drug Bank)

Absorption

Bioavailability is over 80% following oral administration. (source: Drug Bank)

Toxicity

Acute overdose: Inadvertent pediatric overdoses have occurred with doses up to 1.5 mg/kg zalcitabine. Chronic overdose: in an initial dose-finding study in which zalcitabine was administered at doses 25 times (0.25 mg/kg every 8 hours) the currently recommended dose, one patient discontinued zalcitabine after 1½ weeks of treatment subsequent to the development of a rash and fever. (source: Drug Bank)

Isomeric SMILES Code:

c1cn(c(=O)nc1N)C[C@H]2CC[C@H](O2)CO (source: Drug Bank)

A list of non-curated publications that mention this drug along with other genes is available.

A list of non-curated publications that mention this drug along with other drugs is available.

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

Additional Datasets

These datasets are minimally curated and are sorted alphabetically by title.

  1. The Connectivity Map: using gene-expression signatures to connect small molecules, genes, and disease

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00943
KEGG Compound ID:
C07207
KEGG Drug ID:
D00412
PubChem Compound ID:
24066
PubChem Substance ID:
166590

Common Searches

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Non-Curated Publications

A list of non-curated publications that mention this drug is available.

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