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PubChem
| Name: | Zalcitabine |
|---|---|
| PubChem Compound ID: | 10198219 |
| Description: | A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen.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. |
| Molecular formula: | C9H13N3O3 |
| Molecular weight: | 211.218 g/mol |
DrugBank
Identification
| Name: | Zalcitabine |
|---|---|
| Name (isomeric): | DB00943 |
| Drug Type: | small molecule |
| Description: | A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen.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. |
| Synonyms: |
DDCYD; DDC; Dideoxycytidine
|
| Brand: | HIVID |
| Category: | Antimetabolites, Anti-HIV Agents, Nucleoside and Nucleotide Reverse Transcriptase Inhibitors, Reverse Transcriptase Inhibitors |
| CAS number: | 7481-89-2 |
Pharmacology
| Indication: | For the treatment of Human immunovirus (HIV) infections in conjunction with other antivirals. |
|---|---|
| Pharmacology: | Zalcitabine is an analog of 2'-deoxycytidine that is pharmacologically related to but structurally different from other nucleotide reverse transcriptase inhibitors (NRTIs). 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. |
| Mechanism of Action: |
Zalcitabine is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Within cells, zalcitabine is converted to its active metabolite, dideoxycytidine 5'-triphosphate (ddCTP), by the sequential action of cellular enzymes. ddCTP interferes with viral RNA-directed DNA polymerase (reverse...
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| Absorption: | Bioavailability is over 80% following oral administration. |
| Protein binding: | Less than 4% |
| Biotransformation: | Hepatic |
| Route of elimination: | Renal excretion of unchanged drug appears to be the primary route of elimination, accounting for approximately 80% of an intravenous dose and 60% of an orally administered dose within 24 hours after dosing (n=19). Renal clearance exceeds glomerular filtration rate suggesting renal tubular secretion contributes to the elimination of zalcitabine by the kidneys. |
| Half Life: | 2 hours |
| Clearance: | 285 mL/min [HIV-infected patients receiving 1.5 mg IV infusion for 1 hour] |
| 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. |
| Affected organisms: | Human Immunodeficiency Virus |
Interactions
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