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PubChem
| Name: | Zidovudine |
|---|---|
| PubChem Compound ID: | 35370 |
| Description: | A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. 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, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia. |
| Molecular formula: | C10H13N5O4 |
| Molecular weight: | 267.242 g/mol |
| Synonyms: |
DivK1c_000524; Retrovir (TN); KBioGR_000703; AZT & SST; ZIDOVUDINE [AZT]; Zidovudinum [Latin]; Cpd S; AIDS-001803; AIDS-001535; Azidothymidine.
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DrugBank
Identification
| Name: | Zidovudine |
|---|---|
| Name (isomeric): | DB00495 |
| Drug Type: | small molecule |
| Description: | A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. 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, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia. |
| Brand: | Compound S, Azidothymidine, Retrovir, Novo-Azt, Aztec, Apo-Zidovudine, Zidovudine EP III |
| Brand name mixture: | Trizivir(Abacavir sulfate + Lamivudine + Zidovudine), Combivir(Lamivudine + Zidovudine) |
| Category: | Antimetabolites, Anti-HIV Agents, Nucleoside and Nucleotide Reverse Transcriptase Inhibitors, Reverse Transcriptase Inhibitors |
| CAS number: | 30516-87-1 |
Pharmacology
| Indication: | For the treatment of human immunovirus (HIV) infections. |
|---|---|
| Pharmacology: |
Zidovudine is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Zidovudine 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 lac...
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| Mechanism of Action: | Zidovudine, a structural analog of thymidine, inhibits the activity of HIV-1 reverse transcriptase (RT) both by competing with the natural substrate dGTP and by its incorporation into viral DNA. |
| Absorption: | Rapid and nearly complete absorption from the gastrointestinal tract following oral administration; however, because of first-pass metabolism, systemic bioavailability of zidovudine capsules and solution is approximately 65% (range, 52 to 75%). Bioavailability in neonates up to 14 days of age is approximately 89%, and it decreases to approximately 61% and 65% in neonates over 14 days of age and children 3 months to 12 years, respectively. Administration with a high-fat meal may decrease the rate and extent of absorption. |
| Protein binding: | 30-38% |
| Biotransformation: | Hepatic. Metabolized by glucuronide conjugation to major, inactive metabolite, 3′-azido-3′-deoxy-5′- O-beta-D-glucopyranuronosylthymidine (GZDV). |
| Route of elimination: | As in adult patients, the major route of elimination was by metabolism to GZDV. After intravenous dosing, about 29% of the dose was excreted in the urine unchanged and about 45% of the dose was excreted as GZDV |
| Half Life: | 0.5-3 hours |
| Clearance: | 0.65 +/- 0.29 L/hr/kg [HIV-infected, Birth to 14 Days of Age] 1.14 +/- 0.24 L/hr/kg [HIV-infected, 14 Days to 3 Months of Age] 1.85 +/- 0.47 L/hr/kg [HIV-infected, 3 Months to 12 Years of Age] |
| Toxicity: | Symptoms of overdose include fatigue, headache, nausea, and vomiting. LD50 is 3084 mg/kg (orally in mice). |
| Affected organisms: | Human Immunodeficiency Virus |
Interactions
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