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QuickView for Ribavirin (compound)


PubChem
Name: Ribavirin
PubChem Compound ID: 10220469
Description: A nucleoside antimetabolite antiviral agent that blocks nucleic acid synthesis and is used against both RNA and DNA viruses.
Molecular formula: C8H12N4O5
Molecular weight: 244.205 g/mol
DrugBank
Identification
Name: Ribavirin
Name (isomeric): DB00811
Drug Type: small molecule
Description: A nucleoside antimetabolite antiviral agent that blocks nucleic acid synthesis and is used against both RNA and DNA viruses.
Synonyms:
Ribavirinum [INN-Latin]; Ribavirina [INN-Spanish]; Ribavirine [INN-French]; RBV; Ribavirin Triphosphate
Brand: Virazole, Varazid, RTP, Ribamidyl, Rebretron, Tribavirin, RTC, Ribasphere, Ribavirin-TP, RIBAV, Virazid, Viramid, Ribamide, Rebetol, Ribavirin Capsules, Vilona, Ribamidil, Copegus, Rebetron, RTCA, Virazole 5'-triphosphate
Brand name mixture: Rebetron (Schering-Plough)(Ribavirin + Interferon alpha)
Category: Antimetabolites, Antiviral Agents
CAS number: 36791-04-5
Pharmacology
Indication: For the treatment of chronic hepatitis C and for respiratory syncytial virus (RSV).
Pharmacology:
Ribavirin is an anti-viral drug active against a number of DNA and RNA viruses. It is a member of the nucleoside antimetabolite drugs that interfere with duplication of the viral genetic material. The drug inhibits the activity of the enzyme RNA dependent RNA polymerase, due to it's resemblence to building blocks of the RNA molecules. The oral form...
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Mechanism of Action:
Ribavirin is readily phosphorylated intracellularly by adenosine kinase to ribavirin mono-, di-, and triphosphate metabolites. Ribavirin triphosphate (RTP) is a potent competitive inhibitor of inosine monophosphate (IMP) dehydrogenase, viral RNA polymerase and messenger RNA (mRNA) guanylyltransferase (viral) and can be incorporated into RNA in RNA ...
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Absorption: Rapidly and extensively absorbed following oral administration. However, due to first-pass metabolism, the absolute bioavailability averages 64%.
Biotransformation: Hepatic. Results of in vitro studies using both human and rat liver microsome preparations indicated little or no cytochrome P450 enzyme-mediated metabolism of ribavirin, with minimal potential for P450 enzyme-based drug interactions. Ribavirin has two pathways of metabolism: (1) a reversible phosphorylation pathway in nucleated cells; and (2) a degradative pathway involving deribosylation and amide hydrolysis to yield a triazole carboxylic acid metabolite.
Half Life: 9.5 hours
Clearance: Apparent cl=26 L/h [A single oral dose]
Toxicity: Side effects include "flu-like" symptoms, such as headache, fatigue, myalgia, and fever. The LD50 in mice is 2 g/kg orally and is associated with hypoactivity and gastrointestinal symptoms (estimated human equivalent dose of 0.17 g/kg, based on body surface area conversion).
Affected organisms: Hepatitis C virus, RSV and other RNA/DNA viruses
Interactions
Drug interaction:
ZidovudineIncreased risk or severity of anemia. Consider alternate therapy or monitor more closely for anemia.
AbacavirRibavirin may increase the hepatotoxicity of reverse transcriptase inhibitors (nucleoside) such as Abacavir. Lactic acidosis may occur. Consider modifying therapy.
ZalcitabineRibavirin may increase the hepatotoxicity of zalcitabine. May cause lactic acidosis. MOnitor for lactic acidosis during concomitant therapy.

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