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Ribavirin, also known as tribavirin, is an antiviral medication used to treat RSV infection, hepatitis C, and viral hemorrhagic fever.
Common side effects include feeling tired, headache, nausea, fever, muscle pains, and an irritable mood.
Ribavirin was patented in 1971 and approved for medical use in 1986.
1 Medical uses
2 Adverse effects
3 Mechanisms of action
3.1 RNA viruses
3.2 DNA viruses
6 See also
8 External links
Ribavirin is used primarily to treat hepatitis C and viral hemorrhagic fevers (which is an orphan indication in most countries).
It has been used (in combination with ketamine, midazolam, and amantadine ) in treatment of rabies.
Experimental data indicate that ribavirin may have useful activity against canine distemper.
Some interest has been seen in its possible use as a treatment for cancers, especially acute myeloid leukemia.
For a more comprehensive list, see List of adverse effects of ribavirin.
The medication has two FDA “black box” warnings: One raises concerns that use before or during pregnancy by either sex may result in birth defects in the baby, and the other is regarding the risk of red blood cell breakdown.
Ribavirin should not be given with zidovudine because of the increased risk of anemia;
Mechanisms of action
It is a guanosine (ribonucleic) analog used to stop viral RNA synthesis and viral mRNA capping, thus, it is a nucleoside inhibitor. Ribavirin is a prodrug, which when metabolized resembles purine RNA nucleotides. In this form, it interferes with RNA metabolism required for viral replication. Over five direct and indirect mechanisms have been proposed for its mechanism of action.
Ribavirin’s carboxamide group can make the native nucleoside drug resemble adenosine or guanosine, depending on its rotation. For this reason, when ribavirin is incorporated into RNA, as a base analog of either adenine or guanine, it pairs equally well with either uracil or cytosine, inducing mutations in RNA-dependent replication in RNA viruses. Such hypermutation can be lethal to RNA viruses.
Neither of these mechanisms explains ribavirin’s effect on many DNA viruses, which is more of a mystery, especially given the complete inactivity of ribavirin’s 2′ deoxyribose analogue, which suggests that the drug functions only as an RNA nucleoside mimic, and never a DNA nucleoside mimic. Ribavirin 5′-monophosphate inhibits cellular inosine monophosphate dehydrogenase, thereby depleting intracellular pools of GTP.
Ribavirin was first made in 1972.
It was reported that ribavirin was active against a variety of RNA and DNA viruses in culture and in animals, without undue toxicity.
Ribavirin is the INN and USAN, whereas tribavirin is the BAN. Brand names of generic forms include Copegus, Ribasphere, Rebetol.
Ribavirin is possibly best viewed as a ribosyl purine analogue with an incomplete purine 6-membered ring. This structural resemblance historically prompted replacement of the 2′ nitrogen of the triazole with a carbon (which becomes the 5′ carbon in an imidazole), in an attempt to partly “fill out” the second ring— but to no great effect. Such 5′ imidazole riboside derivatives show antiviral activity with 5′ hydrogen or halide, but the larger the substituent, the smaller the activity, and all proved less active than ribavirin. Note that two natural products were already known with this imidazole riboside structure: substitution at the 5′ carbon with OH results in pyrazomycin/pyrazofurin, an antibiotic with antiviral properties but unacceptable toxicity, and replacement with an amino group results in the natural purine synthetic precursor 5-aminoimidazole-4-carboxamide-1-β-D-ribofuranoside ( AICAR ), which has only modest antiviral properties.
Main article: Taribavirin
The most successful ribavirin derivative to date is the 3-carboxamidine derivative of the parent 3-carboxamide, first reported in 1973 by J.T.Witkowski et al.,
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