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Encyclopedia > Ribavirin
Systematic (IUPAC) name
CAS number 36791-04-5
ATC code J05AB04
PubChem 5064
DrugBank APRD00081
Chemical data
Formula C8H12N4O5 
Mol. mass 244.206
Pharmacokinetic data
Bioavailability 45% oral (without food), about 76% with fatty meal
Metabolism Metabolized to 5'phosphates, de-riboside, and deriboside carboxylic acid
Half life 12 days - Multiple Dose; 120-170 hours - Single Dose
Excretion 10% fecal, remainder in urine (30% unchanged, remainder metabolites)
Therapeutic considerations
Pregnancy cat.

US: X; AU: X Image File history File links Ribavirin. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Carbon (disambiguation). ... This article is about the chemistry of hydrogen. ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, symbol, number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, period, block 16, 2, p Appearance colorless (gas) pale blue (liquid) Standard atomic weight 15. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... The biological half-life of a substance is the time required for half of that substance to be removed from an organism by either a physical or a chemical process. ... The kidneys are important excretory organs in vertebrates. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ...

Legal status

Ethical U.S. pharmaceutical; Not DEA-controlled. The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ...

Routes Liquid for inhalation; oral capsule and tablet

Ribavirin (Copegus®; Rebetol®; Ribasphere®; Vilona®,Virazole®, also generics from Sandoz, Teva, Warrick) is an anti-viral drug which is active against a number of DNA and RNA viruses. It is a member of the nucleoside antimetabolite drugs that interfere with duplication of viral genetic material. Though not effective against all viruses, ribavirin is remarkable as a small molecule for its wide range of activity, including important activities against influenzas, flaviviruses and agents of many viral hemorrhagic fevers. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body. ... Antiviral drugs are a class of medication used specifically for treating viral infections. ... The structure of part of a DNA double helix Deoxyribonucleic acid, or DNA, is a nucleic acid molecule that contains the genetic instructions used in the development and functioning of all known living organisms. ... Left: An RNA strand, with its nitrogenous bases. ... This article is about biological infectious particles. ... Nucleosides are glycosylamines made by attaching a nucleobase (often reffered to simply as bases) to a ribose ring. ... Influenza, commonly known as flu, is an infectious disease of birds and mammals caused by RNA viruses of the family Orthomyxoviridae (the influenza viruses). ... Species see text Flavivirus is a genus of the family Flaviviridae. ... Viral hemorrhagic fevers (VHFs) are a group of illnesses that are caused by several distinct families of viruses: Arenavirus, Filoviridae, Bunyaviridae and Flavivirus. ...

Ribavirin is a pro-drug, meaning that it is a chemical precursor for the actual pharmacologically active molecule. When the pro-drug is administered, the body converts it into the desired chemical. Ribavirin is activated by cellular kinases which change it into the 5' triphosphate nucleotide. In this form it interferes with aspects of RNA metabolism related to viral reproduction. A number of mechanisms have been proposed for this (see Mechanisms of Action, below) but none of these is proven. More than one mechanism may be active. In biochemistry, a kinase is a type of enzyme that transfers phosphate groups from, for example, ATP to a specified substrate or target; the process is termed phosphorylation. Typically, the target is activated or energized by being phosphorylated. ... A nucleotide is a chemical compound that consists of a heterocyclic base, a sugar, and one or more phosphate groups. ...

In the U.K. & the U.S. the oral (capsule or tablet) form of ribavirin is used in the treatment of hepatitis C, in combination with interferon drugs. The aerosol form is used to treat respiratory syncytial virus-related diseases in children. In Mexico, ribavirin ("ribavirina") has been sold for use against influenza. This page is for the disease. ... Interferons (IFNs) are natural proteins produced by the cells of the immune system of most vertebrates in response to challenges by foreign agents such as viruses, bacteria, parasites and tumor cells. ... The respiratory syncytial virus (RSV or RS virus) causes a common viral infection of infants and young children. ...

The primary observed serious adverse side-effect of ribavirin is hemolytic anemia, which may worsen preexisting cardiac disease. The mechanism for this effect is unknown. It is dose-dependent and may sometimes be compensated by decreasing dose. Ribavirin is also a teratogen in some animals species and thus poses a theoretical reproductive risk in humans, remaining a hazard as long as the drug is present, which can be as long as 6 months after a course of the drug has ended. Hemolytic anemia is anemia due to hemolysis, the abnormal breakdown of red blood cells either in the blood vessels (intravascular hemolysis) or elsewhere in the body (extravascular). ...



Oral ribavirin, as Rebetol®, was marketed in the U.S. until 2005 by Schering Plough with royalty payments for licensing made to Valeant Pharmaceuticals International (see History below). It was also marketed as Copegas ® tablets by Roche Pharmaceuticals under a separate license to Valeant Pharmaceuticals International. After concluding patent disputes over generic ribavirin availability in 2003, Three Rivers Pharmaceuticals, LLC in conjunction with Par Pharmaceutical, was approved in 2005 to market ribavirin as Ribosphere® capsules. Generic ribavirin (200 mg, no brand name) became available in 2005 from Sandoz, Teva Pharmaceutical Industries, and Warrick Pharmaceuticals, which is the generic arm of Schering Plough. More generics are expected, including one from Geneva. These products are expected to displace the brand name products paying license fees to Valeant Pharmaceuticals International. The only present FDA-approved indication for these products is in conjunction with interferon against chronic hepatitis C with hepatic damage. Schering-Plough Corporation is a pharmaceutical company started in Germany by Ernst Schering in 1851. ... Valeant Pharmaceuticals International is a pharmaceutical company with activities spanning the drug discovery pipeline from target identification through clinical trials and commercialization. ... Hoffmann-La Roche, Ltd. ... Valeant Pharmaceuticals International is a pharmaceutical company with activities spanning the drug discovery pipeline from target identification through clinical trials and commercialization. ... Par Pharmaceutical develops, manufactures and markets generic and branded specialty pharmaceuticals. ... Sandoz is the generics subsidiary of Novartis, one of the Big Pharma pharmaceutical companies. ... Teva Pharmaceutical Industries Ltd. ... Schering-Plough Corporation is a pharmaceutical company started in Germany by Ernst Schering in 1851. ... Geneva (pronunciation //; French: Genève //, German:   //, Italian: Ginevra //, Romansh: Genevra) is the second most populous city in Switzerland (after Zürich), and is the most populous city of Romandy (the French-speaking part of Switzerland). ... Valeant Pharmaceuticals International is a pharmaceutical company with activities spanning the drug discovery pipeline from target identification through clinical trials and commercialization. ...

In Mexico, oral ribavirin has been available since the 1980s as an over-the-counter drug ("ribavirina," ICN pharmaceuticals Spanish tradename Vilona®), for treating influenza. In this form it was occasionally brought into the U.S. for HIV/AIDS patients. However, ribavirin has proven to have little if any clinical usefulness against HIV, and it can greatly increase blood levels and also toxicity of the HIV antiviral didanosine (ddI, Videx®). Other interactions with nucleoside antivirals for HIV should be considered when HIV/AIDS patients use ribavirin to treat hepatitis C (see "aidsinfo" external link).


Ribavirin (originally also known as Virazole) is a synthetic chemical not found in nature. It was first synthesized in 1970 (Lau, 2002-- see hepcassoc.org external link below) at ICN Pharmaceuticals, Inc. (later Valeant Pharmaceuticals International) by chemist Joseph T. Witkowski, under the direction of laboratory director Roland K. Robins. (Robins [1926-92], a purine chemist, had earlier been the inventor of the highly successful purine-analogue pharmaceutical allopurinol). Ribavirin was discovered as part of a systematic ICN search of antiviral and antitumor activity in synthetic nucleosides. This was inspired in part by discovery (in the 1960s) of antiviral activity from naturally-occurring purine-like nucleoside antibiotics like showdomycin, coformycin, and pyrazomycin. These agents had too much toxicity to be clinically useful (and the antiviral activity of them may be incidental), but they served as the starting point for pharmaceutical chemists interested in antivirals and antimetabolic chemotherapeutic agents. Valeant Pharmaceuticals International is a pharmaceutical company with activities spanning the drug discovery pipeline from target identification through clinical trials and commercialization. ... Allopurinol is a drug used primarily to treat conditions arising from excess uric acid, most notably chronic gout. ...

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.[1] Ribavirin protected mice against mortality from both A and B strains of influenza, and ICN originally planned to market it as an anti-influenza drug. Results in human trials against experimental influenza infection were mixed, however, and the FDA ultimately did not approve this indication for ribavirin use in humans, thereby causing a severe financial shock to ICN.

Although ICN was allowed in 1980 to market ribavirin, in inhalant form, for RSV infection in children, the U.S. market for this indication was small. By the time oral ribavirin was finally approved by the FDA as part of a combination treatment (with interferon) for hepatitis C in 1998, the original ICN patents on ribavirin itself had expired, and (notwithstanding subsequent patent disputes) ribavirin had become essentially a generic drug.

Future: Other Viral Activities

Experimental data indicate that ribavirin may have useful activity against many viruses of interest, including avian influenza, hepatitis B, polio, measles and smallpox. Ribavirin is the only known treatment for a variety of viral hemorrhagic fevers, including Lassa fever, Crimean-Congo hemorrhagic fever, and Hantavirus infection. Ribavirin is active in a hamster model of yellow fever, a finding which is not surprising, given the familial relationship of yellow fever and hepatitis C viruses as flaviviridae. Ribavirin is active against other important flaviviridae such as West Nile virus and dengue fever. Influenza, commonly known as flu, is an infectious disease of birds and mammals caused by RNA viruses of the family Orthomyxoviridae (the influenza viruses). ... “HBV” redirects here. ... Poliomyelitis (polio), or infantile paralysis, is a viral paralytic disease. ... Smallpox (also known by the Latin names Variola or Variola vera) is a contagious disease unique to humans. ... Viral hemorrhagic fevers (VHFs) are a group of illnesses that are caused by several distinct families of viruses: Arenavirus, Filoviridae, Bunyaviridae and Flavivirus. ... Lassa fever is an acute viral hemorrhagic fever first described in 1969 in the Nigerian town of Lassa in the Yedseram River valley. ... Crimean-Congo hemorrhagic fever (CCHF) is a widespread tick-borne viral disease, a zoonosis of domestic animals and wild animals, that may affect humans. ... Species Andes virus (ANDV) Bayou virus (BAYV) Black Creek Canal virus (BCCV) Cano Delgadito virus (CADV) Choclo virus (CHOV) Dobrava-Belgrade virus (DOBV) Hantaan virus (HTNV) Isla Vista virus (ISLAV) Khabarovsk virus (KHAV) Laguna Negra virus (LANV) Muleshoe virus (MULV) New York virus (NYV) Prospect Hill virus (PHV) Puumala virus... This page is for the disease. ... Genera Flavivirus Pestivirus Hepacivirus The Flaviviridae are a family of viruses that infect mammals. ... Genera Flavivirus Pestivirus Hepacivirus The Flaviviridae are a family of viruses that infect mammals. ... West Nile virus (WNV) is a virus of the family Flaviviridae; part of the Japanese encephalitis (JE) antigenic complex of viruses, it is found in both tropical and temperate regions. ... “Dengue Fever” redirects here. ...

Ribavirin's present generic status is expected to slow research into new uses, however.


Physically ribavirin is similar to the sugar D-ribose from which it is derived. It is freely soluble in water, and is re-crystallized as fine silvery needles from boiling methanol. It is only sparingly soluble in anhydrous ethanol.

Classically ribavirin is prepared from natural D-ribose by blocking the 2', 3' and 5' OH groups with benzyl groups, then derivatizing the 1' OH with an acetyl group which acts as a suitable leaving group upon nucleophilic attack. The ribose 1' carbon attack is accomplished with 1,2,4 triazole-3-carboxymethyl ester, which directly attaches the 1' nitrogen of the triazole to the 1' carbon of the ribose, in the proper 1-β-D isomeric position. The bulky benzyl groups hinder attack at the other sugar carbons. Following purification of this intermediate, treatment with ammonia in methanolic conditions then simultaneously deblocks the ribose hydroxyls, and converts the triazole carboxymethyl ester to the carboxamide. Following this step, ribavirin may be recovered in good quantity by cooling and crystallization.


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.[2] 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.

Derivatization of the triazole 5' carbon, or replacement of it with a nitrogen (i.e., the 1,2,4,5 tetrazole 3-carboxamide) also results in substantial loss of activity, as does alkyl derivatization of the 3' carboxamide nitrogen.

The 2' deoxyribose version of ribavirin (the DNA nucleoside analogue) is not active as an antiviral, suggesting strongly that ribavirin requires RNA-dependent enzymes for its antiviral activity.

Antiviral activity is retained for acetate and phosphate derivation of the ribose hydroxyls, including the triphosphate and 3', 5' cyclic phosphates, but these compounds are no more active than the parent molecule, reflecting the high efficiency of esterase and kinase activity in the body. An esterase is an hydrolase enzyme that splits esters into a acid and an alcohol in a chemical reaction with water called hydrolysis. ... In biochemistry, a kinase is a type of enzyme that transfers phosphate groups from high-energy donor molecules, such as ATP, to specific target molecules (substrates); the process is termed phosphorylation. ...


The most successful ribavirin derivative to date is the 3-carboxamidine derivative of the parent 3-carboxamide, first reported in 1973 by Witkowski, and now generally called viramidine (also "Ribamidine"). This drug shows a similar spectrum of antiviral activity to ribavirin, which is not surprising as it is now known to be a pro-drug for ribavirin. Viramidine, however, has useful properties of less erythrocyte-trapping and better liver-targeting than ribavirin. The first property is due to viramidine's basic amidine group which inhibits drug entry into RBCs, and the second property is probably due to increased concentration of the enzymes which convert amidine to amide, in liver tissue. Viramidine is in phase III human trials and may one day be used in place of ribavirin, at least against certain kinds of viral hepatitis (see links in viramidine article). Viramidine's slightly superior toxicological properties may eventually cause it to replace ribavirin in all uses of ribavirin. For example, see PMID 16087250. Viramidine (ICN 3142) is an anti-viral drug in Phase III human trials, but not yet approved for pharmaceutical use. ... Viramidine (ICN 3142) is an anti-viral drug in Phase III human trials, but not yet approved for pharmaceutical use. ... Viramidine (ICN 3142) is an anti-viral drug in Phase III human trials, but not yet approved for pharmaceutical use. ...

Mechanism(s) 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.

Ribavirin 5' mono- di- and tri-phosphates, in addition, are all inhibitors of certain viral RNA-dependent RNA polymerases which are a feature of RNA viruses (save for retroviruses).

Neither of these mechanisms explains ribavirin's effect on many DNA viruses, which is more of a mystery. Ribavirin 5'-monophosphate inhibits cellular inosine monophosphate dehydrogenase, thereby depleting intracellular pools of GTP. This mechanism may be useful in explaining the drug's general cytotoxic and anti-DNA replication effect (i.e. its toxicity) as well as some effect on DNA viral replication.

Ribavirin is an inhibitor of some viral RNA guanylyl transferase and (guanine-7N-)-methyl transferase enzymes, and this may contribute to a defective 5'-cap structure of viral mRNA transcripts and therefore inefficient viral translation for certain DNA viruses, such as vaccinia virus (a complex DNA virus). It has been suggested that incorporation of ribavirin into the 5' end of mRNA transcripts would mimic the 7-methyl guanosine endcap of cellular mRNAs, causing poor cellular translation of these. This would be a cell-toxic effect, but it does not seem to be important at therapeutic ribavirin concentrations. Any difference between cellular and viral enzyme handling of ribavirin-containin mRNA transcripts, is a potential mechanism of differential inhibition of ribavirin to translation of mRNAs from viruses (including DNA viruses).

Finally, ribavirin is known to enhance host T-cell-mediated immunity against viral infection through helping to switch the host T-cell phenotype from type 2 to type 1. This may explain rivavirin's antiviral activity against some viruses such as hepatitis C, at doses which do not clearly interfere with replication of the virus when used without interferon (see hepcassoc.org external link below).


Ribavirin is absorbed from the GI tract probably by nucleoside transporters. Absorption is about 45%, and this is modestly increased (to about 75%) by a fatty meal. Once in the plasma, ribavirin is transported through the cell membrane also by nucleoside transporters.

Ribavirin is widely distributed in all tissues, including the CSF and brain. The pharmacokinetics of ribavirin is dominated by trapping of the phosphated form inside cells, particularly red blood cells (RBCs) which lack the enzyme to remove the phosphate once it has been added by kinases, and therefore attain high concentrations of the drug. Most of the kinase activity which converts the drug to active nucleotide form, is provided by adenine kinase. This enzyme is more active in virally infected cells.

The volume of distribution of ribavirin is large (2000 L/kg) and the length of time the drug is trapped varies greatly from tissue to tissue. The mean half-life for multiple doses in the body is about 12 days, but very long-term kinetics are dominated by the kinetics of RBCs (half-life 40 days). RBCs store ribavirin for the lifetime of the cells, releasing it into the body's systems when old cells are degraded in the spleen.

About a third of absorbed ribavirin is excreted into the urine unchanged, and the rest is excreted into urine as the de-ribosylated base 1,2,4-triazole 3-carboxamide, and the oxidation product of this, 1,2,4- triazole 3-carboxylic acid.

Adverse effects

Ribavirin is not substantially incorporated into DNA, but does have a dose-dependent inhibiting effect on DNA synthesis, as well as having other effects on gene-expression. Possibly for these reasons, significant teratogenic effects have been noted in all non-primate animal species on which ribavirin has been tested. Ribavirin did not produce birth defects in baboons, but this should not be an indication that it is safe in humans. Therefore, two simultaneous forms of birth control are recommended during treatment of either partner and continued for six months after treatment. Women who are pregnant or planning to become pregnant are advised not to take ribavirin. Of special concern as regards teratogenicity is the ribavirin's long half-life in the body. Red blood cells (erythrocytes) concentrate the drug and are unable to excrete it, so this pool is not completely eliminated until all red cells have turned over, a process estimated to take as long as 6 months. Thus in theory, ribavirin might remain a reproductive hazard for as long as 6 months after a course of the drug has ended. Drug packaging information materials in the U.S. now reflect this warning. Teratogenesis is a medical term from the Greek, literally meaning monster making. ... For other uses, see Birth control (disambiguation). ... Human red blood cells Red blood cells are the most common type of blood cell and are the vertebrate bodys principal means of delivering oxygen to body tissues via the blood. ...

Ribavirin should not be given with zidovudine because of the increased risk of anaemia[3]; concurrent use with didanosine should likewise be avoided because of an increased risk of mitochondrial toxicity.[4] Zidovudine (INN) or azidothymidine (AZT) (also called ZDV) is an antiretroviral drug, the first one approved for treatment of HIV. It is also sold under the names Retrovir® and Retrovis®, and as an ingredient in Combivir® and Trizivir®. It is an analog of thymidine. ... Didanosine (2-3-dideoxyinosine, ddI) is sold under the trade names Videx® and Videx EC®. It is a reverse transcriptase inhibitor, effective against HIV and usually used in combination with other antiviral drug therapy as part of highly active antiretroviral therapy (HAART). ... Mitochondrial toxicity is a condition in which the mitochondria of a bodys cells become damaged or decline significantly in number; it occurs as a side-effect of certain antiretroviral drugs used to treat human immunodeficiency virus, or HIV. While the exact causes of mitochondrial toxicity are not known, research...


  1. ^ Sidwell RW, Huffman JH, Khare GP, et al. (1972). "Broad-spectrum antiviral activity of Virazole: 1-β-D-ribofuranosyl-1,2,4-triazole-3-carboxamide". Science 177: 705–6. PMID 4340949. 
  2. ^ Smith RA & Kirkpatrick W (eds.) (1980). "Ribavirin: structure and antiviral activity relationships", Ribavirin: A Broad Spectrum Antiviral Agent. New York: Academic Press, 1–21. 
  3. ^ Alvarez D, Dieterich DT, Brau N, Moorehead L, Ball L, Sulkowski MS (2006). "Zidovudine use but not weight-based ribavirin dosing impacts anaemia during HCV treatment in HIV-infected persons". J Viral Hepat 13 (10): 683–89. PMID 16970600. 
  4. ^ Bani-Sadr F, Carrat F, Pol S, et al. (2005). "Risk factors for symptomatic mitochondrial toxicity in HIV/hepatitis C virus-coinfected patients during interferon plus ribavirin-based therapy". J Acquir Immune Defic Syndr 40: 47–52. PMID 16123681. 

External links

  • http://www.hepcassoc.org/news/article39.html
  • http://www.jac.oxfordjournals.org/cgi/content/full/52/4/543
  • http://aidsinfo.nih.gov/drugs/htmldrug_tech.asp?int_id=0028
  • http://www.jac.oxfordjournals.org/cgi/reprint/dki405v1
  • Information on Ribavirin

  Results from FactBites:
Hepatitis C: Current Treatment (1691 words)
The addition of ribavirin to interferon alpha is superior to interferon alpha alone in the treatment of chronic hepatitis C. Ribavirin is a synthetic nucleoside that has activity against a broad spectrum of viruses.
In several studies, oral ribavirin was examined as a single agent for the treatment of adults with chronic hepatitis C. Although decreases in serum ALT activities were seen with treatment, the overall results of these studies were discouraging as sustained-responses were rarely achieved.
Ribavirin is associated with a significant risk of abnormal fetal development and women of childbearing potential should not begin therapy until a report of a negative pregnancy test has been obtained and not become pregnant during treatment.
  More results at FactBites »



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