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Ribavirin information


Ribavirin
Clinical data
Pronunciation/ˌrbəˈvrɪn/ RY-bə-VY-rin
Trade namesCopegus, Rebetol, Virazole, other[1]
Other names1-(β-D-Ribofuranosyl)-1"H"-1,2,4-triazole-3-carboxamide, tribavirin (BAN UK)
AHFS/Drugs.comMonograph
MedlinePlusa605018
License data
  • EU EMA: by INN
  • US DailyMed: Ribavirin
Pregnancy
category
  • AU: X (High risk)
Routes of
administration
Oral, Inhalation
ATC code
  • J05AP01 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)[3]
  • CA: ℞-only[4]
  • UK: POM (Prescription only)
  • US: WARNING[2]Rx-only
  • EU: Rx-only
Pharmacokinetic data
Bioavailability64%[5]
Protein binding0%[5]
Metabolismliver and intracellularly[5]
Elimination half-life298 hours (multiple dose); 43.6 hours (single dose)[5]
ExcretionUrine (61%), faeces (12%)[5]
Identifiers
IUPAC name
  • 1-[(2"R",3"R",4"S",5"R")-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1"H"-1,2,4-triazole-3-carboxamide
CAS Number
  • 36791-04-5 checkY
PubChem CID
  • 37542
IUPHAR/BPS
  • 6842
DrugBank
  • DB00811 checkY
ChemSpider
  • 34439 checkY
UNII
  • 49717AWG6K
KEGG
  • D00423 checkY
ChEMBL
  • ChEMBL1643 checkY
NIAID ChemDB
  • 000053
PDB ligand
  • RBV (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID8023557 Edit this at Wikidata
ECHA InfoCard100.164.587 Edit this at Wikidata
Chemical and physical data
FormulaC8H12N4O5
Molar mass244.207 g·mol−1
3D model (JSmol)
  • Interactive image
Melting point166 to 168 °C (331 to 334 °F)
SMILES
  • OC[C@@H](O1)[C@@H](O)[C@@H](O)[C@@H]1N2N=C(C(N)=O)N=C2
InChI
  • InChI=1S/C8H12N4O5/c9-6(16)7-10-2-12(11-7)8-5(15)4(14)3(1-13)17-8/h2-5,8,13-15H,1H2,(H2,9,16)/t3-,4-,5-,8-/m1/s1 checkY
  • Key:IWUCXVSUMQZMFG-AFCXAGJDSA-N checkY
  (verify)

Ribavirin, also known as tribavirin, is an antiviral medication used to treat RSV infection, hepatitis C and some viral hemorrhagic fevers.[1] For hepatitis C, it is used in combination with other medications such as simeprevir, sofosbuvir, peginterferon alfa-2b or peginterferon alfa-2a.[1] Among the viral hemorrhagic fevers it is sometimes used for Lassa fever, Crimean–Congo hemorrhagic fever, and Hantavirus infection but should not be used for Ebola or Marburg infections.[1] Ribavirin is taken orally (swallowed by mouth) or inhaled.[1] Despite widespread usage, since the 2010s it has faced scrutiny for a lack of efficacy in treating viral infections it has historically been prescribed for.[6][7]

Common side effects include tiredness, headache, nausea, fever, muscle pains, and an irritable mood.[1] Serious side effects include red blood cell breakdown, liver problems, and allergic reactions.[1] Use during pregnancy results in harm to the baby.[1] Effective birth control is recommended for both males and females for at least seven months during and after use.[8] The mechanism of action of ribavirin is not entirely clear.[1]

Ribavirin was patented in 1971 and approved for medical use in 1986.[9] It is on the World Health Organization's List of Essential Medicines.[10] It is available as a generic medication.[1]

  1. ^ a b c d e f g h i j k "Ribavirin". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.
  2. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
  3. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  4. ^ "Ribavirin (Ibavyr)". Catie. 2022. Retrieved 22 August 2022.
  5. ^ a b c d e "PRODUCT INFORMATION REBETOL (RIBAVIRIN) CAPSULES" (PDF). TGA eBusiness Services. Merck Sharp & Dohme (Australia) Pty Limited. 29 April 2013. Archived from the original on 16 August 2017. Retrieved 23 February 2014.
  6. ^ Cite error: The named reference Safrin_2024 was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference Drugs.com_2023 was invoked but never defined (see the help page).
  8. ^ World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 177. hdl:10665/44053. ISBN 9789241547659.
  9. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 504. ISBN 9783527607495. Archived from the original on 2016-12-20.
  10. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

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Ribavirin

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Ribavirin, also known as tribavirin, is an antiviral medication used to treat RSV infection, hepatitis C and some viral hemorrhagic fevers. For hepatitis...

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List of adverse effects of ribavirin

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List of adverse effects of ribavirin by frequency. Abdominal pain Anemia Anxiety Appetite loss Concentration impaired Depression Diarrhea Dizziness Dry...

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Taribavirin

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It is a prodrug of ribavirin, active against a number of DNA and RNA viruses. Taribavirin has better liver-targeting than ribavirin, and has a shorter...

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List of antiviral drugs

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PMID 25387551. Gish RG (January 2006). "Treating HCV with ribavirin analogues and ribavirin-like molecules". The Journal of Antimicrobial Chemotherapy...

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Hepatitis C

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antiviral medications such as sofosbuvir or simeprevir. Peginterferon and ribavirin were earlier generation treatments that proved successful in <50% of cases...

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Viral hemorrhagic fever

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are generally not available. Post-exposure prophylactic (preventive) ribavirin may be effective for some bunyavirus and arenavirus infections. VHF isolation...

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Lassa fever

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addressing dehydration and improving symptoms. The antiviral medication ribavirin has been recommended, but evidence to support its use is weak. Descriptions...

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Respiratory syncytial virus

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respiratory failure, intubation and mechanical ventilation may be required. Ribavirin is an antiviral medication licensed for the treatment of RSV in children...

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Boceprevir

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April, 2009. When used in combination with peginterferon alfa-2b and ribavirin, boceprevir resulted in significantly higher sustained viral response...

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Subacute sclerosing panencephalitis

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Supportive treatment Medication Intrathecal interferon alpha, intravenous ribavirin, isoprinosine Prognosis Usually fatal Frequency 2 in 10,000 for all age...

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Kadmon Corporation

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Ontario, Canada-based Valeant Pharmaceuticals for their Hepatitis C drugs ribavirin and taribavirin (now KD024). Cancer drugs XL647 and XL844 were acquired...

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Yellow fever

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administration of the antiviral ribavirin is an effective treatment of many pathological features of the disease. Ribavirin treatment during the first five...

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Ledipasvir

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used to treat patients with genotypes 1a or 1b without PEG-interferon or ribavirin. Ledipasvir is an inhibitor of NS5A, a hepatitis C virus protein.[citation...

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Interferon

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C virus (HCV) worldwide—genotype I— can be treated with interferon-α, ribavirin and protease inhibitors such as telaprevir, boceprevir or the nucleotide...

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Infection

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interferon-alpha-2b (brand names Pegasys or PEG-Intron) combined with ribavirin, it has been shown that genetic polymorphisms near the human IL28B gene...

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Sofosbuvir

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caused by ribavirin. Females who could potentially become pregnant should undergo a pregnancy test 2 months prior to starting the sofosbuvir/ribavirin/peginterferon...

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Telaprevir

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treatment with peginterferon alfa-2a and ribavirin alone. In patients who received peginterferon alfa-2a and ribavirin for a year, the addition of telaprevir...

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WHO Model List of Essential Medicines

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(isoniazid + pyridoxine + sulfamethoxazole + trimethoprim) Ribavirin Valganciclovir Complementary: Oseltamivirα Valganciclovirα Entecavir Tenofovir...

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Human parainfluenza viruses

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HPIVs during the early stages of life via the colostrum in breast milk. Ribavirin is one medication which has shown good potential for the treatment of...

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SARS

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antipyretics, supplemental oxygen and mechanical ventilation as needed. While ribavirin is commonly used to treat SARS, there seems to have little to no effect...

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RNA

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targeting RNA and approved drugs for human illness therapy is scarce. Ribavirin, branaplam, and ataluren are currently available medications that stabilize...

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Nipah virus infection

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treatment is supportive care. While tentative evidence supports the use of ribavirin, it has not yet been studied in people with the disease. Specific antibodies...

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Brazilian hemorrhagic fever

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who was studying the woman's disease contracted the virus but survived. Ribavirin was not given in these first two cases. Four years later, in 1994, a researcher...

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Glial scar

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as well as chemical signaling events to reduce reactive astrogliosis. Ribavirin is a purine nucleoside analogue that is generally used as an anti-viral...

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Canine distemper

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G, Belloli C, Cirone F, et al. (February 2008). "In vitro efficacy of ribavirin against canine distemper virus". Antiviral Res. 77 (2): 108–113. doi:10...

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Herpes

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LB, Wolf SM, Hintz CJ, Huffman JH, Sidwell RW (March 1977). "Effect of ribavirin on Type 2 Herpesvirus hominis (HVH/2) in vitro and in vivo". Annals of...

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