Structure via PubChem · Public domain (PubChem)
ribavirin
Sign in to saveAlso known as Copegus®, ribofluranosyl carboxamide, Virazole®, 1-beta-D-Ribofuranosyl-1,2,4-triazole-3-carboxamide, 1-beta-D-Ribofuranosyl-1H-1,2,4-triazole-3-carboxamide, RBV, Ribavirinum
Ribavirin, also known as tribavirin, is an antiviral medication used to treat illness caused by respiratory syncytial virus (RSV) and hepatitis C virus (HCV) infections, as well as some viral hemorrhagic fevers. For HCV, it is used in combination with other medications, such as simeprevir, sofosbuvir, peginterferon alfa-2b or peginterferon alfa-2a. It can also be used for viral hemorrhagic fevers—specifically, for Lassa fever, Crimean–Congo hemorrhagic fever, and Hantavirus infections (with exceptions for Ebola or Marburg virus diseases). Ribavirin is usually taken orally (by mouth) or inhaled
Key facts
- Drug.protein_bound
- 0%
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 464382050
- Drug.IUPAC_name
- 1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-1,2,4-triazole-3-carboxamide
- Drug.BAN
- tribavirin
- Drug.image
- Ribavirin.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 175
- Drug.image2
- Ribavirin-from-xtal-Mercury-3D-bs.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 200
- Drug.tradename
- Copegus, Rebetol, Virazole, other
- Drug.MedlinePlus
- a605018
- Drug.DailyMedID
- Ribavirin
- Drug.licence_EU
- yes
- Drug.pregnancy_AU
- X
- Drug.pregnancy_US
- X
- Drug.routes_of_administration
- Oral, Inhalation
via Wikipedia infobox
Chemical data
- Formula
- C8H12N4O5
- Molecular weight
- 244.2 g/mol
- IUPAC name
- 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide
- SMILES
- C1=NC(=NN1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)C(=O)N
- InChIKey
- IWUCXVSUMQZMFG-AFCXAGJDSA-N
- XLogP
- -1.8
- Polar surface area
- 144 Ų
- H-bond donors
- 4
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Research
18,780 papers- Ribavirin pharmacokinetics.The Pediatric infectious disease journal · 1990
- Ribavirin: a clinical overview.European journal of epidemiology · 1986
- Ribavirin's antiviral mechanism of action: lethal mutagenesis?Journal of molecular medicine (Berlin, Germany) · 2002
- Ribavirin as an anti-cancer therapy: acute myeloid leukemia and beyond?Leukemia & lymphoma · 2010
- Ribavirin.Pediatrics · 1987
via PubMed
Wikidata facts
- Mass
- 244.081
Show 5 more facts
- chemical formula
- C₈H₁₂N₄O₅
- canonical SMILES
- C1=NC(=NN1C2C(C(C(O2)CO)O)O)C(=O)N
- isomeric SMILES
- C1=NC(=NN1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)C(=O)N
- World Health Organisation international non-proprietary name
- ribavirin
- Commons category
- Ribavirin
Sources (9)
via Wikidata · CC0
~12 min read
Article
16 sectionsContents
- Medical uses
- Hepatitis C
- Viral hemorrhagic fever
- Experimental uses
- Adverse effects
- Mechanisms of action
- RNA viruses
- DNA viruses
- eIF4E targeting in cancer
- History and culture
- Names
- Derivatives
- Taribavirin
- Notes
- References
- External links
Ribavirin, also known as tribavirin, is an antiviral medication used to treat illness caused by respiratory syncytial virus (RSV) and hepatitis C virus (HCV) infections, as well as some viral hemorrhagic fevers. For HCV, it is used in combination with other medications, such as simeprevir, sofosbuvir, peginterferon alfa-2b or peginterferon alfa-2a. It can also be used for viral hemorrhagic fevers—specifically, for Lassa fever, Crimean–Congo hemorrhagic fever, and Hantavirus infections (with exceptions for Ebola or Marburg virus diseases). Ribavirin is usually taken orally (by mouth) or inhaled. Despite widespread usage, it has faced scrutiny in the 21st century because of lack of proven efficacy in treating viral infections for which it has been prescribed in the past.
Its common side effects include fatigue, headache, nausea, fever, muscle pains, and an irritable mood. Serious side effects include red blood cell breakdown, liver problems, and allergic reactions. Its use during pregnancy can bring harm to the developing fetus. Effective birth control is recommended for both males and females for at least seven months during and after use. The mechanism of action of ribavirin is not entirely clear.