Ribavirin

Ribavirin
Clinical data


Pronunciation	RYE-ba-VYE-rin
Trade names	Copegus, Rebetol, Virazole, other
AHFS/Drugs.com	Monograph
MedlinePlus	a605018
Pregnancy category	AU: X (High risk) US: X (Contraindicated)
Routes of administration	by mouth, solution for inhalation
ATC code	J05AB04 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	64%
Protein binding	0%
Metabolism	liver and intracellularly
Biological half-life	298 hours (multiple dose); 43.6 hours (single dose)
Excretion	Urine (61%), faeces (12%)
Identifiers
IUPAC name 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-1,2,4-triazole-3-carboxamide
Synonyms	1-(β-D-Ribofuranosyl)-1H-1,2,4-triazole-3-carboxamide
CAS Number	36791-04-5^Y
PubChem CID	37542
IUPHAR/BPS	6842
DrugBank	DB00811^Y
ChemSpider	34439^Y
UNII	49717AWG6K
KEGG	D00423^Y
ChEMBL	CHEMBL1643^Y
NIAID ChemDB	000053
PDB ligand	RBV (PDBe, RCSB PDB)
ECHA InfoCard	100.164.587
Chemical and physical data
Formula	C₈H₁₂N₄O₅
Molar mass	244.206
3D model (Jmol)	Interactive image
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^Y Key:IWUCXVSUMQZMFG-AFCXAGJDSA-N^Y

Ribavirin, also known as tribavirin, is an anti-viral medication used to treat RSV infection, hepatitis C, and viral hemorrhagic fever. For hepatitis C it is used with other medications such as simeprevir, sofosbuvir, peginterferon alfa-2b or peginterferon alfa-2a. Among the viral hemorrhagic fevers it is used for Lassa fever, Crimean–Congo hemorrhagic fever, and Hantavirus infection but not Ebola or Marburg. Ribavirin is taken by mouth or inhaled.

Common side effects include feeling tired, headache, nausea, fever, muscle pains, and an irritable mood. Serious side effects include red blood cell breakdown, liver problems, and allergic reactions. Use during pregnancy results in harm to the baby. Effective birth control is recommended for both males and females for 7 months after use. The mechanism of action of ribavirin is not entirely clear.

Ribavirin was patented in 1971 and approved for medical use in 1986. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. It is available as a generic medication. In the United States a course of treatment costs more than 200 USD.

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