Ribavirin

Ribavirin
Clinical data
Pronunciation	/ˌraɪbəˈvaɪrɪn/ RY-bə-VY-rin
Trade names	Copegus, Rebetol, Virazole, other
Other names	1-(β-D-Ribofuranosyl)-1"H"-1,2,4-triazole-3-carboxamide, tribavirin (BAN UK)
AHFS/Drugs.com	Monograph
MedlinePlus	a605018
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); CA: ℞-only; UK: POM (Prescription only); US: WARNINGRx-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	64%
Protein binding	0%
Metabolism	liver and intracellularly
Elimination half-life	298 hours (multiple dose); 43.6 hours (single dose)
Excretion	Urine (61%), faeces (12%)
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 ;
PubChem CID	37542;
IUPHAR/BPS	6842;
DrugBank	DB00811 ;
ChemSpider	34439 ;
UNII	49717AWG6K;
KEGG	D00423 ;
ChEMBL	ChEMBL1643 ;
NIAID ChemDB	000053;
PDB ligand	RBV (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID8023557 ;
ECHA InfoCard	100.164.587
Chemical and physical data
Formula	C8H12N4O5
Molar mass	244.207 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	166 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 ; Key:IWUCXVSUMQZMFG-AFCXAGJDSA-N ;
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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 C, it is used in combination with other medications such as simeprevir, sofosbuvir, peginterferon alfa-2b or peginterferon alfa-2a. 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. Ribavirin is taken orally (swallowed by mouth) or inhaled. 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.

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 at least seven months during and 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. It is available as a generic medication.

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