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-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-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 ;
	(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]

^ ^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.
^ "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.
^ 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.
^ "Ribavirin (Ibavyr)". Catie. 2022. Retrieved 22 August 2022.
^ ^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.
^ Cite error: The named reference Safrin_2024 was invoked but never defined (see the help page).
^ Cite error: The named reference Drugs.com_2023 was invoked but never defined (see the help page).
^ 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.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 504. ISBN 9783527607495. Archived from the original on 2016-12-20.
^ 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.

[AHFS2016-1] ^ ^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.

[FDA-AllBoxedWarnings-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.

[Ribavirin_(Ibavyr)-4] "Ribavirin (Ibavyr)". Catie. 2022. Retrieved 22 August 2022.

[TGA-5] "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.

[Safrin_2024-6] Cite error: The named reference Safrin_2024 was invoked but never defined (see the help page).

[Drugs.com_2023-7] Cite error: The named reference Drugs.com_2023 was invoked but never defined (see the help page).

[WHO2008-8] 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.

[WHO21st-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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Clinical data


Pronunciation	/ˌraɪbəˈvaɪrɪn/ RY-bə-VY-rin
Trade names	Copegus, Rebetol, Virazole, other^[1]
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)^[3] CA: ℞-only^[4] UK: POM (Prescription only) US: WARNING^[2]Rx-only EU: Rx-only
Pharmacokinetic data
Bioavailability	64%^[5]
Protein binding	0%^[5]
Metabolism	liver and intracellularly^[5]
Elimination half-life	298 hours (multiple dose); 43.6 hours (single dose)^[5]
Excretion	Urine (61%), faeces (12%)^[5]
Identifiers
IUPAC name 1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-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)
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^Y Key:IWUCXVSUMQZMFG-AFCXAGJDSA-N^Y
(verify)