Ribavirin

Structural formula
General
Non-proprietary name	Ribavirin
other names	1 - [(2 R , 3 R , 4 R , 5 R ) -3,4-dihydroxy-5-hydroxymethyl-oxolan-2-yl] -1,2,4-triazole-3-carboxamide ( IUPAC )
Molecular formula	C 8 H 12 N 4 O 5
External identifiers / databases
EC number	636-825-3
ECHA InfoCard	100.164.587
PubChem	37542
DrugBank	DB00811
Wikidata	Q421862
Drug information
ATC code	J05 AB04
Drug class	Antivirals
properties
Molar mass	244.20 g · mol -1
Melting point	174–176 ° C (1st morphological form); 166–168 ° C (2nd morphological form); 180-182 ° C (3rd morphological form);
solubility	easily soluble in water; sparingly soluble in ethanol
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances danger
H and P phrases	H: 360
	P: 201-308 + 313
Toxicological data	1.3 g kg −1 ( LD 50 , mouse , ip ) ; 5.3 g kg −1 ( LD 50 , rat , oral ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Ribavirin is a drug from the group of antivirals . It is a nucleoside - analogue and acts virostatic against a number of DNA and RNA viruses such as Hepatitis C virus , the respiratory syncytial virus , influenza viruses, herpes viruses , Arena virus , hantavirus and adenovirus .

Mechanism of action

Ribavirin inhibits the viral enzyme that is used to multiply the genetic material , the polymerase . This prevents both DNA and RNA viruses from multiplying. Ribavirin does not work against retroviruses .

Chemically, ribavirin is an analogue of the nucleoside guanosine and is provided with a phosphate group (ie phosphorylated ) within the cell . In the form of the monophosphate inhibits it then competitively the inosine monophosphate dehydrogenase and thus the formation of guanosine monophosphate , a basic building block of DNA and RNA . Ribavirin also acts on the immune system , but how it works is not fully known.

Analytics

The reliable qualitative and quantitative determination of ribavirin in various examination matrices succeeds after appropriate sample preparation by coupling the HPLC with the mass spectrometry .

application

Ribavirin is administered orally in combination with interferon α -2a or peginterferon α displayed -2a for the treatment of hepatitis C .

Ribavirin was used as an aerosol for severe respiratory syncytial virus (RSV) infections in children and young children. According to the Robert Koch Institute , the effectiveness of the drug has been proven in vitro . However, placebo-controlled studies could not demonstrate any positive effect in patients. For this reason, the Robert Koch Institute no longer recommends ribavirin therapy for RSV infection.

Ribavirin is also used against Lassa fever , Crimean-Congo fever and hantaviruses in the early stages.

For the treatment of herpes there are cheaper and more effective agents available ( acyclovir ).

Trade names

Monopreparations

Copegus (D, A, CH), Rebetol (D, A, CH), Virazole (D)

Individual evidence

↑ ^a ^b ^c ^d ^e ^f The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, ISBN 978-0-911910-00-1 , p. 1413.

↑ ^a ^b Ribavirin data sheet from Sigma-Aldrich , accessed on April 22, 2011 ( PDF ).

↑ Shi X, Zhu D, Lou J, Zhu B, Hu AR, Gan D: Evaluation of a rapid method for the simultaneous quantification of ribavirin, sofosbuvir and its metabolite in rat plasma by UPLC-MS / MS. , J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Oct 1; 1002: 353-7, PMID 26363369

↑ Zhu W, Yang J, Yuan P, Sun Z, Wang C, Sun W, Zhang S: Rapid determination of total residues of ribavirin and its metabolites in chicken and chicken products by ultra-performance hydrophilic interaction chromatography-tandem mass spectrometry , Se Pooh 2013 Oct; 31 (10): 934-8. Chinese, PMID 24432634

↑ Jimmerson LC, Zheng JH, Bushman LR, MacBrayne CE, Anderson PL, Kiser JJ: Development and validation of a dried blood spot assay for the quantification of ribavirin using liquid chromatography coupled to mass spectrometry. , J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Jan 1; 944: 18-24, PMID 24291608

↑ RKI Guide for Doctors: Respiratory Syncytial Viruses (RSV) - information from the Robert Koch Institute , accessed on January 23, 2012.

^ Profiles of rare and imported infectious diseases - information from the Robert Koch Institute , accessed on October 14, 2009.

[MerckIndex-1] ↑ ^a ^b ^c ^d ^e ^f The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, ISBN 978-0-911910-00-1 , p. 1413.