MedKoo Cat#: 326880 | Name: Taribavirin HCl

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Taribavirin, also known as Viramidine, is an antiviral drug candidate. It is a prodrug of ribavirin, active against a number of DNA and RNA viruses. Taribavirin has better liver-targeting than ribavirin, and has a shorter life in the body due to less penetration and storage in red blood cells. It is expected eventually to be the drug of choice for viral hepatitis syndromes in which ribavirin is active. These include hepatitis C and perhaps also hepatitis B and yellow fever.

Chemical Structure

Taribavirin HCl
Taribavirin HCl
CAS#40372-00-7 (HCl)

Theoretical Analysis

MedKoo Cat#: 326880

Name: Taribavirin HCl

CAS#: 40372-00-7 (HCl)

Chemical Formula: C8H14ClN5O4

Exact Mass: 0.0000

Molecular Weight: 279.68

Elemental Analysis: C, 34.36; H, 5.05; Cl, 12.68; N, 25.04; O, 22.88

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Synonym
AVS-206, AVS 206, AVS206, ICN-3142, ICN 3142, ICN3142, KD-024, KD 024, KD024, Taribavirin hydrochloride, Ribamidine, Viramidine, Taribavirin HCl
IUPAC/Chemical Name
1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-1,2,4-triazole-3-carboximidamide hydrochloride
InChi Key
PIGYMBULXKLTCJ-UHSSARMYSA-N
InChi Code
InChI=1S/C8H13N5O4.ClH/c9-6(10)7-11-2-13(12-7)8-5(16)4(15)3(1-14)17-8;/h2-5,8,14-16H,1H2,(H3,9,10);1H/t3-,4-,5-,8-;/m1./s1
SMILES Code
N=C(C1=NN([C@H]2[C@@H]([C@@H]([C@@H](CO)O2)O)O)C=N1)N.[H]Cl
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 279.68 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Soota K, Maliakkal B. Ribavirin induced hemolysis: a novel mechanism of action against chronic hepatitis C virus infection. World J Gastroenterol. 2014 Nov 21;20(43):16184-90. doi: 10.3748/wjg.v20.i43.16184. Review. PubMed PMID: 25473172; PubMed Central PMCID: PMC4239506. 2: Konstantinova ID, Fateev IV, Galegov GA, Deriabin PG, Botikov AG, Muzyka IS, L'vov DK, Miroshnikov AI. [The arsenolysis reaction in the biotechnological method of synthesis of the ribavirin. Inhibition of reproduction of influenza A virus with the combination of ribavirin and ozeltamivir in experiments in vitro and in vivo]. Bioorg Khim. 2013 Sep-Oct;39(5):594-603. Russian. PubMed PMID: 25702418. 3: Brochot E, François C, Castelain S, Helle F, Van Nhien AN, Duchaussoy I, Capron D, Nguyen-Khac E, Duverlie G. A new tool to study ribavirin-induced haemolysis. Antivir Ther. 2012;17(7):1311-7. doi: 10.3851/IMP2308. Epub 2012 Sep 5. PubMed PMID: 22951364. 4: Palmer M, Rubin R, Rustgi V; Taribavirin Viral Kinetic Study Group. Randomised clinical trial: pre-dosing with taribavirin before starting pegylated interferon vs. standard combination regimen in treatment-naïve patients with chronic hepatitis C genotype 1. Aliment Pharmacol Ther. 2012 Aug;36(4):370-8. doi: 10.1111/j.1365-2036.2012.05188.x. Epub 2012 Jun 19. PubMed PMID: 22708649; PubMed Central PMCID: PMC3492905. 5: Deming P, Arora S. Taribavirin in the treatment of hepatitis C. Expert Opin Investig Drugs. 2011 Oct;20(10):1435-43. doi: 10.1517/13543784.2011.606214. Epub 2011 Aug 20. Review. PubMed PMID: 21854301. 6: Kwo PY, Vinayek R. The next step for taribavirin. Hepatology. 2010 Oct;52(4):1185-8. doi: 10.1002/hep.23957. PubMed PMID: 20879028. 7: Poordad F, Lawitz E, Shiffman ML, Hassanein T, Muir AJ, Bacon BR, Heise J, Halliman D, Chun E, Hammond J. Virologic response rates of weight-based taribavirin versus ribavirin in treatment-naive patients with genotype 1 chronic hepatitis C. Hepatology. 2010 Oct;52(4):1208-15. doi: 10.1002/hep.23827. PubMed PMID: 20721883. 8: Singh V, Somvanshi P. Structural modeling of the NS 3 helicase of Tick-borne encephalitis virus and their virtual screening of potent drugs using molecular docking. Interdiscip Sci. 2009 Sep;1(3):168-72. doi: 10.1007/s12539-009-0039-4. Epub 2009 Aug 7. PubMed PMID: 20640834. 9: Godzik P, Komorowski M, Cielecka-Kuszyk J, Madaliński K. [Inhibitors of hepatitis C virus--current standards and status of investigations]. Przegl Epidemiol. 2010;64(4):473-8. Polish. PubMed PMID: 21473060. 10: Samuel D. Focus. J Hepatol. 2010 Jan;52(1):3-4. doi: 10.1016/j.jhep.2009.10.017. Epub 2009 Oct 29. PubMed PMID: 19923033. 11: Marcellin P, Gish RG, Gitlin N, Heise J, Halliman DG, Chun E, Rodriguez-Torres M. Safety and efficacy of viramidine versus ribavirin in ViSER2: randomized, double-blind study in therapy-naive hepatitis C patients. J Hepatol. 2010 Jan;52(1):32-8. doi: 10.1016/j.jhep.2009.10.015. Epub 2009 Oct 23. PubMed PMID: 19913323. 12: Shields WW, Pockros PJ. Ribavirin analogs. Clin Liver Dis. 2009 Aug;13(3):419-27. doi: 10.1016/j.cld.2009.05.006. PubMed PMID: 19628158. 13: Benhamou Y, Afdhal NH, Nelson DR, Shiffman ML, Halliman DG, Heise J, Chun E, Pockros PJ. A phase III study of the safety and efficacy of viramidine versus ribavirin in treatment-naïve patients with chronic hepatitis C: ViSER1 results. Hepatology. 2009 Sep;50(3):717-26. doi: 10.1002/hep.23073. PubMed PMID: 19585653. 14: Kearney KR, Thornton JJ, Navarro VJ. Taribavirin for the treatment of chronic hepatitis C. Expert Opin Pharmacother. 2008 Dec;9(18):3243-9. doi: 10.1517/14656560802594459 . Review. PubMed PMID: 19040344. 15: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2007 Dec;29(10):697-735. PubMed PMID: 18200333. 16: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2007 Nov;29(9):625-55. PubMed PMID: 18193114. 17: Benhamou Y. Anemia and clinical outcomes in hepatitis C. J Hepatol. 2007 Jul;47(1):7-9. Epub 2007 Apr 20. PubMed PMID: 17509719. 18: Gish RG, Arora S, Rajender Reddy K, Nelson DR, O'Brien C, Xu Y, Murphy B. Virological response and safety outcomes in therapy-nai ve patients treated for chronic hepatitis C with taribavirin or ribavirin in combination with pegylated interferon alfa-2a: a randomized, phase 2 study. J Hepatol. 2007 Jul;47(1):51-9. Epub 2007 Mar 12. PubMed PMID: 17470380. 19: Iino S. [Drugs for hepatitis B and C infection]. Nihon Rinsho. 2007 Feb 28;65 Suppl 2 Pt. 1:391-5. Review. Japanese. PubMed PMID: 17455651. 20: McHutchison JG, Manns MP, Brown RS Jr, Reddy KR, Shiffman ML, Wong JB. Strategies for managing anemia in hepatitis C patients undergoing antiviral therapy. Am J Gastroenterol. 2007 Apr;102(4):880-9. Review. PubMed PMID: 17397412.