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MedKoo Cat#: 597905 | Name: Levovirin

Description:

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

Levovirin is a monocyclic L-nucleosides with type 1 cytokine-inducing activity. Levovirin is the L-enantiomer of Ribavirin with similar immunomodulatory activity but does not have direct antiviral activity or hemolytic anemia.

Chemical Structure

Levovirin
CAS#206269-27-4

Theoretical Analysis

MedKoo Cat#: 597905

Name: Levovirin

CAS#: 206269-27-4

Chemical Formula: C8H12N4O5

Exact Mass: 244.0808

Molecular Weight: 244.21

Elemental Analysis: C, 39.35; H, 4.95; N, 22.94; O, 32.76

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Levovirin; L-Ribavirin; ICN17261; ICN 17261; ICN-17261;
IUPAC/Chemical Name
1-((2S,3S,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-1,2,4-triazole-3-carboxamide
InChi Key
IWUCXVSUMQZMFG-RGDLXGNYSA-N
InChi Code
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-/m0/s1
SMILES Code
O=C(C1=NN([C@@H]2[C@H]([C@H]([C@H](CO)O2)O)O)C=N1)N
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
>3 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
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Levovirin is a monocyclic L-nucleosides with type 1 cytokine-inducing activity.
In vitro activity:
TBD
In vivo activity:
TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 244.21 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
Formulation protocol:
TBD
In vitro protocol:
TBD
In vivo protocol:
TBD
1: Huang Y, Ostrowitzki S, Hill G, Navarro M, Berger N, Kopeck P, Mau CI, Alfredson T, Lal R. Single- and multiple-dose pharmacokinetics of levovirin valinate hydrochloride (R1518) in healthy volunteers. J Clin Pharmacol. 2005 May;45(5):578-88. PubMed PMID: 15831782. 2: Fang C, Srivastava P, Lin CC. Effect of ribavirin, levovirin and viramidine on liver toxicological gene expression in rats. J Appl Toxicol. 2003 Nov-Dec;23(6):453-9. PubMed PMID: 14635270. 3: Lin CC, Luu T, Lourenco D, Yeh LT, Lau JY. Absorption, pharmacokinetics and excretion of levovirin in rats, dogs and cynomolgus monkeys. J Antimicrob Chemother. 2003 Jan;51(1):93-9. PubMed PMID: 12493792. 4: Watson J. Prospects for hepatitis C virus therapeutics: levovirin and viramidine as improved derivatives of ribavirin. Curr Opin Investig Drugs. 2002 May;3(5):680-3. Review. PubMed PMID: 12090539. 5: Lin CC, Lau JY. Specific, sensitive and accurate LC-MS/MS method for the measurement of levovirin in rat and monkey plasma. J Pharm Biomed Anal. 2002 Sep 5;30(2):239-46. PubMed PMID: 12191708. 6: Li F, Hong L, Mau CI, Chan R, Hendricks T, Dvorak C, Yee C, Harris J, Alfredson T. Transport of levovirin prodrugs in the human intestinal Caco-2 cell line. J Pharm Sci. 2006 Jun;95(6):1318-25. PubMed PMID: 16634069. 7: Hofmann WP, Polta A, Herrmann E, Mihm U, Kronenberger B, Sonntag T, Lohmann V, Schönberger B, Zeuzem S, Sarrazin C. Mutagenic effect of ribavirin on hepatitis C nonstructural 5B quasispecies in vitro and during antiviral therapy. Gastroenterology. 2007 Mar;132(3):921-30. Epub 2006 Dec 3. PubMed PMID: 17383421. 8: 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. 9: 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. 10: Foster GR. Past, present, and future hepatitis C treatments. Semin Liver Dis. 2004;24 Suppl 2:97-104. Review. PubMed PMID: 15346252. 11: Plöckinger U, Krüger D, Bergk A, Weich V, Wiedenmann B, Berg T. Hepatitis-C patients have reduced growth hormone (GH) secretion which improves during long-term therapy with pegylated interferon-alpha. Am J Gastroenterol. 2007 Dec;102(12):2724-31. Epub 2007 Jul 27. PubMed PMID: 17662104. 12: Mihm U, Hofmann WP, Welsch C, Polta A, Lengauer T, Zeuzem S, Sarrazin C, Herrmann E. Effect of ribavirin on the frequency of RNase L cleavage sites within the hepatitis C viral genome. J Viral Hepat. 2010 Mar;17(3):217-21. doi: 10.1111/j.1365-2893.2009.01171.x. Epub 2009 Sep 15. PubMed PMID: 19758279.