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MedKoo Cat#: 329107 | Name: Clevudine
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Description:

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

Clevudine, also known as L-FMAU, is an antiviral used in the treatment of Hepatitis B. Clevudine is differentiated from other oral agents by an unusual activation pathway to the biochemically active triphosphate, a mechanism of action of clevudine triphosphate that inhibits multiple steps of the hepatitis B virus (HBV) intracellular life cycle, a long half-life, and significant reduction of covalently closed circular DNA (cccDNA) in animal models.

Chemical Structure

Clevudine
Clevudine
CAS#163252-36-6

Theoretical Analysis

MedKoo Cat#: 329107

Name: Clevudine

CAS#: 163252-36-6

Chemical Formula: C10H13FN2O5

Exact Mass: 260.0800

Molecular Weight: 260.22

Elemental Analysis: C, 46.16; H, 5.04; F, 7.30; N, 10.77; O, 30.74

Price and Availability

Size Price Availability Quantity
100mg USD 450.00 2 Weeks
200mg USD 750.00 2 Weeks
500mg USD 1,250.00 2 Weeks
1g USD 2,150.00 2 Weeks
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Related CAS #
No Data
Synonym
Clevudine; L-FMAU; L FMAU; LFMAU; Levovir
IUPAC/Chemical Name
1-((2S,3R,4S,5S)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
InChi Key
GBBJCSTXCAQSSJ-XQXXSGGOSA-N
InChi Code
InChI=1S/C10H13FN2O5/c1-4-2-13(10(17)12-8(4)16)9-6(11)7(15)5(3-14)18-9/h2,5-7,9,14-15H,3H2,1H3,(H,12,16,17)/t5-,6+,7-,9-/m0/s1
SMILES Code
O=C1NC(C(C)=CN1[C@@H]2[C@H](F)[C@H]([C@H](CO)O2)O)=O
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 260.22 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: Li S, Gao S, Jiang Q, Liang Q, Luan J, Zhang R, Zhang F, Ruan H, Li X, Li X, Zhou H, Yang C. Clevudine attenuates bleomycin-induced early pulmonary fibrosis via regulating M2 macrophage polarization. Int Immunopharmacol. 2021 Dec;101(Pt B):108271. doi: 10.1016/j.intimp.2021.108271. Epub 2021 Oct 23. PMID: 34700113. 2: Anderson DL. Clevudine for hepatitis B. Drugs Today (Barc). 2009 May;45(5):331-50. doi: 10.1358/dot.2009.45.5.1354223. PMID: 19584963. 3: Hui CK, Lau GK. Clevudine for the treatment of chronic hepatitis B virus infection. Expert Opin Investig Drugs. 2005 Oct;14(10):1277-84. doi: 10.1517/13543784.14.10.1277. PMID: 16185170. 4: Park SH, Park KS, Kim NH, Cho JY, Koh MS, Lee JH. Clevudine Induced Mitochondrial Myopathy. J Korean Med Sci. 2017 Nov;32(11):1857-1860. doi: 10.3346/jkms.2017.32.11.1857. PMID: 28960041; PMCID: PMC5639069. 5: Asselah T, Lada O, Moucari R, Marcellin P. Clevudine: a promising therapy for the treatment of chronic hepatitis B. Expert Opin Investig Drugs. 2008 Dec;17(12):1963-74. doi: 10.1517/13543780802535760. PMID: 19012511. 6: Kocic I. Clevudine University of Georgia/Abbott/Bukwang/Triangle/Yale University. Curr Opin Investig Drugs. 2000 Nov;1(3):308-13. PMID: 11249713. 7: Korba BE, Furman PA, Otto MJ. Clevudine: a potent inhibitor of hepatitis B virus in vitro and in vivo. Expert Rev Anti Infect Ther. 2006 Aug;4(4):549-61. doi: 10.1586/14787210.4.4.549. PMID: 17009935. 8: Jang JH, Kim JW, Jeong SH, Myung HJ, Kim HS, Park YS, Lee SH, Hwang JH, Kim N, Lee DH. Clevudine for chronic hepatitis B: antiviral response, predictors of response, and development of myopathy. J Viral Hepat. 2011 Feb;18(2):84-90. doi: 10.1111/j.1365-2893.2010.01281.x. PMID: 20196804. 9: Jang YO, Quan X, Das R, Xu S, Chung CH, Ahn CM, Baik SK, Kong ID, Park KS, Kim MY. High-dose clevudine impairs mitochondrial function and glucose- stimulated insulin secretion in INS-1E cells. BMC Gastroenterol. 2012 Jan 10;12:4. doi: 10.1186/1471-230X-12-4. PMID: 22230186; PMCID: PMC3288815. 10: Yoo BC, Kim JH, Kim TH, Koh KC, Um SH, Kim YS, Lee KS, Han BH, Chon CY, Han JY, Ryu SH, Kim HC, Byun KS, Hwang SG, Kim BI, Cho M, Yoo K, Lee HJ, Hwang JS, Kim YS, Lee YS, Choi SK, Lee YJ, Yang JM, Park JW, Lee MS, Kim DG, Chung YH, Cho SH, Choi JY, Kweon YO, Lee HY, Jeong SH, Yoo HW, Lee HS. Clevudine is highly efficacious in hepatitis B e antigen-negative chronic hepatitis B with durable off-therapy viral suppression. Hepatology. 2007 Oct;46(4):1041-8. doi: 10.1002/hep.21800. PMID: 17647293. 11: Lee KS. [Clevudine therapy in patients with chronic hepatitis B]. Korean J Hepatol. 2009 Jun;15(2):119-21. Korean. doi: 10.3350/kjhep.2009.15.2.119. PMID: 19581763. 12: Kim HJ, Park DI, Park JH, Cho YK, Sohn CI, Jeon WK, Kim BI. Comparison between clevudine and entecavir treatment for antiviral-naïve patients with chronic hepatitis B. Liver Int. 2010 Jul;30(6):834-40. doi: 10.1111/j.1478-3231.2010.02245.x. Epub 2010 Apr 8. PMID: 20408946. 13: Tremblay T, Alcée JB, Giguère D. Protecting-group-free synthesis of clevudine (L-FMAU), a treatment of the hepatitis B virus. Org Biomol Chem. 2022 Nov 23;20(45):8859-8863. doi: 10.1039/d2ob01814d. PMID: 36331415. 14: Kim SB, Song IH, Kim YM, Noh R, Kang HY, Lee HIe, Yang HY, Kim AN, Chae HB, Lee SH, Kim HS, Lee TH, Kang YW, Lee ES, Kim SH, Lee BS, Lee HY. Long-term treatment outcomes of clevudine in antiviral-naive patients with chronic hepatitis B. World J Gastroenterol. 2012 Dec 21;18(47):6943-50. doi: 10.3748/wjg.v18.i47.6943. PMID: 23322992; PMCID: PMC3531678. 15: Shouval D. Focus. J Hepatol. 2010 Aug;53(2):219-20. doi: 10.1016/j.jhep.2010.05.006. PMID: 20579760. 16: Yoo BC, Kim JH, Chung YH, Lee KS, Paik SW, Ryu SH, Han BH, Han JY, Byun KS, Cho M, Lee HJ, Kim TH, Cho SH, Park JW, Um SH, Hwang SG, Kim YS, Lee YJ, Chon CY, Kim BI, Lee YS, Yang JM, Kim HC, Hwang JS, Choi SK, Kweon YO, Jeong SH, Lee MS, Choi JY, Kim DG, Kim YS, Lee HY, Yoo K, Yoo HW, Lee HS. Twenty-four-week clevudine therapy showed potent and sustained antiviral activity in HBeAg- positive chronic hepatitis B. Hepatology. 2007 May;45(5):1172-8. doi: 10.1002/hep.21629. PMID: 17464992. 17: Lee HS, Chung YH, Lee K, Byun KS, Paik SW, Han JY, Yoo K, Yoo HW, Lee JH, Yoo BC. A 12-week clevudine therapy showed potent and durable antiviral activity in HBeAg-positive chronic hepatitis B. Hepatology. 2006 May;43(5):982-8. doi: 10.1002/hep.21166. PMID: 16628625. 18: Tak WY, Park SY, Cho CM, Jung MK, Jeon SW, Kweon YO, Park JY, Sohn YK. Clinical, biochemical, and pathological characteristics of clevudine-associated myopathy. J Hepatol. 2010 Aug;53(2):261-6. doi: 10.1016/j.jhep.2010.03.006. Epub 2010 Apr 18. PMID: 20466447. 19: Yoon EL, Yim HJ, Lee HJ, Lee YS, Kim JH, Jung ES, Kim JH, Seo YS, Yeon JE, Lee HS, Um SH, Byun KS. Comparison of clevudine and entecavir for treatment- naive patients with chronic hepatitis B virus infection: two-year follow-up data. J Clin Gastroenterol. 2011 Nov-Dec;45(10):893-9. doi: 10.1097/MCG.0b013e31821f8bdf. PMID: 21617542. 20: Lee HS, Yoo BC, Lee KS, Kim JH, Um SH, Ryu SH, Lee YS, Kim YS, Yoo K, Han JY, Hwang JS, Kim TH, Yang JM, Lee HJ, Chon CY, Cho M, Han BH, Hwang SG, Byun KS, Chung YH, Cho SH, Koh KC, Kim BI, Kim HC, Paik SW, Lee MS, Yoo HW, Han CJ. Clevudine-induced viral response, associated with continued reduction of HBsAg titer, was durable after the withdrawal of therapy. J Gastroenterol. 2011 Mar;46(3):410-4. doi: 10.1007/s00535-010-0354-x. Epub 2010 Dec 23. PMID: 21181212.

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