Clevudine

Clevudine
Clinical data
Routes of; administration	Oral
ATC code	J05AF12 (WHO) [1];
Identifiers
	IUPAC name 1-[(2S,3R,4S,5S)-3-fluoro-4-hydroxy-5- (hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine- 2,4-dione;
CAS Number	69256-17-3 ;
PubChem CID	73115;
ChemSpider	65894 ;
UNII	IN51MVP5F1;
KEGG	D03537 ;
ChEMBL	ChEMBL458875 ;
Chemical and physical data
Formula	C10H13FN2O5
Molar mass	260.219 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C/1NC(=O)N(\C=C\1C)[C@H]2O[C@H]([C@H](O)[C@H]2F)CO;
	InChI 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 ; Key:GBBJCSTXCAQSSJ-XQXXSGGOSA-N ;
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Clevudine (INN) is an antiviral drug for the treatment of hepatitis B (HBV). It is already approved for HBV in South Korea and the Philippines. It is marketed by Bukwang Pharmaceuticals in South Korea under the tradenames Levovir and Revovir.

Under license from Bukwang, Pharmasset was developing the drug, but its phase III clinical trial (international, multicenter, randomized, double-blind, 96-week QUASH studies) was terminated due to some myopathy cases in patients. Its approval in South Korea was revoked following these findings. Researchers in South Korea are testing clevudine at lower doses in combination with adefovir for continued use.[2]

It is a nucleoside analog.[3]

References

WHO International Working Group for Drug Statistics Methodology (August 27, 2008). "ATC/DDD Classification (FINAL): New ATC 5th level codes". WHO Collaborating Centre for Drug Statistics Methodology. Archived from the original on 2008-05-06. Retrieved 2008-09-05.
Tak WY, Yang JM, Kim BI, Baik SK, Cheon GJ, Byun KS, Kim DY, Yoo BC, et al. (May 2014). "A randomized, open-label study comparing low-dose clevudine plus adefovir combination therapy with clevudine monotherapy in naïve chronic hepatitis B patients". Hepatology International. 8 (3): 375–381. doi:10.1007/s12072-014-9537-5. PMC 4116600. PMID 25101150.
Lee HS, Chung YH, Lee K, et al. (May 2006). "A 12-week clevudine therapy showed potent and durable antiviral activity in HBeAg-positive chronic hepatitis B". Hepatology. 43 (5): 982–8. doi:10.1002/hep.21166. PMID 16628625.

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[1] WHO International Working Group for Drug Statistics Methodology (August 27, 2008). "ATC/DDD Classification (FINAL): New ATC 5th level codes". WHO Collaborating Centre for Drug Statistics Methodology. Archived from the original on 2008-05-06. Retrieved 2008-09-05.

[pmid25101150-2] Tak WY, Yang JM, Kim BI, Baik SK, Cheon GJ, Byun KS, Kim DY, Yoo BC, et al. (May 2014). "A randomized, open-label study comparing low-dose clevudine plus adefovir combination therapy with clevudine monotherapy in naïve chronic hepatitis B patients". Hepatology International. 8 (3): 375–381. doi:10.1007/s12072-014-9537-5. PMC 4116600. PMID 25101150.

[pmid16628625-3] Lee HS, Chung YH, Lee K, et al. (May 2006). "A 12-week clevudine therapy showed potent and durable antiviral activity in HBeAg-positive chronic hepatitis B". Hepatology. 43 (5): 982–8. doi:10.1002/hep.21166. PMID 16628625.