Clevudine
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Clevudine
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CAS No:
163252-36-6
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Formula:
C10H13FN2O5
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Chemical Name:
Clevudine
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Synonyms:
2,4(1H,3H)-Pyrimidinedione,1-(2-deoxy-2-fluoro-β-L-arabinofuranosyl)-5-methyl-;1-(2-Deoxy-2-fluoro-β-L-arabinofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione;L-FMAU;Clevudine;1-(2′-Deoxy-2′-fluoro-β-L-arabinofuranosyl)-5-methyluracil;Levovir;850403-37-1
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CAS No:
Description
White SolidClevudine is a fluorinated b-L-nucleoside analog launched for the oral treatment of chronic HBV infection. It is the fifth nucleoside or nucleotide analog to be marketed for this indication. The previous drugs from this class include lamivudine, adefovir, entecavir, and telbivudine. In HBV-expressing human hepatoma cell line 2.2.15, clevudine inhibits HBV DNA synthesis with an EC50 of 0.1 μM, and does not show cytotoxicity up to 200 μM.
Clevudine is a pyrimidine 2'-deoxyribonucleoside.|Clevudine is a synthetic pyrimidine analogue with activity against hepatitis B virus (HBV). Intracellularly, clevudine is phosphorylated to its active metabolites, clevudine monophosphate and triphosphate. The triphosphate metabolite competes with thymidine for incorporation into viral DNA, thereby causing DNA chain termination and inhibiting the function of HBV DNA polymerase (reverse transcriptase). Clevudine has a long half-life and shows significant reduction of covalently closed circular DNA (cccDNA), therefore the patient is less likely to have a relapse after treatment is discontinued.
Clevudine Basic Attributes
260.22
260.22
IN51MVP5F1
DTXSID2057659
C95210
J - Antiinfectives for systemic use
2934999090
Characteristics
99.1
-0.9
1.55±0.1 g/cm3(Predicted)
184-185°
1.592
LD50 in mice, rats (mg/kg): >5000, >3000 orally (Painter)
D25 -111.77° (c = 0.23 in methanol)
Drug Information
Investigated for use/treatment in hepatitis (viral, B).
Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)
1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione,
Computed Properties
Molecular Weight:260.22
XLogP3:-0.9
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:2
Exact Mass:260.08084968
Monoisotopic Mass:260.08084968
Topological Polar Surface Area:99.1
Heavy Atom Count:18
Complexity:413
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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