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163252-36-6,MFCD00935785
Catalog No.:AA001TVD

163252-36-6 | Clevudine

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50mg
≥98%
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$98.00   $68.00
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100mg
95%
in stock  
$105.00   $73.00
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1g
96%
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$851.00   $596.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA001TVD
Chemical Name:
Clevudine
CAS Number:
163252-36-6
Molecular Formula:
C10H13FN2O5
Molecular Weight:
260.2190
MDL Number:
MFCD00935785
SMILES:
OC[C@@H]1O[C@@H]([C@@H]([C@H]1O)F)n1cc(C)c(=O)[nH]c1=O
Properties
Computed Properties
 
Complexity:
413  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
18  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
2  
XLogP3:
-0.9  

Downstream Synthesis Route
69739-34-0    163252-36-6   
CASUnavailable 

[1]CurrentPatentAssignee:EMORYUNIVERSITY-WO2016/99982,2016,A2Locationinpatent:Page/Pagecolumn62

[2]CurrentPatentAssignee:EMORYUNIVERSITY-WO2017/223421,2017,A1Locationinpatent:Page/Pagecolumn75

Literature

Title: Noncompetitive inhibition of hepatitis B virus reverse transcriptase protein priming and DNA synthesis by the nucleoside analog clevudine.

Journal: Antimicrobial agents and chemotherapy 20130901

Title: Microwave-assisted one-pot radiosynthesis of 2'-deoxy-2'-[18F]fluoro-5-methyl-1-β-d-arabinofuranosyluracil ([18F]-FMAU).

Journal: Nuclear medicine and biology 20121001

Title: Simultaneous determination of 1-(2'-deoxy-2'-fluoro-β-D-arabinofuranosyl) uracil (FAU) and 1-(2'-deoxy-2'-fluoro-β-D-arabinofuranosyl) 5-methyluracil (FMAU) in human plasma by liquid chromatography/tandem mass spectrometry.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20120401

Title: [New drugs of treatment of patients with chronic hepatitis B].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20120401

Title: Normal-phase liquid chromatography coupled with electrospray ionization mass spectrometry for chiral separation and quantification of clevudine and its enantiomer in human plasma.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20120215

Title: Structure-guided engineering of human thymidine kinase 2 as a positron emission tomography reporter gene for enhanced phosphorylation of non-natural thymidine analog reporter probe.

Journal: The Journal of biological chemistry 20120102

Title: High-dose clevudine impairs mitochondrial function and glucose-stimulated insulin secretion in INS-1E cells.

Journal: BMC gastroenterology 20120101

Title: [18F]-2'-Fluoro-5-methyl-1-beta-D-arabinofuranosyluracil (18F-FMAU) in prostate cancer: initial preclinical observations.

Journal: Molecular imaging 20120101

Title: [New drugs of treatment of patients with chronic hepatitis B].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20110501

Title: Virologic and biochemical responses to clevudine in patients with chronic HBV infection-associated cirrhosis: data at week 48.

Journal: Journal of viral hepatitis 20110401

Title: 18F-FDG PET/CT of drug-induced myopathy in a patient with chronic hepatitis B on long-term clevudine therapy.

Journal: European journal of nuclear medicine and molecular imaging 20110401

Title: Clevudine-induced viral response, associated with continued reduction of HBsAg titer, was durable after the withdrawal of therapy.

Journal: Journal of gastroenterology 20110301

Title: Clevudine for chronic hepatitis B: antiviral response, predictors of response, and development of myopathy.

Journal: Journal of viral hepatitis 20110201

Title: Automated synthesis of 2'-deoxy-2'-[18F]fluoro-5-methyl-1-β-D-arabinofuranosyluracil ([18F]-FMAU) using a one reactor radiosynthesis module.

Journal: Nuclear medicine and biology 20110201

Title: Comparison of clevudine and entecavir for treatment-naive patients with chronic hepatitis B virus infection: two-year follow-up data.

Journal: Journal of clinical gastroenterology 20110101

Title: [Treatment efficacy of clevudine, entecavir and lamivudine in treatment-naive patients with HBeAg-positive chronic hepatitis B].

Journal: The Korean journal of gastroenterology = Taehan Sohwagi Hakhoe chi 20101201

Title: Efficacy of initial treatment with clevudine in naive patients with chronic hepatitis B.

Journal: The Korean journal of internal medicine 20101201

Title: Different modes of transport for 3H-thymidine, 3H-FLT, and 3H-FMAU in proliferating and nonproliferating human tumor cells.

Journal: Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20100901

Title: Forty-eight weeks treatment with clevudine 30 mg qd versus lamivudine 100 mg qd for chronic hepatitis B infection: a double-blind randomized study.

Journal: The Korean journal of hepatology 20100901

Title: Clinical, biochemical, and pathological characteristics of clevudine-associated myopathy.

Journal: Journal of hepatology 20100801

Title: Focus.

Journal: Journal of hepatology 20100801

Title: Comparison between clevudine and entecavir treatment for antiviral-naïve patients with chronic hepatitis B.

Journal: Liver international : official journal of the International Association for the Study of the Liver 20100701

Title: Treatment outcomes of clevudine versus lamivudine at week 48 in naïve patients with HBeAg positive chronic hepatitis B.

Journal: Journal of Korean medical science 20100501

Title: Clevudine demonstrates potent antiviral activity in naïve chronic hepatitis B patients.

Journal: Intervirology 20100101

Title: Polymyositis in patients taking antiviral clevudine therapy: a report of two cases.

Journal: NeuroRehabilitation 20100101

Title: Evaluation of the in vitro anti-HBV activity of clevudine in combination with other nucleoside/nucleotide inhibitors.

Journal: Antiviral therapy 20100101

Title: Clevudine myopathy in patients with chronic hepatitis B.

Journal: Journal of hepatology 20091001

Title: Myopathy and neuropathy associated with nucleos(t)ide analog therapy for hepatitis B.

Journal: Journal of hepatology 20091001

Title: [Efficacy of 48-week clevudine therapy for chronic hepatitis B].

Journal: The Korean journal of hepatology 20090901

Title: Early development of clevudine resistance during clevudine therapy in a patient with chronic hepatitis B who received prior lamivudine therapy.

Journal: Liver international : official journal of the International Association for the Study of the Liver 20090701

Title: Long-term therapy with clevudine for chronic hepatitis B can be associated with myopathy characterized by depletion of mitochondrial DNA.

Journal: Hepatology (Baltimore, Md.) 20090601

Title: [Clevudine therapy in patients with chronic hepatitis B].

Journal: The Korean journal of hepatology 20090601

Title: [Long-term clevudine therapy in nucleos(t)ide-naïve and lamivudine-experienced patients with hepatitis B virus-related chronic liver diseases].

Journal: The Korean journal of hepatology 20090601

Title: [New molecules in the treatment of chronic hepatitis B].

Journal: Presse medicale (Paris, France : 1983) 20090501

Title: Clevudine for hepatitis B.

Journal: Drugs of today (Barcelona, Spain : 1998) 20090501

Title: Clinical and virological responses to clevudine therapy in chronic hepatitis B patients: results at 1 year of an open-labelled prospective study.

Journal: Antiviral therapy 20090101

Title: Clevudine: a promising therapy for the treatment of chronic hepatitis B.

Journal: Expert opinion on investigational drugs 20081201

Title: [Development of clevudine resistance after switching from lamivudine in a patient with chronic hepatitis B].

Journal: The Korean journal of gastroenterology = Taehan Sohwagi Hakhoe chi 20081101

Title: Tracking cellular stress with labeled FMAU reflects changes in mitochondrial TK2.

Journal: European journal of nuclear medicine and molecular imaging 20080801

Title: Clinical trial: a phase II, randomized study evaluating the safety, pharmacokinetics and anti-viral activity of clevudine for 12 weeks in patients with chronic hepatitis B.

Journal: Alimentary pharmacology & therapeutics 20080601

Title: [Management of chronic hepatitis B in treatment-naive patients].

Journal: The Korean journal of gastroenterology = Taehan Sohwagi Hakhoe chi 20080601

Title: [Management of antiviral-resistant chronic hepatitis B virus infection].

Journal: The Korean journal of gastroenterology = Taehan Sohwagi Hakhoe chi 20080601

Title: Evaluation of 2'-deoxy-2'-[18F]fluoro-5-methyl-1-beta-L: -arabinofuranosyluracil ([18F]-L: -FMAU) as a PET imaging agent for cellular proliferation: comparison with [18F]-D: -FMAU and [18F]FLT.

Journal: European journal of nuclear medicine and molecular imaging 20080501

Title: In vivo measurement of cell proliferation in canine brain tumor using C-11-labeled FMAU and PET.

Journal: Nuclear medicine and biology 20080101

Title: New drugs for chronic hepatitis B: a review.

Journal: American journal of therapeutics 20080101

Title: Clevudine is efficiently phosphorylated to the active triphosphate form in primary human hepatocytes.

Journal: Antiviral therapy 20080101

Title: Clevudine is highly efficacious in hepatitis B e antigen-negative chronic hepatitis B with durable off-therapy viral suppression.

Journal: Hepatology (Baltimore, Md.) 20071001

Title: Tumor imaging using 1-(2'-deoxy-2'-18F-fluoro-beta-D-arabinofuranosyl)thymine and PET.

Journal: Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20070901

Title: Radiosynthesis of 2'-deoxy-2'-[18F]-fluoro-5-methyl-1-beta-L-arabinofuranosyluracil ([18F]-L-FMAU) for PET.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20070801

Title: 6-Chloro-3-(((1-[11C]methyl)-2-(S)-pyrrolidinyl)methoxy)-5-(2-fluoropyridin-4-yl)pyridine ([11C]JHU85270), a potent ligand for nicotinic acetylcholine receptor imaging by positron emission tomography.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20070801

Title: Twenty-four-week clevudine therapy showed potent and sustained antiviral activity in HBeAg-positive chronic hepatitis B.

Journal: Hepatology (Baltimore, Md.) 20070501

Title: Clevudine therapy for 24 weeks further reduced serum hepatitis B virus DNA levels and increased ALT normalization rates without emergence of viral breakthrough than 12 weeks of clevudine therapy.

Journal: Intervirology 20070101

Title: A novel mutation pattern emerging during lamivudine treatment shows cross-resistance to adefovir dipivoxil treatment.

Journal: Antiviral therapy 20070101

Title: Hepatitis B virus treatment in HIV-infected patients.

Journal: Topics in HIV medicine : a publication of the International AIDS Society, USA 20061201

Title: Clevudine: a potent inhibitor of hepatitis B virus in vitro and in vivo.

Journal: Expert review of anti-infective therapy 20060801

Title: [Advances in the study of nucleoside antiviral drugs].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20060801

Title: A 12-week clevudine therapy showed potent and durable antiviral activity in HBeAg-positive chronic hepatitis B.

Journal: Hepatology (Baltimore, Md.) 20060501

Title: [Therapeutic approach to EBV infection].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20060301

Title: Cellular and virological mechanisms of HBV drug resistance.

Journal: Journal of hepatology 20060201

Title: Rapid quantitative determination of L-FMAU-TP from human peripheral-blood mononuclear cells of hepatitis B virus-infected patients treated with L-FMAU by ion-pairing, reverse-phase, liquid chromatography/electrospray tandem mass spectrometry.

Journal: Therapeutic drug monitoring 20060201

Title: Clevudine for the treatment of chronic hepatitis B virus infection.

Journal: Expert opinion on investigational drugs 20051001

Title: Combination of nucleoside analogues in the treatment of chronic hepatitis B virus infection: lesson from experimental models.

Journal: The Journal of antimicrobial chemotherapy 20050501

Title: Imaging DNA synthesis in vivo with 18F-FMAU and PET.

Journal: Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20050201

Title: Imaging DNA synthesis with [18F]FMAU and positron emission tomography in patients with cancer.

Journal: European journal of nuclear medicine and molecular imaging 20050101

Title: Drugs in development for hepatitis B.

Journal: Drugs 20050101

Title: Comparison of [14C]FMAU, [3H]FEAU, [14C]FIAU, and [3H]PCV for monitoring reporter gene expression of wild type and mutant herpes simplex virus type 1 thymidine kinase in cell culture.

Journal: Molecular imaging and biology : MIB : the official publication of the Academy of Molecular Imaging 20050101

Title: Clevudine therapy with vaccine inhibits progression of chronic hepatitis and delays onset of hepatocellular carcinoma in chronic woodchuck hepatitis virus infection.

Journal: Antiviral therapy 20041201

Title: Distribution of 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl) uracil in mice bearing colorectal cancer xenografts: rationale for therapeutic use and as a positron emission tomography probe for thymidylate synthase.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20041001

Title: Adenovirus-based gene therapy during clevudine treatment of woodchucks chronically infected with woodchuck hepatitis virus.

Journal: Virology 20040915

Title: A phase II dose-escalating trial of clevudine in patients with chronic hepatitis B.

Journal: Hepatology (Baltimore, Md.) 20040701

Title: [New approaches in the treatment of hepatitis B].

Journal: Deutsche medizinische Wochenschrift (1946) 20040521

Title: Pharmacokinetics of the thymidine analog 2'-fluoro-5-methyl-1-beta-D-arabinofuranosyluracil (FMAU) in tumor-bearing rats.

Journal: Nuclear medicine and biology 20040501

Title: Direct comparison of radiolabeled probes FMAU, FHBG, and FHPG as PET imaging agents for HSV1-tk expression in a human breast cancer model.

Journal: Molecular imaging 20040401

Title: New treatment of chronic hepatitis B.

Journal: Seminars in liver disease 20040101

Title: Monitoring tumor cell proliferation by targeting DNA synthetic processes with thymidine and thymidine analogs.

Journal: Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20031201

Title: Mechanism of antiviral activities of 3'-substituted L-nucleosides against 3TC-resistant HBV polymerase: a molecular modelling approach.

Journal: Antiviral chemistry & chemotherapy 20031101

Title: Effects of pyrimidine and purine analog combinations in the duck hepatitis B virus infection model.

Journal: Antimicrobial agents and chemotherapy 20030601

Title: Synthesis of 2'-deoxy-2'-[18F]fluoro-beta-D-arabinofuranosyl nucleosides, [18F]FAU, [18F]FMAU, [18F]FBAU and [18F]FIAU, as potential PET agents for imaging cellular proliferation. Synthesis of [18F]labelled FAU, FMAU, FBAU, FIAU.

Journal: Nuclear medicine and biology 20030401

Title: Current and future antiviral agents for chronic hepatitis B.

Journal: The Journal of antimicrobial chemotherapy 20030301

Title: Comparison of anti-hepatitis B virus activities of lamivudine and clevudine by a quantitative assay.

Journal: Antimicrobial agents and chemotherapy 20030101

Title: In vitro activity of potential anti-poxvirus agents.

Journal: Antiviral research 20030101

Title: Entecavir, FTC, L-FMAU, LdT and others.

Journal: Journal of hepatology 20030101

Title: Treatment of HBeAg negative chronic hepatitis B with new drugs (adefovir and others).

Journal: Journal of hepatology 20030101

Title: Understanding the unique mechanism of L-FMAU (clevudine) against hepatitis B virus: molecular dynamics studies.

Journal: Bioorganic & medicinal chemistry letters 20021202

Title: Rat studies comparing 11C-FMAU, 18F-FLT, and 76Br-BFU as proliferation markers.

Journal: Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20021201

Title: Inhibitory activity of dioxolane purine analogs on wild-type and lamivudine-resistant mutants of hepadnaviruses.

Journal: Hepatology (Baltimore, Md.) 20020901

Title: Radiolabeled 2'-fluorodeoxyuracil-beta-D-arabinofuranoside (FAU) and 2'-fluoro-5-methyldeoxyuracil-beta -D-arabinofuranoside (FMAU) as tumor-imaging agents in mice.

Journal: Cancer chemotherapy and pharmacology 20020501

Title: [New management strategies for hepatitis B].

Journal: Gastroenterologie clinique et biologique 20020201

Title: New synthesis of L-FMAU from L-arabinose.

Journal: Nucleosides, nucleotides & nucleic acids 20020101

Title: Immunogenic effects of woodchuck hepatitis virus surface antigen vaccine in combination with antiviral therapy: breaking of humoral and cellular immune tolerance in chronic woodchuck hepatitis virus infection.

Journal: Intervirology 20020101

Title: Evaluation of 2'-deoxy-2'-flouro-5-methyl-1-beta-D-arabinofuranosyluracil as a potential gene imaging agent for HSV-tk expression in vivo.

Journal: Molecular imaging 20020101

Title: Rapid enantiomeric quantification of an antiviral nucleoside agent (D,L-FMAU, 2'-fluoro-5-methyl-beta,D,L-arabinofurano-syluracil) by mass spectrometry.

Journal: Journal of medicinal chemistry 20011025

Title: In vitro susceptibilities of wild-type or drug-resistant hepatitis B virus to (-)-beta-D-2,6-diaminopurine dioxolane and 2'-fluoro-5-methyl-beta-L-arabinofuranosyluracil.

Journal: Antimicrobial agents and chemotherapy 20010901

Title: Antiviral activity of clevudine [L-FMAU, (1-(2-fluoro-5-methyl-beta, L-arabinofuranosyl) uracil)] against woodchuck hepatitis virus replication and gene expression in chronically infected woodchucks (Marmota monax).

Journal: Hepatology (Baltimore, Md.) 20010101

Title: Potential use of antiviral L(-)nucleoside analogues for the prevention or treatment of viral associated cancers.

Journal: Cancer letters 20010101

Title: Structure-activity relationships of L-dioxolane uracil nucleosides as anti-Epstein Barr virus agents.

Journal: Journal of medicinal chemistry 19990617

Title: Sensitivity of L-(-)2,3-dideoxythiacytidine resistant hepatitis B virus to other antiviral nucleoside analogues.

Journal: Biochemical pharmacology 19990615

Title: Synthesis and anti-hepatitis B virus activity of 9-(2-deoxy-2-fluoro-beta-L-arabinofuranosyl) purine nucleosides.

Journal: Journal of medicinal chemistry 19970815

Title: Structure--activity relationships of 1-(2-Deoxy-2-fluoro-beta-L-arabinofuranosyl)pyrimidine nucleosides as anti-hepatitis B virus agents.

Journal: Journal of medicinal chemistry 19960705

Title: Inhibition of Epstein-Barr virus replication by a novel L-nucleoside, 2'-fluoro-5-methyl-beta-L-arabinofuranosyluracil.

Journal: Biochemical pharmacology 19960412

Title: Inhibition of hepatitis B virus by a novel L-nucleoside, 2'-fluoro-5-methyl-beta-L-arabinofuranosyl uracil.

Journal: Antimicrobial agents and chemotherapy 19960201

Title: Inhibitory effects of 2'-fluorinated arabinosyl-pyrimidine nucleosides on woodchuck hepatitis virus replication in chronically infected woodchucks.

Journal: Antimicrobial agents and chemotherapy 19900301

Title: Activity of 1-(2'-deoxy-2'-fluoro-beta-D-arabinofuranosyl)-5-iodouracil against simian varicella virus infections in African green monkeys.

Journal: Antimicrobial agents and chemotherapy 19860101

Title: Comparative anti-herpesvirus activities of 9-(1,3-dihydroxy-2-propoxymethyl)guanine, acyclovir, and two 2'-fluoropyrimidine nucleosides.

Journal: Antiviral research 19851001

Title: Therapeutic activities of 1-(2-fluoro-2-deoxy-beta-D-arabinofuranosyl)-5-iodocytosine and -thymine alone and in combination with acyclovir and vidarabine in mice infected intracerebrally with herpes simplex virus.

Journal: Antimicrobial agents and chemotherapy 19830701

Title: Activity of 1-(2'-fluoro-2'-deoxy-beta-D-arabinofuranosyl)thymine against herpes simplex virus in cell cultures and rabbit eyes.

Journal: Antimicrobial agents and chemotherapy 19830601

Title: Asselah T, et al. Clevudine: a promising therapy for the treatment of chronic hepatitis B. Expert Opin Investig Drugs. 2008;17(12):1963-1974.

Title: Yoo BC, et al. Clevudine is highly efficacious in hepatitis B e antigen-negative chronic hepatitis B with durable off-therapy viral suppression. Hepatology. 2007;46(4):1041-1048.

Title: Smee DF, et, al. Progress in the discovery of compounds inhibiting orthopoxviruses in animal models. Antivir Chem Chemother. 2008;19(3):115-24.

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Tags:163252-36-6 Molecular Formula|163252-36-6 MDL|163252-36-6 SMILES|163252-36-6 Clevudine