Home Other Building Blocks Clevudine

Clevudine

CAS No.:
163252-36-6
Catalog Number:
AG001TY5
Molecular Formula:
C10H13FN2O5
Molecular Weight:
260.2190
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
10mg
99%
1 week
United States
$175
- +
50mg
99%
1 week
United States
$404
- +
100mg
99%
1 week
United States
$682
- +
Product Description
Catalog Number:
AG001TY5
Chemical Name:
Clevudine
CAS Number:
163252-36-6
Molecular Formula:
C10H13FN2O5
Molecular Weight:
260.2190
MDL Number:
MFCD00935785
IUPAC Name:
1-[(2S,3R,4S,5S)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
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
InChI Key:
GBBJCSTXCAQSSJ-XQXXSGGOSA-N
SMILES:
OC[C@@H]1O[C@@H]([C@@H]([C@H]1O)F)n1cc(C)c(=O)[nH]c1=O
UNII:
IN51MVP5F1
Properties
Complexity:
413  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
0
Exact Mass:
260.081g/mol
Formal Charge:
0
Heavy Atom Count:
18  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
260.221g/mol
Monoisotopic Mass:
260.081g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
99.1A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-0.9  
Literature
Title Journal
Noncompetitive inhibition of hepatitis B virus reverse transcriptase protein priming and DNA synthesis by the nucleoside analog clevudine. Antimicrobial agents and chemotherapy 20130901
Microwave-assisted one-pot radiosynthesis of 2'-deoxy-2'-[18F]fluoro-5-methyl-1-β-d-arabinofuranosyluracil ([18F]-FMAU). Nuclear medicine and biology 20121001
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 of chromatography. B, Analytical technologies in the biomedical and life sciences 20120401
[New drugs of treatment of patients with chronic hepatitis B]. Nihon rinsho. Japanese journal of clinical medicine 20120401
Normal-phase liquid chromatography coupled with electrospray ionization mass spectrometry for chiral separation and quantification of clevudine and its enantiomer in human plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20120215
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. The Journal of biological chemistry 20120102
High-dose clevudine impairs mitochondrial function and glucose-stimulated insulin secretion in INS-1E cells. BMC gastroenterology 20120101
[18F]-2'-Fluoro-5-methyl-1-beta-D-arabinofuranosyluracil (18F-FMAU) in prostate cancer: initial preclinical observations. Molecular imaging 20120101
[New drugs of treatment of patients with chronic hepatitis B]. Nihon rinsho. Japanese journal of clinical medicine 20110501
Virologic and biochemical responses to clevudine in patients with chronic HBV infection-associated cirrhosis: data at week 48. Journal of viral hepatitis 20110401
18F-FDG PET/CT of drug-induced myopathy in a patient with chronic hepatitis B on long-term clevudine therapy. European journal of nuclear medicine and molecular imaging 20110401
Clevudine-induced viral response, associated with continued reduction of HBsAg titer, was durable after the withdrawal of therapy. Journal of gastroenterology 20110301
Clevudine for chronic hepatitis B: antiviral response, predictors of response, and development of myopathy. Journal of viral hepatitis 20110201
Automated synthesis of 2'-deoxy-2'-[18F]fluoro-5-methyl-1-β-D-arabinofuranosyluracil ([18F]-FMAU) using a one reactor radiosynthesis module. Nuclear medicine and biology 20110201
Comparison of clevudine and entecavir for treatment-naive patients with chronic hepatitis B virus infection: two-year follow-up data. Journal of clinical gastroenterology 20110101
[Treatment efficacy of clevudine, entecavir and lamivudine in treatment-naive patients with HBeAg-positive chronic hepatitis B]. The Korean journal of gastroenterology = Taehan Sohwagi Hakhoe chi 20101201
Efficacy of initial treatment with clevudine in naive patients with chronic hepatitis B. The Korean journal of internal medicine 20101201
Different modes of transport for 3H-thymidine, 3H-FLT, and 3H-FMAU in proliferating and nonproliferating human tumor cells. Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20100901
Forty-eight weeks treatment with clevudine 30 mg qd versus lamivudine 100 mg qd for chronic hepatitis B infection: a double-blind randomized study. The Korean journal of hepatology 20100901
Clinical, biochemical, and pathological characteristics of clevudine-associated myopathy. Journal of hepatology 20100801
Focus. Journal of hepatology 20100801
Comparison between clevudine and entecavir treatment for antiviral-naïve patients with chronic hepatitis B. Liver international : official journal of the International Association for the Study of the Liver 20100701
Treatment outcomes of clevudine versus lamivudine at week 48 in naïve patients with HBeAg positive chronic hepatitis B. Journal of Korean medical science 20100501
Clevudine demonstrates potent antiviral activity in naïve chronic hepatitis B patients. Intervirology 20100101
Polymyositis in patients taking antiviral clevudine therapy: a report of two cases. NeuroRehabilitation 20100101
Evaluation of the in vitro anti-HBV activity of clevudine in combination with other nucleoside/nucleotide inhibitors. Antiviral therapy 20100101
Clevudine myopathy in patients with chronic hepatitis B. Journal of hepatology 20091001
Myopathy and neuropathy associated with nucleos(t)ide analog therapy for hepatitis B. Journal of hepatology 20091001
[Efficacy of 48-week clevudine therapy for chronic hepatitis B]. The Korean journal of hepatology 20090901
Early development of clevudine resistance during clevudine therapy in a patient with chronic hepatitis B who received prior lamivudine therapy. Liver international : official journal of the International Association for the Study of the Liver 20090701
Long-term therapy with clevudine for chronic hepatitis B can be associated with myopathy characterized by depletion of mitochondrial DNA. Hepatology (Baltimore, Md.) 20090601
[Clevudine therapy in patients with chronic hepatitis B]. The Korean journal of hepatology 20090601
[Long-term clevudine therapy in nucleos(t)ide-naïve and lamivudine-experienced patients with hepatitis B virus-related chronic liver diseases]. The Korean journal of hepatology 20090601
[New molecules in the treatment of chronic hepatitis B]. Presse medicale (Paris, France : 1983) 20090501
Clevudine for hepatitis B. Drugs of today (Barcelona, Spain : 1998) 20090501
Clinical and virological responses to clevudine therapy in chronic hepatitis B patients: results at 1 year of an open-labelled prospective study. Antiviral therapy 20090101
Clevudine: a promising therapy for the treatment of chronic hepatitis B. Expert opinion on investigational drugs 20081201
[Development of clevudine resistance after switching from lamivudine in a patient with chronic hepatitis B]. The Korean journal of gastroenterology = Taehan Sohwagi Hakhoe chi 20081101
Tracking cellular stress with labeled FMAU reflects changes in mitochondrial TK2. European journal of nuclear medicine and molecular imaging 20080801
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. Alimentary pharmacology & therapeutics 20080601
[Management of chronic hepatitis B in treatment-naive patients]. The Korean journal of gastroenterology = Taehan Sohwagi Hakhoe chi 20080601
[Management of antiviral-resistant chronic hepatitis B virus infection]. The Korean journal of gastroenterology = Taehan Sohwagi Hakhoe chi 20080601
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. European journal of nuclear medicine and molecular imaging 20080501
In vivo measurement of cell proliferation in canine brain tumor using C-11-labeled FMAU and PET. Nuclear medicine and biology 20080101
New drugs for chronic hepatitis B: a review. American journal of therapeutics 20080101
Clevudine is efficiently phosphorylated to the active triphosphate form in primary human hepatocytes. Antiviral therapy 20080101
Clevudine is highly efficacious in hepatitis B e antigen-negative chronic hepatitis B with durable off-therapy viral suppression. Hepatology (Baltimore, Md.) 20071001
Tumor imaging using 1-(2'-deoxy-2'-18F-fluoro-beta-D-arabinofuranosyl)thymine and PET. Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20070901
Radiosynthesis of 2'-deoxy-2'-[18F]-fluoro-5-methyl-1-beta-L-arabinofuranosyluracil ([18F]-L-FMAU) for PET. Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20070801
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. Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20070801
Twenty-four-week clevudine therapy showed potent and sustained antiviral activity in HBeAg-positive chronic hepatitis B. Hepatology (Baltimore, Md.) 20070501
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. Intervirology 20070101
A novel mutation pattern emerging during lamivudine treatment shows cross-resistance to adefovir dipivoxil treatment. Antiviral therapy 20070101
Hepatitis B virus treatment in HIV-infected patients. Topics in HIV medicine : a publication of the International AIDS Society, USA 20061201
Clevudine: a potent inhibitor of hepatitis B virus in vitro and in vivo. Expert review of anti-infective therapy 20060801
[Advances in the study of nucleoside antiviral drugs]. Yao xue xue bao = Acta pharmaceutica Sinica 20060801
A 12-week clevudine therapy showed potent and durable antiviral activity in HBeAg-positive chronic hepatitis B. Hepatology (Baltimore, Md.) 20060501
[Therapeutic approach to EBV infection]. Nihon rinsho. Japanese journal of clinical medicine 20060301
Cellular and virological mechanisms of HBV drug resistance. Journal of hepatology 20060201
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. Therapeutic drug monitoring 20060201
Clevudine for the treatment of chronic hepatitis B virus infection. Expert opinion on investigational drugs 20051001
Combination of nucleoside analogues in the treatment of chronic hepatitis B virus infection: lesson from experimental models. The Journal of antimicrobial chemotherapy 20050501
Imaging DNA synthesis in vivo with 18F-FMAU and PET. Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20050201
Imaging DNA synthesis with [18F]FMAU and positron emission tomography in patients with cancer. European journal of nuclear medicine and molecular imaging 20050101
Drugs in development for hepatitis B. Drugs 20050101
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. Molecular imaging and biology : MIB : the official publication of the Academy of Molecular Imaging 20050101
Clevudine therapy with vaccine inhibits progression of chronic hepatitis and delays onset of hepatocellular carcinoma in chronic woodchuck hepatitis virus infection. Antiviral therapy 20041201
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. Clinical cancer research : an official journal of the American Association for Cancer Research 20041001
Adenovirus-based gene therapy during clevudine treatment of woodchucks chronically infected with woodchuck hepatitis virus. Virology 20040915
A phase II dose-escalating trial of clevudine in patients with chronic hepatitis B. Hepatology (Baltimore, Md.) 20040701
[New approaches in the treatment of hepatitis B]. Deutsche medizinische Wochenschrift (1946) 20040521
Pharmacokinetics of the thymidine analog 2'-fluoro-5-methyl-1-beta-D-arabinofuranosyluracil (FMAU) in tumor-bearing rats. Nuclear medicine and biology 20040501
Direct comparison of radiolabeled probes FMAU, FHBG, and FHPG as PET imaging agents for HSV1-tk expression in a human breast cancer model. Molecular imaging 20040401
New treatment of chronic hepatitis B. Seminars in liver disease 20040101
Monitoring tumor cell proliferation by targeting DNA synthetic processes with thymidine and thymidine analogs. Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20031201
Mechanism of antiviral activities of 3'-substituted L-nucleosides against 3TC-resistant HBV polymerase: a molecular modelling approach. Antiviral chemistry & chemotherapy 20031101
Effects of pyrimidine and purine analog combinations in the duck hepatitis B virus infection model. Antimicrobial agents and chemotherapy 20030601
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. Nuclear medicine and biology 20030401
Current and future antiviral agents for chronic hepatitis B. The Journal of antimicrobial chemotherapy 20030301
Comparison of anti-hepatitis B virus activities of lamivudine and clevudine by a quantitative assay. Antimicrobial agents and chemotherapy 20030101
In vitro activity of potential anti-poxvirus agents. Antiviral research 20030101
Entecavir, FTC, L-FMAU, LdT and others. Journal of hepatology 20030101
Treatment of HBeAg negative chronic hepatitis B with new drugs (adefovir and others). Journal of hepatology 20030101
Understanding the unique mechanism of L-FMAU (clevudine) against hepatitis B virus: molecular dynamics studies. Bioorganic & medicinal chemistry letters 20021202
Rat studies comparing 11C-FMAU, 18F-FLT, and 76Br-BFU as proliferation markers. Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20021201
Inhibitory activity of dioxolane purine analogs on wild-type and lamivudine-resistant mutants of hepadnaviruses. Hepatology (Baltimore, Md.) 20020901
Radiolabeled 2'-fluorodeoxyuracil-beta-D-arabinofuranoside (FAU) and 2'-fluoro-5-methyldeoxyuracil-beta -D-arabinofuranoside (FMAU) as tumor-imaging agents in mice. Cancer chemotherapy and pharmacology 20020501
[New management strategies for hepatitis B]. Gastroenterologie clinique et biologique 20020201
New synthesis of L-FMAU from L-arabinose. Nucleosides, nucleotides & nucleic acids 20020101
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. Intervirology 20020101
Evaluation of 2'-deoxy-2'-flouro-5-methyl-1-beta-D-arabinofuranosyluracil as a potential gene imaging agent for HSV-tk expression in vivo. Molecular imaging 20020101
Rapid enantiomeric quantification of an antiviral nucleoside agent (D,L-FMAU, 2'-fluoro-5-methyl-beta,D,L-arabinofurano-syluracil) by mass spectrometry. Journal of medicinal chemistry 20011025
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. Antimicrobial agents and chemotherapy 20010901
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). Hepatology (Baltimore, Md.) 20010101
Potential use of antiviral L(-)nucleoside analogues for the prevention or treatment of viral associated cancers. Cancer letters 20010101
Structure-activity relationships of L-dioxolane uracil nucleosides as anti-Epstein Barr virus agents. Journal of medicinal chemistry 19990617
Sensitivity of L-(-)2,3-dideoxythiacytidine resistant hepatitis B virus to other antiviral nucleoside analogues. Biochemical pharmacology 19990615
Synthesis and anti-hepatitis B virus activity of 9-(2-deoxy-2-fluoro-beta-L-arabinofuranosyl) purine nucleosides. Journal of medicinal chemistry 19970815
Structure--activity relationships of 1-(2-Deoxy-2-fluoro-beta-L-arabinofuranosyl)pyrimidine nucleosides as anti-hepatitis B virus agents. Journal of medicinal chemistry 19960705
Inhibition of Epstein-Barr virus replication by a novel L-nucleoside, 2'-fluoro-5-methyl-beta-L-arabinofuranosyluracil. Biochemical pharmacology 19960412
Inhibition of hepatitis B virus by a novel L-nucleoside, 2'-fluoro-5-methyl-beta-L-arabinofuranosyl uracil. Antimicrobial agents and chemotherapy 19960201
Inhibitory effects of 2'-fluorinated arabinosyl-pyrimidine nucleosides on woodchuck hepatitis virus replication in chronically infected woodchucks. Antimicrobial agents and chemotherapy 19900301
Activity of 1-(2'-deoxy-2'-fluoro-beta-D-arabinofuranosyl)-5-iodouracil against simian varicella virus infections in African green monkeys. Antimicrobial agents and chemotherapy 19860101
Comparative anti-herpesvirus activities of 9-(1,3-dihydroxy-2-propoxymethyl)guanine, acyclovir, and two 2'-fluoropyrimidine nucleosides. Antiviral research 19851001
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. Antimicrobial agents and chemotherapy 19830701
Activity of 1-(2'-fluoro-2'-deoxy-beta-D-arabinofuranosyl)thymine against herpes simplex virus in cell cultures and rabbit eyes. Antimicrobial agents and chemotherapy 19830601
Properties