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923604-59-5,MFCD25563225
Catalog No.:AA00GRIM

923604-59-5 | Simeprevir

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Purity
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Price(USD)
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1mg
98%
in stock  
$14.00   $10.00
- +
5mg
98%
in stock  
$45.00   $32.00
- +
50mg
98%
in stock  
$349.00   $244.00
- +
100mg
98%
in stock  
$543.00   $380.00
- +
200mg
98%
in stock  
$932.00   $653.00
- +
  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00GRIM
Chemical Name:
Simeprevir
CAS Number:
923604-59-5
Molecular Formula:
C38H47N5O7S2
Molecular Weight:
749.9391
MDL Number:
MFCD25563225
SMILES:
COc1ccc2c(c1C)nc(cc2O[C@@H]1C[C@@H]2[C@@H](C1)C(=O)N(C)CCCC/C=C\[C@H]1[C@](NC2=O)(C1)C(=O)NS(=O)(=O)C1CC1)c1scc(n1)C(C)C
Properties
Computed Properties
 
Complexity:
1490  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
52  
Hydrogen Bond Acceptor Count:
10  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
8  
XLogP3:
4.8  

Literature

Title: Mechanisms of Hepatitis C Viral Resistance to Direct Acting Antivirals.

Journal: Viruses 20151201

Title: Interferon-free therapy for hepatitis C: The hurdles amid a golden era.

Journal: Digestive and liver disease : official journal of the Italian Society of Gastroenterology and the Italian Association for the Study of the Liver 20150901

Title: Hepatitis C virus: Virology, diagnosis and treatment.

Journal: World journal of hepatology 20150608

Title: An update on the management of chronic hepatitis C: 2015 Consensus guidelines from the Canadian Association for the Study of the Liver.

Journal: Canadian journal of gastroenterology & hepatology 20150101

Title: Changing the face of hepatitis C management - the design and development of sofosbuvir.

Journal: Drug design, development and therapy 20150101

Title: Cost-effectiveness of sofosbuvir-based treatments for chronic hepatitis C in the US.

Journal: BMC gastroenterology 20150101

Title: Discovery and development of simeprevir (TMC435), a HCV NS3/4A protease inhibitor.

Journal: Journal of medicinal chemistry 20140313

Title: Highly efficient infectious cell culture of three hepatitis C virus genotype 2b strains and sensitivity to lead protease, nonstructural protein 5A, and polymerase inhibitors.

Journal: Hepatology (Baltimore, Md.) 20140201

Title: New treatments for genotype 1 chronic hepatitis C - focus on simeprevir.

Journal: Therapeutics and clinical risk management 20140101

Title: Simeprevir for the treatment of hepatitis C virus infection.

Journal: Pharmacogenomics and personalized medicine 20140101

Title: Synthesis and antiviral activity of novel HCV NS3 protease inhibitors with P4 capping groups.

Journal: Bioorganic & medicinal chemistry letters 20121215

Title: Antiviral activity of TMC435 monotherapy in patients infected with HCV genotypes 2-6: TMC435-C202, a phase IIa, open-label study.

Journal: Journal of hepatology 20120601

Title: Discovery of novel urea-based hepatitis C protease inhibitors with high potency against protease-inhibitor-resistant mutants.

Journal: Journal of medicinal chemistry 20120412

Title: Molecular modeling study on the resistance mechanism of HCV NS3/4A serine protease mutants R155K, A156V and D168A to TMC435.

Journal: Antiviral research 20120101

Title: Differential efficacy of protease inhibitors against HCV genotypes 2a, 3a, 5a, and 6a NS3/4A protease recombinant viruses.

Journal: Gastroenterology 20110901

Title: Second-wave protease inhibitors: choosing an heir.

Journal: Clinics in liver disease 20110801

Title: Therapeutics: new drugs hit the target.

Journal: Nature 20110608

Title: Emerging therapeutic options in hepatitis C virus infection.

Journal: The American journal of managed care 20110301

Title: Rapid viral response of once-daily TMC435 plus pegylated interferon/ribavirin in hepatitis C genotype-1 patients: a randomized trial.

Journal: Antiviral therapy 20110101

Title: Synthesis and biological evaluations of P4-benzoxaborole-substituted macrocyclic inhibitors of HCV NS3 protease.

Journal: Bioorganic & medicinal chemistry letters 20101215

Title: Susceptibility of treatment-naive hepatitis C virus (HCV) clinical isolates to HCV protease inhibitors.

Journal: Antimicrobial agents and chemotherapy 20101201

Title: Improved P2 phenylglycine-based hepatitis C virus NS3 protease inhibitors with alkenylic prime-side substituents.

Journal: Bioorganic & medicinal chemistry 20100715

Title: In vitro resistance profile of the hepatitis C virus NS3/4A protease inhibitor TMC435.

Journal: Antimicrobial agents and chemotherapy 20100501

Title: Rapid HCV-RNA decline with once daily TMC435: a phase I study in healthy volunteers and hepatitis C patients.

Journal: Gastroenterology 20100301

Title: Induced-fit binding of the macrocyclic noncovalent inhibitor TMC435 to its HCV NS3/NS4A protease target.

Journal: Angewandte Chemie (International ed. in English) 20100222

Title: Advances in the development of macrocyclic inhibitors of hepatitis C virus NS3-4A protease.

Journal: Current topics in medicinal chemistry 20100101

Title: [New antiviral agents against hepatitis C in clinical trials. Hope for a cure--but resistance problems must be overcomed].

Journal: Lakartidningen 20091101

Title: TMC-435, an NS3/4A protease inhibitor for the treatment of HCV infection.

Journal: Current opinion in investigational drugs (London, England : 2000) 20090801

Title: In vitro activity and preclinical profile of TMC435350, a potent hepatitis C virus protease inhibitor.

Journal: Antimicrobial agents and chemotherapy 20090401

Title: Structure-activity relationship study on a novel series of cyclopentane-containing macrocyclic inhibitors of the hepatitis C virus NS3/4A protease leading to the discovery of TMC435350.

Journal: Bioorganic & medicinal chemistry letters 20080901

Title: Raboisson P, et al. Structure-activity relationship study on a novel series of cyclopentane-containing macrocyclic inhibitors of the hepatitis C virus NS3/4A protease leading to the discovery of TMC435350. Bioorg Med Chem Lett. 2008 Sep 1;18(17):4853-8.

Title: Lin TI, et al. In vitro activity and preclinical profile of TMC435350, a potent hepatitis C virus protease inhibitor.Antimicrob Agents Chemother. 2009 Apr;53(4):1377-85. Epub 2009 Jan 26.

Title: Rajagopalan R, et al. Preclinical Characterization and Human Microdose Pharmacokinetics of ITMN-8187, a Nonmacrocyclic Inhibitor of the Hepatitis C Virus NS3 Protease. Antimicrob Agents Chemother. 2016 Dec 27;61(1). pii: e01569-16.

Title: Lo HS, et al. Simeprevir Potently Suppresses SARS-CoV-2 Replication and Synergizes with Remdesivir. ACS Cent Sci. 2021 May 26;7(5):792-802.

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