Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C35H46ClN5O9S |
Molecular Weight | 748.286 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CN=C(O[C@@H]2C[C@H](N(C2)C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)C(=O)N[C@@]3(C[C@H]3C=C)C(=O)NS(=O)(=O)C4CC4)C5=C1C=CC(Cl)=C5
InChI
InChIKey=XRWSZZJLZRKHHD-WVWIJVSJSA-N
InChI=1S/C35H46ClN5O9S/c1-9-19-16-35(19,31(44)40-51(46,47)22-11-12-22)39-28(42)25-15-21(49-29-24-14-20(36)10-13-23(24)26(48-8)17-37-29)18-41(25)30(43)27(33(2,3)4)38-32(45)50-34(5,6)7/h9-10,13-14,17,19,21-22,25,27H,1,11-12,15-16,18H2,2-8H3,(H,38,45)(H,39,42)(H,40,44)/t19-,21-,25+,27-,35-/m1/s1
DescriptionCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25117197 | https://news.bms.com/press-release/japan-approves-first-all-oral-interferon-and-ribavirin-free-hepatitis-c-treatment-dakl | https://www.tga.gov.au/auspar/auspar-asunaprevir | http://www.hepctip.ca/drug-pipeline-2/sunvepra-asunaprevir-canada/
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25117197 | https://news.bms.com/press-release/japan-approves-first-all-oral-interferon-and-ribavirin-free-hepatitis-c-treatment-dakl | https://www.tga.gov.au/auspar/auspar-asunaprevir | http://www.hepctip.ca/drug-pipeline-2/sunvepra-asunaprevir-canada/
Asunaprevir is a direct acting antiviral agent (DAA) against the hepatitis C virus Asunaprevir is an inhibitor of the HCV NS3/4A serine protease complex. This NS3/4A enzyme complex is responsible for processing the HCV polyprotein to yield mature viral proteins required for viral replication. The combination of daclatasvir + asunaprevir [Daklinza(®) + Sunvepra(®)], two direct-acting antiviral agents, has been developed by Bristol-Myers Squibb for the treatment of patients with chronic hepatitis C virus (HCV) genotype 1 infections, including those with compensated cirrhosis.
CNS Activity
Originator
Sources: http://adisinsight.springer.com/drugs/800027520
Curator's Comment: # Bristol-Myers Squibb
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2095231 |
0.3 nM [IC50] | ||
Target ID: CHEMBL1697668 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25670521 |
0.3 µM [IC50] | ||
Target ID: CHEMBL1743124 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25670521 |
0.27 µM [IC50] | ||
Target ID: CHEMBL1743121 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25670521 |
3.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | SUNVEPRA Approved UseSUNVEPRA (asunaprevir) is indicated in combination with other medicinal products for the treatment of chronic hepatitis C virus (HCV) infection in adults with compensated liver disease (including cirrhosis) |
Sample Use Guides
The recommended dose of SUNVEPRA (asunaprevir) is 100 mg twice daily. SUNVEPRA must be administered in combination with DAKLINZA or with DAKLINZA, peginterferon alfa, and ribavirin.
Route of Administration:
Oral
In cell-based HCV replicon assays, asunaprevir inhibited HCV genotypes 1a(H77 strain) and, 1b(Con1 strain) with effective concentration (50% reduction, EC50) values of 4 nM and 1.2 nM, , respectively. The EC50 values against a genotype 2a replicon and hybrid replicons encoding the NS3 protease domain representing HCV genotypes 2b and 3a were 230 nM, 480 nM, and 1162 nM, respectively. Against hybrid replicons encoding the NS3 protease domain representing HCV genotype 4a, observed EC50 values ranged from 1.8 nM to 7.6 nM
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NCI_THESAURUS |
C783
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WHO-ATC |
J05AP06
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WHO-ATC |
J05AE15
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630420-16-5
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16076883
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DB11586
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S9X0KRJ00S
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SUB124458
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CHEMBL2105735
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C114982
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DTXSID201026065
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C571889
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4889
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ASUNAPREVIR
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m11765
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XX-150
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9472
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1652103
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100000145687
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)