BOCEPREVIR

Search structure
Trade Names:
Synonyms:
Status: Approved (2011)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: J05AP03
UNII: 89BT58KELH

Structure
InChI Key LHHCSNFAOIFYRV-DOVBMPENSA-N
Smile CC(C)(C)NC(=O)N[C@H](C(=O)N1C[C@H]2[C@@H]([C@H]1C(=O)NC(CC1CCC1)C(=O)C(N)=O)C2(C)C)C(C)(C)C
InChI
InChI=1S/C27H45N5O5/c1-25(2,3)20(30-24(37)31-26(4,5)6)23(36)32-13-15-17(27(15,7)8)18(32)22(35)29-16(19(33)21(28)34)12-14-10-9-11-14/h14-18,20H,9-13H2,1-8H3,(H2,28,34)(H,29,35)(H2,30,31,37)/t15-,16?,17-,18-,20+/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C27H45N5O5
Molecular Weight 519.69
AlogP 1.71
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 4.0
Number of Rotational Bond 8.0
Polar Surface Area 150.7
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 37.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Hepatitis C virus serine protease, NS3/NS4A inhibitor Expert DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Protease Cysteine protease Cysteine protease CA clan Cysteine protease C1A family
- 1100 - - -
Enzyme Protease Serine protease Serine protease PA clan Serine protease S1A subfamily
- 17000 - - -
Enzyme Protease Serine protease Serine protease PA clan Serine protease S29 family Serine protease S29 regulatory subfamily
- - - 14 -
Enzyme Protease Serine protease Serine protease PA clan Serine protease S29 family
- - - 14 -
Unclassified protein
- - - 14 -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Hepatitis C, Chronic 4 D019698 FDA
Hepatitis C 3 D006526 ClinicalTrials
Thrombocytopenia 1 D013921 ClinicalTrials

Related Entries

MCS

Side Effects from Label

Side effects Relative Frequency (%) Labels
General disorders and administration site conditions Asthenia 59.0
General disorders and administration site conditions Fatigue 59.0
General disorders and administration site conditions Asthenia 50.0
General disorders and administration site conditions Fatigue 50.0
Nervous system disorders Headache 48.0
Gastrointestinal disorders Nausea 42.0
Gastrointestinal disorders Nausea 38.0
Nervous system disorders Insomnia 34.0
Blood and lymphatic system disorders Anaemia 30.0
General disorders and administration site conditions Chills 30.0
General disorders and administration site conditions Chills 29.0
Skin and subcutaneous tissue disorders Alopecia 27.0
General disorders and administration site conditions Influenza like illness 25.0
General disorders and administration site conditions Decreased appetite 24.0
Nervous system disorders Insomnia 24.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 24.0
Musculoskeletal and connective tissue disorders Myalgia 24.0
General disorders and administration site conditions Irritability 23.0
Gastrointestinal disorders Diarrhoea 22.0
Investigations Body temperature increased 21.0
Blood and lymphatic system disorders Anaemia 20.0
Nervous system disorders Insomnia 20.0
Musculoskeletal and connective tissue disorders Arthralgia 19.0
Skin and subcutaneous tissue disorders Dermatitis 19.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 19.0
Blood and lymphatic system disorders Neutropenia 19.0
Skin and subcutaneous tissue disorders Rash 19.0
General disorders and administration site conditions Asthenia 18.0
Skin and subcutaneous tissue disorders Dry skin 18.0
Skin and subcutaneous tissue disorders Pruritus 18.0
Skin and subcutaneous tissue disorders Alopecia 16.0
Musculoskeletal and connective tissue disorders Arthralgia 16.0
General disorders and administration site conditions Asthenia 16.0
General disorders and administration site conditions Decreased appetite 16.0
Gastrointestinal disorders Diarrhoea 16.0
Cardiac disorders Dizziness 16.0
Gastrointestinal disorders Dysgeusia 16.0
Cardiac disorders Dyspnoea 16.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 16.0
Respiratory, thoracic and mediastinal disorders Cough 15.0
Psychiatric disorders Depression 15.0
Gastrointestinal disorders Diarrhoea 15.0
Musculoskeletal and connective tissue disorders Arthralgia 14.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 14.0
General disorders and administration site conditions Irritability 13.0
Gastrointestinal disorders Vomiting 13.0
Gastrointestinal disorders Dysgeusia 11.0
Cardiac disorders Dizziness 10.0
Gastrointestinal disorders Dry mouth 10.0
Blood and lymphatic system disorders Neutropenia 10.0
Gastrointestinal disorders Dry mouth 9.0
Skin and subcutaneous tissue disorders Dry skin 9.0
Investigations Weight decreased 9.0
Gastrointestinal disorders Dry mouth 8.0
Skin and subcutaneous tissue disorders Dry skin 8.0
Cardiac disorders Dyspnoea exertional 8.0
Gastrointestinal disorders Vomiting 8.0
Psychiatric disorders Anxiety 6.0
Skin and subcutaneous tissue disorders Dermatitis 6.0
Skin and subcutaneous tissue disorders Rash 6.0
Skin and subcutaneous tissue disorders Dermatitis 5.0
Cardiac disorders Dyspnoea exertional 5.0
Skin and subcutaneous tissue disorders Rash 5.0
General disorders and administration site conditions Pain 4.0

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
16.06
Gastrointestinal disorders
13.34
Nervous system disorders
9.95
Investigations
8.13
Skin and subcutaneous tissue disorders
7.55
Psychiatric disorders
6.75
Blood and lymphatic system disorders
5.54
Respiratory, thoracic and mediastinal disorders
5.5
Cardiac disorders
4.04
Vascular disorders
3.75
Infections and infestations
3.44
Musculoskeletal and connective tissue disorders
3.41
Metabolism and nutrition disorders
2.64
Injury, poisoning and procedural complications
2.17

Cross References

Resources Reference
CAS NUMBER 394730-60-0
ChEBI 68621
ChEMBL CHEMBL218394
DrugBank DB08873
DrugCentral 4172
FDA SRS 89BT58KELH
Guide to Pharmacology 7876
KEGG D08876
PDB HU5
PharmGKB PA165948902
PubChem 10324367
SureChEMBL SCHEMBL640836
ZINC ZINC14210457
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