ENTACAPONE

Search structure
Trade Names:
Synonyms:
Status: Approved (1999)
Entry Type: Small molecule
Molecule Category: Parent
ATC: N04BX02
UNII: 4975G9NM6T

Structure
InChI Key JRURYQJSLYLRLN-BJMVGYQFSA-N
Smile CCN(CC)C(=O)/C(C#N)=C/c1cc(O)c(O)c([N+](=O)[O-])c1
InChI
InChI=1S/C14H15N3O5/c1-3-16(4-2)14(20)10(8-15)5-9-6-11(17(21)22)13(19)12(18)7-9/h5-7,18-19H,3-4H2,1-2H3/b10-5+

Physicochemical Descriptors

Property Name Value
Molecular Formula C14H15N3O5
Molecular Weight 305.29
AlogP 1.78
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 5.0
Polar Surface Area 127.7
Molecular species ACID
Aromatic Rings 1.0
Heavy Atoms 22.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Catechol O-methyltransferase inhibitor DailyMed
Primary Target
Catechol-O-methyltransferase
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Protease Serine protease Serine protease PA clan Serine protease S1A subfamily
- - - - 22
Enzyme Transferase
- 3-12800 - - 20-98
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Carboxylic acid receptor Kynurenic acid receptor
5660-65600 - - - -
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 55600 - - -
Transporter Primary active transporter ATP-binding cassette ABCC subfamily
- 35100 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Parkinson Disease 4 D010300 ClinicalTrials
Cocaine-Related Disorders 2 D019970 ClinicalTrials
Epilepsy 1 D004827 ClinicalTrials
Obesity 1 D009765 ClinicalTrials
Amphetamine-Related Disorders 0 D019969 ClinicalTrials
Gastrointestinal Stromal Tumors 0 D046152 ClinicalTrials

Related Entries

Mixture

Side Effects from Label

Side effects Relative Frequency (%) Labels
Nervous system disorders Dyskinesia 27.0
Nervous system disorders Dyskinesia 25.2
Nervous system disorders Dyskinesia 25.0
Nervous system disorders Dyskinesia
Nervous system disorders Dyskinesia
Nervous system disorders Parkinsonism
Gastrointestinal disorders Nausea 14.0
Nervous system disorders Parkinsonism 13.9
Gastrointestinal disorders Nausea 13.8
Gastrointestinal disorders Nausea 11.0
Nervous system disorders Agitation 10.0
Renal and urinary disorders Chromaturia 10.0
Gastrointestinal disorders Diarrhoea 10.0
Nervous system disorders Hyperkinesia 10.0
Nervous system disorders Agitation 9.5
Renal and urinary disorders Chromaturia 9.5
Nervous system disorders Hyperkinesia 9.5
Nervous system disorders Hypokinesia 9.0
Nervous system disorders Hypokinesia 8.6
Gastrointestinal disorders Abdominal pain 8.1
Gastrointestinal disorders Gastrointestinal pain 8.1
Gastrointestinal disorders Abdominal pain 8.0
Gastrointestinal disorders Diarrhoea 8.0
Cardiac disorders Dizziness 8.0
Gastrointestinal disorders Gastrointestinal pain 8.0
Nervous system disorders Hypokinesia
Gastrointestinal disorders Nausea
Cardiac disorders Dizziness 7.5
Nervous system disorders Hypokinesia
Gastrointestinal disorders Nausea
Nervous system disorders Insomnia
Gastrointestinal disorders Abdominal pain 7.0
Gastrointestinal disorders Gastrointestinal pain 7.0
Nervous system disorders Tremor
Gastrointestinal disorders Constipation 6.3
Nervous system disorders Insomnia 6.3
General disorders and administration site conditions Asthenia 6.1
General disorders and administration site conditions Fatigue 6.1
General disorders and administration site conditions Asthenia 6.0
Gastrointestinal disorders Constipation 6.0
Cardiac disorders Dizziness
General disorders and administration site conditions Fatigue 6.0
General disorders and administration site conditions Pain 6.0
Nervous system disorders Agitation
Musculoskeletal and connective tissue disorders Back pain 5.0
Nervous system disorders Hyperkinesia
Nervous system disorders Tremor 5.0
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Gastrointestinal pain
General disorders and administration site conditions Pain
Gastrointestinal disorders Constipation
Nervous system disorders Headache
Gastrointestinal disorders Dry mouth 4.2
Psychiatric disorders Hallucination 4.1
Gastrointestinal disorders Abdominal pain
General disorders and administration site conditions Asthenia
Musculoskeletal and connective tissue disorders Back pain 4.0
Gastrointestinal disorders Constipation
Gastrointestinal disorders Diarrhoea
General disorders and administration site conditions Fatigue
Gastrointestinal disorders Gastrointestinal pain
Psychiatric disorders Hallucination
Gastrointestinal disorders Vomiting 4.0
General disorders and administration site conditions Hyperhidrosis 3.6
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Fatigue
Nervous system disorders Headache 3.5
Musculoskeletal and connective tissue disorders Muscle spasms
Psychiatric disorders Depression
Ear and labyrinth disorders Vertigo
Psychiatric disorders Depression 3.2
Musculoskeletal and connective tissue disorders Back pain
Gastrointestinal disorders Dry mouth 3.0
Cardiac disorders Dyspnoea 3.0
General disorders and administration site conditions Hyperhidrosis
Musculoskeletal and connective tissue disorders Muscle spasms 3.0
Nervous system disorders Orthostatic hypotension
Nervous system disorders Orthostatic hypotension 2.7
Ear and labyrinth disorders Vertigo 2.3
Psychiatric disorders Anxiety 2.0
General disorders and administration site conditions Asthenia 2.0
Musculoskeletal and connective tissue disorders Back pain
Musculoskeletal and connective tissue disorders Back pain 2.0
Gastrointestinal disorders Dyspepsia 2.0
Gastrointestinal disorders Flatulence 2.0
General disorders and administration site conditions Hyperhidrosis 2.0
Blood and lymphatic system disorders Purpura 2.0
Nervous system disorders Somnolence 2.0
Blood and lymphatic system disorders Vascular purpura 2.0
Nervous system disorders Agitation 1.0
Psychiatric disorders Anxiety
General disorders and administration site conditions Asthenia
Musculoskeletal and connective tissue disorders Back pain
Infections and infestations Bacterial infection 1.0
Gastrointestinal disorders Dysgeusia 1.0
Gastrointestinal disorders Dyspepsia
Cardiac disorders Dyspnoea
Gastrointestinal disorders Gastritis 1.0
Gastrointestinal disorders Gastrointestinal disorder 1.0
General disorders and administration site conditions Hyperhidrosis
Blood and lymphatic system disorders Purpura
Blood and lymphatic system disorders Vascular purpura
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Dry mouth

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Nervous system disorders
21.92
Psychiatric disorders
14.94
General disorders and administration site conditions
10.87
Gastrointestinal disorders
8.57
Musculoskeletal and connective tissue disorders
7.53
Investigations
5.94
Injury, poisoning and procedural complications
5.3
Vascular disorders
5.23
Respiratory, thoracic and mediastinal disorders
4.25
Cardiac disorders
2.79
Metabolism and nutrition disorders
2.57
Renal and urinary disorders
2.08

Cross References

Resources Reference
CAS NUMBER 130929-57-6
ChEBI 4798
ChEMBL CHEMBL953
DrugBank DB00494
DrugCentral 1018
EPA CompTox DTXSID5046439
FDA SRS 4975G9NM6T
Human Metabolome Database HMDB0012226
Guide to Pharmacology 6647
KEGG C07943
PDB PD9
PharmGKB PA164748726
PubChem 5281081
SureChEMBL SCHEMBL34504
ZINC ZINC000035342787
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