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Compound Detail

CHEMBL953

ENTACAPONE
💊 Approved Drug
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💊 Approved Drug
CCN(CC)C(=O)/C(C#N)=C/c1cc(O)c(O)c([N+](=O)[O-])c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL953
Name ENTACAPONE
Phase Approved
Structure Type MOL
InChI Key JRURYQJSLYLRLN-BJMVGYQFSA-N
Therapeutic ✓ Yes

Known Names

Comtan Comtess Entacapona Entacapone Entacapone component of corbilta Entacapone component of levodopa/carbidopa/ orion Entacapone component of stalevo Entacapone orion Entacapone teva OR-611
8
Targets
19
Activities
2
Assay Types
30
PK Parameters
20
Publications
10
Known Names
7
Indications
1
Mechanisms

Molecular Properties

305.3
MW (Da)
1.78
ALogP
6
HBA
2
HBD
127.7
PSA (Ų)
0.28
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1998
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -capone
USAN Year 1997

Extended Properties

Molecular Formula C14H15N3O5
MW 305.29
Aromatic Rings 1
Heavy Atoms 22
NP-Likeness -0.89

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Catechol O-methyltransferase inhibitor INHIBITOR Catechol O-methyltransferase ✓ ✓

Indications

Parkinson Disease Cocaine-Related Disorders Cocaine-Related Disorders Epilepsy Obesity Amphetamine-Related Disorders Gastrointestinal Stromal Tumors

ATC Classification

N04BX02
entacapone
Level 1: NERVOUS SYSTEM
Level 2: ANTI-PARKINSON DRUGS

Activity Summary

IC50 17 meas. best 8.52
EC50 2 meas. best 5.25

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Catechol O-methyltransferase
CHEMBL2372
 IC50 8.52 7.07 3.0 7
Catechol O-methyltransferase
CHEMBL2023
 IC50 7.22 6.815 60.0 2
Unchecked
CHEMBL612545
 IC50 5.72 5.72 1900.0 1
Alpha-ketoglutarate-dependent dioxygenase FTO
CHEMBL2331065
 IC50 5.52 5.48 3000.0 3
G-protein coupled receptor 35
CHEMBL1293267
 EC50 5.25 4.715 5660.0 2
ATP-binding cassette sub-family C member 4
CHEMBL1743128
 IC50 5.17 5.17 6800.0 1
ATP-binding cassette sub-family C member 3
CHEMBL5918
 IC50 4.46 4.46 35100.0 1
Bile salt export pump
CHEMBL6020
 IC50 4.25 4.25 55600.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1615.9 ng.hr.mL-1 Homo sapiens
CL 11.7 mL.min-1.kg-1 Homo sapiens
CL 5.3 mL.min-1.kg-1 Homo sapiens
CL 11.7 mL.min-1.kg-1 Homo sapiens
CL 12.0 mL.min-1.kg-1 Homo sapiens
CL - mL.min-1.kg-1 Homo sapiens
CL 12.0 mL.min-1.kg-1 Homo sapiens
CL 27.0 mL.min-1.g-1 Homo sapiens
CL 27.0 mL.min-1.g-1 Homo sapiens
CL - - Homo sapiens
CL 850.0 mL/min Homo sapiens
Cmax 3930.69 nM Homo sapiens
Excretion 10.0 % Homo sapiens
Excretion 90.0 % Homo sapiens
F 35.0 % Homo sapiens
Fu 0.02 - Homo sapiens
Fu 0.02 - Homo sapiens
Fu 0.025 - Homo sapiens
Fu 0.031 - Macaca fascicularis
Fu 0.02 - Canis lupus familiaris
Fu 0.019 - Cavia porcellus
Fu 0.026 - Mus musculus
Fu 0.017 - Rattus norvegicus
Fu 1.0 - Homo sapiens
Fu - - Homo sapiens
Fu 0.021 - Rattus norvegicus
Inhibition 65.0 % Homo sapiens
Inhibition 82.0 % Homo sapiens
MRT 0.38 hr Homo sapiens
T1/2 0.9667 hr Oryctolagus cuniculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Catechol O-methyltransferase IC50 = 3.02 nM 8.52 Inhibition of MB-COMT in Wistar rat brain assessed as metanephrine formation pre... 27463695
Catechol O-methyltransferase IC50 = 3.47 nM 8.46 Inhibition of MB-COMT in Wistar rat brain assessed as metanephrine formation pre... 27463695
Catechol O-methyltransferase IC50 = 12.8 nM 7.89 Inhibition of Catechol O-methyltransferase activity in rat brain 11806720
Catechol O-methyltransferase IC50 = 34.45 nM 7.46 Inhibition of S-COMT in Wistar rat liver assessed as metanephrine formation prei... 27463695
Catechol O-methyltransferase IC50 = 60.0 nM 7.22 Inhibition of COMT (unknown origin) in presence of AdoMet and Esculetin by react... -
Catechol O-methyltransferase IC50 = 230.0 nM 6.64 Inhibition of rat liver COMT using esculetin as substrate by fluorescence based ... 32299731
Catechol O-methyltransferase IC50 = 386.0 nM 6.41 Inhibition of human recombinant His-tagged soluble COMT expressed in Escherichia... 27074629
Unchecked IC50 = 1900.0 nM 5.72 Inhibition of human OAT2 tv.1 variant expressed in HEK293 cells assessed as inhi... 36270005
Catechol O-methyltransferase IC50 = 2320.0 nM 5.63 Inhibitory activity against COMT in rat liver 16335931
Alpha-ketoglutarate-dependent dioxygenase FTO IC50 = 3000.0 nM 5.52 Inhibition of FTO (unknown origin) assessed as reduction in demethylation by mea... -
Alpha-ketoglutarate-dependent dioxygenase FTO IC50 = 3500.0 nM 5.46 Inhibition of FTO (unknown origin) expressed in Escherichia coli BL21(DE3) using... 38805939
Alpha-ketoglutarate-dependent dioxygenase FTO IC50 = 3500.0 nM 5.46 Inhibition of FTO (unknown origin) demethylation activity 34792334
G-protein coupled receptor 35 EC50 = 5660.0 nM 5.25 Agonist activity at GPR35 in human HT-29 cells assessed as induction of whole ce... -
ATP-binding cassette sub-family C member 4 IC50 = 6800.0 nM 5.17 Inhibition of human MRP4 overexpressed in Sf9 cell membrane vesicles assessed as... 23956101
Catechol O-methyltransferase IC50 = 12800.0 nM 4.89 Inhibitory activity against COMT in rat brain 16335931
ATP-binding cassette sub-family C member 3 IC50 = 35100.0 nM 4.46 Inhibition of human MRP3 overexpressed in Sf9 insect cell membrane vesicles asse... 23956101
Bile salt export pump IC50 = 55600.0 nM 4.25 Inhibition of human BSEP overexpressed in Sf9 cell membrane vesicles assessed as... 23956101
G-protein coupled receptor 35 EC50 = 65600.0 nM 4.18 Agonist activity at GPR35 in human U2OS cells assessed as induction of beta-arre... -

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 36
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
11806720 10.1021/jm0109964 Catechol O-methyltransferase 13
16335931 10.1021/jm0580454 Catechol O-methyltransferase 13
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
20070106 10.1021/jm901371v Homo sapiens 8
- 10.1039/C2MD20210G G-protein coupled receptor 35 6
27463695 10.1021/acs.jmedchem.6b00666 No relevant target 6
15566291 10.1021/jm040848o Catechol O-methyltransferase 5
21474681 10.1124/dmd.111.038778 Brain 5
27074629 10.1021/acs.jmedchem.5b01970 Catechol O-methyltransferase 4
34846885 10.1021/acs.jmedchem.1c01333 ADMET 4
18426954 10.1124/dmd.108.020479 ADMET 4
22685216 10.1124/dmd.112.045476 ADMET 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
33691794 10.1186/s13148-021-01037-1 A549 4
20014752 10.1021/tx900326k Hepatotoxicity 3
23956101 10.1093/toxsci/kft176 Unchecked 3
27463695 10.1021/acs.jmedchem.6b00666 Catechol O-methyltransferase 3

Data from ChEMBL 36 via Core Engine