Details of the Drug

General Information of Drug (ID: DMLBVKQ)

Drug Name

Entacapone

Synonyms

Comtan; Comtess; Entacapona; Entacaponum; Novartis brand of entacapone; Orion brand of entacapone; KB475572; OR 611; COM-998; Comtan (TN); Entacapona [INN-Spanish]; Entacapone [USAN:INN]; Entacaponum [INN-Latin]; OR-611; Stalevo (TN); Entacapone (JAN/USAN/INN); N,N-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl) acrylamide; (2E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylprop-2-enamide; (E)-2-Cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-2-propenamide; (E)-2-cyano-3-(3,4-dihydroxy-5-nitro-phenyl)-N,N-diethyl-prop-2-enamide; (E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylprop-2-enamide; (E)-alpha-Cyano-N,N-diethyl-3,4-dihydroxy-5-nitrocinnamamide; 2-Cyano-N,N-diethyl-3-(3,4-dihydroxy-5-nitrophenyl)propenamide

Indication

Disease Entry	ICD 11	Status	REF
Parkinson disease	8A00.0	Approved	[1], [2]

Therapeutic Class

Antiparkinson Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

305.29

Topological Polar Surface Area (xlogp)

2.1

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [3]
Bioavailability: The bioavailability of drug is 35% [4]
Clearance: The clearance of drug is 850 mL/min [5]
Elimination: 0.2% of drug is excreted from urine in the unchanged form [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 0.4 - 0.7 hours [6]
Metabolism: The drug is metabolized via the isomerization to the cis-isomer, followed by direct glucuronidation of the parent and cis-isomer [4]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 87.3486 micromolar/kg/day [7]
Unbound Fraction: The unbound fraction of drug in plasma is 0.02% [6]
Vd: The volume of distribution (Vd) of drug is 20 L [5]
Water Solubility: The ability of drug to dissolve in water is measured as 0.0166 mg/mL [3]

Chemical Identifiers

Formula: C14H15N3O5
IUPAC Name: (E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylprop-2-enamide
Canonical SMILES: CCN(CC)C(=O)/C(=C/C1=CC(=C(C(=C1)O)O)[N+](=O)[O-])/C#N
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+
InChIKey: JRURYQJSLYLRLN-BJMVGYQFSA-N

Cross-matching ID

PubChem CID: 5281081
ChEBI ID: CHEBI:4798
CAS Number: 130929-57-6
DrugBank ID: DB00494
TTD ID: D0J1VY
VARIDT ID: DR01275
INTEDE ID: DR0581
ACDINA ID: D00231

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Catechol-O-methyl-transferase (COMT)	TTKWFB8	COMT_HUMAN	Inhibitor	[8], [9]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Breast cancer resistance protein (ABCG2)	DTI7UX6	ABCG2_HUMAN	Substrate	[10]
Organic anion transporting polypeptide 1B1 (SLCO1B1)	DT3D8F0	SO1B1_HUMAN	Substrate	[11]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
UDP-glucuronosyltransferase 1A9 (UGT1A9)_{Main DME}	DE85D2P	UD19_HUMAN	Substrate	[12]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Parkinson disease

ICD Disease Classification

8A00.0

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Catechol-O-methyl-transferase (COMT)	DTT	COMT	9.24E-02	0.17	1.09
Breast cancer resistance protein (ABCG2)	DTP	BCRP	9.26E-01	-9.37E-02	-1.15E-01
Organic anion transporting polypeptide 1B1 (SLCO1B1)	DTP	OATP1B1	8.03E-01	8.37E-02	4.07E-01

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Entacapone

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Disease	REF
Levodopa	DMN3E57	Moderate	Decreased metabolism of Entacapone caused by Levodopa mediated inhibition of non-CYP450 enzyme.	Parkinsonism [8A00]	[45]
Dopamine	DMPGUCF	Moderate	Decreased metabolism of Entacapone caused by Dopamine mediated inhibition of non-CYP450 enzyme.	Parkinsonism [8A00]	[46]
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Coadministration of a Drug Treating the Disease Different from Entacapone (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Epinephrine	DM3KJBC	Moderate	Decreased metabolism of Entacapone caused by Epinephrine mediated inhibition of non-CYP450 enzyme.	Allergic/hypersensitivity disorder [4A80-4A8Z]	[46]
Memantine	DMD9WSC	Minor	Additive dopaminergic effects by the combination of Entacapone and Memantine.	Alzheimer disease [8A20]	[47]
Isoproterenol	DMK7MEY	Moderate	Decreased metabolism of Entacapone caused by Isoproterenol mediated inhibition of non-CYP450 enzyme.	Conduction disorder [BC63]	[46]
Olopatadine	DMKMWQG	Moderate	Additive CNS depression effects by the combination of Entacapone and Olopatadine.	Conjunctiva disorder [9A60]	[48]
Ethanol	DMDRQZU	Moderate	Additive CNS depression effects by the combination of Entacapone and Ethanol.	Cystitis [GC00]	[48]
OPC-34712	DMHG57U	Moderate	Additive hypotensive effects by the combination of Entacapone and OPC-34712.	Depression [6A70-6A7Z]	[49]
Amoxapine	DMKITQE	Moderate	Antagonize the effect of Entacapone when combined with Amoxapine.	Depression [6A70-6A7Z]	[49]
Esketamine	DMVU687	Moderate	Additive CNS depression effects by the combination of Entacapone and Esketamine.	Depression [6A70-6A7Z]	[50]
Dobutamine	DMD1B8Z	Moderate	Decreased metabolism of Entacapone caused by Dobutamine mediated inhibition of non-CYP450 enzyme.	Heart failure [BD10-BD1Z]	[46]
Methyldopa	DM5I621	Moderate	Decreased metabolism of Entacapone caused by Methyldopa mediated inhibition of non-CYP450 enzyme.	Hypertension [BA00-BA04]	[46]
Propiomazine	DMKY8V1	Moderate	Antagonize the effect of Entacapone when combined with Propiomazine.	Insomnia [7A00-7A0Z]	[49]
ITI-007	DMUQ1DO	Moderate	Antagonize the effect of Entacapone when combined with ITI-007.	Insomnia [7A00-7A0Z]	[49]
Iron	DMAP8MV	Moderate	Decreased absorption of Entacapone due to formation of complexes caused by Iron.	Iron deficiency anaemia [3A00]	[51]
Allopregnanolone	DMNLHAC	Moderate	Additive CNS depression effects by the combination of Entacapone and Allopregnanolone.	Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z]	[52]
Lasmiditan	DMXLVDT	Moderate	Additive CNS depression effects by the combination of Entacapone and Lasmiditan.	Migraine [8A80]	[53]
Flibanserin	DM70DTN	Moderate	Additive CNS depression effects by the combination of Entacapone and Flibanserin.	Mood disorder [6A60-6E23]	[54]
Thalidomide	DM70BU5	Moderate	Additive CNS depression effects by the combination of Entacapone and Thalidomide.	Multiple myeloma [2A83]	[55]
Promethazine	DM6I5GR	Moderate	Additive hypotensive effects by the combination of Entacapone and Promethazine.	Nausea/vomiting [MD90]	[49]
Metoclopramide	DMFA5MY	Moderate	Additive CNS depression effects by the combination of Entacapone and Metoclopramide.	Nausea/vomiting [MD90]	[49]
Apraclonidine	DMO4PVE	Moderate	Additive CNS depression effects by the combination of Entacapone and Apraclonidine.	Optic nerve disorder [9C40]	[56]
Dextropropoxyphene	DM23HCX	Major	Additive CNS depression effects by the combination of Entacapone and Dextropropoxyphene.	Pain [MG30-MG3Z]	[57]
Levomepromazine	DMIKFEL	Moderate	Antagonize the effect of Entacapone when combined with Levomepromazine.	Psychotic disorder [6A20-6A25]	[49]
Fluphenazine	DMIT8LX	Moderate	Antagonize the effect of Entacapone when combined with Fluphenazine.	Psychotic disorder [6A20-6A25]	[49]
Triflupromazine	DMKFQJP	Moderate	Additive hypotensive effects by the combination of Entacapone and Triflupromazine.	Psychotic disorder [6A20-6A25]	[49]
Quetiapine	DM1N62C	Moderate	Antagonize the effect of Entacapone when combined with Quetiapine.	Schizophrenia [6A20]	[49]
Mesoridazine	DM2ZGAN	Moderate	Antagonize the effect of Entacapone when combined with Mesoridazine.	Schizophrenia [6A20]	[49]
Thioridazine	DM35M8J	Moderate	Antagonize the effect of Entacapone when combined with Thioridazine.	Schizophrenia [6A20]	[49]
Aripiprazole	DM3NUMH	Moderate	Antagonize the effect of Entacapone when combined with Aripiprazole.	Schizophrenia [6A20]	[49]
Iloperidone	DM6AUFY	Moderate	Antagonize the effect of Entacapone when combined with Iloperidone.	Schizophrenia [6A20]	[49]
Paliperidone	DM7NPJS	Moderate	Additive CNS depression effects by the combination of Entacapone and Paliperidone.	Schizophrenia [6A20]	[49]
Haloperidol	DM96SE0	Moderate	Antagonize the effect of Entacapone when combined with Haloperidol.	Schizophrenia [6A20]	[49]
Perphenazine	DMA4MRX	Moderate	Additive CNS depression effects by the combination of Entacapone and Perphenazine.	Schizophrenia [6A20]	[49]
Molindone	DMAH70G	Moderate	Antagonize the effect of Entacapone when combined with Molindone.	Schizophrenia [6A20]	[49]
Thiothixene	DMDINC4	Moderate	Antagonize the effect of Entacapone when combined with Thiothixene.	Schizophrenia [6A20]	[49]
Trifluoperazine	DMKBYWI	Moderate	Antagonize the effect of Entacapone when combined with Trifluoperazine.	Schizophrenia [6A20]	[49]
Risperidone	DMN6DXL	Moderate	Antagonize the effect of Entacapone when combined with Risperidone.	Schizophrenia [6A20]	[49]
Amisulpride	DMSJVAM	Moderate	Antagonize the effect of Entacapone when combined with Amisulpride.	Schizophrenia [6A20]	[49]
Asenapine	DMSQZE2	Moderate	Antagonize the effect of Entacapone when combined with Asenapine.	Schizophrenia [6A20]	[49]
Tizanidine	DMR2IQ4	Moderate	Additive CNS depression effects by the combination of Entacapone and Tizanidine.	Tonus and reflex abnormality [MB47]	[58]
Methdilazine	DMAUHQX	Moderate	Antagonize the effect of Entacapone when combined with Methdilazine.	Vasomotor/allergic rhinitis [CA08]	[49]
Trimeprazine	DMEMV9D	Moderate	Antagonize the effect of Entacapone when combined with Trimeprazine.	Vasomotor/allergic rhinitis [CA08]	[59]
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⏷ Show the Full List of 41 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Mannitol	E00103	6251	Diluent; Flavoring agent; Lyophilization aid; Plasticizing agent; Tonicity agent
Quinoline yellow WS	E00309	24671	Colorant
Sucralose	E00370	71485	Flavoring agent
Sunset yellow FCF	E00255	17730	Colorant
Carmellose sodium	E00625	Not Available	Disintegrant
Eisenoxyd	E00585	56841934	Colorant
Ferric hydroxide oxide yellow	E00539	23320441	Colorant
Glycerin	E00026	753	Antimicrobial preservative; Emollient; Flavoring agent; Humectant; Lubricant; Plasticizing agent; Solvent; Suppository base; Tonicity agent; Viscosity-controlling agent
Hydrogenated polyoxyl 40 castor oil	E00662	Not Available	Emulsifying agent; Solubilizing agent; Surfactant
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Polysorbate 80	E00665	Not Available	Dispersing agent; Emollient; Emulsifying agent; Plasticizing agent; Solubilizing agent; Surfactant; Suspending agent
Povidone	E00667	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Saccharose	E00091	5988	Binding agent; Coating agent; Cryoprotectant; Diluent; Flavoring agent; Suspending agent; Viscosity-controlling agent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Triacetin	E00080	5541	Humectant; Plasticizing agent; Solvent
Water	E00035	962	Solvent
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⏷ Show the Full List of 20 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Entacapone 200 mg tablet	200 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

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