Details of the Drug

General Information of Drug (ID: DM8MNVO)

Drug Name

Tolcapone

Synonyms

Tasmar; Roche brand of tolcapone; Ro 40-7592; Tasmar (TN); Tolcapone [USAN:INN]; Ro-40-7592; Tolcapone (JAN/USAN/INN); Methanone,(3,4-dihydroxy-5-nitrophenyl)(4-methylphenyl); (3,4-Dihydroxy-5-nitrophenyl)(4-methylphenyl)methanone; (3,4-dihydroxy-5-nitrophenyl)-(4-methylphenyl)methanone; 3,4-Dihydroxy-4'-methyl-5-nitrobenzophenone; 3,4-dihydroxy-5'-methyl-5-nitrobenzophenone

Indication

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

Therapeutic Class

Antiparkinson Agents

Affected Organisms

Humans and other mammals

ATC Code

N04BX01: Tolcapone

N04BX: Other dopaminergic agents

N04B: DOPAMINERGIC AGENTS

N04: ANTI-PARKINSON DRUGS

N: NERVOUS SYSTEM

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

273.24

Logarithm of the Partition Coefficient (xlogp)

3.3

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 [2]
Bioavailability: The bioavailability of drug is 65% []
Clearance: The clearance of drug is 7 L/h []
Elimination: 0.5% of drug is excreted from urine in the unchanged form [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 2 - 3.5 hours [3]
Metabolism: The drug is metabolized via the glucuronidation []
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 12.2 micromolar/kg/day [4]
Unbound Fraction: The unbound fraction of drug in plasma is 0.0012% [3]
Vd: The volume of distribution (Vd) of drug is 9 L []

Chemical Identifiers

Formula: C14H11NO5
IUPAC Name: (3,4-dihydroxy-5-nitrophenyl)-(4-methylphenyl)methanone
Canonical SMILES: CC1=CC=C(C=C1)C(=O)C2=CC(=C(C(=C2)O)O)[N+](=O)[O-]
InChI: InChI=1S/C14H11NO5/c1-8-2-4-9(5-3-8)13(17)10-6-11(15(19)20)14(18)12(16)7-10/h2-7,16,18H,1H3
InChIKey: MIQPIUSUKVNLNT-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 4659569
ChEBI ID: CHEMBL63630
CAS Number: 134308-13-7
UNII: CIF6334OLY
DrugBank ID: DB00323
TTD ID: D0Y7PG
ACDINA ID: D00686

Drug-Molecule Activity Atlas (DMA)^NEW

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Drug Pharmacogenomic Perturbation (DPP)^NEW

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Drug ADMET Endpoint Profile (DAE)^NEW

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Combinatorial Drugs (CBD)

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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	[5]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Antileukoproteinase (SLPI)	OTUNFUU8	SLPI_HUMAN	Gene/Protein Processing	[6]
Bile salt export pump (ABCB11)	OTRU7THO	ABCBB_HUMAN	Gene/Protein Processing	[7]
Hepatocyte growth factor receptor (MET)	OT7K55MU	MET_HUMAN	Gene/Protein Processing	[6]
Interleukin-8 (CXCL8)	OTS7T5VH	IL8_HUMAN	Gene/Protein Processing	[6]
Lipid transferase CIDEA (CIDEA)	OTDUTSOV	CIDEA_HUMAN	Gene/Protein Processing	[8]
Long-chain-fatty-acid--CoA ligase 1 (ACSL1)	OTB06ESI	ACSL1_HUMAN	Gene/Protein Processing	[8]
Long-chain-fatty-acid--CoA ligase 5 (ACSL5)	OT3L9XO3	ACSL5_HUMAN	Gene/Protein Processing	[8]
Microsomal triglyceride transfer protein large subunit (MTTP)	OTNUVSDT	MTP_HUMAN	Gene/Protein Processing	[8]
Proepiregulin (EREG)	OTRM4NQY	EREG_HUMAN	Gene/Protein Processing	[6]
Superoxide dismutase , mitochondrial (SOD2)	OTIWXGZ9	SODM_HUMAN	Gene/Protein Processing	[9]

Molecular Interaction Atlas (MIA)

MIA Detail

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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

Molecular Expression Atlas (MEA)

MEA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Tolcapone

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Disease	REF
Levodopa	DMN3E57	Moderate	Decreased metabolism of Tolcapone caused by Levodopa mediated inhibition of non-CYP450 enzyme.	Parkinsonism [8A00]	[10]
Dopamine	DMPGUCF	Moderate	Decreased metabolism of Tolcapone caused by Dopamine mediated inhibition of non-CYP450 enzyme.	Parkinsonism [8A00]	[11]

Coadministration of a Drug Treating the Disease Different from Tolcapone (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Remdesivir	DMBFZ6L	Moderate	Increased risk of hepatotoxicity by the combination of Tolcapone and Remdesivir.	1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019]	[12]
Thioguanine	DM7NKEV	Moderate	Increased risk of hepatotoxicity by the combination of Tolcapone and Thioguanine.	Acute myeloid leukaemia [2A60]	[13]
Epinephrine	DM3KJBC	Moderate	Decreased metabolism of Tolcapone caused by Epinephrine mediated inhibition of non-CYP450 enzyme.	Allergic/hypersensitivity disorder [4A80-4A8Z]	[11]
Memantine	DMD9WSC	Minor	Additive dopaminergic effects by the combination of Tolcapone and Memantine.	Alzheimer disease [8A20]	[14]
Promazine	DMZAL7W	Moderate	Additive hypotensive effects by the combination of Tolcapone and Promazine.	Appearance/behaviour symptom [MB23]	[15]
Pexidartinib	DMS2J0Z	Major	Increased risk of hepatotoxicity by the combination of Tolcapone and Pexidartinib.	Bone/articular cartilage neoplasm [2F7B]	[16]
Anisindione	DM2C48U	Minor	Decreased metabolism of Tolcapone caused by Anisindione mediated inhibition of CYP450 enzyme.	Coagulation defect [3B10]	[17]
Isoproterenol	DMK7MEY	Moderate	Decreased metabolism of Tolcapone caused by Isoproterenol mediated inhibition of non-CYP450 enzyme.	Conduction disorder [BC63]	[11]
Olopatadine	DMKMWQG	Moderate	Additive CNS depression effects by the combination of Tolcapone and Olopatadine.	Conjunctiva disorder [9A60]	[18]
Ethanol	DMDRQZU	Moderate	Additive CNS depression effects by the combination of Tolcapone and Ethanol.	Cystitis [GC00]	[18]
OPC-34712	DMHG57U	Moderate	Antagonize the effect of Tolcapone when combined with OPC-34712.	Depression [6A70-6A7Z]	[15]
Amoxapine	DMKITQE	Moderate	Antagonize the effect of Tolcapone when combined with Amoxapine.	Depression [6A70-6A7Z]	[15]
Esketamine	DMVU687	Moderate	Additive CNS depression effects by the combination of Tolcapone and Esketamine.	Depression [6A70-6A7Z]	[12]
Cannabidiol	DM0659E	Moderate	Increased risk of hepatotoxicity by the combination of Tolcapone and Cannabidiol.	Epileptic encephalopathy [8A62]	[14]
Brimonidine	DMQLT4N	Moderate	Additive CNS depression effects by the combination of Tolcapone and Brimonidine.	Glaucoma [9C61]	[19]
Dobutamine	DMD1B8Z	Moderate	Decreased metabolism of Tolcapone caused by Dobutamine mediated inhibition of non-CYP450 enzyme.	Heart failure [BD10-BD1Z]	[11]
Brentuximab vedotin	DMWLC57	Moderate	Increased risk of hepatotoxicity by the combination of Tolcapone and Brentuximab vedotin.	Hodgkin lymphoma [2B30]	[20]
Efavirenz	DMC0GSJ	Moderate	Increased risk of hepatotoxicity by the combination of Tolcapone and Efavirenz.	Human immunodeficiency virus disease [1C60-1C62]	[21]
Mipomersen	DMGSRN1	Major	Increased risk of hepatotoxicity by the combination of Tolcapone and Mipomersen.	Hyper-lipoproteinaemia [5C80]	[22]
Teriflunomide	DMQ2FKJ	Major	Increased risk of hepatotoxicity by the combination of Tolcapone and Teriflunomide.	Hyper-lipoproteinaemia [5C80]	[23]
BMS-201038	DMQTAGO	Major	Increased risk of hepatotoxicity by the combination of Tolcapone and BMS-201038.	Hyper-lipoproteinaemia [5C80]	[24]
Methyldopa	DM5I621	Moderate	Decreased metabolism of Tolcapone caused by Methyldopa mediated inhibition of non-CYP450 enzyme.	Hypertension [BA00-BA04]	[11]
Propiomazine	DMKY8V1	Moderate	Additive CNS depression effects by the combination of Tolcapone and Propiomazine.	Insomnia [7A00-7A0Z]	[15]
ITI-007	DMUQ1DO	Moderate	Antagonize the effect of Tolcapone when combined with ITI-007.	Insomnia [7A00-7A0Z]	[15]
Methotrexate	DM2TEOL	Moderate	Increased risk of hepatotoxicity by the combination of Tolcapone and Methotrexate.	Leukaemia [2A60-2B33]	[14]
Calaspargase pegol	DMQZBXI	Moderate	Increased risk of hepatotoxicity by the combination of Tolcapone and Calaspargase pegol.	Malignant haematopoietic neoplasm [2B33]	[25]
Idelalisib	DM602WT	Moderate	Increased risk of hepatotoxicity by the combination of Tolcapone and Idelalisib.	Mature B-cell leukaemia [2A82]	[26]
Clofarabine	DMCVJ86	Moderate	Increased risk of hepatotoxicity by the combination of Tolcapone and Clofarabine.	Mature B-cell lymphoma [2A85]	[27]
Allopregnanolone	DMNLHAC	Moderate	Additive CNS depression effects by the combination of Tolcapone and Allopregnanolone.	Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z]	[28]
Lasmiditan	DMXLVDT	Moderate	Additive CNS depression effects by the combination of Tolcapone and Lasmiditan.	Migraine [8A80]	[29]
Flibanserin	DM70DTN	Moderate	Additive CNS depression effects by the combination of Tolcapone and Flibanserin.	Mood disorder [6A60-6E23]	[30]
Droperidol	DM0DXA8	Moderate	Antagonize the effect of Tolcapone when combined with Droperidol.	Nausea/vomiting [MD90]	[15]
Prochlorperazine	DM53SRA	Moderate	Antagonize the effect of Tolcapone when combined with Prochlorperazine.	Nausea/vomiting [MD90]	[15]
Promethazine	DM6I5GR	Moderate	Antagonize the effect of Tolcapone when combined with Promethazine.	Nausea/vomiting [MD90]	[15]
Metoclopramide	DMFA5MY	Moderate	Additive CNS depression effects by the combination of Tolcapone and Metoclopramide.	Nausea/vomiting [MD90]	[15]
Thiethylperazine	DMU3IET	Moderate	Antagonize the effect of Tolcapone when combined with Thiethylperazine.	Nausea/vomiting [MD90]	[15]
Apraclonidine	DMO4PVE	Moderate	Additive CNS depression effects by the combination of Tolcapone and Apraclonidine.	Optic nerve disorder [9C40]	[19]
Dextropropoxyphene	DM23HCX	Major	Additive CNS depression effects by the combination of Tolcapone and Dextropropoxyphene.	Pain [MG30-MG3Z]	[31]
Levomepromazine	DMIKFEL	Moderate	Antagonize the effect of Tolcapone when combined with Levomepromazine.	Psychotic disorder [6A20-6A25]	[15]
Fluphenazine	DMIT8LX	Moderate	Antagonize the effect of Tolcapone when combined with Fluphenazine.	Psychotic disorder [6A20-6A25]	[15]
Triflupromazine	DMKFQJP	Moderate	Antagonize the effect of Tolcapone when combined with Triflupromazine.	Psychotic disorder [6A20-6A25]	[15]
Leflunomide	DMR8ONJ	Major	Increased risk of hepatotoxicity by the combination of Tolcapone and Leflunomide.	Rheumatoid arthritis [FA20]	[23]
Mesoridazine	DM2ZGAN	Moderate	Antagonize the effect of Tolcapone when combined with Mesoridazine.	Schizophrenia [6A20]	[15]
Aripiprazole	DM3NUMH	Moderate	Antagonize the effect of Tolcapone when combined with Aripiprazole.	Schizophrenia [6A20]	[15]
Iloperidone	DM6AUFY	Moderate	Antagonize the effect of Tolcapone when combined with Iloperidone.	Schizophrenia [6A20]	[15]
Paliperidone	DM7NPJS	Moderate	Antagonize the effect of Tolcapone when combined with Paliperidone.	Schizophrenia [6A20]	[15]
Loxapine	DM8AI9U	Moderate	Antagonize the effect of Tolcapone when combined with Loxapine.	Schizophrenia [6A20]	[15]
Haloperidol	DM96SE0	Moderate	Antagonize the effect of Tolcapone when combined with Haloperidol.	Schizophrenia [6A20]	[15]
Molindone	DMAH70G	Moderate	Antagonize the effect of Tolcapone when combined with Molindone.	Schizophrenia [6A20]	[15]
Chlorpromazine	DMBGZI3	Moderate	Antagonize the effect of Tolcapone when combined with Chlorpromazine.	Schizophrenia [6A20]	[15]
Thiothixene	DMDINC4	Moderate	Antagonize the effect of Tolcapone when combined with Thiothixene.	Schizophrenia [6A20]	[15]
Clozapine	DMFC71L	Moderate	Antagonize the effect of Tolcapone when combined with Clozapine.	Schizophrenia [6A20]	[15]
Trifluoperazine	DMKBYWI	Moderate	Antagonize the effect of Tolcapone when combined with Trifluoperazine.	Schizophrenia [6A20]	[15]
Risperidone	DMN6DXL	Moderate	Additive CNS depression effects by the combination of Tolcapone and Risperidone.	Schizophrenia [6A20]	[15]
Olanzapine	DMPFN6Y	Moderate	Antagonize the effect of Tolcapone when combined with Olanzapine.	Schizophrenia [6A20]	[15]
Amisulpride	DMSJVAM	Moderate	Antagonize the effect of Tolcapone when combined with Amisulpride.	Schizophrenia [6A20]	[15]
Asenapine	DMSQZE2	Moderate	Antagonize the effect of Tolcapone when combined with Asenapine.	Schizophrenia [6A20]	[15]
Pimozide	DMW83TP	Moderate	Antagonize the effect of Tolcapone when combined with Pimozide.	Schizophrenia [6A20]	[15]
Norepinephrine	DMOUC09	Moderate	Decreased metabolism of Tolcapone caused by Norepinephrine mediated inhibition of non-CYP450 enzyme.	Sepsis [1G40-1G41]	[11]
Trabectedin	DMG3Y89	Moderate	Increased risk of hepatotoxicity by the combination of Tolcapone and Trabectedin.	Solid tumour/cancer [2A00-2F9Z]	[14]
Epirubicin	DMPDW6T	Moderate	Increased risk of hepatotoxicity by the combination of Tolcapone and Epirubicin.	Solid tumour/cancer [2A00-2F9Z]	[12]
Naltrexone	DMUL45H	Moderate	Increased risk of hepatotoxicity by the combination of Tolcapone and Naltrexone.	Substance abuse [6C40]	[32]
Warfarin	DMJYCVW	Minor	Decreased metabolism of Tolcapone caused by Warfarin mediated inhibition of CYP450 enzyme.	Supraventricular tachyarrhythmia [BC81]	[17]
Tizanidine	DMR2IQ4	Moderate	Additive CNS depression effects by the combination of Tolcapone and Tizanidine.	Tonus and reflex abnormality [MB47]	[33]
Methdilazine	DMAUHQX	Moderate	Antagonize the effect of Tolcapone when combined with Methdilazine.	Vasomotor/allergic rhinitis [CA08]	[15]
Trimeprazine	DMEMV9D	Moderate	Antagonize the effect of Tolcapone when combined with Trimeprazine.	Vasomotor/allergic rhinitis [CA08]	[34]
Cetirizine	DMOMP9U	Moderate	Additive CNS depression effects by the combination of Tolcapone and Cetirizine.	Vasomotor/allergic rhinitis [CA08]	[35]


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

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Calcium hydrogenphosphate	E00294	24441	Diluent
Eisenoxyd	E00585	56841934	Colorant
Ferric hydroxide oxide yellow	E00539	23320441	Colorant
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Polyvinyl alcohol	E00666	Not Available	Coating agent; Emulsion stabilizing agent; Film/Membrane-forming 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
Vinylpyrrolidone	E00668	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent


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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Tolcapone 200 mg tablet	200 mg	Oral Tablet	Oral
Tolcapone 100 mg tablet	100 mg	Oral Tablet	Oral

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References

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7	Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development. Toxicol Sci. 2010 Dec; 118(2):485-500.
8	Effect of the Catechol-O-Methyltransferase Inhibitors Tolcapone and Entacapone on Fatty Acid Metabolism in HepaRG Cells. Toxicol Sci. 2018 Aug 1;164(2):477-488.
9	The catechol-O-methyltransferase inhibitors tolcapone and entacapone uncouple and inhibit the mitochondrial respiratory chain in HepaRG cells. Toxicol In Vitro. 2017 Aug;42:337-347.
10	Dingemanse J, Jorga K, Zurcher G, Schmitt M, Sedek G, Da Prada M, Van Brummelen P "Pharmacokinetic-pharmacodynamic interaction between the COMT inhibitor tolcapone and single-dose levodopa." Br J Clin Pharmacol 40 (1995): 253-62. [PMID: 8527287]
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16	Product Information. Turalio (pexidartinib). Daiichi Sankyo, Inc., Parsippany, NJ.
17	Product Information. Tasmar (tolcapone). Valeant Pharmaceuticals, Costa Mesa, CA.
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22	Product Information. Kynamro (mipomersen). Genzyme Corporation, Cambridge, MA.
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24	Product Information. Juxtapid (lomitapide). Aegerion Pharmaceuticals Inc, Cambridge, MA.
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26	Product Information. Zydelig (idelalisib). Gilead Sciences, Foster City, CA.
27	Product Information. Clolar (clofarabine). sanofi-aventis, Bridgewater, NJ.
28	Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA.
29	Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN.
30	Product Information. Addyi (flibanserin). Sprout Pharmaceuticals, Raleigh, NC.
31	Hansen BS, Dam M, Brandt J, et al "Influence of dextropropoxyphene on steady state serum levels and protein binding of three anti-epileptic drugs in man." Acta Neurol Scand 61 (1980): 357-67. [PMID: 6998251]
32	Product Information. ReVia (naltrexone). DuPont Pharmaceuticals, Wilmington, DE.
33	Product Information. Zanaflex (tizanidine). Acorda Therapeutics, Hawthorne, NY.
34	Product Information. Norprolac (quinagolide). Ferring Inc, North York, IA.
35	Product Information. Zyrtec (cetirizine). Pfizer US Pharmaceuticals, New York, NY.