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
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) 2
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 5
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
CHEBI:63630
CAS Number
134308-13-7
DrugBank ID
DB00323
TTD ID
D0Y7PG
ACDINA ID
D00686
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

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]
Apolipoprotein B-100 (APOB) OTH0UOCZ APOB_HUMAN Gene/Protein Processing [7]
Bile salt export pump (ABCB11) OTRU7THO ABCBB_HUMAN Gene/Protein Processing [8]
Catechol O-methyltransferase (COMT) OTPWKTQG COMT_HUMAN Gene/Protein Processing [9]
Cystine/glutamate transporter (SLC7A11) OTKJ6PXW XCT_HUMAN Gene/Protein Processing [6]
Cytochrome P450 1A1 (CYP1A1) OTE4EFH8 CP1A1_HUMAN Gene/Protein Processing [10]
Cytochrome P450 1B1 (CYP1B1) OTYXFLSD CP1B1_HUMAN Gene/Protein Processing [10]
Cytochrome P450 3A4 (CYP3A4) OTQGYY83 CP3A4_HUMAN Drug Response [11]
Hepatocyte growth factor receptor (MET) OT7K55MU MET_HUMAN Gene/Protein Processing [6]
Interleukin-24 (IL24) OT4VUWH1 IL24_HUMAN Gene/Protein Processing [6]
Molecular Interaction Atlas (MIA) 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
Molecular Expression Atlas (MEA) 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 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] [12]
Dopamine DMPGUCF Moderate Decreased metabolism of Tolcapone caused by Dopamine mediated inhibition of non-CYP450 enzyme. Parkinsonism [8A00] [13]
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] [14]
Thioguanine DM7NKEV Moderate Increased risk of hepatotoxicity by the combination of Tolcapone and Thioguanine. Acute myeloid leukaemia [2A60] [15]
Epinephrine DM3KJBC Moderate Decreased metabolism of Tolcapone caused by Epinephrine mediated inhibition of non-CYP450 enzyme. Allergic/hypersensitivity disorder [4A80-4A8Z] [13]
Memantine DMD9WSC Minor Additive dopaminergic effects by the combination of Tolcapone and Memantine. Alzheimer disease [8A20] [16]
Promazine DMZAL7W Moderate Additive hypotensive effects by the combination of Tolcapone and Promazine. Appearance/behaviour symptom [MB23] [17]
Pexidartinib DMS2J0Z Major Increased risk of hepatotoxicity by the combination of Tolcapone and Pexidartinib. Bone/articular cartilage neoplasm [2F7B] [18]
Anisindione DM2C48U Minor Decreased metabolism of Tolcapone caused by Anisindione mediated inhibition of CYP450 enzyme. Coagulation defect [3B10] [19]
Isoproterenol DMK7MEY Moderate Decreased metabolism of Tolcapone caused by Isoproterenol mediated inhibition of non-CYP450 enzyme. Conduction disorder [BC63] [13]
Olopatadine DMKMWQG Moderate Additive CNS depression effects by the combination of Tolcapone and Olopatadine. Conjunctiva disorder [9A60] [20]
Ethanol DMDRQZU Moderate Additive CNS depression effects by the combination of Tolcapone and Ethanol. Cystitis [GC00] [20]
OPC-34712 DMHG57U Moderate Antagonize the effect of Tolcapone when combined with OPC-34712. Depression [6A70-6A7Z] [17]
Amoxapine DMKITQE Moderate Antagonize the effect of Tolcapone when combined with Amoxapine. Depression [6A70-6A7Z] [17]
Esketamine DMVU687 Moderate Additive CNS depression effects by the combination of Tolcapone and Esketamine. Depression [6A70-6A7Z] [14]
Cannabidiol DM0659E Moderate Increased risk of hepatotoxicity by the combination of Tolcapone and Cannabidiol. Epileptic encephalopathy [8A62] [16]
Brimonidine DMQLT4N Moderate Additive CNS depression effects by the combination of Tolcapone and Brimonidine. Glaucoma [9C61] [21]
Dobutamine DMD1B8Z Moderate Decreased metabolism of Tolcapone caused by Dobutamine mediated inhibition of non-CYP450 enzyme. Heart failure [BD10-BD1Z] [13]
Brentuximab vedotin DMWLC57 Moderate Increased risk of hepatotoxicity by the combination of Tolcapone and Brentuximab vedotin. Hodgkin lymphoma [2B30] [22]
Efavirenz DMC0GSJ Moderate Increased risk of hepatotoxicity by the combination of Tolcapone and Efavirenz. Human immunodeficiency virus disease [1C60-1C62] [23]
Mipomersen DMGSRN1 Major Increased risk of hepatotoxicity by the combination of Tolcapone and Mipomersen. Hyper-lipoproteinaemia [5C80] [24]
Teriflunomide DMQ2FKJ Major Increased risk of hepatotoxicity by the combination of Tolcapone and Teriflunomide. Hyper-lipoproteinaemia [5C80] [25]
BMS-201038 DMQTAGO Major Increased risk of hepatotoxicity by the combination of Tolcapone and BMS-201038. Hyper-lipoproteinaemia [5C80] [26]
Methyldopa DM5I621 Moderate Decreased metabolism of Tolcapone caused by Methyldopa mediated inhibition of non-CYP450 enzyme. Hypertension [BA00-BA04] [13]
Propiomazine DMKY8V1 Moderate Additive CNS depression effects by the combination of Tolcapone and Propiomazine. Insomnia [7A00-7A0Z] [17]
ITI-007 DMUQ1DO Moderate Antagonize the effect of Tolcapone when combined with ITI-007. Insomnia [7A00-7A0Z] [17]
Methotrexate DM2TEOL Moderate Increased risk of hepatotoxicity by the combination of Tolcapone and Methotrexate. Leukaemia [2A60-2B33] [16]
Calaspargase pegol DMQZBXI Moderate Increased risk of hepatotoxicity by the combination of Tolcapone and Calaspargase pegol. Malignant haematopoietic neoplasm [2B33] [27]
Idelalisib DM602WT Moderate Increased risk of hepatotoxicity by the combination of Tolcapone and Idelalisib. Mature B-cell leukaemia [2A82] [28]
Clofarabine DMCVJ86 Moderate Increased risk of hepatotoxicity by the combination of Tolcapone and Clofarabine. Mature B-cell lymphoma [2A85] [29]
Allopregnanolone DMNLHAC Moderate Additive CNS depression effects by the combination of Tolcapone and Allopregnanolone. Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z] [30]
Lasmiditan DMXLVDT Moderate Additive CNS depression effects by the combination of Tolcapone and Lasmiditan. Migraine [8A80] [31]
Flibanserin DM70DTN Moderate Additive CNS depression effects by the combination of Tolcapone and Flibanserin. Mood disorder [6A60-6E23] [32]
Droperidol DM0DXA8 Moderate Antagonize the effect of Tolcapone when combined with Droperidol. Nausea/vomiting [MD90] [17]
Prochlorperazine DM53SRA Moderate Antagonize the effect of Tolcapone when combined with Prochlorperazine. Nausea/vomiting [MD90] [17]
Promethazine DM6I5GR Moderate Antagonize the effect of Tolcapone when combined with Promethazine. Nausea/vomiting [MD90] [17]
Metoclopramide DMFA5MY Moderate Additive CNS depression effects by the combination of Tolcapone and Metoclopramide. Nausea/vomiting [MD90] [17]
Thiethylperazine DMU3IET Moderate Antagonize the effect of Tolcapone when combined with Thiethylperazine. Nausea/vomiting [MD90] [17]
Apraclonidine DMO4PVE Moderate Additive CNS depression effects by the combination of Tolcapone and Apraclonidine. Optic nerve disorder [9C40] [21]
Dextropropoxyphene DM23HCX Major Additive CNS depression effects by the combination of Tolcapone and Dextropropoxyphene. Pain [MG30-MG3Z] [33]
Levomepromazine DMIKFEL Moderate Antagonize the effect of Tolcapone when combined with Levomepromazine. Psychotic disorder [6A20-6A25] [17]
Fluphenazine DMIT8LX Moderate Antagonize the effect of Tolcapone when combined with Fluphenazine. Psychotic disorder [6A20-6A25] [17]
Triflupromazine DMKFQJP Moderate Antagonize the effect of Tolcapone when combined with Triflupromazine. Psychotic disorder [6A20-6A25] [17]
Leflunomide DMR8ONJ Major Increased risk of hepatotoxicity by the combination of Tolcapone and Leflunomide. Rheumatoid arthritis [FA20] [25]
Mesoridazine DM2ZGAN Moderate Antagonize the effect of Tolcapone when combined with Mesoridazine. Schizophrenia [6A20] [17]
Aripiprazole DM3NUMH Moderate Antagonize the effect of Tolcapone when combined with Aripiprazole. Schizophrenia [6A20] [17]
Iloperidone DM6AUFY Moderate Antagonize the effect of Tolcapone when combined with Iloperidone. Schizophrenia [6A20] [17]
Paliperidone DM7NPJS Moderate Antagonize the effect of Tolcapone when combined with Paliperidone. Schizophrenia [6A20] [17]
Loxapine DM8AI9U Moderate Antagonize the effect of Tolcapone when combined with Loxapine. Schizophrenia [6A20] [17]
Haloperidol DM96SE0 Moderate Antagonize the effect of Tolcapone when combined with Haloperidol. Schizophrenia [6A20] [17]
Molindone DMAH70G Moderate Antagonize the effect of Tolcapone when combined with Molindone. Schizophrenia [6A20] [17]
Chlorpromazine DMBGZI3 Moderate Antagonize the effect of Tolcapone when combined with Chlorpromazine. Schizophrenia [6A20] [17]
Thiothixene DMDINC4 Moderate Antagonize the effect of Tolcapone when combined with Thiothixene. Schizophrenia [6A20] [17]
Clozapine DMFC71L Moderate Antagonize the effect of Tolcapone when combined with Clozapine. Schizophrenia [6A20] [17]
Trifluoperazine DMKBYWI Moderate Antagonize the effect of Tolcapone when combined with Trifluoperazine. Schizophrenia [6A20] [17]
Risperidone DMN6DXL Moderate Additive CNS depression effects by the combination of Tolcapone and Risperidone. Schizophrenia [6A20] [17]
Olanzapine DMPFN6Y Moderate Antagonize the effect of Tolcapone when combined with Olanzapine. Schizophrenia [6A20] [17]
Amisulpride DMSJVAM Moderate Antagonize the effect of Tolcapone when combined with Amisulpride. Schizophrenia [6A20] [17]
Asenapine DMSQZE2 Moderate Antagonize the effect of Tolcapone when combined with Asenapine. Schizophrenia [6A20] [17]
Pimozide DMW83TP Moderate Antagonize the effect of Tolcapone when combined with Pimozide. Schizophrenia [6A20] [17]
Norepinephrine DMOUC09 Moderate Decreased metabolism of Tolcapone caused by Norepinephrine mediated inhibition of non-CYP450 enzyme. Sepsis [1G40-1G41] [13]
Trabectedin DMG3Y89 Moderate Increased risk of hepatotoxicity by the combination of Tolcapone and Trabectedin. Solid tumour/cancer [2A00-2F9Z] [16]
Epirubicin DMPDW6T Moderate Increased risk of hepatotoxicity by the combination of Tolcapone and Epirubicin. Solid tumour/cancer [2A00-2F9Z] [14]
Naltrexone DMUL45H Moderate Increased risk of hepatotoxicity by the combination of Tolcapone and Naltrexone. Substance abuse [6C40] [34]
Warfarin DMJYCVW Minor Decreased metabolism of Tolcapone caused by Warfarin mediated inhibition of CYP450 enzyme. Supraventricular tachyarrhythmia [BC81] [19]
Tizanidine DMR2IQ4 Moderate Additive CNS depression effects by the combination of Tolcapone and Tizanidine. Tonus and reflex abnormality [MB47] [35]
Methdilazine DMAUHQX Moderate Antagonize the effect of Tolcapone when combined with Methdilazine. Vasomotor/allergic rhinitis [CA08] [17]
Trimeprazine DMEMV9D Moderate Antagonize the effect of Tolcapone when combined with Trimeprazine. Vasomotor/allergic rhinitis [CA08] [36]
Cetirizine DMOMP9U Moderate Additive CNS depression effects by the combination of Tolcapone and Cetirizine. Vasomotor/allergic rhinitis [CA08] [37]
⏷ Show the Full List of 67 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
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
⏷ Show the Full List of 11 Pharmaceutical Excipients of This Drug
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
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

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