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    Chemistry

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    Also known as: 134308-13-7, Tasmar, Ro 40-7592, 3,4-dihydroxy-4'-methyl-5-nitrobenzophenone, (3,4-dihydroxy-5-nitrophenyl)(4-methylphenyl)methanone, Ro-40-7592
    Molecular Formula
    C14H11NO5
    Molecular Weight
    273.24  g/mol
    InChI Key
    MIQPIUSUKVNLNT-UHFFFAOYSA-N
    FDA UNII
    CIF6334OLY
    Tolcapone
    A benzophenone and nitrophenol compound that acts as an inhibitor of CATECHOL O-METHYLTRANSFERASE, an enzyme involved in the metabolism of DOPAMINE and LEVODOPA. It is used in the treatment of PARKINSON DISEASE in patients for whom levodopa is ineffective or contraindicated.
    Tolcapone is a Catechol-O-Methyltransferase Inhibitor. The mechanism of action of tolcapone is as a Catechol O-Methyltransferase Inhibitor.
    1 2D Structure

    Tolcapone

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (3,4-dihydroxy-5-nitrophenyl)-(4-methylphenyl)methanone
    2.1.2 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
    2.1.3 InChI Key
    MIQPIUSUKVNLNT-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=CC=C(C=C1)C(=O)C2=CC(=C(C(=C2)O)O)[N+](=O)[O-]
    2.2 Other Identifiers
    2.2.1 UNII
    CIF6334OLY
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 3,4 Dihydroxy 5' Methyl 5 Nitrobenzophenone

    2. 3,4-dihydroxy-5'-methyl-5-nitrobenzophenone

    3. Ro 40 7592

    4. Ro 40-7592

    5. Ro 407592

    6. Ro-40-7592

    7. Ro407592

    8. Som0226

    9. Tasmar

    2.3.2 Depositor-Supplied Synonyms

    1. 134308-13-7

    2. Tasmar

    3. Ro 40-7592

    4. 3,4-dihydroxy-4'-methyl-5-nitrobenzophenone

    5. (3,4-dihydroxy-5-nitrophenyl)(4-methylphenyl)methanone

    6. Ro-40-7592

    7. (3,4-dihydroxy-5-nitrophenyl)(p-tolyl)methanone

    8. (3,4-dihydroxy-5-nitrophenyl)-(4-methylphenyl)methanone

    9. Methanone, (3,4-dihydroxy-5-nitrophenyl)(4-methylphenyl)-

    10. Mfcd00866569

    11. Ro-407592

    12. Chembl1324

    13. Cif6334oly

    14. Chebi:63630

    15. Ncgc00181767-01

    16. 3,4-dihydroxy-5-nitro-4'-methylbenzophenone

    17. 4'-methyl-3,4-dihydroxy-5-nitrobenzophenone

    18. Dsstox_cid_3685

    19. Dsstox_rid_77146

    20. Dsstox_gsid_23685

    21. Talcapone

    22. Unii-cif6334oly

    23. Tasmar (tn)

    24. Ccris 7904

    25. Cas-134308-13-7

    26. Tolcapone [usan:usp:inn:ban]

    27. Tolcapone- Bio-x

    28. Tcw

    29. Tolcapone [inn]

    30. Tolcapone [jan]

    31. Tolcapone [mi]

    32. Tolcapone [usan]

    33. Tolcapone [vandf]

    34. Tolcapone [mart.]

    35. Tolcapone [usp-rs]

    36. Tolcapone [who-dd]

    37. Tolcapone (jan/usp/inn)

    38. Schembl33869

    39. Tolcapone [ema Epar]

    40. Mls006012044

    41. Bidd:gt0032

    42. Gtpl6646

    43. Tolcapone [orange Book]

    44. Dtxsid3023685

    45. Tolcapone, >=98% (hplc)

    46. Methanone,(3,4-dihydroxy-5-nitrophenyl)(4-methylphenyl)-

    47. Tolcapone [usp Monograph]

    48. 3s68

    49. Hms2089k14

    50. Hms3652m17

    51. Hms3715d16

    52. Hms3872f03

    53. Hms3885g18

    54. Bcp09156

    55. Tox21_112963

    56. Tox21_302414

    57. 3,4-dihydroxy-4 Inverted Exclamation Mark -methyl-5-nitrobenzophenone

    58. Ac-791

    59. Bdbm50108877

    60. S4021

    61. Zinc35342789

    62. Akos015902328

    63. Tox21_112963_1

    64. As-7085

    65. Ccg-221217

    66. Cs-1173

    67. Db00323

    68. Ks-1314

    69. Ncgc00181767-02

    70. Ncgc00181767-03

    71. Ncgc00255188-01

    72. Bt164481

    73. Hy-17406

    74. Smr001614567

    75. Sy102278

    76. Db-013561

    77. Ft-0631149

    78. Sw219511-1

    79. T3856

    80. C07949

    81. D00786

    82. O10068

    83. Ab01275441-01

    84. Ab01275441_02

    85. (3,4-dihydroxy-5-nitro-phenyl)-p-tolyl-methanone

    86. 308t137

    87. Q413840

    88. Sr-05000001444

    89. Q-201840

    90. Sr-05000001444-1

    91. Brd-k10852020-001-01-1

    92. 5-[(4-methylphenyl)carbonyl]-3-nitrobenzene-1,2-diol

    93. Tolcapone, United States Pharmacopeia (usp) Reference Standard

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 273.24 g/mol
    Molecular Formula C14H11NO5
    XLogP33.3
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count2
    Exact Mass273.06372245 g/mol
    Monoisotopic Mass273.06372245 g/mol
    Topological Polar Surface Area103 Ų
    Heavy Atom Count20
    Formal Charge0
    Complexity372
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameTasmar
    PubMed HealthTolcapone (By mouth)
    Drug ClassesAntiparkinsonian
    Drug LabelTASMAR is available as tablets containing 100 mg tolcapone.Tolcapone, an inhibitor of catechol-O-methyltransferase (COMT), is used in the treatment of Parkinson's disease as an adjunct to levodopa/carbidopa therapy. It is a yellow, odorless, non-hy..
    Active IngredientTolcapone
    Dosage FormTablet
    RouteOral
    Strength100mg
    Market StatusPrescription
    CompanyValeant Pharms

    2 of 2  
    Drug NameTasmar
    PubMed HealthTolcapone (By mouth)
    Drug ClassesAntiparkinsonian
    Drug LabelTASMAR is available as tablets containing 100 mg tolcapone.Tolcapone, an inhibitor of catechol-O-methyltransferase (COMT), is used in the treatment of Parkinson's disease as an adjunct to levodopa/carbidopa therapy. It is a yellow, odorless, non-hy..
    Active IngredientTolcapone
    Dosage FormTablet
    RouteOral
    Strength100mg
    Market StatusPrescription
    CompanyValeant Pharms

    4.2 Drug Indication

    Used as an adjunct to levodopa/carbidopa therapy for the symptomatic treatment of Parkinson's Disease. This drug is generally reserved for patients with parkinsonian syndrome receiving levodopa/carbidopa who are experiencing symptom fluctuations and are not responding adequately to or are not candidates for other adjunctive therapies.

    FDA Label

    Tasmar is indicated in combination with levodopa / benserazide or levodopa / carbidopa for use in patients with levodopa-responsive idiopathic Parkinsons disease and motor fluctuations, who failed to respond to or are intolerant of other catechol-O-methyltransferase (COMT) inhibitors.

    Because of the risk of potentially fatal, acute liver injury, Tasmar should not be considered as a first-line adjunct therapy to levodopa / benserazide or levodopa / carbidopa.

    Since Tasmar should be used only in combination with levodopa / benserazide and levodopa / carbidopa, the prescribing information for these levodopa preparations is also applicable to their concomitant use with Tasmar.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Tolcapone is a potent, selective, and reversible inhibitor of catechol-O-methyltransferase (COMT). In humans, COMT is distributed throughout various organs. COMT catalyzes the transfer of the methyl group of S-adenosyl-L-methionine to the phenolic group of substrates that contain a catechol structure. Physiological substrates of COMT include dopa, catecholamines (dopamine, norepinephrine, epinephrine) and their hydroxylated metabolites. The function of COMT is the elimination of biologically active catechols and some other hydroxylated metabolites. COMT is responsible for the elimination of biologically active catechols and some other hydroxylated metabolites. In the presence of a decarboxylase inhibitor, COMT becomes the major metabolizing enzyme for levodopa catalyzing it to 3-methoxy-4-hydroxy-L-phenylalanine (3-OMD) in the brain and periphery. When tolcapone is given in conjunction with levodopa and an aromatic amino acid decarboxylase inhibitor, such as carbidopa, plasma levels of levodopa are more sustained than after administration of levodopa and an aromatic amino acid decarboxylase inhibitor alone. It is believed that these sustained plasma levels of levodopa result in more constant dopaminergic stimulation in the brain, leading to greater effects on the signs and symptoms of Parkinson's disease in patients as well as increased levodopa adverse effects, sometimes requiring a decrease in the dose of levodopa.

    5.2 MeSH Pharmacological Classification

    Antiparkinson Agents

    Agents used in the treatment of Parkinson's disease. The most commonly used drugs act on the dopaminergic system in the striatum and basal ganglia or are centrally acting muscarinic antagonists. (See all compounds classified as Antiparkinson Agents.)

    Catechol O-Methyltransferase Inhibitors

    Compounds and drugs that inhibit or block the activity of CATECHOL O-METHYLTRANSFERASE enzymes. Drugs in this class are used in management of central nervous system disorders such as PARKINSON DISEASE. (See all compounds classified as Catechol O-Methyltransferase Inhibitors.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    TOLCAPONE
    5.3.2 FDA UNII
    CIF6334OLY
    5.3.3 Pharmacological Classes
    Catechol-O-Methyltransferase Inhibitor [EPC]; Catechol O-Methyltransferase Inhibitors [MoA]
    5.4 ATC Code

    N04BX01

    N04BX01

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    N - Nervous system

    N04 - Anti-parkinson drugs

    N04B - Dopaminergic agents

    N04BX - Other dopaminergic agents

    N04BX01 - Tolcapone

    5.5 Absorption, Distribution and Excretion

    Absorption

    Rapidly absorbed (absolute bioavailability is about 65%)

    Route of Elimination

    Tolcapone is almost completely metabolized prior to excretion, with only a very small amount (0.5% of dose) found unchanged in urine. The glucuronide conjugate of tolcapone is mainly excreted in the urine but is also excreted in the bile.

    Volume of Distribution

    9 L

    Clearance

    7 L/h

    5.6 Metabolism/Metabolites

    The main metabolic pathway of tolcapone is glucuronidation

    Tolcapone has known human metabolites that include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-[2-hydroxy-4-(4-methylbenzoyl)-6-nitrophenoxy]oxane-2-carboxylic acid.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.7 Biological Half-Life

    2-3.5 hours

    5.8 Mechanism of Action

    The precise mechanism of action of tolcapone is unknown, but it is believed to be related to its ability to inhibit COMT and alter the plasma pharmacokinetics of levodopa, resulting in an increase in plasma levodopa concentrations. The inhibition of COMT also causes a reduction in circulating 3-OMD as a result of decreased peripheral metabolism of levodopa. This may lead to an increase distribution of levodopa into the CNS through the reduction of its competitive substrate, 3-OMD, for transport mechanisms. Sustained levodopa concentrations presumably result in more consistent dopaminergic stimulation, resulting in greater reduction in the manifestations of parkinsonian syndrome.

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