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Tolcapone

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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

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 Formula	C₁₄H₁₁NO₅
Molecular Weight	273.24 g/mol
XLogP3	3.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	2
Exact Mass	273.06372245 g/mol
Monoisotopic Mass	273.06372245 g/mol
Topological Polar Surface Area	103 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	372
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Tasmar
PubMed Health	Tolcapone (By mouth)
Drug Classes	Antiparkinsonian
Drug Label	TASMAR 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 Ingredient	Tolcapone
Dosage Form	Tablet
Route	Oral
Strength	100mg
Market Status	Prescription
Company	Valeant Pharms

2 of 2
Drug Name	Tasmar
PubMed Health	Tolcapone (By mouth)
Drug Classes	Antiparkinsonian
Drug Label	TASMAR 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 Ingredient	Tolcapone
Dosage Form	Tablet
Route	Oral
Strength	100mg
Market Status	Prescription
Company	Valeant 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

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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