Product Name

Entacapone

CAS Number

130929-57-6

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Product Name:
Entacapone
CAS Number:
130929-57-6
Indication:
Used as an adjunct to levodopa / carbidopa in the symptomatic treatment of patients with idiopathic Parkinson’s Disease who experience the signs and symptoms of end-of-dose “wearing-off”.
Mode of Action:

The mechanism of action of entacapone is believed to be through its ability to inhibit COMT in peripheral tissues, altering the plasma pharmacokinetics of levodopa. When entacapone is given in conjunction with levodopa and an aromatic amino acid decarboxylase inhibitor, such as carbidopa, plasma levels of levodopa are greater and more sustained than after administration of levodopa and an aromatic amino acid decarboxylase inhibitor alone. It is believed that at a given frequency of levodopa administration, these more sustained plasma levels of levodopa result in more constant dopaminergic stimulation in the brain, leading to a greater reduction in the manifestations of parkinsonian syndrome.

Pharmacodynamics:

Entacapone is structurally and pharmacologically related to tolcapone, but unlike tolcapone, is not associated with hepatotoxicity. Entacapone is used in the treatment of Parkinson’s disease as an adjunct to levodopa/carbidopa therapy. Entacapone is a selective and reversible inhibitor of catechol-O-methyltransferase (COMT). In mammals, COMT is distributed throughout various organs with the highest activities in the liver and kidney. COMT also occurs in the heart, lung, smooth and skeletal muscles, intestinal tract, reproductive organs, various glands, adipose tissue, skin, blood cells and neuronal tissues, especially in glial cells. 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, and 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 the it to 3-methoxy-4-hydroxy-L-phenylalanine (3-OMD) in the brain and periphery.

Metabolism:

Metabolized via isomerization to the cis-isomer, followed by direct glucuronidation of the parent and cis-isomer.

Toxicity:

Side effect include increase the occurrence of orthostatic hypotension, severe rhabdomyolysis, dyskinesia, hallucinations, hyperkinesia, hypokinesia, dizziness, fatigu, e gastrointestinal effects including abdominal pain constipation diarrhea nausea

IUPAC:
(E)-alpha-Cyano-N, N-diethyl-3, 4-dihydroxy-5-nitrocinnamamide 2-Propenamide, 2-cyano-3-(3, 4-dihydroxy-5-nitrophenyl)-N, N-diethyl-, (2E)-
ATC:
N04BX02
PubChem:
5281081
DrugBank:
DB00494 (APRD00416)
Formula:
C14-H15-N3-O5
Molecular Mass:
305.2885
Synonyms:
(E)-2-cyano-3-(3,4-dihydroxy-5-nitro-phenyl)-N,N-diethyl-prop-2-enamide, (E)-Entacapone, 2-Cyano-N,N-diethyl-3-(3,4-dihydroxy-5-nitrophenyl)propenamide, Comtan, Comtess, Entacapona, Entacapona [INN-Spanish], Entacapone, Entacaponum, Entacaponum [INN-Latin], Entacom, OR 611, OR-611, UNII-4975G9NM6T
SMILES:
CCN(CC)C(=O)C(=Cc1cc(O)c(O)c(c1)[N+](=O)[O-])C#N
AHFS Code:
29:32.0
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+
General Reference:
General Reference:
  1. Najib J: Entacapone: a catechol-O-methyltransferase inhibitor for the adjunctive treatment of Parkinson’s disease. Clin Ther. 2001 Jun;23(6):802-32; discussion 771. [PubMed:11440283 ]
  2. Chong BS, Mersfelder TL: Entacapone. Ann Pharmacother. 2000 Sep;34(9):1056-65. [PubMed:10981253 ]
  3. Poewe WH, Deuschl G, Gordin A, Kultalahti ER, Leinonen M: Efficacy and safety of entacapone in Parkinson’s disease patients with suboptimal levodopa response: a 6-month randomized placebo-controlled double-blind study in Germany and Austria (Celomen study). Acta Neurol Scand. 2002 Apr;105(4):245-55. [PubMed:11939936 ]
  4. Brooks DJ, Sagar H: Entacapone is beneficial in both fluctuating and non-fluctuating patients with Parkinson’s disease: a randomised, placebo controlled, double blind, six month study. J Neurol Neurosurg Psychiatry. 2003 Aug;74(8):1071-9. [PubMed:12876237 ]
  5. Forsberg M, Lehtonen M, Heikkinen M, Savolainen J, Jarvinen T, Mannisto PT: Pharmacokinetics and pharmacodynamics of entacapone and tolcapone after acute and repeated administration: a comparative study in the rat. J Pharmacol Exp Ther. 2003 Feb;304(2):498-506. [PubMed:12538800 ]
  6. Kaakkola S: Clinical pharmacology, therapeutic use and potential of COMT inhibitors in Parkinson’s disease. Drugs. 2000 Jun;59(6):1233-50. [PubMed:10882160 ]

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