Entacapone (CED0005201)

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:01 UTC

Update Date

2026-05-14 16:40:25 UTC

SynCED ID

CED0005201

Secondary Accession Numbers

CHEM002210
T3D2808

Identification

Common Name

Entacapone

Class

Small Molecule

Description

Entacapone is an exogenous solid with the formula C14H15N3O5 and an average molecular weight of 305.29 g/mol. Entacapone belongs to the hydroxycinnamic acids and derivatives, a subclass of cinnamic acids and derivatives within the organic compounds. It is classified as a central nervous system drug, an antiparkinson drug, and an antidyskinesia agent. The compound acts as a biological and chemical inhibitor of catechol O-methyltransferase (EC 2.1.1.6), which is its recorded protein target. The mechanism of action involves inhibiting COMT to alter the plasma pharmacokinetics of levodopa. When administered in conjunction with levodopa and an aromatic amino acid decarboxylase inhibitor, such as carbidopa, plasma levels of levodopa are more sustained and greater than after the administration of levodopa and an aromatic amino acid decarboxylase inhibitor alone. Entacapone is found in dopaminergic agents within healthcare, pharmaceuticals, and veterinary products, as well as in household cleaning and consumer products, specifically other smoking requisites and non-electric simulated smoking devices. The recorded exposure route for this compound is oral.

Contaminant Type

Amide
Amine
Antidyskinetic
Antiparkinson Agent
Central Nervous System Agent
Drug
Enzyme Inhibitor
Ester
Food Toxin
Human Neurotoxin
Metabolite
Nitrile
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF 3D SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(e)-alpha-Cyano-N,N-diethyl-3,4-dihydroxy-5-nitrocinnamamide	ChEBI
Comtan	ChEBI
Comtess	ChEBI
Entacapona	ChEBI
Entacaponum	ChEBI
N,N-Diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl) acrylamide	ChEBI
(e)-a-Cyano-N,N-diethyl-3,4-dihydroxy-5-nitrocinnamamide	Generator
(e)-Α-cyano-N,N-diethyl-3,4-dihydroxy-5-nitrocinnamamide	Generator
2-Cyano-N,N-diethyl-3-(3,4-dihydroxy-5-nitrophenyl)propenamide	HMDB
Orion brand OF entacapone	HMDB
Novartis brand OF entacapone	HMDB

Chemical Formula

C₁₄H₁₅N₃O₅

Average Molecular Mass

305.286 g/mol

Monoisotopic Mass

305.101 g/mol

CAS Registry Number

130929-57-6

IUPAC Name

(2E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylprop-2-enamide

Traditional Name

entacapone

SMILES

CCN(CC)C(=O)C(=C\C1=CC(=C(O)C(O)=C1)[N+]([O-])=O)\C#N

InChI Identifier

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+

InChI Key

JRURYQJSLYLRLN-BJMVGYQFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids and derivatives

Alternative Parents

Substituents

Hydroxycinnamic acid or derivatives
Nitrophenol
Nitrobenzene
Nitroaromatic compound
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
C-nitro compound
Organic nitro compound
Allyl-type 1,3-dipolar organic compound
Propargyl-type 1,3-dipolar organic compound
Carboxylic acid derivative
Carbonitrile
Nitrile
Organic oxoazanium
Organic 1,3-dipolar compound
Organic nitrogen compound
Organic zwitterion
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:4798 )
catechols (CHEBI:4798 )
nitrile (CHEBI:4798 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Biological Roles

EC 2.1.1.6 (catechol O-methyltransferase) inhibitor (PMC7930641 , PMC7930641 )?An EC 2.1.1.* (methyltransferase) inhibitor that interferes with the action of catechol O-methyltransferase (EC 2.1.1.6).

Chemical Roles

EC 2.1.1.6 (catechol O-methyltransferase) inhibitor ?

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.08 g/L	ALOGPS
logP	2.5	ALOGPS
logP	1.63	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	5.68	ChemAxon
pKa (Strongest Basic)	-0.036	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	130.38 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	80.51 m³·mol⁻¹	ChemAxon
Polarizability	29.48 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-003r-4190000000-da6b28638ec4920bd58a	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0059-6004900000-14645ab585cbbed0ca38	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0329000000-8d20a5650e9c1b1c8275	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0329000000-8d20a5650e9c1b1c8275	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0009000000-6e08b463d5af43617517	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udr-1069000000-5075a6f93c2b72c3483a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0fkc-9240000000-27e088a40b83e29661e0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0009000000-29c32f9a04e379fce5fe	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-2009000000-6d53b89d8a9ecd3b180e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00dl-9100000000-5f330d3ad8cb0af17a9a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0009000000-62e9f24f62db1840e2e0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-1292000000-28b9a09056bdc465cd19	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-1590000000-58fe447bc05aa8420188	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0039000000-85f49c3b07fd9b1dd7bd	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0pb9-1693000000-bf7093c3dc0b31a75e5d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4j-5910000000-658aee735015de149a67	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
827.0 Log mg/kg [460:1500]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

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.

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Minimum Risk Level

Not Available

Symptoms

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.

Treatment

Management of Entacapone overdose is symptomatic; there is no known antidote to Comtan. Hospitalization is advised, and general supportive care is indicated. There is no experience with hemodialysis or hemoperfusion, but these procedures are unlikely to be of benefit, because Entacapone is highly bound to plasma proteins. An immediate gastric lavage and repeated doses of charcoal over time may hasten the elimination of Entacapone by decreasing its absorption/reabsorption from the GI tract. The adequacy of the respiratory and circulatory systems should be carefully monitored and appropriate supportive measures employed. (9)

Health Effects

Health Effect	Relationship	Direction	Description	Reference
Parkinson's disease	Not Available	Not Available	A long-term degenerative disorder of the central nervous system that mainly affects the motor system. The symptoms generally come on slowly over time.	PMC7930641
Dyskinesia	Associated With?	increase	Not Available	PMC7930641
severe diarrhea	Associated With?	Not Available	Not Available	PMC7930641

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000373	Dopaminergic agents?Dopaminergic agents are compounds that influence the dopamine system, primarily through agonistic or antagonistic actions at dopamine receptors.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000518	Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.	Electrical & Electronic Equipment	PubChem
CEDs000545	Food Preservation?Food preservation often involves the use of synthetic chemicals, such as preservatives, flavor enhancers, and color additives, to extend shelf life and enhance the sensory qualities of food products.	Food, food processing & cookware	PubChem
CEDs000556	Cigar Cigarettes?Cigar cigarettes are a source of synthetic chemical contamination due to the combustion of various tobacco blends and additives.	Household cleaning & consumer products	PubChem
CEDs000559	Non Electric Simulated Smoking Devices?Non-electric simulated smoking devices, often designed to mimic the experience of smoking without combustion, can be sources of synthetic chemical contamination due to the materials and chemicals used in their construction and operation.	Household cleaning & consumer products	PubChem
CEDs000560	Other Smoking Requisites?Other smoking requisites, including items such as lighters, matches, and rolling papers, can introduce synthetic chemical contamination through various components and additives.	Household cleaning & consumer products	PubChem
CEDs000563	Soap Detergents?Soap detergents are synthetic surfactants designed to enhance the cleaning efficacy of water by reducing surface tension, allowing for better interaction with dirt and grease.	Household cleaning & consumer products	PubChem
CEDs000569	Tobacco Smoke Filters?Tobacco smoke filters are designed to reduce the inhalation of harmful substances in cigarette smoke, including tar and other particulate matter.	Household cleaning & consumer products	PubChem
CEDs000580	Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.	Industrial manufacturing & chemical processing	PubChem
CEDs000596	Acaricides?Acaricides are synthetic chemicals specifically designed to target and control mite populations that can damage crops and plants.	Agriculture & land management	PubChem
CEDs000611	Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000615	Eye Makeup Products?Eye makeup products, including mascaras, eyeliners, and eyeshadows, often contain a variety of synthetic chemicals such as pigments, preservatives, and film-forming agents.	Personal care & cosmetics	PubChem
CEDs000632	Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.	Textiles, leather & furnishings	PubChem
CEDs000671	Airplanes And Helicopters?Airplanes and helicopters are significant sources of synthetic chemical contamination primarily through the use of aviation fuels, lubricants, and de-icing agents.	Aviation & Aerospace	PubChem
CEDs000678	Nitrogenous Fertilisers?Nitrogenous fertilizers are synthetic chemical compounds primarily used to enhance plant growth by supplying essential nitrogen, a crucial nutrient for photosynthesis and protein synthesis.	Agriculture & land management	PubChem
CEDs000679	Phosphatic Fertilisers?Phosphatic fertilizers are synthetic chemical products primarily composed of phosphorus, which is essential for plant growth.	Agriculture & land management	PubChem
CEDs000685	Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.	Building & Construction	PubChem
CEDs000688	Glass Coatings?Glass coatings are synthetic chemical formulations applied to glass surfaces to enhance properties such as durability, UV resistance, and aesthetic appeal.	Building & Construction	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs000735	Explosives?Explosives are chemical compounds or mixtures designed to undergo rapid decomposition, releasing energy in the form of gas and heat.	Defense & military infrastructure	PubChem
CEDs000742	Leather Tanning?Leather tanning is a process that transforms raw animal hides into durable leather through the application of various chemicals, including chromium salts, aldehydes, and vegetable tannins.	Textiles, leather & furnishings	PubChem
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	PubChem

Pathways

2 pathwaysPathway Source: PathBank

Entacapone Drug Metabolism Action Pathway

Entacapone Predicted Metabolism Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	UDP-glucuronosyltransferase 1A9	O60656	Humans	Known	Not Available
Click to view 3D structure	Catechol O-methyltransferase	P22734	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.594 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 15 E-value 0.0778492
Click to view 3D structure	Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	Humans	Predicted (SEA)	Prediction Confidence Score 0.588 Applicability Domain 1.0 Statistical Significance 2.00e-05 Supporting Reference Compounds 36 E-value 0.155698
Click to view 3D structure	G-protein coupled receptor 35	Q9HC97	Humans	Predicted (SEA)	Prediction Confidence Score 0.52 Applicability Domain 1.0 Statistical Significance 7.00e-05 Supporting Reference Compounds 115 E-value 0.544945
Click to view 3D structure	Catechol O-methyltransferase	P21964	Humans	Predicted (SEA)	Prediction Confidence Score 0.467 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 9 E-value 0.0778492
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	Prediction Confidence Score 0.364 Applicability Domain 1.0 Statistical Significance 0.0329 Supporting Reference Compounds 1245 E-value 255.813
Click to view 3D structure	Catechol O-methyltransferase	Q99028	Sus scrofa	Predicted (SEA)	Prediction Confidence Score 0.35 Applicability Domain 0.468 Statistical Significance 8.00e-05 Supporting Reference Compounds 2 E-value 0.622794
Click to view 3D structure	Epidermal growth factor receptor	P00533	Humans	Predicted (SEA)	Prediction Confidence Score 0.341 Applicability Domain 0.354 Statistical Significance 0.064 Supporting Reference Compounds 1301 E-value 498.235
Click to view 3D structure	Fatty acid synthase	P49327	Humans	Predicted (SEA)	Prediction Confidence Score 0.314 Applicability Domain 0.348 Statistical Significance 0.0027 Supporting Reference Compounds 117 E-value 21.4085
Click to view 3D structure	ATP-binding cassette sub-family C member 4	O15439	Humans	Predicted (SEA)	Prediction Confidence Score 0.308 Applicability Domain 1.0 Statistical Significance 9.00e-05 Supporting Reference Compounds 30 E-value 0.700643
Click to view 3D structure	Protein RecA	P9WHJ3	Mycobacterium tuberculosis	Predicted (SEA)	Prediction Confidence Score 0.296 Applicability Domain 0.368 Statistical Significance 0.0131 Supporting Reference Compounds 296 E-value 101.982
Click to view 3D structure	Large T antigen	P03070	Simian virus 40	Predicted (SEA)	Prediction Confidence Score 0.29 Applicability Domain 0.339 Statistical Significance 0.0036 Supporting Reference Compounds 78 E-value 27.7922
Click to view 3D structure	Transthyretin	P02766	Humans	Predicted (SEA)	Prediction Confidence Score 0.289 Applicability Domain 0.375 Statistical Significance 0.0047 Supporting Reference Compounds 55 E-value 36.2777
Click to view 3D structure	Alkaline phosphatase, tissue-nonspecific isozyme	P05186	Humans	Predicted (SEA)	Prediction Confidence Score 0.28 Applicability Domain 0.339 Statistical Significance 0.0018 Supporting Reference Compounds 48 E-value 14.1686
Click to view 3D structure	Intestinal-type alkaline phosphatase	P24822	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.28 Applicability Domain 0.339 Statistical Significance 0.0028 Supporting Reference Compounds 58 E-value 21.6421
Click to view 3D structure	Induced myeloid leukemia cell differentiation protein Mcl-1	Q07820	Humans	Predicted (SEA)	Prediction Confidence Score 0.274 Applicability Domain 0.347 Statistical Significance 0.0448 Supporting Reference Compounds 343 E-value 348.609
Click to view 3D structure	Intestinal-type alkaline phosphatase	P09923	Humans	Predicted (SEA)	Prediction Confidence Score 0.257 Applicability Domain 0.339 Statistical Significance 0.0036 Supporting Reference Compounds 37 E-value 28.1814
Click to view 3D structure	Catechol O-methyltransferase	O88587	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.257 Applicability Domain 0.257 Low confidence Statistical Significance 2.50e-04 Supporting Reference Compounds 1 E-value 1.94623
Click to view 3D structure	Ribosomal protein S6 kinase alpha-3	P51812	Humans	Predicted (SEA)	Prediction Confidence Score 0.254 Applicability Domain 0.317 Statistical Significance 0.2816 Supporting Reference Compounds 733 E-value 2192.31
Click to view 3D structure	DNA damage-inducible transcript 3 protein	P35639	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.254 Applicability Domain 0.368 Statistical Significance 0.0669 Supporting Reference Compounds 226 E-value 520.889
Click to view 3D structure	X-box-binding protein 1	P17861	Humans	Predicted (SEA)	Prediction Confidence Score 0.254 Applicability Domain 0.368 Statistical Significance 0.0669 Supporting Reference Compounds 227 E-value 521.123
Click to view 3D structure	DNA (cytosine-5)-methyltransferase 1	P26358	Humans	Predicted (SEA)	Prediction Confidence Score 0.252 Applicability Domain 0.268 Low confidence Statistical Significance 0.0324 Supporting Reference Compounds 116 E-value 252.621
Click to view 3D structure	Monocarboxylate transporter 1	P53987	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.249 Applicability Domain 0.357 Statistical Significance 1.30e-04 Supporting Reference Compounds 4 E-value 1.01204
Click to view 3D structure	Genome polyprotein	P29990	dengue virus type 2	Predicted (SEA)	Prediction Confidence Score 0.248 Applicability Domain 0.357 Statistical Significance 0.0265 Supporting Reference Compounds 58 E-value 206.69
Click to view 3D structure	Metabotropic glutamate receptor 4	Q68EF4	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.243 Applicability Domain 0.243 Low confidence Statistical Significance 6.80e-04 Supporting Reference Compounds 1 E-value 5.29375
Click to view 3D structure	Tyrosine-protein kinase JAK3	P52333	Humans	Predicted (SEA)	Prediction Confidence Score 0.243 Applicability Domain 0.298 Low confidence Statistical Significance 0.4283 Supporting Reference Compounds 961 E-value 3334.44
Click to view 3D structure	UDP-glucuronosyltransferase 1A8	Q9HAW9	Humans	Known	Not Available
Click to view 3D structure	Catechol O-methyltransferase	P21964	Humans	Known	The mechanism of action of entacapone is believed to be through its ability to inhibit COMT and alter 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 greater effects on the signs and symptoms of Parkinson's disease.

Concentrations

Not Available

External Links

DrugBank ID

DB00494

HMDB ID

HMDB0012226

FooDB ID

FDB028870

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

CPD-7662

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Pandurang Deshpande, Parven Luthra, Anand Pandey, Dharmesh Dhameliya, “Process for the preparation of (E)-2-cyano-3-(3, 4-dihydroxy-5-nitrophenyl)-N, N-diethyl-2-propenamide (entacapone).” U.S. Patent US20060258877, issued November 16, 2006.

MSDS

Not Available

General References

Bonifati V, Meco G: New, selective catechol-O-methyltransferase inhibitors as therapeutic agents in Parkinson's disease. Pharmacol Ther. 1999 Jan;81(1):1-36. [PubMed: 10051176]
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]
Kaakkola S: Clinical pharmacology, therapeutic use and potential of COMT inhibitors in Parkinson's disease. Drugs. 2000 Jun;59(6):1233-50. [PubMed: 10882160]
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]
Chong BS, Mersfelder TL: Entacapone. Ann Pharmacother. 2000 Sep;34(9):1056-65. [PubMed: 10981253]
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]
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]
Drugs.com - http://www.drugs.com/cons/Entacapone.html
RxList: The Internet Drug Index (2009). - http://www.rxlist.com/

Entacapone (CED0005201)

Structure for CHEM002210: Entacapone

Structure