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Merck

SML0654

Sigma-Aldrich

Entacapone

≥98% (HPLC), COMT inhibitor, powder

Synonym(s):

2-Cyano-N,N-diethyl-3-(3,4-dihydroxy-5-nitrophenyl)propenamide

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About This Item

Empirical Formula (Hill Notation):
C14H15N3O5
CAS Number:
130929-57-6
Molecular Weight:
305.29
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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Product Name

Entacapone, ≥98% (HPLC)

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to light brown

solubility

DMSO: 20 mg/mL, clear

storage temp.

room temp

SMILES string

[N+](=O)([O-])c1c(c(cc(c1)\C=C(\C(=O)N(CC)CC)/C#N)O)O

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

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Application

Entacapone has been used in high-performance bioaffinity chromatography.

Biochem/physiol Actions

Entacapone acts predominantly in the intestine. It increases the bioavailability of levodopa. Levodopa is known to be associated with many complications such as motor fluctuations. COMT inhibitors have been used to overcome these adverse effects of levodopa by reducing its metabolism. Entacapone exhibits its inhibition action on COMT in the peripheral nervous system.
Entacapone is a catechol-O-methyl transferase (COMT) inhibitor. Used in treatment of Parkinson′s disease, entacapone is administered with L-DOPA to inihibit COMT from converting L-DOPA into a compound that cannot cross the blood brain barrier.
Entacapone is a catechol-O-methyl transferase (COMT) inhibitor. Antiparkinson; anti-Dyskinesia.

Features and Benefits

This compound is featured on the Dopamine and Norepinephrine Metabolism page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
086M4704V
076M4704V
065M4722V
073M4735V
033M4717V

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Principles of Treatment in Parkinson's Disease, 133-133 (2005)
Entacapone in the treatment of Parkinson's disease
Schrag Anette
Lancet Neurology, 4(6), 366-370 (2005)
Maximiliano Rapanelli et al.
Behavioural brain research, 280, 92-100 (2014-12-02)
Dopamine encodes reward and its prediction in reinforcement learning. Catechol-O-methyltransferase (COMT) activity in the medial prefrontal cortex (mPFC) has been shown to influence cognitive abilities by modifying dopamine clearance. Nevertheless, it is unknown how COMT in the mPFC influences operant
Expanding LogP: Present possibilities
Vraka C, et al.
Nuclear Medicine and Biology, 58(6), 20-32 (2018)
Paul E Polak et al.
Journal of neuroimmunology, 276(1-2), 135-141 (2014-09-23)
Reduced levels of noradrenaline (NA) in CNS of multiple sclerosis patients could be due to metabolism by catechol-O-methyltransferase (COMT). In mice immunized with myelin oligodendrocyte glycoprotein peptide, the BBB-permeable COMT inhibitor dinitrocatechol (DNC) reduced clinical signs, while entacapone, a non-BBB-permeable
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