Entacapone

Names

[ Name ]:
Entacapone

[Synonym ]:
(E)-2-Cyano-N,N-diethyl-3-(3,4-dihydroxy-5-nitrophenyl)acrylamide
(2E)-2-Cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylacrylamide
Comtan
Comtes
(2Z)-2-Cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylacrylamide
OR-611
2-Cyano-N,N-diethyl-3-(3,4-dihydroxy-5-nitrophenyl)propenamide
MFCD00866580
2-Propenamide, 2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-, (2E)-
(2E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylprop-2-enamide
Comtess
(E)-a-Cyano-N,N-diethyl-3,4-dihydroxy-5-nitrocinnamamide
Entacapone
2-Propenamide, 2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-, (2Z)-

Biological Activity

[Description]:

Entacapone is a specific, potent, peripherally acting catechol-O-methyltransferase (COMT) inhibitor with IC50 of 151 nM for PD treatment.IC50 Value: 151 nMTarget: COMTin vitro: Entacapone inhibits catechol-O-methyltransferase(COMT) with similar IC50 in different tissues including live, duodenum, kidney and lung, but entacapone is more active than tolcapone in those tissues. Entacapone (< 100 μM) is a potent inhibitor of α-syn and β-amyloid (Aβ) oligomerization and fibrillogenesis, and also protects against extracellular toxicity induced by the aggregation of both proteins in PC12 cells.in vivo: Levodopa/carbidopa/entacapone has been shown to improve the pharmacokinetic profile of levodopa and provide superior symptomatic control compared with conventional levodopa/dopa decarboxylase inhibitor therapy. We report four case histories describing clinical experience of using levodopa/carbidopa/entacapone 200/50/200 mg, one of the latest doses of this formulation, in a range of patients with Parkinson's disease. These cases illustrate that levodopa/carbidopa/entacapone 200/50/200 mg provides improvements in symptomatic control.Clinical trial: The combination product carbidopa/levodopa/entacapone (CLE) was approved in 2003 for the treatment of PD patients.

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> COMT

Signaling Pathways >> Neuronal Signaling >> COMT

Research Areas >> Neurological Disease

[References]

[1]. Piccini P, Brooks DJ, Korpela K, The catechol-O-methyltransferase(COMT) inhibitor entacapone enhances the pharmacokinetic and clinical response to Sinemet CR in Parkinson's disease. J Neurol Neurosurg Psychiatry. 2000 May;68(5):589-94.

[2]. Di Giovanni S, Eleuteri S, Paleologou KE, Entacapone and tolcapone, two catechol O-methyltransferase inhibitors, block fibril formation of alpha-synuclein and beta-amyloid and protect against amyloid-induced toxicity. J Biol Chem. 2010 May 14;285(20):1494

[3]. Sethi KD, Hauser RA, Isaacson SH, Levodopa/carbidopa/entacapone 200/50/200 mg (Stalevo 200) in the treatment of Parkinson's disease: a case series. Cases J. 2009 Jul 30;2:7134.

[4]. Poulopoulos M, Waters C. Carbidopa/levodopa/entacapone: the evidence for its place in the treatment of Parkinson's disease. Core Evid. 2010 Jul 27;5:1-10.

[Related Small Molecules]

Serotonin hydrochloride | Tolcapone | Opicapone | Flopropione | Entacapone sodium salt

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
526.6±50.0 °C at 760 mmHg

[ Melting Point ]:
162-1630C

[ Molecular Formula ]:
C₁₄H₁₅N₃O₅

[ Molecular Weight ]:
305.286

[ Flash Point ]:
272.3±30.1 °C

[ Exact Mass ]:
305.101166

[ PSA ]:
130.38000

[ LogP ]:
2.38

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.642

[ Storage condition ]:
-20°C Freezer

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Codes ]:
Xn,T,F

[ Risk Phrases ]:
R10:Flammable. R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . R37/38:Irritating to respiratory system and skin . R41:Risk of serious damage to eyes. R62:Possible risk of impaired fertility. R38:Irritating to the skin. R36/37/38:Ir

[ Safety Phrases ]:
S26-S36-S39-S45-S36/37/39-S16

[ RIDADR ]:
UN 1986 3/PG 3

[ WGK Germany ]:
1

[ RTECS ]:
KM5250000

[ Packaging Group ]:
III

[ Hazard Class ]:
3

[ HS Code ]:
2942000000

Synthetic Route

Click to get detail synthetic route

Customs

[ HS Code ]: 2942000000

Articles

Dog UDP-glucuronosyltransferase enzymes of subfamily 1A: cloning, expression, and activity.

Drug Metab. Dispos. 43(1) , 107-18, (2014)

Understanding drug glucuronidation in the dog, a preclinical animal, is important but currently poorly characterized at the level of individual enzymes. We have constructed cDNAs for the 10 dog UDP-gl...

Comparison of IPX066 with carbidopa-levodopa plus entacapone in advanced PD patients.

Parkinsonism Relat. Disord. 20(12) , 1335-40, (2014)

IPX066, an investigational extended-release carbidopa-levodopa (CD-LD) preparation, has demonstrated a rapid attainment and prolonged maintenance of therapeutic LD plasma concentrations in advanced Pa...

Entacapone and prostate cancer risk in patients with Parkinson's disease.

Mov. Disord 30(5) , 724-8, (2015)

The association between Parkinson's disease (PD) and prostate cancer, both common in elderly men, is disputable. In the STRIDE-PD study, prostate cancer developed in 9 patients (3.7%) receiving levodo...