CAS 130929-57-6|Entacapone

Introduction：Basic information about CAS 130929-57-6|Entacapone, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Entacapone BiologicalActivity
3. Chemical & Physical Properties
4. Safety Information
5. Customs
6. Articles5
7. Synonyms

Common Name	Entacapone
CAS Number	130929-57-6	Molecular Weight	305.286
Density	1.4±0.1 g/cm3	Boiling Point	526.6±50.0 °C at 760 mmHg
Molecular Formula	C₁₄H₁₅N₃O₅	Melting Point	162-1630C
MSDS	USA	Flash Point	272.3±30.1 °C

Names

Name	entacapone
Synonym	More Synonyms

Entacapone BiologicalActivity

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 >>COMTSignaling Pathways >>Neuronal Signaling >>COMTResearch 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.

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 >>COMTSignaling Pathways >>Neuronal Signaling >>COMTResearch 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.

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
InChIKey	JRURYQJSLYLRLN-BJMVGYQFSA-N
SMILES	CCN(CC)C(=O)C(C#N)=Cc1cc(O)c(O)c([N+](=O)[O-])c1
Storage condition	-20°C Freezer

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

Customs

HS Code	2942000000

Articles5

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...

Synonyms

(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)-

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