ChemicalBook
Chinese Japanese Germany Korea

Entacapone

Anti-Parkinson's disease drugs Pharmacokinetics Chemical property Uses Production method
Entacapone
Entacapone structure
CAS No.
130929-57-6
Chemical Name:
Entacapone
Synonyms
Comtan;Comtes; OR-611;Comtess;ENTACAPONE;ENTACAPONE F·S;Entacapone (150 mg);Entacapone (isomer E);(E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylacrylamide;(E)-2-Cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-2-pmpenamide
CBNumber:
CB5726435
Molecular Formula:
C14H15N3O5
Formula Weight:
305.29
MOL File:
130929-57-6.mol

Entacapone Properties

Melting point:
162-1630C
storage temp. 
-20°C Freezer
solubility 
DMSO: soluble20mg/mL, clear
pka
pKa ~4.5(at 25℃)
form 
powder
color 
white to light brown
CAS DataBase Reference
130929-57-6(CAS DataBase Reference)
SAFETY
  • Risk and Safety Statements
WGK Germany  3
HS Code  2926900005

Entacapone price More Price(9)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich SML0654 Entacapone ≥98% (HPLC) 130929-57-6 10mg $60.2 2018-11-13 Buy
Sigma-Aldrich 1235933 Entacapone United States Pharmacopeia (USP) Reference Standard 130929-57-6 150mg $666 2018-11-13 Buy
Cayman Chemical 14153 Entacapone ≥98% 130929-57-6 25mg $61 2018-11-13 Buy
Cayman Chemical 14153 Entacapone ≥98% 130929-57-6 10mg $35 2018-11-13 Buy
Sigma-Aldrich 1235933 Entacapone United States Pharmacopeia (USP) Reference Standard 130929-57-6 200mg $676.2 2018-11-23 Buy

Entacapone Chemical Properties,Uses,Production

Anti-Parkinson's disease drugs

Entacapone is an anti-Parkinson's disease drug which is successfully developed by Orion Pharma company in Swedish. It is a highly selective potent catechol-O-methyltransferase (COMT) inhibitor, rarely penetrating the blood-brain barrier, and primarily acting in the intestinal tract. It is dose-dependent to decrease levels of 3-OMD in serum and the brain, increasing levodopa, dopamine and DOPAC levels in the brain and significantly reducing the dose which is required to increase dopamine concentration in striatal. Levodopa and carbidopa combining with COMTI can significantly increase the bioavailability of levodopa (3-4 times). Activity of COMTI in red blood cell is reversible. When in 800mg dose, the maximum inhibitory activity is up to 82%, so Entacapone combines with levodopa and carbidopa, which can be used for adjuvant therapy of idiopathic Parkinson's disease.

Pharmacokinetics

This product is rapid oral absorption, the bioavailability is a dose-dependent with the range of 30% to 45%. In the range of 5~800 mg, pharmacokinetics of Entacapone (abbreviation: Ent) is linear, peak plasma concentration is related to AUC and dose. Food does not affect the absorption of this product, 98% Ent combines with plasma albumin, rarely distributing in tissues. In patients with Parkinson disease (abbreviated: PD), and is required to take levodopa/carbidopa, the peak concentration of Ent arrives within 1~2h. The rate of Ent through the blood-brain barrier is low, the plasma elimination half-life is 1.5~3.5h. After oral administration, Ent (E-configuration) is metabolized to Z-isomer in the blood and is present in plasma and red blood cells. Z-isomer has little impact on the clinical efficacy. Its drug-time curve is similar to Ent. Z-Ent accounts for about 5% of the total AUC. Ent and Z-Ent are acidified by glucose in the liver. After metabolism of Ent: 10% excreted in the urine, 90% of Ent excreted in the feces, only 0.2% excreted in the urine in phony drugs. While taking levodopa in PD patients, and oral Ent 200 mg after elimination half-life of about 1 h, the body has no savings.
Pharmacokinetic study shows that in healthy persons and patients with PD, Ent can increase the bioavailability of levodopa. In the short-term PD patients taking Ent, AUC of levodopa increase 25%, while the long-term taking Ent can increase 50%. AUC of 3-OMD relatively reduces 60%. In these studies, they found that plasma peak time of levodopa will be extended. Single dose of Entacapone (while not taking levodopa/carbidopa), in patients with liver disease, the patient's AUC and Cmax is 2 times of the patients with normal liver function. We should adjust the dosage of the patient. In patients with mild to moderate kidney disease, it is not necessary to adjust the dosage. Kidney patients receiving dialysis can extend dosing interval.
The above information is edited by the Chemicalbook of Liu Yujie.

Chemical property

Crystals, melting point 162--163 ℃.

Uses

As COMT inhibitors, it is used to treat Parkinson's disease.

Production method

1.83 g 3,4-dihydroxy-5-nitrobenzaldehyde and 1.5g N, N-diethyl-cyanoacetamide and a catalytic amount of piperidine acetate are dissolved in 40ml of dry ethanol , followed by stirring overnight , 2.23 g crude product is obtained, yield 73%, melting point 153~156 ℃.
Heated at 90 ℃, the 3.0 kg crude product is dissolved in 8.0kg acetic acid (or formic acid) containing 80 g HBr (or 40gHCl).It is slowly cooled to 20 ℃, and stirred at this temperature for 20h, then at 15 ℃ stirred for 6h. The precipitated crystals were collected by filtration, carefully washed with cool (4 ℃) 1L toluene-acetic acid (1: l v/v) mixed solution, and washed with 1L cold toluene. It is dried at 45 ℃under vacuum and 2.4kg crystalline pure Entacapone is obtained, yield 80%, melting point 162-163 ℃.

Description

Entacapone was introduced in Finland, Germany and Sweden as an adjunctive treatment with L-dopa in Parkinson’s disease. Entacapone is the second drug in its class to reach the market; it can be obtained by basecatalyzed condensation of the corresponding benzaldehyde with a cyanoacetamide. Entacapone is a highly selective and orally-active catechol-0- methyltransferase (COMT) inhibitor ; by inhibiting metabolism of L-dopa when given as an adjuvant in patients with Parkinson’s disease, Entacapone markedly prolongs the effects of L-dopa and improves its bioavailability. Results from clinical studies showed that 200mglday Entacapone coadministered with L-dopa lowered the dose of the latter required to reduce fluctuations in motor performance.

Chemical Properties

Yellow Crystalline Solid

Originator

Orion Pharma (Finland)

Uses

(E)-Isomer of Entacapone polymorphic form A. Peripherally acting inhibitor of catechol-O-methyl transferase (COMT), an enzyme involved in the metabolism of catecholamine neurotransmitters and related drugs. Antiparkinsonian

Uses

antiparkinsinian;catechol-O-methyl transferase inhibitor

Uses

This compound belongs to the cinnamic acid amides. These are amides of cinnamic acids. 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-

Definition

ChEBI: A monocarboxylic acid amide that is N,N-diethylprop-2-enamide in which the hydrogen at position 2 is substituted by a cyano group and the hydrogen at the 3E position is substituted by a 3,4-dihydroxy-5 nitrophenyl group.

brand name

Comtan(Orion);Comtess.

General Description

Entacapone, (E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-2-propenamide (Comtan),is a nitrocatechol that is practically insoluble in water (pKa=4.50). Entacapone is rapidly absorbed after oral administrationand does not cross the BBB. Entacapone does not distributewidely into tissues because of its high plasma proteinbinding and it is completely metabolized before excretion.The main metabolic pathway is by isomerization to the cisisomerfollowed by direct glucuronidation of the parent andthe cis-isomer. The glucuronide conjugates are inactive.Entacapone is eliminated in the feces (90%) and urine (10%).Entacapone is indicated as an adjunct to levodopa/carbidopato treat patients with idiopathic PD who experience the signsand symptoms of end-of-dose wearing off.

Entacapone Preparation Products And Raw materials

Raw materials

Preparation Products


Entacapone Suppliers

Global( 181)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Capot Chemical Co.,Ltd.
+86 (0)571-855 867 18
+86 (0)571-858 647 95 sales@capotchem.com China 19918 60
Shenzhen Sendi Biotechnology Co.Ltd.
0755-23311925 18102838259
0755-23311925 Abel@chembj.com CHINA 3194 55
Henan DaKen Chemical CO.,LTD.
+86-371-55531817
info@dakenchem.com CHINA 21707 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 20672 55
Mainchem Co., Ltd.
+86-0592-6210733
+86-0592-6210733 sales@mainchem.com CHINA 32447 55
PI & PI BIOTECH INC.
020-81716320
020-81716319 Sales@pipitech.com CHINA 2543 55
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 29955 58
GIHI CHEMICALS CO.,LIMITED
08657186217390
sales@gihichemicals.com CHINA 308 58
Hubei Jusheng Technology Co.,Ltd.
86-18871470254
027-59599243 sales@jushengtech.com CHINA 28236 58
QUALITY CONTROL CHEMICALS INC.
(323) 306-3136
(626) 453-0409 orders@qcchemical.com United States 8407 58

View Lastest Price from Entacapone manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2018-12-24 Entacapone
130929-57-6
US $2.00 / kg 1kg 99% 100kg career henan chemical co

130929-57-6(Entacapone)Related Search:


Copyright 2017 © ChemicalBook. All rights reserved