Entacapone

• CAT Number: A001088
• CAS Number: 130929-57-6
• Molecular Formula: C₁₄H₁₅N₃O₅
• Molecular Weight: 305.29
• Purity: ≥95%
• Synonyms: OR-611
• Target: Neuronal Signaling
• Solubility: >13.1mg/mL in DMSO
• Storage: 3 years -20C powder
• IUPAC Name: (E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylprop-2-enamide
• InChI: 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+
• InChIKey: JRURYQJSLYLRLN-BJMVGYQFSA-N
• SMILES: CCN(CC)C(=O)/C(=C/C1=CC(=C(C(=C1)O)O)[N+](=O)[O-])/C#N

Entacapone（Cat No.:A001088）is a peripheral catechol-O-methyltransferase (COMT) inhibitor with the molecular formula C14H15N3O5, used in the treatment of Parkinson’s disease. It enhances the effect of levodopa by inhibiting its peripheral breakdown, thereby increasing its availability to the brain and prolonging its therapeutic action. Entacapone is administered orally, typically in combination with levodopa/carbidopa, to manage “wearing-off” symptoms in advanced Parkinson’s patients. It does not cross the blood-brain barrier and works solely in peripheral tissues. Common side effects include diarrhea, urine discoloration, and dizziness. Regular monitoring is recommended during therapy.

Reference

1:Levodopa-entacapone-carbidopa intestinal gel in Parkinson/’s disease: A randomized crossover study. Senek M, Nielsen EI, Nyholm D.Mov Disord. 2017 Feb;32(2):283-286. doi: 10.1002/mds.26855. Epub 2016 Dec 17. PMID: 27987231 2:Micelle-enhanced spectrofluorimetric method for quantification of entacapone in tablets and human plasma. Belal F, Ibrahim F, Sheribah ZA, Alaa H.Luminescence. 2016 Dec 5. doi: 10.1002/bio.3241. [Epub ahead of print] PMID: 27917581 3:Investigation of different spectrophotometric and chemometric methods for determination of entacapone, levodopa and carbidopa in ternary mixture. Abdel-Ghany MF, Hussein LA, Ayad MF, Youssef MM.Spectrochim Acta A Mol Biomol Spectrosc. 2017 Jan 15;171:236-245. doi: 10.1016/j.saa.2016.07.053. Epub 2016 Aug 2. PMID: 27541796 4:Homocysteine Levels in Parkinson/’s Disease: Is Entacapone Effective? Kocer B, Guven H, Comoglu SS.Biomed Res Int. 2016;2016:7563705. doi: 10.1155/2016/7563705. Epub 2016 Jul 17. PMID: 27493964 Free PMC Article5:Conformational, Optoelectronic and Vibrational Properties of the Entacapone Molecule: A Quantum Chemistry Study. Frazão NF, Albuquerque EL, Fulco UL, Mauriz PW, Azevedo DL.J Nanosci Nanotechnol. 2016 May;16(5):4825-34. PMID: 27483829 6:A novel way for detection of antiparkinsonism drug entacapone via electrodeposition of silver nanoparticles/functionalized multi-walled carbon nanotubes as an amperometric sensor. Baghayeri M, Tehrani MB, Amiri A, Maleki B, Farhadi S.Mater Sci Eng C Mater Biol Appl. 2016 Sep 1;66:77-83. doi: 10.1016/j.msec.2016.03.077. Epub 2016 Mar 24. PMID: 27207040 7:Development and Validation of a RP-HPLC Method for Determination of Related Substances and Degradants in Entacapone. Purnachand D, Veerareddy A, Ramadevi B, Kameswarrao ChV, Madhusudhanreddy B.J Chromatogr Sci. 2016 Sep;54(8):1310-23. doi: 10.1093/chromsci/bmw083. Epub 2016 May 10. PMID: 27165569 8:Comparison of the inhibitory effects of tolcapone and entacapone against human UDP-glucuronosyltransferases. Lv X, Wang XX, Hou J, Fang ZZ, Wu JJ, Cao YF, Liu SW, Ge GB, Yang L.Toxicol Appl Pharmacol. 2016 Jun 15;301:42-9. doi: 10.1016/j.taap.2016.04.009. Epub 2016 Apr 16. PMID: 27089846 9:Entacapone is an Antioxidant More Potent than Vitamin C and Vitamin E for Scavenging of Hypochlorous Acid and Peroxynitrite, and the Inhibition of Oxidative Stress-Induced Cell Death. Chen AY, Lü JM, Yao Q, Chen C.Med Sci Monit. 2016 Mar 1;22:687-96. PMID: 26927838 Free PMC Article10:Effects of levodopa-carbidopa-entacapone and smoked cocaine on facial affect recognition in cocaine smokers. Bedi G, Shiffrin L, Vadhan NP, Nunes EV, Foltin RW, Bisaga A.J Psychopharmacol. 2016 Apr;30(4):370-7. doi: 10.1177/0269881115626308. Epub 2016 Feb 26. PMID: 26921145 Free PMC Article