Entacapone | CAS#130929-57-6 | COMT inhibitor

MedKoo Cat#: 540117 | Name: Entacapone

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Entacapone is a COMT inhibitor used to treat Parkinson's Disease. It reduces clearance of L-DOPA, improves motor function, and prevents α-synuclein and amyloid-β oligomerization and fibril formation.

Chemical Structure

Entacapone

CAS#130929-57-6 (E isomer)

Theoretical Analysis

MedKoo Cat#: 540117

Name: Entacapone

CAS#: 130929-57-6 (E isomer)

Chemical Formula: C14H15N3O5

Exact Mass: 305.1012

Molecular Weight: 305.29

Elemental Analysis: C, 55.08; H, 4.95; N, 13.76; O, 26.20

Price and Availability

Size	Price	Availability
250mg	USD 250.00	2 Weeks
500mg	USD 450.00	2 Weeks
1g	USD 750.00	2 Weeks
2g	USD 1,250.00	2 Weeks

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Related CAS #

130929-57-6 (E isomer) 145195-63-7 (Z isomer)

Synonym

Comtan; Entacapone; Comtess; Entacapona; Entacaponum; (E)-Entacapone; OR-611; OR 611; OR611

IUPAC/Chemical Name

(E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylacrylamide

InChi Key

JRURYQJSLYLRLN-BJMVGYQFSA-N

InChi Code

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+

SMILES Code

O=C(N(CC)CC)/C(C#N)=C/C1=CC([N+]([O-])=O)=C(O)C(O)=C1

Appearance

Solid powder

Purity

>95% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Entacapone is a potent, reversible, peripherally acting and orally active catechol-O-methyltransferase (COMT) inhibitor.

In vitro activity:

After incubation at pH 2.2, 60 °C for 192 h, HL formed aggregates. However, under the same conditions, when HL (70 μM) was incubated together with Ent (Entacapone) at a concentration ranging from 70 μM to 700 μM, a noticeable decrease in RLS scattering was observed (Fig. 1). This result allowed us to infer that Ent might be the reason for reducing the aggregation of HL amyloid fibrillation. The inhibition constant (Λ) of Ent against HL aggregation was further obtained by Eq. (1), and the fitted curve is shown in Fig. 1. The Λ value of Ent was determined to be (3.0 ± 0.5) × 103 M−1. Hence, scattering results indicated that Ent inhibits HL aggregation. Reference: Int J Biol Macromol. 2020 Oct 15;161:1393-1404. https://pubmed.ncbi.nlm.nih.gov/32750483/

In vivo activity:

Pre-treatment with either entacapone or FeTPPS improved renal function as indicated by a significant reduction in serum creatinine and urea when compared to I/R group (P < 0.05). I/R injury increased renal levels of NO (4-folds, P < 0.05), iNOS (4-folds, P < 0.05), and 3-nitrotyrosine (5-folds, P < 0.05) compared to sham control. These effects were abrogated in animals pre-treated with entacapone or FeTPPS before being subjected to I/R (P < 0.05). In addition, entacapone or FeTPPS significantly inhibited I/R-induced elevation in renal TNF-α levels (78% and 58%, respectively) and caspase-3 activity (72% and 56%, respectively) indicating the reduction of both inflammation and apoptosis in the kidney (P < 0.05). The two drugs also improved kidney and liver functions in rats with renal I/R injury. Reference: Int Urol Nephrol. 2021 Aug;53(8):1713-1721. https://pubmed.ncbi.nlm.nih.gov/33675481/

	Solvent	mg/mL	mM
Solubility
	DMSO	38.7	126.83
	DMSO:PBS (pH 7.2) (1:1)	0.5	1.64
	DMF	30.0	98.27
	Ethanol	3.4	10.97
	Water	2.0	6.55

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 305.29 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Jin L, Gao W, Liu C, Zhang N, Mukherjee S, Zhang R, Dong H, Bhunia A, Bednarikova Z, Gazova Z, Liu M, Han J, Siebert HC. Investigating the inhibitory effects of entacapone on amyloid fibril formation of human lysozyme. Int J Biol Macromol. 2020 Oct 15;161:1393-1404. doi: 10.1016/j.ijbiomac.2020.07.296. Epub 2020 Aug 1. PMID: 32750483. 2. Peng S, Xiao W, Ju D, Sun B, Hou N, Liu Q, Wang Y, Zhao H, Gao C, Zhang S, Cao R, Li P, Huang H, Ma Y, Wang Y, Lai W, Ma Z, Zhang W, Huang S, Wang H, Zhang Z, Zhao L, Cai T, Zhao YL, Wang F, Nie Y, Zhi G, Yang YG, Zhang EE, Huang N. Identification of entacapone as a chemical inhibitor of FTO mediating metabolic regulation through FOXO1. Sci Transl Med. 2019 Apr 17;11(488):eaau7116. doi: 10.1126/scitranslmed.aau7116. PMID: 30996080. 3. Soliman E, Shewaikh SM, Fahmy A, Elshazly S. Entacapone scavenges peroxynitrite and protects against kidney and liver injuries induced by renal ischemia/reperfusion in rats. Int Urol Nephrol. 2021 Aug;53(8):1713-1721. doi: 10.1007/s11255-021-02827-5. Epub 2021 Mar 6. PMID: 33675481. 4. Yoo DY, Jung HY, Kim W, Hahn KR, Kwon HJ, Nam SM, Chung JY, Yoon YS, Kim DW, Hwang IK. Entacapone promotes hippocampal neurogenesis in mice. Neural Regen Res. 2021 Jun;16(6):1005-1110. doi: 10.4103/1673-5374.300447. PMID: 33269743; PMCID: PMC8224137.

In vitro protocol:

In vivo protocol:

1. Soliman E, Shewaikh SM, Fahmy A, Elshazly S. Entacapone scavenges peroxynitrite and protects against kidney and liver injuries induced by renal ischemia/reperfusion in rats. Int Urol Nephrol. 2021 Aug;53(8):1713-1721. doi: 10.1007/s11255-021-02827-5. Epub 2021 Mar 6. PMID: 33675481. 2. Yoo DY, Jung HY, Kim W, Hahn KR, Kwon HJ, Nam SM, Chung JY, Yoon YS, Kim DW, Hwang IK. Entacapone promotes hippocampal neurogenesis in mice. Neural Regen Res. 2021 Jun;16(6):1005-1110. doi: 10.4103/1673-5374.300447. PMID: 33269743; PMCID: PMC8224137.

1: Kuoppamäki M, Leinonen M, Poewe W. Efficacy and safety of entacapone in levodopa/carbidopa versus levodopa/benserazide treated Parkinson's disease patients with wearing-off. J Neural Transm (Vienna). 2015 Dec;122(12):1709-14. doi: 10.1007/s00702-015-1449-6. Epub 2015 Sep 7. PubMed PMID: 26347184; PubMed Central PMCID: PMC4644189. 2: Li LS, Liu CZ, Xu JD, Zheng LF, Feng XY, Zhang Y, Zhu JX. Effect of entacapone on colon motility and ion transport in a rat model of Parkinson's disease. World J Gastroenterol. 2015 Mar 28;21(12):3509-18. doi: 10.3748/wjg.v21.i12.3509. PubMed PMID: 25834315; PubMed Central PMCID: PMC4375572. 3: Kuoppamäki M, Vahteristo M, Ellmén J, Kieburtz K. Pooled analysis of phase III with entacapone in Parkinson's disease. Acta Neurol Scand. 2014 Oct;130(4):239-47. doi: 10.1111/ane.12278. Epub 2014 Sep 3. PubMed PMID: 25186800. 4: Alqahtani S, Kaddoumi A. Development of a physiologically based pharmacokinetic/pharmacodynamic model to identify mechanisms contributing to entacapone low bioavailability. Biopharm Drug Dispos. 2015 Dec;36(9):587-602. doi: 10.1002/bdd.1986. PubMed PMID: 26295926. 5: Korhonen P, Kuoppamäki M, Prami T, Hoti F, Christopher S, Ellmén J, Aho V, Vahteristo M, Pukkala E, Haukka J. Entacapone and prostate cancer risk in patients with Parkinson's disease. Mov Disord. 2015 Apr 15;30(5):724-8. doi: 10.1002/mds.26140. Epub 2015 Jan 16. PubMed PMID: 25639262. 6: Hsu A, Yao HM, Gupta S, Modi NB. Comparison of the pharmacokinetics of an oral extended-release capsule formulation of carbidopa-levodopa (IPX066) with immediate-release carbidopa-levodopa (Sinemet(®)), sustained-release carbidopa-levodopa (Sinemet(®) CR), and carbidopa-levodopa-entacapone (Stalevo(®)). J Clin Pharmacol. 2015 Sep;55(9):995-1003. doi: 10.1002/jcph.514. Epub 2015 May 20. PubMed PMID: 25855267; PubMed Central PMCID: PMC5032972. 7: Rocha JF, Falcão A, Santos A, Pinto R, Lopes N, Nunes T, Wright LC, Vaz-da-Silva M, Soares-da-Silva P. Effect of opicapone and entacapone upon levodopa pharmacokinetics during three daily levodopa administrations. Eur J Clin Pharmacol. 2014 Sep;70(9):1059-71. doi: 10.1007/s00228-014-1701-2. Epub 2014 Jun 14. PubMed PMID: 24925090. 8: Kaphzan H, Ben-Shachar D, Klein E. Entacapone augmentation of antipsychotic treatment in schizophrenic patients with negative symptoms; a double-blind placebo-controlled study. Int J Neuropsychopharmacol. 2014 Feb;17(2):337-40. doi: 10.1017/S1461145713001387. Epub 2013 Nov 12. PubMed PMID: 24229565. 9: Lv X, Wang XX, Hou J, Fang ZZ, Wu JJ, Cao YF, Liu SW, Ge GB, Yang L. Comparison of the inhibitory effects of tolcapone and entacapone against human UDP-glucuronosyltransferases. Toxicol Appl Pharmacol. 2016 Jun 15;301:42-9. doi: 10.1016/j.taap.2016.04.009. Epub 2016 Apr 16. PubMed PMID: 27089846. 10: Alshammari TM, AlMutairi EN. Use of an entacapone-containing drug combination and risk of death: Analysis of the FDA AERS (FAERS) database. Saudi Pharm J. 2015 Jan;23(1):28-32. doi: 10.1016/j.jsps.2014.04.005. Epub 2014 Apr 30. PubMed PMID: 25685040; PubMed Central PMCID: PMC4311018. 11: Tambasco N, Muti M, Chiarini P, Tarducci R, Caproni S, Castrioto A, Nigro P, Parnetti L, Floridi P, Rossi A, Calabresi P. Entacapone reduces cortical activation in Parkinson's disease with wearing-off: a f-MRI study. PLoS One. 2014 May 15;9(5):e96806. doi: 10.1371/journal.pone.0096806. eCollection 2014. PubMed PMID: 24830331; PubMed Central PMCID: PMC4022515. 12: Stocchi F, Hsu A, Khanna S, Ellenbogen A, Mahler A, Liang G, Dillmann U, Rubens R, Kell S, Gupta S. Comparison of IPX066 with carbidopa-levodopa plus entacapone in advanced PD patients. Parkinsonism Relat Disord. 2014 Dec;20(12):1335-40. doi: 10.1016/j.parkreldis.2014.08.004. Epub 2014 Aug 15. PubMed PMID: 25306200. 13: Longo DM, Yang Y, Watkins PB, Howell BA, Siler SQ. Elucidating Differences in the Hepatotoxic Potential of Tolcapone and Entacapone With DILIsym(®), a Mechanistic Model of Drug-Induced Liver Injury. CPT Pharmacometrics Syst Pharmacol. 2016 Jan;5(1):31-9. doi: 10.1002/psp4.12053. Epub 2016 Jan 13. PubMed PMID: 26844013; PubMed Central PMCID: PMC4728295. 14: Madias JE. Entacapone, Parkinson's disease, "functional adrenergic denervation", and Takotsubo syndrome. Parkinsonism Relat Disord. 2015 Apr;21(4):426. doi: 10.1016/j.parkreldis.2014.11.011. Epub 2014 Nov 20. PubMed PMID: 25443553. 15: Graham DJ, Williams JR, Hsueh YH, Calia K, Levenson M, Pinheiro SP, Macurdy TE, Shih D, Worrall C, Kelman JA. Cardiovascular and mortality risks in Parkinson's disease patients treated with entacapone. Mov Disord. 2013 Apr;28(4):490-7. doi: 10.1002/mds.25351. Epub 2013 Feb 26. PubMed PMID: 23443994. 16: Baldacci F, Vergallo A, Del Dotto P, Ulivi M, Palombo C, Casolo G, Bonuccelli U. RE response to: "Entacapone, Parkinson's disease, "functional adrenergic denervation", and Takotsubo syndrome". Parkinsonism Relat Disord. 2015 Apr;21(4):427. doi: 10.1016/j.parkreldis.2014.11.010. Epub 2014 Nov 20. PubMed PMID: 25630888. 17: Kocer B, Guven H, Comoglu SS. Homocysteine Levels in Parkinson's Disease: Is Entacapone Effective? Biomed Res Int. 2016;2016:7563705. doi: 10.1155/2016/7563705. Epub 2016 Jul 17. PubMed PMID: 27493964; PubMed Central PMCID: PMC4967439. 18: Li LS, Zheng LF, Xu JD, Ji T, Guo H, Li XF, Li Y, Zhang Y, Zhu JX. Entacapone promotes cAMP-dependent colonic Cl(-) secretion in rats. Neurogastroenterol Motil. 2011 Jul;23(7):657-e277. doi: 10.1111/j.1365-2982.2011.01715.x. Epub 2011 Apr 19. PubMed PMID: 21501335. 19: Ribeiro RP, Gasparetto JC, de Oliveira Vilhena R, Guimarães de Francisco TM, Martins CA, Cardoso MA, Pontarolo R, de Carvalho KA. Simultaneous determination of levodopa, carbidopa, entacapone, tolcapone, 3-O-methyldopa and dopamine in human plasma by an HPLC-MS/MS method. Bioanalysis. 2015;7(2):207-20. doi: 10.4155/bio.14.230. Erratum in: Bioanalysis. 2015;7(7):924. de Francisco, Thais Martins Guimarães [corrected to Guimarães de Francisco, Thais Martins]. PubMed PMID: 25587837. 20: Elrington GM. Review on initial drug treatment in Parkinson's disease did not mention entacapone. BMJ. 2015 Nov 3;351:h5843. doi: 10.1136/bmj.h5843. PubMed PMID: 26530214.