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MedKoo Cat#: 591366 | Name: Entacapone acid

Description:

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

Entacapone is a selective and reversible inhibitor of catechol-O-methyltransferase (COMT).

Chemical Structure

Entacapone acid
Entacapone acid
CAS#160391-70-8

Theoretical Analysis

MedKoo Cat#: 591366

Name: Entacapone acid

CAS#: 160391-70-8

Chemical Formula: C10H6N2O6

Exact Mass: 250.0226

Molecular Weight: 250.17

Elemental Analysis: C, 48.01; H, 2.42; N, 11.20; O, 38.37

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Entacapone acid; Entacapone impurity F; Tyrphostin; AG 1290; AG-1290; AG1290
IUPAC/Chemical Name
2-Propenoic acid, 2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-, (2E)-
InChi Key
XDDDOLQEZBJWFZ-LZCJLJQNSA-N
InChi Code
InChI=1S/C10H6N2O6/c11-4-6(10(15)16)1-5-2-7(12(17)18)9(14)8(13)3-5/h1-3,13-14H,(H,15,16)/b6-1+
SMILES Code
O=C(O)/C(C#N)=C/C1=CC([N+]([O-])=O)=C(O)C(O)=C1
Appearance
Solid powder
Purity
>98% (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

Preparing Stock Solutions

The following data is based on the product molecular weight 250.17 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.

Recalculate based on batch purity %
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
1: Belal F, Ibrahim F, Sheribah ZA, Alaa H. Micellar HPLC-UV method for the simultaneous determination of levodopa, carbidopa and entacapone in pharmaceuticals and human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2018 May 22;1091:36-45. doi: 10.1016/j.jchromb.2018.05.030. [Epub ahead of print] PubMed PMID: 29843067. 2: Engelbrecht I, Petzer JP, Petzer A. Nitrocatechol Derivatives of Chalcone as Inhibitors of Monoamine Oxidase and Catechol-O-Methyltransferase. Cent Nerv Syst Agents Med Chem. 2018 Apr 26. doi: 10.2174/1871524918666180426125714. [Epub ahead of print] PubMed PMID: 29697034. 3: Grünig D, Felser A, Duthaler U, Bouitbir J, Krähenbühl S. Effect of the catechol-O-methyltransferase inhibitors tolcapone and entacapone on fatty acid metabolism in HepaRG cells. Toxicol Sci. 2018 Apr 23. doi: 10.1093/toxsci/kfy101. [Epub ahead of print] PubMed PMID: 29688484. 4: Ware BR, McVay M, Sunada WY, Khetani SR. Exploring Chronic Drug Effects on Microengineered Human Liver Cultures Using Global Gene Expression Profiling. Toxicol Sci. 2017 Jun 1;157(2):387-398. doi: 10.1093/toxsci/kfx059. PubMed PMID: 28369597. 5: Mittur A, Gupta S, Modi NB. Pharmacokinetics of Rytary(®), An Extended-Release Capsule Formulation of Carbidopa-Levodopa. Clin Pharmacokinet. 2017 Sep;56(9):999-1014. doi: 10.1007/s40262-017-0511-y. Review. PubMed PMID: 28236251; PubMed Central PMCID: PMC5563351. 6: Zhu J, Yu F. [Feeding difficulty and developmental delay for 8 months and nystagmus for 4 months in an infant]. Zhongguo Dang Dai Er Ke Za Zhi. 2017 Jan;19(1):68-72. Chinese. PubMed PMID: 28100326. 7: Belal F, Ibrahim F, Sheribah ZA, Alaa H. Micelle-enhanced spectrofluorimetric method for quantification of entacapone in tablets and human plasma. Luminescence. 2017 Aug;32(5):713-722. doi: 10.1002/bio.3241. Epub 2016 Dec 5. PubMed PMID: 27917581. 8: Scott LJ. Opicapone: A Review in Parkinson's Disease. Drugs. 2016 Sep;76(13):1293-1300. doi: 10.1007/s40265-016-0623-y. Review. Erratum in: Drugs. 2016 Oct;76(15):1505. Drugs. 2017 Nov 21;:. PubMed PMID: 27498199. 9: 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. 10: Silva T, Mohamed T, Shakeri A, Rao PP, Martínez-González L, Pérez DI, Martínez A, Valente MJ, Garrido J, Uriarte E, Serrão P, Soares-da-Silva P, Remião F, Borges F. Development of Blood-Brain Barrier Permeable Nitrocatechol-Based Catechol O-Methyltransferase Inhibitors with Reduced Potential for Hepatotoxicity. J Med Chem. 2016 Aug 25;59(16):7584-97. doi: 10.1021/acs.jmedchem.6b00666. Epub 2016 Aug 5. PubMed PMID: 27463695. 11: Purnachand D, Veerareddy A, Ramadevi B, Kameswarrao ChV, Madhusudhanreddy B. Development and Validation of a RP-HPLC Method for Determination of Related Substances and Degradants in Entacapone. J Chromatogr Sci. 2016 Sep;54(8):1310-23. doi: 10.1093/chromsci/bmw083. Epub 2016 May 10. PubMed PMID: 27165569. 12: Chen AY, Lü JM, Yao Q, Chen C. 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. Med Sci Monit. 2016 Mar 1;22:687-96. PubMed PMID: 26927838; PubMed Central PMCID: PMC4777242. 13: Tian DD, Jia WW, Liu XW, Wang DD, Liu JH, Dong JJ, Li L, Du FF, Xu F, Wang FQ, Sun Y, Huang YX, Li MJ, Hu LH, Zhu Y, Gao XM, Li C, Yang JL. Methylation and its role in the disposition of tanshinol, a cardiovascular carboxylic catechol from Salvia miltiorrhiza roots (Danshen). Acta Pharmacol Sin. 2015 May;36(5):627-43. doi: 10.1038/aps.2015.20. Epub 2015 Apr 20. PubMed PMID: 25891082; PubMed Central PMCID: PMC4422947. 14: 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. 15: 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. 16: Rapanelli M, Frick LR, Miguelez Fernández AM, Zanutto BS. Dopamine bioavailability in the mPFC modulates operant learning performance in rats: an experimental study with a computational interpretation. Behav Brain Res. 2015 Mar 1;280:92-100. doi: 10.1016/j.bbr.2014.11.031. Epub 2014 Nov 27. PubMed PMID: 25435314. 17: Ma JY, Zhou X, Fu J, Hu T, Or PM, Feng R, He CY, Chen WJ, Zhang X, Chen Y, Wang Y, Yeung JH. Metabolite profiling analysis of FR429, an ellagitannin purified from Polygonum capitatum, in rat and human liver microsomes, cytosol and rat primary hepatocytes in vitro. Chem Biol Interact. 2014 Sep 5;220:33-40. doi: 10.1016/j.cbi.2014.06.002. Epub 2014 Jun 11. PubMed PMID: 24928742. 18: Zhao P, Yang JF, Liu W, Wang Y, Sun YN, Li Q, Zhang W, Zhang BS. [Effects of entacapone on plasma homocysteine in Parkinson's disease patients on levodopa]. Zhonghua Yi Xue Za Zhi. 2013 Feb 19;93(7):512-5. Chinese. PubMed PMID: 23660319. 19: Vemić A, Jančić Stojanović B, Stamenković I, Malenović A. Chaotropic agents in liquid chromatographic method development for the simultaneous analysis of levodopa, carbidopa, entacapone and their impurities. J Pharm Biomed Anal. 2013 Apr 15;77:9-15. doi: 10.1016/j.jpba.2013.01.007. Epub 2013 Jan 8. PubMed PMID: 23354116. 20: Robinson RG, Smith SM, Wolkenberg SE, Kandebo M, Yao L, Gibson CR, Harrison ST, Polsky-Fisher S, Barrow JC, Manley PJ, Mulhearn JJ, Nanda KK, Schubert JW, Trotter BW, Zhao Z, Sanders JM, Smith RF, McLoughlin D, Sharma S, Hall DL, Walker TL, Kershner JL, Bhandari N, Hutson PH, Sachs NA. Characterization of non-nitrocatechol pan and isoform specific catechol-O-methyltransferase inhibitors and substrates. ACS Chem Neurosci. 2012 Feb 15;3(2):129-40. doi: 10.1021/cn200109w. Epub 2011 Nov 14. PubMed PMID: 22860182; PubMed Central PMCID: PMC3369789.