Nebicapone | BIA-3202 | CAS#274925-86-9 | Catechol-O-Methyltransferase Inhibitor

MedKoo Cat#: 528423 | Name: Nebicapone

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Description:

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

Nebicapone, also known as BIA-3202, is a catechol-O-methyltransferase inhibitor potentially for the treatment of Parkinson's disease. Nebicapone dose dependently and significantly decreased COMT activity. Nebicapone also increased systemic exposure to levodopa and improved motor response.

Chemical Structure

Nebicapone

CAS#274925-86-9

Theoretical Analysis

MedKoo Cat#: 528423

Name: Nebicapone

CAS#: 274925-86-9

Chemical Formula: C14H11NO5

Exact Mass: 273.0637

Molecular Weight: 273.24

Elemental Analysis: C, 61.54; H, 4.06; N, 5.13; O, 29.28

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 500.00	2 Weeks

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Related CAS #

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Synonym

Nebicapone; BIA-3202; BIA 3202; BIA3202

IUPAC/Chemical Name

1-(3,4-dihydroxy-5-nitrophenyl)-2-phenylethan-1-one

InChi Key

MRFOLGFFTUGAEB-UHFFFAOYSA-N

InChi Code

InChI=1S/C14H11NO5/c16-12(6-9-4-2-1-3-5-9)10-7-11(15(19)20)14(18)13(17)8-10/h1-5,7-8,17-18H,6H2

SMILES Code

O=[N+](C1=C(O)C(O)=CC(C(CC2=CC=CC=C2)=O)=C1)[O-]

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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Nebicapone (BIA 3-202), a reversible catechol-O-methyltransferase (COMT) inhibitor.

In vitro activity:

TBD

In vivo activity:

Upon oral administration of nebicapone the extent of mouse liver catechol-O-methyltransferase (COMT) inhibition is half that in the rat. Furthermore, nebicapone inhibited rat liver COMT with a lower K(i) than mouse liver COMT (respectively 0.2nM vs. 1.2nM). In conclusion, the results from the present study show that mice and rats respond differently to COMT inhibition by nebicapone. Reference: Biochem Pharmacol. 2009 Oct 15;78(8):1043-51. https://pubmed.ncbi.nlm.nih.gov/19505437/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	365.97

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 273.24 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. Bonifácio MJ, Loureiro AI, Torrão L, Fernandes-Lopes C, Wright L, Pinho MJ, Soares-da-Silva P. Species differences in pharmacokinetic and pharmacodynamic properties of nebicapone. Biochem Pharmacol. 2009 Oct 15;78(8):1043-51. doi: 10.1016/j.bcp.2009.05.036. Epub 2009 Jun 6. PMID: 19505437. 2. Soares-da-Silva P, Vieira-Coelho MA, Parada A. Catechol-O-methyltransferase inhibition in erythrocytes and liver by BIA 3-202 (1-[3,4-dibydroxy-5-nitrophenyl]-2-phenyl-ethanone). Pharmacol Toxicol. 2003 Jun;92(6):272-8. doi: 10.1034/j.1600-0773.2003.920604.x. PMID: 12787259.

In vitro protocol:

TBD

In vivo protocol:

1: Bicker J, Alves G, Fortuna A, Soares-da-Silva P, Falcão A. A new PAMPA model using an in-house brain lipid extract for screening the blood-brain barrier permeability of drug candidates. Int J Pharm. 2016 Mar 30;501(1-2):102-11. doi: 10.1016/j.ijpharm.2016.01.074. PubMed PMID: 26836708. 2: Kiss LE, Soares-da-Silva P. Medicinal chemistry of catechol O-methyltransferase (COMT) inhibitors and their therapeutic utility. J Med Chem. 2014 Nov 13;57(21):8692-717. doi: 10.1021/jm500572b. PubMed PMID: 25080080. 3: Marsala SZ, Gioulis M, Ceravolo R, Tinazzi M. A systematic review of catechol-0-methyltransferase inhibitors: efficacy and safety in clinical practice. Clin Neuropharmacol. 2012 Jul-Aug;35(4):185-90. doi: 10.1097/WNF.0b013e31825c034a. Review. PubMed PMID: 22805229. 4: Gonçalves D, Alves G, Soares-da-Silva P, Falcão A. Bioanalytical chromatographic methods for the determination of catechol-O-methyltransferase inhibitors in rodents and human samples: a review. Anal Chim Acta. 2012 Jan 13;710:17-32. doi: 10.1016/j.aca.2011.10.026. Review. PubMed PMID: 22123108. 5: Sousa e Silva JP, Lobo JS, Bonifácio MJ, Machado R, Falcão A, Soares-da-Silva P. In-vivo evaluation of prolonged release bilayer tablets of anti-Parkinson drugs in Göttingen minipigs. J Pharm Pharmacol. 2011 Jun;63(6):780-5. doi: 10.1111/j.2042-7158.2011.01278.x. PubMed PMID: 21585375. 6: Kaakkola S. Problems with the present inhibitors and a relevance of new and improved COMT inhibitors in Parkinson's disease. Int Rev Neurobiol. 2010;95:207-25. doi: 10.1016/B978-0-12-381326-8.00009-0. Review. PubMed PMID: 21095464. 7: Haasio K. Toxicology and safety of COMT inhibitors. Int Rev Neurobiol. 2010;95:163-89. doi: 10.1016/B978-0-12-381326-8.00007-7. Review. PubMed PMID: 21095462. 8: Ferreira JJ, Rascol O, Poewe W, Sampaio C, Rocha JF, Nunes T, Almeida L, Soares-da-Silva P; BIA-3202-202 Study Investigators.. A double-blind, randomized, placebo and active-controlled study of nebicapone for the treatment of motor fluctuations in Parkinson's disease. CNS Neurosci Ther. 2010 Dec;16(6):337-47. doi: 10.1111/j.1755-5949.2010.00145.x. PubMed PMID: 20653695. 9: Wright LC, Maia J, Loureiro AI, Almeida L, Soares-Da-Silva P. Pharmacokinetics, disposition, and metabolism of [14C]-nebicapone in humans. Drug Metab Lett. 2010 Aug;4(3):149-62. PubMed PMID: 20642448. 10: Almeida L, Loureiro AI, Vaz-da-Silva M, Torrão L, Maia J, Fernandes-Lopes C, Falcão A, Igreja B, Wright L, Soares-da-Silva P. Chronopharmacology of nebicapone, a new catechol-O-methyltransferase inhibitor. Curr Med Res Opin. 2010 May;26(5):1097-108. doi: 10.1185/03007991003694472. PubMed PMID: 20225994. 11: Nunes T, Machado R, Rocha JF, Fernandes-Lopes C, Costa R, Torrão L, Loureiro AI, Falcão A, Vaz-da-Silva M, Wright L, Almeida L, Soares-da-Silva P. Pharmacokinetic-pharmacodynamic interaction between nebicapone and controlled-release levodopa/benserazide: a single-center, Phase I, double-blind, randomized, placebo-controlled, four-way crossover study in healthy subjects. Clin Ther. 2009 Oct;31(10):2258-71. doi: 10.1016/j.clinthera.2009.10.019. PubMed PMID: 19922897. 12: Bonifácio MJ, Loureiro AI, Torrão L, Fernandes-Lopes C, Wright L, Pinho MJ, Soares-da-Silva P. Species differences in pharmacokinetic and pharmacodynamic properties of nebicapone. Biochem Pharmacol. 2009 Oct 15;78(8):1043-51. doi: 10.1016/j.bcp.2009.05.036. PubMed PMID: 19505437. 13: Vaz-da-Silva M, Loureiro AI, Nunes T, Lopes C, Rocha J, Machado R, Costa R, Torrão L, Falcão A, Wright L, Almeida L, Soares-da-Silva P. Pharmacokinetic-pharmacodynamic interaction between nebicapone, a novel catechol-o-methyltransferase inhibitor, and controlled-release levodopa/carbidopa 200 mg/50 mg : randomized, double-blind, placebo-controlled, crossover study in healthy subjects. Drugs R D. 2008;9(6):435-46. doi: 10.2165/0126839-200809060-00006. PubMed PMID: 18989992. 14: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2008 May;30(4):313-31. PubMed PMID: 18773127. 15: Almeida L, Falcão A, Vaz-da-Silva M, Nunes T, Santos AT, Rocha JF, Neta C, Macedo T, Fontes-Ribeiro C, Soares-da-Silva P. Effect of nebicapone on the pharmacokinetics and pharmacodynamics of warfarin in healthy subjects. Eur J Clin Pharmacol. 2008 Oct;64(10):961-6. doi: 10.1007/s00228-008-0534-2. PubMed PMID: 18679669. 16: Ferreira JJ, Almeida L, Cunha L, Ticmeanu M, Rosa MM, Januário C, Mitu CE, Coelho M, Correia-Guedes L, Morgadinho A, Nunes T, Wright LC, Falcão A, Sampaio C, Soares-da-Silva P. Effects of nebicapone on levodopa pharmacokinetics, catechol-O-methyltransferase activity, and motor fluctuations in patients with Parkinson disease. Clin Neuropharmacol. 2008 Jan-Feb;31(1):2-18. doi: 10.1097/wnf.0b013e3180645cb0. PubMed PMID: 18303486. 17: Bonifácio MJ, Palma PN, Almeida L, Soares-da-Silva P. Catechol-O-methyltransferase and its inhibitors in Parkinson's disease. CNS Drug Rev. 2007 Fall;13(3):352-79. Review. PubMed PMID: 17894650. 18: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2007 Apr;29(3):231-45. PubMed PMID: 17520107. 19: Loureiro AI, Bonifácio MJ, Fernandes-Lopes C, Almeida L, Wright LC, Soares-Da-Silva P. Human metabolism of nebicapone (BIA 3-202), a novel catechol-o-methyltransferase inhibitor: characterization of in vitro glucuronidation. Drug Metab Dispos. 2006 Nov;34(11):1856-62. PubMed PMID: 16790555. 20: Almeida L, Vaz-da-Silva M, Silveira P, Falcão A, Maia J, Loureiro A, Torrão L, Machado R, Wright L, Soares-da-Silva P. Pharmacokinetic-pharmacodynamic interaction between BIA 3-202, a novel COMT inhibitor, and levodopa/carbidopa. Clin Neuropharmacol. 2004 Jan-Feb;27(1):17-24. PubMed PMID: 15090932.