Nebicapone
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MedKoo CAT#: 528423

CAS#: 274925-86-9

Description: 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.


Price and Availability

Size Price Shipping out time Quantity
5mg USD 430 2 Weeks
25mg USD 1000 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-09-28. Prices are subject to change without notice.

Nebicapone (BIA-3202), purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 528423
Name: Nebicapone
CAS#: 274925-86-9
Chemical Formula: C14H11NO5
Exact Mass: 273.0637
Molecular Weight: 273.244
Elemental Analysis: C, 61.54; H, 4.06; N, 5.13; O, 29.28


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-]


Technical Data

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


References

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.