Nitecapone | OR-462 | CAS#116313-94-1 | COMT inhibitor

MedKoo Cat#: 328037 | Name: Nitecapone

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Description:

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

Nitecapone, also known as OR-462, is a catechol-O-methyltransferase inhibitor potentially for the treatment of peptic ulcer. Nitecapone reduces development and symptoms of neuropathic pain after spinal nerve ligation in rats. Nitecapone reduces cardiac neutrophil accumulation in clinical open heart surgery. Nitecapone inhibits myeloperoxidase in vitro and enhances functional performance after 8 h of ischemia in experimental heart transplantation.

Chemical Structure

Nitecapone

CAS#116313-94-1

Theoretical Analysis

MedKoo Cat#: 328037

Name: Nitecapone

CAS#: 116313-94-1

Chemical Formula: C12H11NO6

Exact Mass: 265.0586

Molecular Weight: 265.22

Elemental Analysis: C, 54.34; H, 4.18; N, 5.28; O, 36.19

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 210.00
10mg	USD 360.00
25mg	USD 690.00

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Related CAS #

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Synonym

Nitecapone; OR-462; OR 462; OR462.

IUPAC/Chemical Name

3-(3,4-Dihydroxy-5-nitrobenzylidene)-2,4-pentanedione

InChi Key

UPMRZALMHVUCIN-UHFFFAOYSA-N

InChi Code

InChI=1S/C12H11NO6/c1-6(14)9(7(2)15)3-8-4-10(13(18)19)12(17)11(16)5-8/h3-5,16-17H,1-2H3

SMILES Code

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

Nitecapone (OR-462) is an orally active and short-acting catechol-O-methyltransferase (COMT) inhibitor.

In vitro activity:

The present study was executed to evaluate the effect of NC (nitecapone) on preservation of grafts in heart transplantation and the role of NC in the inhibition of granulocyte infiltration. In vitro studies demonstrated that NC inhibits 50% of purified MPO activity at a concentration of 10 microM. Reference: Res Exp Med (Berl). 1999 Apr;198(6):299-306. https://pubmed.ncbi.nlm.nih.gov/10369086/

In vivo activity:

Both nitecapone treatments significantly reduced mechanical allodynia and withdrawal thresholds were 80-95% higher compared with the control group. In the acetone test, both nitecapone groups also showed less signs of cold allodynia than the control groups. In nitecapone-naïve rats a single dose of nitecapone also reduced mechanical allodynia on the 14th day after the surgery. Reference: Eur J Pain. 2011 Aug;15(7):732-40. https://pubmed.ncbi.nlm.nih.gov/21216640/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	113.11
	DMSO	40.0	150.82
	DMSO:PBS (pH 7.2) (1:1)	0.5	1.89
	Ethanol	5.0	18.85

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 265.22 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. Vento AE, Rämö OJ, Nemlander AT, Ahotupa M, Nissinen E, Holopainen A, Mattila SP. Nitecapone inhibits myeloperoxidase in vitro and enhances functional performance after 8 h of ischemia in experimental heart transplantation. Res Exp Med (Berl). 1999 Apr;198(6):299-306. doi: 10.1007/s004330050113. PMID: 10369086. 2. Pentikäinen MO, Lindstedt KA, Kovanen PT. Inhibition of the oxidative modification of LDL by nitecapone. Arterioscler Thromb Vasc Biol. 1995 Jun;15(6):740-7. doi: 10.1161/01.atv.15.6.740. PMID: 7773727. 3. Kambur O, Männistö PT, Pusa AM, Käenmäki M, Kalso EA, Kontinen VK. Nitecapone reduces development and symptoms of neuropathic pain after spinal nerve ligation in rats. Eur J Pain. 2011 Aug;15(7):732-40. doi: 10.1016/j.ejpain.2010.12.001. Epub 2011 Jan 8. PMID: 21216640. 4. Singh A, Kulkarni SK. Nitecapone and selegiline as effective adjuncts to L-DOPA in reserpine-induced catatonia in mice. Methods Find Exp Clin Pharmacol. 2002 Jan-Feb;24(1):23-9. doi: 10.1358/mf.2002.24.1.677124. PMID: 11980384.

In vitro protocol:

In vivo protocol:

1. Kambur O, Männistö PT, Pusa AM, Käenmäki M, Kalso EA, Kontinen VK. Nitecapone reduces development and symptoms of neuropathic pain after spinal nerve ligation in rats. Eur J Pain. 2011 Aug;15(7):732-40. doi: 10.1016/j.ejpain.2010.12.001. Epub 2011 Jan 8. PMID: 21216640. 2. Singh A, Kulkarni SK. Nitecapone and selegiline as effective adjuncts to L-DOPA in reserpine-induced catatonia in mice. Methods Find Exp Clin Pharmacol. 2002 Jan-Feb;24(1):23-9. doi: 10.1358/mf.2002.24.1.677124. PMID: 11980384.

1: Kambur O, Männistö PT, Pusa AM, Käenmäki M, Kalso EA, Kontinen VK. Nitecapone reduces development and symptoms of neuropathic pain after spinal nerve ligation in rats. Eur J Pain. 2011 Aug;15(7):732-40. doi: 10.1016/j.ejpain.2010.12.001. PubMed PMID: 21216640. 2: Singh A, Kulkarni SK. Nitecapone and selegiline as effective adjuncts to L-DOPA in reserpine-induced catatonia in mice. Methods Find Exp Clin Pharmacol. 2002 Jan-Feb;24(1):23-9. PubMed PMID: 11980384. 3: Pertovaara A, Wei H, Kalmari J, Ruotsalainen M. Pain behavior and response properties of spinal dorsal horn neurons following experimental diabetic neuropathy in the rat: modulation by nitecapone, a COMT inhibitor with antioxidant properties. Exp Neurol. 2001 Feb;167(2):425-34. PubMed PMID: 11161631. 4: Vainikka T, Heikkilä L, Toivonen HJ, Rämö J, Hyytinen TA, Mattila SP. The effect of nitecapone on early graft function in experimental single lung transplantation. Scand Cardiovasc J. 2000 Aug;34(4):415-20. PubMed PMID: 10983677. 5: Vento AE, Aittomäki J, Verkkala KA, Heikkilä LJ, Salo JA, Sipponen J, Rämö OJ. Nitecapone as an additive to crystalloid cardioplegia in patients who had coronary artery bypass grafting. Ann Thorac Surg. 1999 Aug;68(2):413-20. PubMed PMID: 10475405. 6: Pesonen EJ, Vento AE, Rämo J, Vuorte J, Jansson SE, Repo H. Nitecapone reduces cardiac neutrophil accumulation in clinical open heart surgery. Anesthesiology. 1999 Aug;91(2):355-61. PubMed PMID: 10443596. 7: Vento AE, Rämö OJ, Nemlander AT, Ahotupa M, Nissinen E, Holopainen A, Mattila SP. Nitecapone inhibits myeloperoxidase in vitro and enhances functional performance after 8 h of ischemia in experimental heart transplantation. Res Exp Med (Berl). 1999 Apr;198(6):299-306. PubMed PMID: 10369086. 8: Vento AE, Rämö OJ, Pesonen EJ, Heikkilä L, Nissinen E, Holopainen A, Mattila SP. The Effect of Nitecapone, a New Antioxidant, on Myocardial Function After Aortic Cross-clamping in Experimental Heart Ischemia. Int J Angiol. 1999 Jan;8(1):16-21. PubMed PMID: 9826401. 9: Lautala P, Kivimaa M, Salomies H, Elovaara E, Taskinen J. Glucuronidation of entacapone, nitecapone, tolcapone, and some other nitrocatechols by rat liver microsomes. Pharm Res. 1997 Oct;14(10):1444-8. PubMed PMID: 9358559. 10: Vento AE, Rämö OJ, Nemlander AT, Nissinen E, Holopainen A, Mattila SP. Nitecapone is of benefit to functional performance in experimental heart transplantation. Res Exp Med (Berl). 1997;197(3):137-46. PubMed PMID: 9406281. 11: Haramaki N, Stewart DB, Aggarwal S, Kawabata T, Packer L. Role of ascorbate in protection by nitecapone against cardiac ischemia-reperfusion injury. Biochem Pharmacol. 1995 Sep 7;50(6):839-43. PubMed PMID: 7575646. 12: Pentikäinen MO, Lindstedt KA, Kovanen PT. Inhibition of the oxidative modification of LDL by nitecapone. Arterioscler Thromb Vasc Biol. 1995 Jun;15(6):740-7. PubMed PMID: 7773727. 13: Nissinen E, Lindén IB, Pohto P. Antioxidant properties of nitecapone are potentiated by glutathione. Biochem Mol Biol Int. 1995 Feb;35(2):387-95. PubMed PMID: 7663394. 14: Marcocci L, Maguire JJ, Packer L. Nitecapone: a nitric oxide radical scavenger. Biochem Mol Biol Int. 1994 Oct;34(3):531-41. PubMed PMID: 7833830. 15: Salmela KS, Roine RP, Höök-Nikanne J, Kosunen TU, Salaspuro M. Effect of bismuth and nitecapone on acetaldehyde production by Helicobacter pylori. Scand J Gastroenterol. 1994 Jun;29(6):528-31. PubMed PMID: 8079111. 16: Wikberg T, Vuorela A. Metabolite profiles of two [14C]-labelled catechol O-methyltransferase inhibitors, nitecapone and entacapone, in rat and mouse urine and rat bile. Eur J Drug Metab Pharmacokinet. 1994 Apr-Jun;19(2):125-35. PubMed PMID: 8001593. 17: Marcocci L, Suzuki YJ, Tsuchiya M, Packer L. Antioxidant activity of nitecapone and its analog OR-1246: effect of structural modification on antioxidant action. Methods Enzymol. 1994;234:526-41. PubMed PMID: 7808329. 18: Tu Y, Ranta S, Nissinen E, Lindén IB. Protection by nitecapone against sodium taurocholate-induced damage to cultured gastric cells. Dig Dis Sci. 1993 Apr;38(4):701-7. PubMed PMID: 7681749. 19: Slomiany BL, Murty VL, Piotrowski J, Morita M, Slomiany A. Glycosulfatase activity of Helicobacter pylori towards gastric sulfomucin: effect of nitecapone. J Physiol Pharmacol. 1993 Mar;44(1):7-16. PubMed PMID: 8518427. 20: Valenza M, Serbinova E, Packer L, Khwaja S, Catudioc J. Nitecapone protects the Langendorff perfused heart against ischemia-reperfusion injury. Biochem Mol Biol Int. 1993 Mar;29(3):443-9. Erratum in: Biochem Mol Biol Int 1993 May;30(1):197. PubMed PMID: 8485462.