Nitroflurbiprofen

Orders received during 11/25~11/29 will be shipped in 11/30/2020 due to Thanksgiving holiday.

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

MedKoo CAT#: 529908

CAS#: 158836-71-6

Description: Nitroflurbiprofen is a nitric oxide (NO) donor potentially for the treatment of Paget's disease and overactive bladder.


Price and Availability

Size Price Shipping out time Quantity
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Pricing updated 2020-11-25. Prices are subject to change without notice.

Nitroflurbiprofen is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 529908
Name: Nitroflurbiprofen
CAS#: 158836-71-6
Chemical Formula: C19H20FNO5
Exact Mass: 361.13
Molecular Weight: 361.37
Elemental Analysis: C, 63.15; H, 5.58; F, 5.26; N, 3.88; O, 22.14


Synonym: HCT-1026; NCX-1026; HCT1026; NCX1026; HCT 1026; NCX 1026; NO-flurbiprofen

IUPAC/Chemical Name: 4-(nitrooxy)butyl 2-(2-fluoro-[1,1'-biphenyl]-4-yl)propanoate

InChi Key: DLWSRGHNJVLJAH-UHFFFAOYSA-N

InChi Code: InChI=1S/C19H20FNO5/c1-14(19(22)25-11-5-6-12-26-21(23)24)16-9-10-17(18(20)13-16)15-7-3-2-4-8-15/h2-4,7-10,13-14H,5-6,11-12H2,1H3

SMILES Code: O=C(OCCCCO[N+]([O-])=O)C(C)C1=CC=C(C2=CC=CC=C2)C(F)=C1


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: Laleman W, Van Landeghem L, Van der Elst I, Zeegers M, Fevery J, Nevens F. Nitroflurbiprofen, a nitric oxide-releasing cyclooxygenase inhibitor, improves cirrhotic portal hypertension in rats. Gastroenterology. 2007 Feb;132(2):709-19. PubMed PMID: 17258737.

2: Zacharowski P, Zacharowski K, Donnellan C, Johnston A, Vojnovic I, Forte P, Del Soldato P, Benjamin N, O'Byrne S. The effects and metabolic fate of nitroflurbiprofen in healthy volunteers. Clin Pharmacol Ther. 2004 Oct;76(4):350-8. PubMed PMID: 15470334.

3: Cilurzo F, Selmin F, Vistoli G, Minghetti P, Montanari L. Binary polymeric blends to microencapsulate nitroflurbiprofen: physicochemical and in silico studies. Eur J Pharm Sci. 2007 Jul;31(3-4):202-10. PubMed PMID: 17482436.

4: Scatena R. Nitroflurbiprofen (NicOx). Curr Opin Investig Drugs. 2004 May;5(5):551-6. Review. PubMed PMID: 15202730.

5: Yuan J, Murrell GA, Wei AQ, Appleyard RC, Del Soldato P, Wang MX. Addition of nitric oxide via nitroflurbiprofen enhances the material properties of early healing of young rat Achilles tendons. Inflamm Res. 2003 Jun;52(6):230-7. PubMed PMID: 12835894.

6: Ajmone-Cat MA, Nicolini A, Minghetti L. Differential effects of the nonsteroidal antiinflammatory drug flurbiprofen and its nitric oxide-releasing derivative, nitroflurbiprofen, on prostaglandin E(2), interleukin-1beta, and nitric oxide synthesis by activated microglia. J Neurosci Res. 2001 Nov 15;66(4):715-22. PubMed PMID: 11746392.

7: Fujihara CK, Malheiros DM, Donato JL, Poli A, De Nucci G, Zatz R. Nitroflurbiprofen, a new nonsteroidal anti-inflammatory, ameliorates structural injury in the remnant kidney. Am J Physiol. 1998 Mar;274(3 Pt 2):F573-9. PubMed PMID: 9530274.

8: Wang X. Nitroflurbiprofen NicOx SA. IDrugs. 1998 Nov;1(7):807-12. PubMed PMID: 18465650.

9: Mariotto S, Cuzzolin L, Adami A, Del Soldato P, Suzuki H, Benoni G. Effect of a new non-steroidal anti-inflammatory drug, nitroflurbiprofen, on the expression of inducible nitric oxide synthase in rat neutrophils. Br J Pharmacol. 1995 May;115(2):225-6. PubMed PMID: 7545516; PubMed Central PMCID: PMC1908334.

10: Adami A, Cuzzolin L, Minuz P, Crivellente F, Lechi A, Benoni G. Vasodilating properties of a new non-steroidal anti-inflammatory drug, nitroflurbiprofen, on rat aortic rings. Pharmacol Res. 1996 Apr-May;33(4-5):239-44. PubMed PMID: 8938015.

11: Mariotto S, Menegazzi M, Carcereri de Prati A, Cuzzolin L, Adami A, Suzuki H, Benoni G. Protective effect of NO on gastric lesions and inhibition of expression of gastric inducible NOS by flurbiprofen and its nitro-derivative, nitroflurbiprofen. Br J Pharmacol. 1995 Sep;116(2):1713-4. PubMed PMID: 8528547; PubMed Central PMCID: PMC1909099.

12: Anuar F, Whiteman M, Bhatia M, Moore PK. Flurbiprofen and its nitric oxide-releasing derivative protect against septic shock in rats. Inflamm Res. 2006 Nov;55(11):498-503. PubMed PMID: 17122968.

13: Anuar F, Whiteman M, Siau JL, Kwong SE, Bhatia M, Moore PK. Nitric oxide-releasing flurbiprofen reduces formation of proinflammatory hydrogen sulfide in lipopolysaccharide-treated rat. Br J Pharmacol. 2006 Apr;147(8):966-74. PubMed PMID: 16491094; PubMed Central PMCID: PMC1760720.

14: Flurkey K, Astle CM, Harrison DE. Life extension by diet restriction and N-acetyl-L-cysteine in genetically heterogeneous mice. J Gerontol A Biol Sci Med Sci. 2010 Dec;65(12):1275-84. doi: 10.1093/gerona/glq155. PubMed PMID: 20819793; PubMed Central PMCID: PMC2990268.

15: Strong R, Miller RA, Astle CM, Floyd RA, Flurkey K, Hensley KL, Javors MA, Leeuwenburgh C, Nelson JF, Ongini E, Nadon NL, Warner HR, Harrison DE. Nordihydroguaiaretic acid and aspirin increase lifespan of genetically heterogeneous male mice. Aging Cell. 2008 Oct;7(5):641-50. doi: 10.1111/j.1474-9726.2008.00414.x. PubMed PMID: 18631321; PubMed Central PMCID: PMC2695675.

16: Miller RA, Harrison DE, Astle CM, Floyd RA, Flurkey K, Hensley KL, Javors MA, Leeuwenburgh C, Nelson JF, Ongini E, Nadon NL, Warner HR, Strong R. An Aging Interventions Testing Program: study design and interim report. Aging Cell. 2007 Aug;6(4):565-75. Erratum in: Aging Cell. 2008 Jun;7(3):445. PubMed PMID: 17578509.

17: Huang J, Moochhala SM, Moore PK, Bhatia M. Flurbiprofen and HCT1026 protect mice against acute pancreatitis-associated lung injury. Shock. 2005 Aug;24(2):182-7. PubMed PMID: 16044091.

18: Govoni M, Tocchetti P, Lundberg JO. Metabolism and pathways for denitration of organic nitrates in the human liver. J Pharmacol Exp Ther. 2013 Jul;346(1):96-104. doi: 10.1124/jpet.113.203356. PubMed PMID: 23596058.

19: Gonçalves AR, Fujihara CK, Mattar AL, Malheiros DM, Noronha Ide L, de Nucci G, Zatz R. Renal expression of COX-2, ANG II, and AT1 receptor in remnant kidney: strong renoprotection by therapy with losartan and a nonsteroidal anti-inflammatory. Am J Physiol Renal Physiol. 2004 May;286(5):F945-54. PubMed PMID: 15075190.

20: Okamoto K, Ishiguro T, Midorikawa Y, Ohata H, Izumiya M, Tsuchiya N, Sato A, Sakai H, Nakagama H. miR-493 induction during carcinogenesis blocks metastatic settlement of colon cancer cells in liver. EMBO J. 2012 Apr 4;31(7):1752-63. doi: 10.1038/emboj.2012.25. PubMed PMID: 22373578; PubMed Central PMCID: PMC3321205.