Naproxcinod

Naproxcinod
Clinical data
Other namesAZD-3582, HCT-3012
ATC code
Identifiers
  • 4-nitrooxybutyl (2S)-2-(6-methoxynaphthalen-2-yl)propanoate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H21NO6
Molar mass347.367 g·mol−1
3D model (JSmol)
  • C[C@@H](C1=CC2=C(C=C1)C=C(C=C2)OC)C(=O)OCCCCO[N+](=O)[O-]
  • InChI=1S/C18H21NO6/c1-13(18(20)24-9-3-4-10-25-19(21)22)14-5-6-16-12-17(23-2)8-7-15(16)11-14/h5-8,11-13H,3-4,9-10H2,1-2H3/t13-/m0/s1 ☒N
  • Key:AKFJWRDCWYYTIG-ZDUSSCGKSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Naproxcinod (nitronaproxen) is a nonsteroidal anti-inflammatory drug (NSAID) developed by the French pharmaceutical company NicOx. It is a derivative of naproxen with a nitroxybutyl ester to allow it to also act as a nitric oxide (NO) donor. This second mechanism of action makes naproxcinod the first in a new class of drugs, the cyclooxygenase inhibiting nitric oxide donators (CINODs), that are hoped to produce similar analgesic efficacy to traditional NSAIDs, but with less gastrointestinal and cardiovascular side effects.[1][2]

In December 2006, Scientific American distinguished naproxcinod as one of the ten most promising treatments for the world's biggest health threats.[3] However, in 2010 the U.S. Food and Drug Administration determined that further clinical trials would be needed to obtain approval.[4]

  1. ^ Ellis JL, Augustyniak ME, Cochran ED, Earl RA, Garvey DS, Gordon LJ, et al. (2005). "NMI-1182, a gastro-protective cyclo-oxygenase-inhibiting nitric oxide donor". Inflammopharmacology. 12 (5–6): 521–534. doi:10.1163/156856005774382661. PMID 16259719. S2CID 3231846.
  2. ^ Cirino G, Distrutti E, Wallace JL (April 2006). "Nitric oxide and inflammation". Inflammation & Allergy - Drug Targets. 5 (2): 115–119. CiteSeerX 10.1.1.628.532. doi:10.2174/187152806776383143. PMID 16613570.
  3. ^ Special Report: 10 Promising Treatments for World's Biggest Health Threats, By Charles Q. Choi. 2006
  4. ^ Cite error: The named reference FDA-2010 was invoked but never defined (see the help page).