Compound: Naproxcinod
SMILES: O=[N+](OCCCCOC(=O)[C@H](c1cc2c(cc(OC)cc2)cc1)C)[O-]
InChIKey: AKFJWRDCWYYTIG-ZDUSSCGKSA-N
Synonyms: Naproxcinod, 163133-43-5, Nitronaproxen, AZD3582, naproxen-n-butyl nitrate, HCT 3012, NO-naproxen, AZD-3582, HCT-3012, AR-P900758XX, AZD 3582, naproxcinodum, V24GR4LI3I, 4-(Nitrooxy)butyl (2S)-2-(6-methoxynaphthalen-2-yl)propanoate, HCT3012, (S)-2-(6-Methoxy-2-naphthyl)propanoic acid 4-nitrooxybutyl ester, CHEBI:76254, DTXSID20167523, 4-nitrooxybutyl (2S)-2-(6-methoxynaphthalen-2-yl)propanoate, NicOx, 2-Naphthaleneacetic acid, 6-methoxy-alpha-methyl-, 4-(nitrooxy)butyl ester, (alphaS)-, nitric oxide naproxen, nitric oxide-releasing naproxen, RefChem:832053, DTXCID3090014, M01AE18, 4-(nitrooxy)butyl-(2S)-2-(6-methoxy-2-naphthyl)propanoate, 2-Naphthaleneacetic Acid, 6-Methoxy-Alpha-Methyl-, 4-(Nitrooxy)Butyl Ester, (Alpha-S)-, 4-nitrooxybutyl (2S)-2-(6-methoxy-2-naphthyl)propanoate, 4-(NITROOXY)BUTYL (2S)-2-(6-METHOXY-2-NAPHTHYL)PROPANOATE, Naproxcinod [USAN], Naproxcinod [USAN:INN], UNII-V24GR4LI3I, HCT 3012; Naproxcinod; Nitronaproxen, NAPROXCINOD [MI], NAPROXCINOD [INN], Naproxcinod (USAN/INN), Naproxen nitroxybutyl ester, NAPROXCINOD [WHO-DD], GTPL9551, orb1695959, SCHEMBL1170879, CHEMBL2103831, SCHEMBL29663794, AKFJWRDCWYYTIG-ZDUSSCGKSA-N, 4-(nitrooxy)butyl (S)-2-(6-methoxynaphthalen-2-yl)propanoate, MFCD08705752, AKOS015914063, AKOS015994779, AKOS040753214, DB06682, ME-0138, ZD-3582, AC-23946, HY-14931, DB-228899, CS-0003642, NS00068606, D09568, E87348, Q3335996, 4-(nitrooxy)butyl(2s)-2-(6-methoxy-2-naphthyl)propanoate, 4-(nitrooxy)butyl-(2s)-2-(6-methoxy-2 naphthyl)propanoate, (S)-2-(6-Methoxy-2-naphtyl) propionic acid 4-nitrooxybutyl ester, 2-Naphthaleneacetic acid, 6-methoxy-alpha-methyl-, 4-(nitrooxy)butyl ester, (S)-, 2-NAPHTHALENEACETIC ACID, 6-METHOXY-.ALPHA.-METHYL-, 4-(NITROOXY)BUTYL ESTER, (.ALPHA.S)-
Theoretical properties:
molecular_formula: C18H21NO6
molecular_weight: 347.4 g/mol
exact_mass: 347.13688739 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 9
heavy_atom_count: 25
topological_polar_surface_area: 90.6 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Naproxcinod is a carboxylic ester obtained by formal condensation of the carboxy group of naproxen with the hydroxy group of 4-(nitrooxy)butanol. A cyclooxygenase-inhibiting nitric oxide donator that is metabolised to naproxen and a nitric oxide donating moiety, effective in treatment of osteoarthritis. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor, a prodrug and a nitric oxide donor. It is a carboxylic ester, a methoxynaphthalene and a nitrate ester. It is functionally related to a butane-1,4-diol and a naproxen.
chebi: A carboxylic ester obtained by formal condensation of the carboxy group of naproxen with the hydroxy group of 4-(nitrooxy)butanol. A cyclooxygenase-inhibiting nitric oxide donator that is metabolised to naproxen and a nitric oxide donating moiety, effective in treatment of osteoarthritis.
chembl: NAPROXCINOD is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: 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.
In December 2006, Scientific American distinguished naproxcinod as one of the ten most promising treatments for the world's biggest health threats. However, in 2010 the U.S. Food and Drug Administration determined that further clinical trials would be needed to obtain approval.