CHEBI:76254 - naproxcinod

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ChEBI Name naproxcinod
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C18H21NO6
Net Charge 0
Average Mass 347.36240
Monoisotopic Mass 347.13689
InChI 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
SMILES COc1ccc2cc(ccc2c1)[C@H](C)C(=O)OCCCCO[N+]([O-])=O
Roles Classification
Chemical Role(s): nitric oxide donor
An agent, with unique chemical structure and biochemical requirements, which generates nitric oxide.
Biological Role(s): non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
EC (prostaglandin-endoperoxide synthase) inhibitor
A compound or agent that combines with cyclooxygenases (EC and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.
Application(s): non-steroidal anti-inflammatory drug
An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
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ChEBI Ontology
Outgoing naproxcinod (CHEBI:76254) has functional parent butane-1,4-diol (CHEBI:41189)
naproxcinod (CHEBI:76254) has functional parent naproxen (CHEBI:7476)
naproxcinod (CHEBI:76254) has role EC (prostaglandin-endoperoxide synthase) inhibitor (CHEBI:35544)
naproxcinod (CHEBI:76254) has role nitric oxide donor (CHEBI:50566)
naproxcinod (CHEBI:76254) has role non-narcotic analgesic (CHEBI:35481)
naproxcinod (CHEBI:76254) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
naproxcinod (CHEBI:76254) has role prodrug (CHEBI:50266)
naproxcinod (CHEBI:76254) is a carboxylic ester (CHEBI:33308)
naproxcinod (CHEBI:76254) is a methoxynaphthalene (CHEBI:48851)
naproxcinod (CHEBI:76254) is a nitrate ester (CHEBI:51080)
4-(nitrooxy)butyl (2S)-2-(6-methoxy-2-naphthyl)propanoate
INNs Sources
naproxcinod KEGG DRUG
naproxcinod WHO MedNet
naproxcinod WHO MedNet
naproxcinodum WHO MedNet
Synonyms Sources
(S)-2-(6-Methoxy-2-naphthyl)propanoic acid 4-nitrooxybutyl ester ChemIDplus
AZD 3582 ChemIDplus
AZD3582 ChemIDplus
HCT 3012 ChemIDplus
Naproxen-N-butyl nitrate ChemIDplus
Nitronaproxen ChemIDplus
Manual Xrefs Databases
4674 DrugCentral
Naproxcinod Wikipedia
US2008269323 Patent
WO2009000723 Patent
WO2012152438 Patent
View more database links
Registry Numbers Types Sources
163133-43-5 CAS Registry Number ChemIDplus
8432594 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017