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CHEBI:76254 - naproxcinod

ChEBI IDCHEBI:76254
ChEBI Namenaproxcinod
Stars
DefinitionA 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.
Last Modified22 February 2017
SubmitterSteve
DownloadsMolfile
FormulaC18H21NO6
Net Charge0
Average Mass347.367
Monoisotopic Mass347.13689
SMILESCOc1ccc2cc([C@H](C)C(=O)OCCCCO[N+](=O)[O-])ccc2c1
InChIInChI=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
InChIKeyAKFJWRDCWYYTIG-ZDUSSCGKSA-N
Wikipedia
Roles Classification
Chemical Role:
nitric oxide donor  An agent, with unique chemical structure and biochemical requirements, which generates nitric oxide.
Biological Roles:
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor  A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.
non-narcotic analgesic  A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
Applications:
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.
prodrug  A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
non-narcotic analgesic  A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
ChEBI Ontology
Outgoing Relation(s)
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 1.14.99.1 (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)
IUPAC Name 
4-(nitrooxy)butyl (2S)-2-(6-methoxy-2-naphthyl)propanoate
INNs  Source
naproxcinodKEGG DRUG
naproxcinodWHO MedNet
naproxcinodumWHO MedNet
naproxcinodWHO MedNet
Synonyms  Source
Naproxen-N-butyl nitrateChemIDplus
AZD 3582ChemIDplus
NitronaproxenChemIDplus
HCT 3012ChemIDplus
(S)-2-(6-Methoxy-2-naphthyl)propanoic acid 4-nitrooxybutyl esterChemIDplus
AZD3582ChemIDplus
Manual XrefsDatabases
D09568KEGG DRUG
US2008269323Patent
WO2012152438Patent
WO2009000723Patent
NaproxcinodWikipedia
4674DrugCentral
Registry NumbersSources
Reaxys:8432594Reaxys
CAS:163133-43-5ChemIDplus
Citations