CHEBI:77428 - nitroflurbiprofen

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ChEBI Name nitroflurbiprofen
ChEBI ID CHEBI:77428
Definition A carboxylic ester obtained by formal condensation of the carboxy group of flurbiprofen with the free hydroxy group of 4-(nitrooxy)butanol. It is a non-steroidal anti-inflammatory agent showing inhibitory effects against the cyclooxygenases COX1 and COX2.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Matthias Ziehm
Supplier Information
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Formula C19H20FNO5
Net Charge 0
Average Mass 361.365
Monoisotopic Mass 361.13255
InChI 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
InChIKey DLWSRGHNJVLJAH-UHFFFAOYSA-N
SMILES C=1C=C(C=CC1)C2=C(F)C=C(C(C(=O)OCCCCO[N+](=O)[O-])C)C=C2
Roles Classification
Biological Role(s): cyclooxygenase 1 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.
cyclooxygenase 2 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
EC 1.14.13.39 (nitric oxide synthase) inhibitor
An EC 1.14.13.* (oxidoreductase acting on paired donors, incorporating 1 atom of oxygen, with NADH or NADPH as one donor) inhibitor that interferes with the action of nitric oxide synthase (EC 1.14.13.39).
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.
vasodilator agent
A drug used to cause dilation of the blood vessels.
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ChEBI Ontology
Outgoing nitroflurbiprofen (CHEBI:77428) has functional parent flurbiprofen (CHEBI:5130)
nitroflurbiprofen (CHEBI:77428) has role cyclooxygenase 1 inhibitor (CHEBI:50630)
nitroflurbiprofen (CHEBI:77428) has role cyclooxygenase 2 inhibitor (CHEBI:50629)
nitroflurbiprofen (CHEBI:77428) has role EC 1.14.13.39 (nitric oxide synthase) inhibitor (CHEBI:61908)
nitroflurbiprofen (CHEBI:77428) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
nitroflurbiprofen (CHEBI:77428) has role vasodilator agent (CHEBI:35620)
nitroflurbiprofen (CHEBI:77428) is a biphenyls (CHEBI:22888)
nitroflurbiprofen (CHEBI:77428) is a carboxylic ester (CHEBI:33308)
nitroflurbiprofen (CHEBI:77428) is a nitrate ester (CHEBI:51080)
nitroflurbiprofen (CHEBI:77428) is a organofluorine compound (CHEBI:37143)
IUPAC Name
4-(nitrooxy)butyl 2-(2-fluorobiphenyl-4-yl)propanoate
Synonyms Sources
4-(Nitrooxy)butyl 2-fluoro-alpha-methyl-(1,1'-biphenyl)-4-acetate ChemIDplus
Flurbinitroxybutylester ChemIDplus
Nitroxybutyl flurbiprofen ChemIDplus
Registry Numbers Types Sources
158836-71-6 CAS Registry Number ChemIDplus
8433798 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
06 July 2016