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Naproxen

Naproxen is a propionic acid derivative and a non-steroidal anti-inflammatory drug (NSAID) with anti-inflammatory, antipyretic and analgesic activities. Naproxen inhibits the activity of the enzymes cyclo-oxygenase I and II, resulting in a decreased formation of precursors of prostaglandins and thromboxanes. The resulting decrease in prostaglandin synthesis is responsible for the therapeutic effects of naproxen. Naproxen also causes a decrease in the formation of thromboxane A2 synthesis, by thromboxane synthase, thereby inhibiting platelet aggregation. It is the product of hydrolysis of Pro-Drugs Naproxen-Methyl-Ester by Hormone-sensitive_lipase_like enzymes. Enantioselective esterification of naproxen by lipases is studied to produce pro-drug

General

Type : Drug, Naphthalen

Chemical_Nomenclature : (2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid

Canonical SMILES : CC(C1=CC2=C(C=C1)C=C(C=C2)OC)C(=O)O

InChI : InChI=1S\/C14H14O3\/c1-9(14(15)16)10-3-4-12-8-13(17-2)6-5-11(12)7-10\/h3-9H,1-2H3,(H,15,16)\/t9-\/m0\/s1

InChIKey : CMWTZPSULFXXJA-VIFPVBQESA-N

Other name(s) : (S)-Naproxen  ||  (+)-Naproxen  ||  Naprosyn  ||  CHEBI:7476  ||  CHEMBL154  ||  SCHEMBL3046  ||  ZINC105216  ||  DB00788

MW : 230.26

Formula : C14H14O3

CAS_number : 22204-53-1

PubChem : 156391, 169118

UniChem : CMWTZPSULFXXJA-VIFPVBQESA-N

Target

Families : 6_AlphaBeta_hydrolase, Canar_LipB, Hormone-sensitive_lipase_like

Protein : bacsu-cbxnp, canar-LipB, 9delt-EstD11

References (6)

Title : Crystal structures of two Bacillus carboxylesterases with different enantioselectivities - Rozeboom_2014_Biochim.Biophys.Acta_1844_567
Author(s) : Rozeboom HJ , Godinho LF , Nardini M , Quax WJ , Dijkstra BW
Ref : Biochimica & Biophysica Acta , 1844 :567 , 2014
Abstract :
PubMedSearch : Rozeboom_2014_Biochim.Biophys.Acta_1844_567
PubMedID: 24418394
Gene_locus related to this paper: bacsu-cbxnp , bacsu-ybfk

Title : Immobilization of Candida rugosa lipase on glass beads for enantioselective hydrolysis of racemic naproxen methyl ester - Yilmaz_2011_Bioresour.Technol_102_499
Author(s) : Yilmaz E , Can K , Sezgin M , Yilmaz M
Ref : Bioresour Technol , 102 :499 , 2011
Abstract :
PubMedSearch : Yilmaz_2011_Bioresour.Technol_102_499
PubMedID: 20846857
Gene_locus related to this paper: canru-1lipa

Title : Efficient production of (S)-naproxen with (R)-substrate recycling using an overexpressed carboxylesterase BsE-NP01 - Liu_2010_Appl.Biochem.Biotechnol_162_1574
Author(s) : Liu X , Xu JH , Pan J , Zhao J
Ref : Appl Biochem Biotechnol , 162 :1574 , 2010
Abstract :
PubMedSearch : Liu_2010_Appl.Biochem.Biotechnol_162_1574
PubMedID: 20237863
Gene_locus related to this paper: bacsu-cbxnp

Title : Lipase-catalyzed esterification of (S)-naproxen ethyl ester in supercritical carbon dioxide - Kwon_2009_J.Microbiol.Biotechnol_19_1596
Author(s) : Kwon CH , Lee JH , Kim SW , Kang JW
Ref : J Microbiol Biotechnol , 19 :1596 , 2009
Abstract :
PubMedSearch : Kwon_2009_J.Microbiol.Biotechnol_19_1596
PubMedID: 20075625
Gene_locus related to this paper: canar-LipB

Title : Hydrolytic resolution of (R,S)-naproxen 2,2,2-trifluoroethyl thioester by Carica papaya lipase in water-saturated organic solvents - Ng_2005_Biotechnol.Bioeng_89_88
Author(s) : Ng IS , Tsai SW
Ref : Biotechnol Bioeng , 89 :88 , 2005
Abstract :
PubMedSearch : Ng_2005_Biotechnol.Bioeng_89_88
PubMedID: 15543625

Title : Lipase-catalyzed naproxen methyl ester hydrolysis in water-saturated ionic liquid: significantly enhanced enantioselectivity and stability - Xin_2005_World.J.Microbiol.Biotechnol_21_193
Author(s) : Xin JY , Zhao YJ , Shi YG , Xia CG , Li SB
Ref : World J Microbiol Biotechnol , 21 :193 , 2005
Abstract :
PubMedSearch : Xin_2005_World.J.Microbiol.Biotechnol_21_193
PubMedID: