Naproxen (CHEM017580)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:28:29 UTC
Update Date2016-10-28 10:04:39 UTC
Accession NumberCHEM017580
Identification
Common NameNaproxen
ClassSmall Molecule
DescriptionNaproxen is classified as a nonsteroidal anti-inflammatory dug (NSAID) and was initially approved for prescription use in 1976 and then for over-the-counter (OTC) use in 1994. It can effectively manage acute pain as well as pain related to rheumatic diseases, and has a well studied adverse effect profile. Given it's overall tolerability and effectiveness, naproxen can be considered a first line treatment for a variety of clinical situations requiring analgesia. Naproxen is available in both immediate and delayed release formulations, in combination with sumatriptan to treat migraines, and in combination with esomeprazole to lower the risk of developing gastric ulcers.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • Suspected Compounds
  • Suspected Compounds - Waste Water
  • Suspected Compounds – Schymanski Project
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-(S)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acidChEBI
(+)-(S)-NaproxenChEBI
(+)-2-(6-Methoxy-2-naphthyl)propionic acidChEBI
(+)-2-(Methoxy-2-naphthyl)-propionic acidChEBI
(+)-2-(Methoxy-2-naphthyl)-propionsaeureChEBI
(+)-NaproxenChEBI
(S)-(+)-2-(6-Methoxy-2-naphthyl)propionic acidChEBI
(S)-(+)-NaproxenChEBI
(S)-2-(6-Methoxy-2-naphthyl)propanoic acidChEBI
(S)-2-(6-Methoxy-2-naphthyl)propionic acidChEBI
(S)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acidChEBI
(S)-NaproxenChEBI
NaproxeneChEBI
NaproxenoChEBI
NaproxenumChEBI
NaprosynKegg
(+)-(S)-6-Methoxy-a-methyl-2-naphthaleneacetateGenerator
(+)-(S)-6-Methoxy-a-methyl-2-naphthaleneacetic acidGenerator
(+)-(S)-6-Methoxy-alpha-methyl-2-naphthaleneacetateGenerator
(+)-(S)-6-Methoxy-α-methyl-2-naphthaleneacetateGenerator
(+)-(S)-6-Methoxy-α-methyl-2-naphthaleneacetic acidGenerator
(+)-2-(6-Methoxy-2-naphthyl)propionateGenerator
(+)-2-(Methoxy-2-naphthyl)-propionateGenerator
(S)-(+)-2-(6-Methoxy-2-naphthyl)propionateGenerator
(S)-2-(6-Methoxy-2-naphthyl)propanoateGenerator
(S)-2-(6-Methoxy-2-naphthyl)propionateGenerator
(S)-6-Methoxy-a-methyl-2-naphthaleneacetateGenerator
(S)-6-Methoxy-a-methyl-2-naphthaleneacetic acidGenerator
(S)-6-Methoxy-alpha-methyl-2-naphthaleneacetateGenerator
(S)-6-Methoxy-α-methyl-2-naphthaleneacetateGenerator
(S)-6-Methoxy-α-methyl-2-naphthaleneacetic acidGenerator
2-(6-Methoxy-2-naphthyl)propionic acidHMDB
AcusprainHMDB
AnexopenHMDB
ApronaxHMDB
ArtagenHMDB
ArthrisilHMDB
ArtrixenHMDB
ArtroxenHMDB
AtiflanHMDB
AxerHMDB
BipronylHMDB
CalosenHMDB
ClinosynHMDB
CongexHMDB
D-NaproxenHMDB
DanaproxHMDB
DaproxHMDB
DiocodalHMDB
DL NaproxenHMDB
DL-NaproxenHMDB
DukHMDB
DysmenalgitHMDB
Dysmenalgit NHMDB
Ec-naprosynHMDB
EquiproxenHMDB
FlexipenHMDB
FloginaxHMDB
FuxenHMDB
GenoxenHMDB
LefaineHMDB
LeniartilHMDB
NafasolHMDB
NaixanHMDB
NalyxanHMDB
NapflamHMDB
NapmelHMDB
NaposinHMDB
NaprosyneHMDB
Naproxen sodiumHMDB
NovonaproxHMDB
NycoprenHMDB
OpipramolHMDB
AnaproxHMDB
MethoxypropiocinHMDB
NaprosinHMDB
ProxenHMDB
AleveHMDB
Sodium, naproxenHMDB
MNPAHMDB
SynflexHMDB
Naproxenate, sodiumHMDB
Sodium naproxenateHMDB
Chemical FormulaC14H14O3
Average Molecular Mass230.259 g/mol
Monoisotopic Mass230.094 g/mol
CAS Registry Number22204-53-1
IUPAC Name(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid
Traditional Namenaproxen
SMILESCOC1=CC2=C(C=C1)C=C(C=C2)[C@H](C)C(O)=O
InChI IdentifierInChI=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
InChI KeyCMWTZPSULFXXJA-VIFPVBQESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNot Available
Direct ParentNaphthalenes
Alternative Parents
Substituents
  • Naphthalene
  • Anisole
  • Alkyl aryl ether
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.051 g/LALOGPS
logP3.29ALOGPS
logP2.99ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)4.19ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity64.85 m³·mol⁻¹ChemAxon
Polarizability24.81 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0540-1920000000-dfcdd431a9b1898cd2d2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0079-9840000000-4be264b19923ce29c773Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-001i-0190000000-64cc22cce1238357760eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0f79-0900000000-17f4e93fda31d93027a1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0fr6-0900000000-4dd08568cff27d62d867Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-0910000000-149b16cac2d80de64d8aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-0900000000-e7dfead967f29853140dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-01b9-0900000000-f5f45cee188a08ef62b1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-014i-0900000000-6c076658da1c69f1b909Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-014i-0900000000-2e1269f26d5b927bca33Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000i-0900000000-68cd0c5a3fcc15470c14Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00di-0900000000-64e5ecb5632e32f89b2dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0910000000-149b16cac2d80de64d8aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0900000000-e7dfead967f29853140dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-01b9-0900000000-f5f45cee188a08ef62b1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-6c076658da1c69f1b909Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-2e1269f26d5b927bca33Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-000i-0900000000-b913db958cba90673250Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-01b9-0900000000-f35f797484d025dc2013Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-004l-4900000000-e4dd2dd07b393d508ee4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0390000000-8bab8d5b4ea21227ea6cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q0-0960000000-f66eabdbaeb345d69ff8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zi0-0900000000-74f939f129b9072f0315Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0390000000-b9c68cf2920eb7b41eacSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00n0-0950000000-7e56ebeb218436f98f52Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066r-2910000000-2191f1b5cabc1a005c8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00n0-0920000000-eca41f81604c83496084Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
StatusValueUnitSample LocationReference
DrugBank IDDB00788
HMDB IDHMDB0001923
FooDB IDFDB022741
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID1461
PDB IDNot Available
Wikipedia LinkNaproxen
Chemspider ID137720
ChEBI ID7476
PubChem Compound ID156391
Kegg Compound IDC01517
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Haupt D, Pettersson C, Westerlund D: Separation of (R)- and (S)-naproxen using micellar chromatography and an alpha 1-acid-glycoprotein column: application for chiral monitoring in human liver microsomes by coupled-column chromatography. J Biochem Biophys Methods. 1992 Dec;25(4):273-84.
2. Rossat J, Maillard M, Nussberger J, Brunner HR, Burnier M: Renal effects of selective cyclooxygenase-2 inhibition in normotensive salt-depleted subjects. Clin Pharmacol Ther. 1999 Jul;66(1):76-84.
3. Cakrt M, Hercegova A, Lesko J, Polonsky J, Sadecka J, Skacani I: Isotachophoretic determination of naproxen in the presence of its metabolite in human serum. J Chromatogr A. 2001 May 4;916(1-2):207-14.
4. Bertin P, Lapicque F, Payan E, Rigaud M, Bailleul F, Jaeger S, Treves R, Netter P: Sodium naproxen: concentration and effect on inflammatory response mediators in human rheumatoid synovial fluid. Eur J Clin Pharmacol. 1994;46(1):3-7.
5. Ozkaya-Bayazit E: Topical provocation in fixed drug eruption due to metamizol and naproxen. Clin Exp Dermatol. 2004 Jul;29(4):419-22.
6. Bruno R, Iliadis A, Jullien I, Guego M, Pinhas H, Cunci S, Cano JP: Naproxen kinetics in synovial fluid of patients with osteoarthritis. Br J Clin Pharmacol. 1988 Jul;26(1):41-4.
7. Fagerholm U, Breuer O, Swedmark S, Hoogstraate J: Pre-clinical pharmacokinetics of the cyclooxygenase-inhibiting nitric oxide donor (CINOD) AZD3582. J Pharm Pharmacol. 2005 May;57(5):587-97.
8. Schwartz JI, Vandormael K, Malice MP, Kalyani RN, Lasseter KC, Holmes GB, Gertz BJ, Gottesdiener KM, Laurenzi M, Redfern KJ, Brune K: Comparison of rofecoxib, celecoxib, and naproxen on renal function in elderly subjects receiving a normal-salt diet. Clin Pharmacol Ther. 2002 Jul;72(1):50-61.
9. Hercegova A, Sadecka J, Polonsky J: Determination of some antirheumatics by capillary isotachophoresis. Electrophoresis. 2000 Aug;21(14):2842-7.
10. Jick H, Derby LE, Garcia Rodriguez LA, Jick SS, Dean AD: Nonsteroidal antiinflammatory drugs and certain rare, serious adverse events: a cohort study. Pharmacotherapy. 1993 May-Jun;13(3):212-7.
11. Toothaker RD, Barker SH, Gillen MV, Helsinger SA, Kindberg CG, Hunt TL, Powell JH: Absence of pharmacokinetic interaction between orally co-administered naproxen sodium and diphenhydramine hydrochloride. Biopharm Drug Dispos. 2000 Sep;21(6):229-33.
12. el Mouelhi M, Beck S, Bock KW: Stereoselective glucuronidation of (R)- and (S)-naproxen by recombinant rat phenol UDP-glucuronosyltransferase (UGT1A1) and its human orthologue. Biochem Pharmacol. 1993 Oct 5;46(7):1298-300.
13. van Hecken A, Depre M, Wynants K, Vanbilloen H, Verbruggen A, Arnout J, Vanhove P, Cariou R, De Schepper PJ: Effect of clopidogrel on naproxen-induced gastrointestinal blood loss in healthy volunteers. Drug Metabol Drug Interact. 1998;14(3):193-205.
14. Mikami E, Goto T, Ohno T, Matsumoto H, Nishida M: Simultaneous analysis of naproxen, nabumetone and its major metabolite 6-methoxy-2-naphthylacetic acid in pharmaceuticals and human urine by high-performance liquid chromatography. J Pharm Biomed Anal. 2000 Oct;23(5):917-25.
15. Rodrigues AD, Kukulka MJ, Roberts EM, Ouellet D, Rodgers TR: [O-methyl 14C]naproxen O-demethylase activity in human liver microsomes: evidence for the involvement of cytochrome P4501A2 and P4502C9/10. Drug Metab Dispos. 1996 Jan;24(1):126-36.
16. Albrecht C, Melgert BN, Reichen J, Poelstra K, Meijer DK: Effect of chronic bile duct obstruction and LPS upon targeting of naproxen to the liver using naproxen-albumin conjugate. J Drug Target. 1998;6(2):105-17.
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=18044350
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=24478225
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=9784154