Record Information
Version1.0
Creation date2011-09-21 00:18:54 UTC
Update date2015-10-09 22:31:18 UTC
Primary IDFDB022741
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNaproxen
DescriptionNaproxen (INN) is a non-steroidal anti-inflammatory drug (NSAID) commonly used for the reduction of mild to moderate pain, fever, inflammation and stiffness caused by conditions such as osteoarthritis, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, injury (like fractures), menstrual cramps, tendonitis, bursitis, and the treatment of primary dysmenorrhea. Naproxen and naproxen sodium are marketed under various trade names including: Aleve, Anaprox, Naprogesic, Naprosyn, Naprelan; Naproxen is a non-steroidal anti-inflammatory drug (NSAID) commonly used for the reduction of mild to moderate pain, fever, inflammation and stiffness caused by conditions such as osteoarthritis, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, injury (like fractures), menstrual cramps, tendonitis, bursitis, and the treatment of primary dysmenorrhea. Naproxen and naproxen sodium are marketed under various trade names including: Aleve, Anaprox, Naprogesic, Naprosyn, Naprelan. Naproxen was first marketed as the prescription drug Naprosyn in 1976 and naproxen sodium was first marketed under the trade name Anaprox in 1980. It remains a prescription-only drug in much of the world. The U.S. Food and Drug Administration (FDA) approved the use of naproxen sodium as an over-the-counter (OTC) drug in 1991, where OTC preparations are sold under the trade name Aleve. In Australia, small packets of lower-strength preparations of naproxen sodium are Schedule 2 Pharmacy Medicines; Naproxen is a member of the 2-arylpropionic acid (profen) family of NSAIDs. It is an odorless, white to off-white crystalline substance. It is lipid-soluble, practically insoluble in water with a low pH (below pH 4), while freely soluble in water at 6 pH and above. Naproxen has a melting point of 153 degree centigrade. [HMDB]
CAS Number22204-53-1
Structure
Thumb
Synonyms
SynonymSource
(+)-(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
d-Naproxenhmdb
Ec-Naprosynhmdb
Naproxenhmdb
Naproxen Sodiumhmdb
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC14H14O3
IUPAC name(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid
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
Isomeric SMILESCOC1=CC2=C(C=C1)C=C(C=C2)[C@H](C)C(O)=O
Average Molecular Weight230.2592
Monoisotopic Molecular Weight230.094294314
Classification
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
Ontology
Disposition

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSNaproxen, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0540-1920000000-dfcdd431a9b1898cd2d2Spectrum
Predicted GC-MSNaproxen, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0079-9840000000-4be264b19923ce29c773Spectrum
Predicted GC-MSNaproxen, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNaproxen, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-001i-0190000000-64cc22cce1238357760e2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0f79-0900000000-17f4e93fda31d93027a12012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0fr6-0900000000-4dd08568cff27d62d8672012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-0910000000-149b16cac2d80de64d8a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-0900000000-e7dfead967f29853140d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-01b9-0900000000-f5f45cee188a08ef62b12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-014i-0900000000-6c076658da1c69f1b9092012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-014i-0900000000-2e1269f26d5b927bca332012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000i-0900000000-68cd0c5a3fcc15470c142012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00di-0900000000-64e5ecb5632e32f89b2d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0910000000-149b16cac2d80de64d8a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0900000000-e7dfead967f29853140d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-01b9-0900000000-f5f45cee188a08ef62b12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-6c076658da1c69f1b9092017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-2e1269f26d5b927bca332017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-000i-0900000000-b913db958cba906732502017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-01b9-0900000000-f35f797484d025dc20132021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-004l-4900000000-e4dd2dd07b393d508ee42021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0390000000-8bab8d5b4ea21227ea6c2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q0-0960000000-f66eabdbaeb345d69ff82017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zi0-0900000000-74f939f129b9072f03152017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0390000000-b9c68cf2920eb7b41eac2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00n0-0950000000-7e56ebeb218436f98f522017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066r-2910000000-2191f1b5cabc1a005c8c2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00n0-0920000000-eca41f81604c834960842021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Spectrum
ChemSpider ID137720
ChEMBL IDCHEMBL154
KEGG Compound IDC01517
Pubchem Compound ID156391
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB08298
HMDB IDHMDB01923
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNPS
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNaproxen
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference