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Record Information
Version3.6
Creation Date2006-05-18 08:33:38 UTC
Update Date2016-02-11 01:05:07 UTC
HMDB IDHMDB01923
Secondary Accession NumbersNone
Metabolite Identification
Common 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.
Structure
Thumb
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
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
Chemical FormulaC14H14O3
Average Molecular Weight230.2592
Monoisotopic Molecular Weight230.094294314
IUPAC Name(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid
Traditional Namenaproxen
CAS Registry Number22204-53-1
SMILES
COC1=CC2=C(C=C1)C=C(C=C2)[C@H](C)C(O)=O
InChI Identifier
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
InChI KeyInChIKey=CMWTZPSULFXXJA-VIFPVBQESA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as naphthalenes. These 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Drug
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point153 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0159 mg/mL at 25 °CNot Available
LogP3.18HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.051 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity64.85 m3·mol-1ChemAxon
Polarizability24.81 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-001i-0190000000-64cc22cce1238357760eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0f79-0900000000-17f4e93fda31d93027a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0fr6-0900000000-4dd08568cff27d62d867View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-0910000000-149b16cac2d80de64d8aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-0900000000-e7dfead967f29853140dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-01b9-0900000000-f5f45cee188a08ef62b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-014i-0900000000-6c076658da1c69f1b909View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-014i-0900000000-2e1269f26d5b927bca33View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000i-0900000000-68cd0c5a3fcc15470c14View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00di-0900000000-64e5ecb5632e32f89b2dView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Kidney
  • Liver
  • Skin
Pathways
NameSMPDB LinkKEGG Link
Naproxen PathwaySMP00120Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified302.0 +/- 53.0 uMAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022741
KNApSAcK IDNot Available
Chemspider ID137720
KEGG Compound IDC01517
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNaproxen
NuGOwiki LinkHMDB01923
Metagene LinkHMDB01923
METLIN ID1461
PubChem Compound156391
PDB IDNPS
ChEBI ID7476
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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. [1494036 ]
  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. [10430112 ]
  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. [11382293 ]
  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. [8005184 ]
  5. Ozkaya-Bayazit E: Topical provocation in fixed drug eruption due to metamizol and naproxen. Clin Exp Dermatol. 2004 Jul;29(4):419-22. [15245546 ]
  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. [3203059 ]
  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. [15901348 ]
  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. [12152004 ]
  9. Hercegova A, Sadecka J, Polonsky J: Determination of some antirheumatics by capillary isotachophoresis. Electrophoresis. 2000 Aug;21(14):2842-7. [11001292 ]
  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. [8321735 ]
  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. [11304721 ]
  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. [8216382 ]
  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. [10366994 ]
  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. [11022916 ]
  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. [8825200 ]
  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. [9886235 ]

Enzymes

General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular weight:
68995.625
General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82