You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2006-05-18 08:33:38 UTC
Update Date2013-02-09 00:11:01 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
  1. (+)-(S)-Naproxen
  2. (+)-Naproxen
  3. (S)-Naproxen
  4. 2-(6-Methoxy-2-naphthyl)propionic acid
  5. Acusprain
  6. Anexopen
  7. Apronax
  8. Artagen
  9. Arthrisil
  10. Artrixen
  11. Artroxen
  12. Atiflan
  13. Axer
  14. Bipronyl
  15. Calosen
  16. Clinosyn
  17. Congex
  18. D-Naproxen
  19. Danaprox
  20. Daprox
  21. Diocodal
  22. DL Naproxen
  23. DL-Naproxen
  24. Duk
  25. Dysmenalgit
  26. Dysmenalgit N
  27. Ec-Naprosyn
  28. Equiproxen
  29. Flexipen
  30. Floginax
  31. Fuxen
  32. Genoxen
  33. Lefaine
  34. Leniartil
  35. Nafasol
  36. Naixan
  37. Nalyxan
  38. Napflam
  39. Napmel
  40. Naposin
  41. Naprosyne
  42. Naproxen
  43. Naproxen Sodium
  44. Naproxene
  45. Naproxeno
  46. Naproxenum
  47. Novonaprox
  48. Nycopren
  49. Opipramol
Chemical FormulaC14H14O3
Average Molecular Weight230.2592
Monoisotopic Molecular Weight230.094294314
IUPAC Name(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid
Traditional IUPAC 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 KeyCMWTZPSULFXXJA-VIFPVBQESA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassAcenes
Sub ClassNaphthalenes
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Aromatic Homopolycyclic Compounds
  • Phenylacetic Acid Derivatives
  • monocarboxylic acid(ChEBI)
Substituents
  • Alkyl Aryl Ether
  • Anisole
  • Carboxylic Acid
Direct ParentNaphthalenes
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 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 Area46.53ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity64.85ChemAxon
Polarizability24.64ChemAxon
Spectra
SpectraMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Kidney
  • Liver
  • Skin
PathwaysNot 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. Pubmed: 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. Pubmed: 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. Pubmed: 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. Pubmed: 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. Pubmed: 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. Pubmed: 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. Pubmed: 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. Pubmed: 12152004
  9. Hercegova A, Sadecka J, Polonsky J: Determination of some antirheumatics by capillary isotachophoresis. Electrophoresis. 2000 Aug;21(14):2842-7. Pubmed: 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. Pubmed: 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. Pubmed: 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. Pubmed: 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. Pubmed: 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. Pubmed: 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. Pubmed: 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. Pubmed: 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