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Human Metabolome Database Version 3.5

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Showing metabocard for Naproxen (HMDB01923)

Record Information
Version 3.5
Creation Date 2006-05-18 02:33:38 -0600
Update Date 2013-02-08 17:11:01 -0700
HMDB ID HMDB01923
Secondary Accession Numbers None
Metabolite Identification
Common Name Naproxen
Description Naproxen (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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C14H14O3
Average Molecular Weight 230.2592
Monoisotopic Molecular Weight 230.094294314
IUPAC Name (2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid
Traditional IUPAC Name naproxen
CAS Registry Number 22204-53-1
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 Key CMWTZPSULFXXJA-VIFPVBQESA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Acenes
Sub Class Naphthalenes
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Aromatic Homopolycyclic Compounds
  • Phenylacetic Acid Derivatives
  • monocarboxylic acid(ChEBI)
Substituents
  • Alkyl Aryl Ether
  • Anisole
  • Carboxylic Acid
Direct Parent Naphthalenes
Ontology
Status Detected and Quantified
Origin
  • Drug
Biofunction Not Available
Application Not Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 153 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 0.0159 mg/mL at 25 °C Not Available
LogP 3.18 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 0.051 g/L ALOGPS
LogP 3.29 ALOGPS
LogP 2.99 ChemAxon
LogS -3.65 ALOGPS
pKa (strongest acidic) 4.19 ChemAxon
pKa (strongest basic) -4.8 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 46.53 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 64.85 ChemAxon
Polarizability 24.64 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies)
MS/MS Spectrum LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies)
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Kidney
  • Liver
  • Skin
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
302.0 +/- 53.0 uM Adult (>18 years old) Female Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022741
KNApSAcK ID Not Available
Chemspider ID 137720 Link_out
KEGG Compound ID C01517 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Naproxen Link_out
NuGOwiki Link HMDB01923 Link_out
Metagene Link HMDB01923 Link_out
METLIN ID 1461 Link_out
PubChem Compound 156391 Link_out
PDB ID NPS Link_out
ChEBI ID 7476 Link_out
References
Synthesis Reference Not 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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  9. Hercegova A, Sadecka J, Polonsky J: Determination of some antirheumatics by capillary isotachophoresis. Electrophoresis. 2000 Aug;21(14):2842-7. Pubmed: 11001292 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
Enzymes
Name: Prostaglandin G/H synthase 2
Reactions:
  • arachidonate + AH2 + 2 O2 = prostaglandin H2 + A + H2O [RN:R01599]
Gene Name: PTGS2
Uniprot ID: P35354 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Prostaglandin G/H synthase 1
Reactions:
  • arachidonate + AH2 + 2 O2 = prostaglandin H2 + A + H2O [RN:R01599]
Gene Name: PTGS1
Uniprot ID: P23219 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA