Naproxen

• Formula: C₁₄H₁₄O₃
• Molecular weight: 230.2592
• IUPAC Standard InChI: 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-/m1/s1 Copy

  
• IUPAC Standard InChIKey: CMWTZPSULFXXJA-SECBINFHSA-N Copy
• CAS Registry Number: 22204-53-1
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Stereoisomers:
  • (±)-2-(6-methoxy-2-naphthyl)propionic acid
• Other names: 2-Naphthaleneacetic acid, 6-methoxy-α-methyl-, (S)-; (+)-6-Methoxy-α-methyl-2-naphthaleneacetic acid; Propionic acid, 2-(6-methoxy-2-naphthyl)-, (+)-; CG 3117; Equiproxen; Floginax; (S)-6-Methoxy-α-methyl-2-naphthalene acetic acid; (+)-2-(Methoxy-2-naphthyl)-propionic acid; d-2-(6-Methoxy-2-naphthyl)propionic acid; d-2-(6'-Methoxy-2'-naphthyl)-propionsaeure; (+)-2-(Methoxy-2-naphthyl)-propionsaeure; MNPA; Naixan; 2-Naphthaleneacetic acid, 6-methoxy-α-methyl-, (+)-; Naprosine; Naprosyn; Naprux; Naxen; Naxyn; Proxen; RS-3540; (+)-6-Methoxy-α-methyl-2-napthaleneacetic acid; Bonyl; Diocodal; Dysmenalgit; Laraflex; Laser; Napren; Naprium; Naprius; Naprosyne; Nycopren; Panoxen; Prexan; Proxine; Reuxen; Veradol; Xenar; 2-(6-Methoxy-2-naphthyl)propanoic acid , (+)-; (S)-(+)-Naproxen; (+)-2-(6-Methoxy-2-naphthyl)propionic acid; (+)-Naproxen; (S)-2-(6-Methoxy-2-naphthyl)propionic acid; (S)-Naproxen; Apo-Naproxen; d-Naproxen; (S)-(+)-2-(6-METHOXY-2-NAPHTHYL)PROPIONIC ACID; 6-Methoxy-α-methyl-2-naphthaleneacetic acid (naproxen)
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Phase change data
  • References
  • Notes
• Other data available:
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Options:
  • Switch to calorie-based units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Phase change data

Go To: Top, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: William E. Acree, Jr., James S. Chickos

Enthalpy of sublimation

Enthalpy of fusion

References

Go To: Top, Phase change data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Perlovich, Kurkov, et al., 2004
Perlovich, German L.; Kurkov, Sergey V.; Kinchin, Andrey N.; Bauer-Brandl, Annette, Thermodynamics of solutions III: comparison of the solvation of (+)-naproxen with other NSAIDs, European Journal of Pharmaceutics and Biopharmaceutics, 2004, 57, 2, 411-420, https://doi.org/10.1016/j.ejpb.2003.10.021 . [all data]

Wassvik, Holmén, et al., 2006
Wassvik, Carola M.; Holmén, Anders G.; Bergström, Christel A.S.; Zamora, Ismael; Artursson, Per, Contribution of solid-state properties to the aqueous solubility of drugs, European Journal of Pharmaceutical Sciences, 2006, 29, 3-4, 294-305, https://doi.org/10.1016/j.ejps.2006.05.013 . [all data]

Neau, Bhandarkar, et al., 1997
Neau, Steven H.; Bhandarkar, Satej V.; Hellmuth, Eckhard W., Pharmaceutical Research, 1997, 14, 5, 601-605, https://doi.org/10.1023/A:1012148910975 . [all data]

Claramonte, Vialard, et al., 1993
Claramonte, M.D. Contreras; Vialard, A. Parera; Vilchez, F. Girela, An application of regular solution theory in the study of the solubility of naproxen in some solvents used in topical preparations, International Journal of Pharmaceutics, 1993, 94, 1-3, 23-30, https://doi.org/10.1016/0378-5173(93)90005-Z . [all data]

Notes

Go To: Top, Phase change data, References

• Symbols used in this document:
  

  ΔfusH	Enthalpy of fusion
  ΔsubH	Enthalpy of sublimation

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.