Indomethacin

• Formula: C₁₉H₁₆ClNO₄
• Molecular weight: 357.788
• IUPAC Standard InChI: InChI=1S/C19H16ClNO4/c1-11-15(10-18(22)23)16-9-14(25-2)7-8-17(16)21(11)19(24)12-3-5-13(20)6-4-12/h3-9H,10H2,1-2H3,(H,22,23) Copy

  
• IUPAC Standard InChIKey: CGIGDMFJXJATDK-UHFFFAOYSA-N Copy
• CAS Registry Number: 53-86-1
• Chemical structure:
  This structure is also available as a 2d Mol file
• Other names: 1H-Indole-3-acetic acid, 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-; Indole-3-acetic acid, 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-; Amuno; Artrinovo; Artrivia; Confortid; Dolovin; Idomethine; Inacid; Indacin; Indo-Rectolmin; Indocid; Indocin; Indomecol; Indomed; Indomee; Indometacin; Indomethacine; Infrocin; Metacen; Metartril; Methazine; Metindol; Mezolin; Reumacide; Sadoreum; Artracin; N-p-Chlorbenzoyl-5-methoxy-2-methylindole-3-acetic acid; 1-(p-Chlorobenzoyl)-5-methoxy-2-methylindole-3-acetic acid; (1-p-Chlorobenzoyl-5-methoxy-2-methylindol-3-yl)acetic acid; 1-(p-Chlorobenzoyl)-2-methyl-5-methoxyindole-3-acetic acid; 1-(p-Chlorobenzoyl)-2-methyl-5-methoxy-3-indole-acetic acid; α-(1-(p-Chlorobenzoyl)-2-methyl-5-methoxy-3-indolyl)acetic acid; 1-p-Cloro-benzoil-5-metoxi-2-metilindol-3-acido acetico; Imbrilon; Indometacine; Indometacyna; Indomethazine; Indometicina; Indoptic; Indo-tablinen; Inflazon; Inteban sp; Kwas 1-(p-chlorobenzoilo)-2-metylo-5-metoksy-3-indolilooctowy; Lausit; Mikametan; Mobilan; NCI-C56144; Tannex; 1-(p-Chlorobenzoyl)-5-methoxy-2-methylindol-3-acetic acid; Argun; Bonidin; Catlep; Chibro-amuno; Chrono-indicid; Dolcidium; Durametacin; Elmetacin; Indo-phlogont; Indomethine; Indomod; Indoptol; Indorektal; Indoxen; Miametan; Rheumacin LA; Vonum; 1-(4-Chlorobenzoyl)-5-methoxy-2-methylindole-3-acetic acid; 1-(4-Chlorobenzoyl)-2-methyl-5-methoxyindole-3-acetic acid; 1-(p-Chlorobenzoyl)-5-methoxy-2-methyl-3-indolylacetic acid; Innamit; Inteban; N-(p-Chlorobenzoyl)-2-methyl-5-methoxy-3-indolylacetic acid; Indonol; Indocollyre; 1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-acetic acid (indomethacin)
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• Information on this page:
  • Phase change data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Mass spectrum (electron ionization)
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Phase change data

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

Data compiled as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of fusion

Gas Chromatography

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

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, custom temperature program

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Normal alkane RI, non-polar column, custom temperature program

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References

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

Grady, Hays, et al., 1973
Grady, L.T.; Hays, S.E.; King, R.H.; Klein, H.R.; Mader, W.J.; Wyatt, D.K.; Zimmere, R.O., Drug purity profiles, J. Pharm. Sci., 1973, 62, 459. [all data]

Aceves-Hernandez, Nicolás-Vázquez, et al., 2009
Aceves-Hernandez, J.M.; Nicolás-Vázquez, I.; Aceves, F.J.; Hinojosa-Torres, J.; Paz, M.; Castaño, V.M., Indomethacin polymorphs: Experimental and conformational analysis, J. Pharm. Sci., 2009, 98, 7, 2448-2463, https://doi.org/10.1002/jps.21626 . [all data]

Murdande, Pikal, et al., 2009
Murdande, Sharad B.; Pikal, Michael J.; Shanker, Ravi M.; Bogner, Robin H., Solubility advantage of amorphous pharmaceuticals: I. A thermodynamic analysis, J. Pharm. Sci., 2009, 99, 3, 1254-1264, https://doi.org/10.1002/jps.21903 . [all data]

Basavoju, Boström, et al., 2008
Basavoju, Srinivas; Boström, Dan; Velaga, Sitaram P., Indomethacin--Saccharin Cocrystal: Design, Synthesis and Preliminary Pharmaceutical Characterization, Pharm Res, 2008, 25, 3, 530-541, https://doi.org/10.1007/s11095-007-9394-1 . [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]

Legendre and Feutelais, 2004
Legendre, B.; Feutelais, Y., Polymorphic and Thermodynamic Study of Indomethacin, Journal of Thermal Analysis and Calorimetry, 2004, 76, 1, 255-264, https://doi.org/10.1023/B:JTAN.0000027824.55280.37 . [all data]

Bergström, Wassvik, et al., 2007
Bergström, Christel A.S.; Wassvik, Carola M.; Johansson, Kajsa; Hubatsch, Ina, Poorly Soluble Marketed Drugs Display Solvation Limited Solubility, J. Med. Chem., 2007, 50, 23, 5858-5862, https://doi.org/10.1021/jm0706416 . [all data]

Hancock and Parks, 2000
Hancock, Bruno C.; Parks, Michael, Organometallics, 2000, 17, 4, 397-404, https://doi.org/10.1023/A:1007516718048 . [all data]

McLinden and Stenhouse, 1979
McLinden, V.J.; Stenhouse, A.M., A chromatography system for drug identification, Forensic Sci. Int., 1979, 13, 71-79, https://doi.org/10.1016/0379-0738(79)90265-2 . [all data]

Ardrey and Moffat, 1981
Ardrey, R.E.; Moffat, A.C., Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase, J. Chromatogr., 1981, 220, 3, 195-252, https://doi.org/10.1016/S0021-9673(00)81925-1 . [all data]

Notes

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• Symbols used in this document:
  

  Tfus	Fusion (melting) point
  ΔfusH	Enthalpy of fusion

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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