Phenytoin

• Formula: C₁₅H₁₂N₂O₂
• Molecular weight: 252.2680
• IUPAC Standard InChI: InChI=1S/C15H12N2O2/c18-13-15(17-14(19)16-13,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H,(H2,16,17,18,19) Copy

  
• IUPAC Standard InChIKey: CXOFVDLJLONNDW-UHFFFAOYSA-N Copy
• CAS Registry Number: 57-41-0
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Other names: 2,4-Imidazolidinedione, 5,5-diphenyl-; Hydantoin, 5,5-diphenyl-; Aleviatin; Denyl; Di-Hydan; Di-Lan; Dihycon; Dilabid; Dintoina; Diphantoin; Diphedan; Diphenine; Diphenylhydantoin; DPH; Lepitoin; Phenytoine; Sodanton; Zentropil; 5,5-Diphenyl-2,4-Imidazolidinedione; 5,5-Diphenylhydantoin; Auranile; Causoin; Comitoina; Convul; Danten; Dantinal; Dantoinal; Dantoinal klinos; Di-Phetine; Didan TDC 250; Difenilhidantoina; Difenin; Difetoin; Difhydan; Dihydantoin; Dilantin; Dilantin acid; Dilantine; Dillantin; Dintoin; Diphedal; Diphenin; Diphentyn; Diphenylan; Diphenylhydatanoin; Ditoinate; Ekko; Ekko capsules; Elepsindon; Enkelfel; Epamin; Epasmir "5"; Epdantoine simple; Epelin; Epifenyl; Epihydan; Epilan-D; Epilantin; Epinat; Epised; Eptal; Fenidantoin "s"; Fenitoina; Fentoin; Fenylepsin; Fenytoine; Gerot-epilan-D; Hidan; Hidantilo; Hidantina; Hidantina senosian; Hidantina vitoria; Hidantomin; Hindatal; Hydantal; Hydantin; Hydantoinal; Ictalis simple; Idantoil; Idantoin; Kessodanten; Labopal; Lehydan; Lepsin; Neos-Hidantoina; Neosidantoina; Novantoina; Om hidantoina simple; Om-Hydantoine; Oxylan; Phanantin; Phanatine; Phenatine; Phenatoine; Phentoin; Ritmenal; Saceril; Sanepil; Silantin; Sodantoin; Solantin; Sylantoic; Thilophenyl; Toin unicelles; TOIN; Zentronal; 5,5-Diphenylimidazolidin-2,4-dione; Citrulliamon; Dantoine; Diphentoin; Diphenylhydantoine; 5,5-Dwufenylohydantoina; Epanutin; Eptoin; Hidantal; Minetoin; NCI-C55765; Phenitoin; Solantoin; Solantyl; Diphenat; 5,5-Diphenyl-1H-imidazolidine-2,4-dione; Epasmir ''5''; Fenidantoin ''s''; Mebroin (Salt/Mix); Antisacer (Salt/Mix); Aladdin (Salt/Mix); Alepsin (Salt/Mix); Fenigramon (Salt/Mix); Soluble phenytoin (Salt/Mix); Tacosal (Salt/Mix); Epdantoin (Salt/Mix); Epileptin (Salt/Mix); Episar (Salt/Mix); Epsolin (Salt/Mix); Citrullamon (Salt/Mix); 5,5-Diphenyl-2,4-imidazolidinedione (phenytoin)
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• Information on this page:
  • Phase change data
  • UV/Visible spectrum
  • 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 by: William E. Acree, Jr., James S. Chickos

Enthalpy of fusion

UV/Visible spectrum

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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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

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, isothermal

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Kovats' RI, non-polar column, temperature ramp

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

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, temperature ramp

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

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References

Go To: Top, Phase change data, UV/Visible spectrum, Gas Chromatography, Notes

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

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]

Wassvik, Holmén, et al., 2008
Wassvik, Carola M.; Holmén, Anders G.; Draheim, Rieke; Artursson, Per; Bergström, Christel A.S., Molecular Characteristics for Solid-State Limited Solubility, J. Med. Chem., 2008, 51, 10, 3035-3039, https://doi.org/10.1021/jm701587d . [all data]

Nokhodchi, Bolourtchian, et al., 2003
Nokhodchi, A.; Bolourtchian, N.; Dinarvand, R., Crystal modification of phenytoin using different solvents and crystallization conditions, International Journal of Pharmaceutics, 2003, 250, 1, 85-97, https://doi.org/10.1016/S0378-5173(02)00488-X . [all data]

Ohm and Lippold, 1985
Ohm, A.; Lippold, B.C., Surface tension of solid drugs and its correlation with solubility, Int. J. Pharm. Tech. Prod. Mfg., 1985, 6, 4, 1. [all data]

Lang (editor), 1967
Lang (editor), L., Absorption Spectra in the Ultraviolet and Visible Region, 1967, 8, 313. [all data]

Phillips, Logan, et al., 1990
Phillips, A.M.; Logan, B.K.; Stafford, D.T., Further applications for capillary gas chromatography in routine quantitative toxicological analyses, J. Hi. Res. Chromatogr., 1990, 13, 11, 754-758, https://doi.org/10.1002/jhrc.1240131106 . [all data]

Japp, Gill, et al., 1987
Japp, M.; Gill, R.; Osselton, M.D., Comparison of drug retention indices determined on packed, wide bore capillary and narrow bore capillary columns, J. Forensic Sci., 1987, 32, 6, 1574-1586. [all data]

Lora-Tamayo, Rams, et al., 1986
Lora-Tamayo, C.; Rams, M.A.; Chacon, J.M.R., Gas Chromatographic Data for 187 Nitrogen- or Phosphorus-Containing Drugs and Metabolites of Toxicological Interest Analysed on Methyl Silicone Capillary Columns, J. Chromatogr., 1986, 374, 73-85, https://doi.org/10.1016/S0378-4347(00)83254-5 . [all data]

Berninger and Möller, 1977
Berninger, H.; Möller, M.R., Retentionsindices zur gaschromatographischen Identifizierung von Arzneimitteln, Arch. Toxicol., 1977, 37, 4, 295-305, https://doi.org/10.1007/BF00330821 . [all data]

Schepers, Wijsbeek, et al., 1982
Schepers, P.; Wijsbeek, J.; Franke, J.P.; de Zeeuw, R.A., Applicability of capillary gas chromatography to substance identification in toxicology by means of retention indices, J. Forensic Sci., 1982, 27, 1, 49-60. [all data]

Berninger, Grunnagel, et al., 1975
Berninger, H.; Grunnagel, R.; Mall, S.; Moller, M.R., Gas chromatographic identification of unknown substances from body fluids by menas of retention indices, Beitr. Gerichtl. Med., 1975, 33, 185-191. [all data]

Christ, Noomano, et al., 1988
Christ, D.W.; Noomano, P.; Rosas, M.; Rhone, D., Retention indices by wide-bore capillary gas chromatography with nitrogen-phosphorus detection, J. Anal. Toxicol., 1988, 12, 2, 84-88, https://doi.org/10.1093/jat/12.2.84 . [all data]

Sharp, 1987
Sharp, M.E., A rapid screening procedure for acidic and neutral drugs in blood by high resolution gas chromatography, J. Anal. Toxicol., 1987, 11, 1, 8-11, https://doi.org/10.1093/jat/11.1.8 . [all data]

Marozzi, Gambaro, et al., 1982
Marozzi, E.; Gambaro, V.; Saligari, E.; Mariani, R.; Lodi, F., Use of the retention index in gas chromatographic studies of drugs, J. Anal. Toxicol., 1982, 6, 4, 185-192, https://doi.org/10.1093/jat/6.4.185 . [all data]

Stowell and Wilson, 1985
Stowell, A.; Wilson, L., Use of retention indices in drug screening by capillary gas chromatography, Rep. # CD 2362, Department of Scientific and Industrial Reseach, Chemistry Division, Lower Hutt, NZ, 1985, 32. [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

Go To: Top, Phase change data, UV/Visible spectrum, Gas Chromatography, References

• Symbols used in this document:
  

  ΔfusH

  Enthalpy of fusion

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