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)
- IUPAC Standard InChIKey: CXOFVDLJLONNDW-UHFFFAOYSA-N
- 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
The 3d structure may be viewed using Java or Javascript. - 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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Phase change data
Go To: Top, Gas Chromatography, 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 fusion
| ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 9.58 | 568.8 | DSC | Wassvik, Holmén, et al., 2006 | See also Wassvik, Holmén, et al., 2008. |
| 11.25 | 570.8 | DSC | Nokhodchi, Bolourtchian, et al., 2003 | |
| 8.674 | 574. | N/A | Ohm and Lippold, 1985 |
Gas Chromatography
Go To: Top, Phase change data, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Capillary | DB-5 | 220. | 2369. | Phillips, Logan, et al., 1990 | 15. m/0.25 mm/0.2 μm, He |
| Capillary | BP-1 | 275. | 2350. | Japp, Gill, et al., 1987 | 25. m/0.22 mm/0.25 μm, N2 |
| Capillary | BP-1 | 275. | 2365. | Japp, Gill, et al., 1987 | 25. m/0.53 mm/1. μm, N2 |
| Capillary | SPB-1 | 250. | 2347. | Lora-Tamayo, Rams, et al., 1986 | He; Column length: 25. m; Column diameter: 0.20 mm |
| Packed | OV-1 | 250. | 2340. | Berninger and Möller, 1977 |
Kovats' RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | SE-30 | 2308. | Schepers, Wijsbeek, et al., 1982 | 25. m/0.49 mm/1.14 μm, 100. C @ 2. min, 8. K/min, 275. C @ 15. min |
Kovats' RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Packed | OV-1 | 2380. | Berninger, Grunnagel, et al., 1975 | N2, Chromosorb G, AW-DMCS; Column length: 2. m; Program: not specified |
| Packed | OV-1 | 2360. | Berninger, Grunnagel, et al., 1975 | N2, Chromosorb G, AW-DMCS; Column length: 2. m; Program: not specified |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | SPB-1 | 2310. | Christ, Noomano, et al., 1988 | 30. m/0.75 mm/1.0 μm, He, 10. K/min, 280. C @ 12. min; Tstart: 160. C |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-1 | 2292. | Sharp, 1987 | 15. m/0.25 mm/0.25 μm, He, 130. C @ 1. min, 10. K/min, 290. C @ 10. min |
| Packed | OV-1 | 2385. | Marozzi, Gambaro, et al., 1982 | Gas Chrom P, 5. K/min; Column length: 2. m; Tstart: 150. C; Tend: 300. C |
| Packed | SE-30 | 2310. | Marozzi, Gambaro, et al., 1982 | Gas Chrom P, 5. K/min; Column length: 2. m; Tstart: 150. C; Tend: 300. C |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | BP-1 | 2335. | Stowell and Wilson, 1985 | 12. m/0.22 mm/0.25 μm, He; Program: not specified |
| Other | Methyl Silicone | 2330. | Ardrey and Moffat, 1981 | Program: not specified |
References
Go To: Top, Phase change data, 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]
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, 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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