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Substance Name: Phenytoin sodium [USP:JAN]
RN: 630-93-3
UNII: 4182431BJH
InChIKey: FJPYVLNWWICYDW-UHFFFAOYSA-M

Note

  • An anticonvulsant that is used in a wide variety of seizures. It is also an anti-arrhythmic and a muscle relaxant. The mechanism of therapeutic action is not clear, although several cellular actions have been described including effects on ion channels, active transport, and general membrane stabilization. The mechanism of its muscle relaxant effect appears to involve a reduction in the sensitivity of muscle spindles to stretch. Phenytoin has been proposed for several other therapeutic uses, but its use has been limited by its many adverse effects and interactions with other drugs.

Molecular Formula

  • C15-H12-N2-O2.Na

Molecular Weight

  • 274.2539
 

Classification Codes

  • Anticonvulsant
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Reproductive Effect
  • Tumor Data

Names and Synonyms

Name of Substance

  • Phenytoin sodium [USP:JAN]

Synonyms

  • 2,4-Imidazolidinedione, 5,5-diphenyl-, monosodium salt
  • 5,5-Diphenylhydantoin sodium
  • 5,5-Diphenylhydantoin sodium salt
  • Aladdin
  • Alepsin
  • Aleviatin sodium
  • Antilepsin
  • Antisacer
  • Auranile
  • Citrullamon
  • Cumatil
  • Danten
  • Dantoin
  • Decatona
  • Denyl
  • Denyl sodium
  • Derizene
  • Di-len
  • Difenin
  • Difetoin
  • Difhydan
  • Dihydan
  • Dilantin
  • Dilantin Infatabs
  • Dilantin Injection
  • Dilantin sodium
  • Dilantin Suspension
  • Diphantoine
  • Diphedan
  • Diphenin
  • Diphenine
  • Diphenine sodium
  • Diphentoin
  • Diphenylan sodium
  • Diphenylhydantoin sodium
  • Ditoin
  • Ditomed
  • EINECS 211-148-2
  • Enkefal
  • Epanutin
  • Epdantoin
  • Epelin
  • Epilan-D
  • Epilantin-E
  • Epileptin
  • Epinat
  • Episar
  • Epsolin
  • Eptoin
  • Eptolin
  • Extended Phenytoin sodium
  • Fenidantoin
  • Fenigramon
  • Fenitoin sodium
  • Fenitoina Sodica
  • Fenitron
  • Fenytoin
  • Hidantal sodium
  • Hidantin
  • Hydantin
  • Hydantoin, 5,5-diphenyl-, sodium salt
  • Hydantoinal
  • Lepitoin sodium
  • Metinal Idantoina
  • Minetoin
  • Muldis
  • Novodiphenyl
  • OM-Hydantoine sodium
  • Phenilep
  • Phenytek
  • Phenytex
  • Phenytoin sodium
  • Phenytoin sodium salt
  • Prompt Phenytoin sodium
  • SDPH
  • Sodium 5,5-diphenyl hydantoinate
  • Sodium 5,5-diphenyl-2,4-imidazolidinedione
  • Sodium 5,5-diphenylhydantoinate
  • Sodium diphenyl hydantoinate
  • Sodium diphenylhydantoin
  • Sodium phenytoin
  • Solantoin
  • Solantyl
  • Soluble phenytoin
  • Tacosal
  • UNII-4182431BJH

Systematic Names

  • 2,4-Imidazolidinedione, 5,5-diphenyl-, monosodium salt
  • 2,4-Imidazolidinedione, 5,5-diphenyl-, sodium salt (1:1)
  • Hydantoin, 5,5-diphenyl-, monosodium salt
  • Phenytoin sodium

Superlist Names

  • Diphenylhydantoin, sodium salt
  • Phenytoin, sodium salt

Registry Numbers

CAS Registry Number

  • 630-93-3

FDA UNII

  • 4182431BJH

Other Registry Numbers

  • 1421-15-4
  • 143-75-9
  • 8017-52-5

System Generated Number

  • 0000630933

Molecular Formulas

Molecular Formula

  • C15-H12-N2-O2.Na

Molecular Formula Fragments

  • C15-H12-N2-O2
  • COMPONENT
  • Na

Structure Descriptors

InChI

1S/C15H12N2O2.Na/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);/q;+1/p-1

InChIKey

FJPYVLNWWICYDW-UHFFFAOYSA-M

Smiles

c1ccc(cc1)C2(C(=O)[N-]C(=O)N2)c3ccccc3.[Na+]

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 90mg/kg (90mg/kg) BLOOD: HEMORRHAGE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

CARDIAC: OTHER CHANGES
Archives of Pathology. Vol. 28, Pg. 761, 1939.
guinea pig LD50 subcutaneous 280mg/kg (280mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 137, Pg. 375, 1962.
guinea pig LDLo intravenous 38600ug/kg (38.6mg/kg)   Farmaco, Edizione Pratica. Vol. 35, Pg. 49, 1980.
man LDLo intravenous 7143ug/kg/14M (7.143mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

CARDIAC: OTHER CHANGES
American Journal of Emergency Medicine. Vol. 6, Pg. 255, 1988.
man LDLo intravenous 12571ug/kg/25 (12.571mg/kg) CARDIAC: OTHER CHANGES

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

CARDIAC: PULSE RATE
American Journal of Emergency Medicine. Vol. 6, Pg. 255, 1988.
man LDLo oral 647mg/kg/21W- (647mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE" Archives of Internal Medicine. Vol. 81, Pg. 605, 1948.
man LDLo unreported 29mg/kg (29mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
man TDLo oral 70mg/kg/17D-I (70mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: ANOREXIA (HUMAN

SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE"
New England Journal of Medicine. Vol. 242, Pg. 897, 1950.
mouse LD50 intraperitoneal 103mg/kg (103mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 30, Pg. 12, 1980.
mouse LD50 intravenous 98mg/kg (98mg/kg)   Farmaco, Edizione Pratica. Vol. 35, Pg. 49, 1980.
mouse LD50 oral 165mg/kg (165mg/kg)   Indian Journal of Experimental Biology. Vol. 19, Pg. 1047, 1981.
mouse LD50 subcutaneous 400mg/kg (400mg/kg)   Biochemical Pharmacology. Vol. 17, Pg. 369, 1968.
mouse LD50 unreported 540mg/kg (540mg/kg)   United States Patent Document. Vol. #4056540,
rabbit LDLo intravenous 157mg/kg (157mg/kg)   Farmaco, Edizione Pratica. Vol. 35, Pg. 49, 1980.
rat LD50 intraperitoneal 138mg/kg (138mg/kg)   Indian Journal of Physiology and Pharmacology. Vol. 10, Pg. 5, 1966.
rat LD50 intravenous 90mg/kg (90mg/kg)   Acta Pharmaceutica Jugoslavica. Vol. 37, Pg. 123, 1987.
rat LD50 oral 1530mg/kg (1530mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 138, Pg. 224, 1962.
rat LD50 subcutaneous 230mg/kg (230mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 56, Pg. 377, 1960.
rat LD50 unreported 153mg/kg (153mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Journal of Pharmacy and Pharmacology. Vol. 14, Pg. 253, 1962.
women LDLo oral 78mg/kg (78mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

BLOOD: HEMORRHAGE
Archives of Dermatology and Syphilology. Vol. 46, Pg. 856, 1942.
women TDLo oral 4mg/kg/D (4mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

ENDOCRINE: OTHER CHANGES
JAMA, Journal of the American Medical Association. Vol. 176, Pg. 491, 1961.
women TDLo oral 148mg/kg/28D- (148mg/kg)   Archives of Neurology and Psychiatry. Vol. 45, Pg. 769, 1941.
women TDLo oral 148mg/kg/28D- (148mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

BEHAVIORAL: HEADACHE
Archives of Neurology and Psychiatry. Vol. 45, Pg. 769, 1941.