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Phenytoin sodium

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Name

Phenytoin sodium

EINECS 211-148-2
CAS No. 630-93-3 Density N/A
PSA 49.41000 LogP 2.21300
Solubility aqueous base: soluble Melting Point 290-299oC
Formula C15H11N2NaO2 Boiling Point 428.2 °C at 760 mmHg
Molecular Weight 274.254 Flash Point 212.8 °C
Transport Information UN 2811 6.1/PG 3 Appearance White powder.
Safety 22-36/37/39-45 Risk Codes 22-43-62-63
Molecular Structure Molecular Structure of 630-93-3 (Phenytoin sodium) Hazard Symbols HarmfulXn
Synonyms

2,4-Imidazolidinedione,5,5-diphenyl-, monosodium salt (9CI);5,5-Diphenylhydantoin sodium;Aleviatin sodium;Difenin;Ditoin;Enkefal;Epanutin;Epilan D;Eptoin;Hydantin;M-toin;Phenyloin;Prompt;Sodium5,5-diphenyl-2,4-imidazolidinedione;Sodiumdiphenylhydantoin;Sodium phenytoin;

Article Data 3

Phenytoin sodium Chemical Properties

Molecular Structure:

Molecular Formula: C15H12N2NaO2
Molecular Weight: 275.2577
IUPAC Name: Sodium 5,5-diphenylimidazolidin-3-ide-2,4-dione
Synonyms of Dilantin (CAS NO.630-93-3): 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 ; Diphenylhydantoin, sodium salt ; Phenytoin, sodium salt
CAS NO: 630-93-3
Classification Code: Anticonvulsant ; Drug / Therapeutic Agent ; Human Data ; Mutation data ; Reproductive Effect ; Tumor data 
 
H bond acceptors: 4
H bond donors: 2
Freely Rotating Bonds: 2
Polar Surface Area: 40.62 Å2 
Solubility: aqueous base soluble
Merck: 7322

Phenytoin sodium Uses

  Dilantin (CAS NO.630-93-3) 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.
 

Phenytoin sodium Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 90mg/kg (90mg/kg) CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BLOOD: HEMORRHAGE
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) CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
American Journal of Emergency Medicine. Vol. 6, Pg. 255, 1988.
man LDLo intravenous 12571ug/kg/25 (12.571mg/kg) CARDIAC: PULSE RATE

CARDIAC: OTHER CHANGES

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
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) BEHAVIORAL: ANOREXIA (HUMAN

GASTROINTESTINAL: NAUSEA OR VOMITING

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

BLOOD: HEMORRHAGE

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Archives of Dermatology and Syphilology. Vol. 46, Pg. 856, 1942.
women TDLo oral 4mg/kg/D (4mg/kg) ENDOCRINE: OTHER CHANGES

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
JAMA, Journal of the American Medical Association. Vol. 176, Pg. 491, 1961.
women TDLo oral 148mg/kg/28D- (148mg/kg) BEHAVIORAL: HEADACHE

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
Archives of Neurology and Psychiatry. Vol. 45, Pg. 769, 1941.

Phenytoin sodium Consensus Reports

IARC Cancer Review: Animal Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 13 , 1977,p. 201.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory.

Phenytoin sodium Safety Profile

Confirmed carcinogen. Experimental teratogen. Other experimental reproductive effects. Poison by ingestion, subcutaneous, intravenous, and intraperitoneal routes. Human systemic effects by ingestion: anorexia, respiratory depression, nausea or vomiting, hemorrhage, dermatitis, and endocrine effects. Mutation data reported. An anticonvulsant and cardiac depressant used for the treatment of grand mal and psychomotor seizures. When heated to decomposition it emits very toxic fumes of NOx and Na2O.
Safety Information of Dilantin (CAS NO.630-93-3):
Hazard Codes : HarmfulXn 
Risk Statements : 22-43-62-63 (  Harmful if swallowed;May cause sensitization by skin contact;Possible risk of impaired fertility ;Possible risk of harm to the unborn child  )Safety Statements : 22-36/37/39-45 (Do not breathe dust ;Wear suitable protective clothing, gloves and eye/face protection ; In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) ) 
RIDADR : UN 2811 6.1/PG 3
WGK Germany : 3
RTECS :MU1400000
HazardClass : 6.1(b)
PackingGroup:III
 

Phenytoin sodium Specification

Production methods of Dilantin (CAS NO.630-93-3):
Benzaldehyde by condensation and oxidation in conjunction benzoyl, and then with urea rearrangement, cyclization to be phenytoin. Water, urea and inter-benzoyl turn to join Fan Yingguo, stirring heated to 98 ℃, with 30% NaOH, reflux 1.5h. Add water and a small amount of carbon bleaching, cold to 26-28 ℃, filtration, the filtrate with 5% hydrochloric acid to pH = 5-6, temperature 45-55 ℃, filtration, water washing, was phenytoin. Phenytoin into the heated lye dissolved, adjust pH with sodium hydroxide solution to 11-11.5, plus live Blues Wong, Mandala charcoal decolorization and a half hours at 75-80 ℃. Pressure filtration, cooling to 37-38 ℃, adding seed crystals placed. Cooling to 25 ℃ filtration, crystallization with distilled water washing, drying, grinding, drying at about 80 ℃, may phenytoin.

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