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