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Fosphenytoin

ISO 17034:
Catalog Number : CS-ED-02004
CAS Number : 93390-81-9
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What is the Chemical Information of Fosphenytoin?

Chemical Name : Fosphenytoin
Category : API Standards
Synonyms : (2,5-dioxo-4,4-diphenylimidazolidin-1-yl)methyl dihydrogen phosphate
Molecular Weight : 362.27 mol/g
Molecular Formula : C16H15N2O6P

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Fosphenytoin was developed in 1996. On 18 November 2004, Sicor (a subsidiary of Teva) received a tentative approval letter from the United States Food and Drug Administration for a generic version of fosphenytoin.
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Canonical SMILES : C1=CC=C(C=C1)C2(C(=O)N(C(=O)N2)COP(=O)(O)O)C3=CC=CC=C3
Isomeric SMILES : C1=CC=C(C=C1)C2(C(=O)N(C(=O)N2)COP(=O)(O)O)C3=CC=CC=C3
InChI : InChI=1S/C16H15N2O6P/c19-14-16(12-7-3-1-4-8-12,13-9-5-2-6-10-13)17-15(20)18(14)11-24-25(21,22)23/h1-10H,11H2,(H,17,20)(H2,21,22,23)
InchIKey : XWLUWCNOOVRFPX-UHFFFAOYSA-N
Related CAS : 92134-98-0 (di-hydrochloride salt)
IUPAC Name : (2,5-dioxo-4,4-diphenylimidazolidin-1-yl)methyl dihydrogen phosphate
Exact Mass : 362.06677320
Color : White crystals from acetone
Melting Point : 173-176.5 °C
Solubility : Mol wt: 406.24. White crystals as the dihydrate from water-ethanol-acetone, mp 220 °C (softens). pH of a saturated aqueous solution: approx 9. Solubility at 25 °C (mg/mL): 142 in water /Disodium salt/
Use Classification : Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients
Description : Fosphenytoin is an imidazolidine-2,4-dione.
Disposal Methods : SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Vapor Pressure : 6.1X10+11 mm Hg at 25 °C (est)
Toxicity Summary : Nausea, vomiting, lethargy, tachycardia, bradycardia, asystole, cardiac arrest, hypotension, syncope, hypocalcemia, metabolic acidosis, and death have been reported in cases of overdosage with fosphenytoin. The median lethal dose of fosphenytoin given intravenously in mice and rats was 156 mg PE/kg and approximately 250 mg PE/kg, or about 0.6 and 2 times, respectively, the maximum human loading dose on a mg/m2 basis. Signs of acute toxicity in animals included ataxia, labored breathing, ptosis, and hypoactivity.
Antidoteand Emergency Treatment : Since there is no specific antidote for overdose with hydantoin anticonvulsants, treatment is symptomatic and supportive and may include the following. ... Multiple oral doses of charcoal and cathartic may shorten the duration of symptoms. Supportive care - oxygen, vasopressors, and assisted ventilation may be necessary for CNS, respiratory, or cardiovascular depression. Patients in whom intentional overdose is confirmed or suspected should be referred for psychiatric consultation. Following recovery, careful evaluation of blood-forming organs is advisable. /Hydantoin anticonvulsants/
Human Toxicity Excerpts : /CASE REPORTS/ Following surgery for a chronic subdural hematoma, a 74-year-old patient received fosphenytoin as prophylaxis for epilepsy. The patient received 10 times the prescribed dose. This error in the administration of fosphenytoin was facilitated by a confusing labeling of the product. The phenytoin blood level was 79 micrograms.mL-1. The main adverse effect was a coma requiring 5 days of mechanical ventilation. No adverse cardiovascular event was noted. The phenytoin blood levels returned toward the therapeutic range in 8 days. At discharge from the hospital 20 days after surgery, the patient did not have any sequela from the fosphenytoin intoxication.