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Fosphenytoin Sodium
Also known as: 92134-98-0, Fosphenytoin disodium salt, Cerebyx, Pro-epanutin, Ci 982, Ci-982
Molecular Formula
C16H13N2Na2O6P
Molecular Weight
406.24  g/mol
InChI Key
GQPXYJNXTAFDLT-UHFFFAOYSA-L
FDA UNII
7VLR55452Z

Fosphenytoin Sodium is the sodium salt form of fosphenytoin, a prodrug that is hydrolyzed to the anticonvulsant phenytoin upon parental administration. Phenytoin exerts its effect most likely through an enhancement of sodium efflux from neurons in the motor cortex. This leads to a suppression of excessive neuronal firing and spread of seizure activity. Other physiologic effects from actions of phenytoin include modulation of the voltage-dependent calcium channels of neurons, inhibition of calcium flux across neuronal membranes and enhancement of sodium-potassium ATPase activity of neurons and glial cells. (NCI05)
1 2D Structure

Fosphenytoin Sodium

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
disodium;(2,5-dioxo-4,4-diphenylimidazolidin-1-yl)methyl phosphate
2.1.2 InChI
InChI=1S/C16H15N2O6P.2Na/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);;/q;2*+1/p-2
2.1.3 InChI Key
GQPXYJNXTAFDLT-UHFFFAOYSA-L
2.1.4 Canonical SMILES
C1=CC=C(C=C1)C2(C(=O)N(C(=O)N2)COP(=O)([O-])[O-])C3=CC=CC=C3.[Na+].[Na+]
2.2 Other Identifiers
2.2.1 UNII
7VLR55452Z
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 3-(hydroxymethyl)phenytoin Disodium Phosphate

2. 3-(hydroxymethyl)phenytoin Phosphate Ester

3. Acc 9653

4. Acc-9653

5. Cerebyx

6. Fosphenytoin

7. Fosphenytoin, Disodium Salt

8. Hmpdp

9. Prodilantin

2.3.2 Depositor-Supplied Synonyms

1. 92134-98-0

2. Fosphenytoin Disodium Salt

3. Cerebyx

4. Pro-epanutin

5. Ci 982

6. Ci-982

7. Fosphenytoin (sodium)

8. Acc-9653

9. Acc-9653-010 (sodium Salt)

10. Disodium;(2,5-dioxo-4,4-diphenylimidazolidin-1-yl)methyl Phosphate

11. Fosphenytoin (disodium)

12. 3-(hydroxymethyl)-5,5-diphenylhydantoin, Disodium Phosphate (ester)

13. 7vlr55452z

14. 92134-98-0 (sodium)

15. Acc-9653-010

16. 2,4-imidazolidinedione, 5,5-diphenyl-3-((phosphonooxy)methyl)-, Disodium Salt

17. Fosphenytoin Disodium

18. Sodium (2,5-dioxo-4,4-diphenylimidazolidin-1-yl)methyl Phosphate

19. Fosphenytoinsodium

20. Acc 9653

21. Fosphenytoin Sodium [usan]

22. Fosphenytoin_sodium

23. Fosphenytoin Disodium Salt Hydrate

24. Acc 9653-010

25. Fostoin

26. Unii-7vlr55452z

27. Fosphenytoin Sodium [usan:usp]

28. Phosphenytoin Sodium

29. Cerebyx (tn)

30. Fosphenytoin Sodium Salt

31. Chembl919

32. Fosphenytoin Sodium (usp)

33. Schembl119417

34. Npc-06

35. Dtxsid1044271

36. Fosphenytoin Sodium [vandf]

37. Bcp13859

38. Fosphenytoin Sodium [mart.]

39. Disodium,(2,5-dioxo-4,4-diphenylimidazolidin-1-yl)methyl Phosphate

40. Fosphenytoin Sodium [usp-rs]

41. Fosphenytoin Sodium [who-dd]

42. 5,5-diphenyl-3-[(phosphonooxy)methyl]-2,4-imidazolidinedione Disodium Salt

43. Akos015915510

44. Ac-1705

45. Fosphenytoin Disodium Salt [mi]

46. Fosphenytoin Sodium [orange Book]

47. Fosphenytoin Sodium [usp Impurity]

48. Fosphenytoin Sodium [usp Monograph]

49. Db-057291

50. Ft-0630980

51. D02096

52. D81920

53. A844152

54. Acc 9653 Pound>>acc9653 Pound>>acc-9653

55. Q27268914

56. Disodium (2,5-dioxo-4,4-diphenyl-1-imidazolidinyl)methyl Phosphate

57. Disodium [2,5-bis(oxidanylidene)-4,4-diphenyl-imidazolidin-1-yl]methyl Phosphate

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 406.24 g/mol
Molecular Formula C16H13N2Na2O6P
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count6
Rotatable Bond Count4
Exact Mass406.03066170 g/mol
Monoisotopic Mass406.03066170 g/mol
Topological Polar Surface Area122 Ų
Heavy Atom Count27
Formal Charge0
Complexity536
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count3
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameCerebyx
PubMed Healthfosphenytoin
Drug ClassesAnticonvulsant
Drug LabelCEREBYX (fosphenytoin sodium injection) is a prodrug intended for parenteral administration; its active metabolite is phenytoin. 1.5 mg of fosphenytoin sodium is equivalent to 1 mg phenytoin sodium, and is referred to as 1 mg phenytoin sodium equiv...
Active IngredientFosphenytoin sodium
Dosage FormInjectable

2 of 4  
Drug NameFosphenytoin sodium
PubMed Healthfosphenytoin
Drug LabelFosphenytoin Sodium Injection, USP is a prodrug intended for parenteral administration; its active metabolite is phenytoin.1.5 mg of fosphenytoin sodium is equivalent to 1 mg phenytoin sodium, and is referred to as 1 mg phenytoin sodium equivalents...
Active IngredientFosphenytoin sodium
Dosage FormInjectable

3 of 4  
Drug NameCerebyx
PubMed Healthfosphenytoin
Drug ClassesAnticonvulsant
Drug LabelCEREBYX (fosphenytoin sodium injection) is a prodrug intended for parenteral administration; its active metabolite is phenytoin. 1.5 mg of fosphenytoin sodium is equivalent to 1 mg phenytoin sodium, and is referred to as 1 mg phenytoin sodium equiv...
Active IngredientFosphenytoin sodium
Dosage FormInjectable

4 of 4  
Drug NameFosphenytoin sodium
PubMed Healthfosphenytoin
Drug LabelFosphenytoin Sodium Injection, USP is a prodrug intended for parenteral administration; its active metabolite is phenytoin.1.5 mg of fosphenytoin sodium is equivalent to 1 mg phenytoin sodium, and is referred to as 1 mg phenytoin sodium equivalents...
Active IngredientFosphenytoin sodium
Dosage FormInjectable

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Sodium Channel Blockers

A class of drugs that act by inhibition of sodium influx through cell membranes. Blockade of sodium channels slows the rate and amplitude of initial rapid depolarization, reduces cell excitability, and reduces conduction velocity. (See all compounds classified as Sodium Channel Blockers.)


Anticonvulsants

Drugs used to prevent SEIZURES or reduce their severity. (See all compounds classified as Anticonvulsants.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Cytochrome P450 1A2 Inducers [MoA]; Cytochrome P450 2B6 Inducers [MoA]; Cytochrome P450 2C19 Inducers [MoA]; Cytochrome P450 2C8 Inducers [MoA]; Cytochrome P450 2C9 Inducers [MoA]; Cytochrome P450 2D6 Inducers [MoA]; Cytochrome P450 3A Inducers [MoA]; Decreased Central Nervous System Disorganized Electrical Activity [PE]; Anti-epileptic Agent [EPC]
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