Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0751)
Drug Name
Fosphenytoin sodium
Synonyms
Fosphenytoin (disodium); Fosphenytoin (sodium); Fosphenytoin disodium; Fosfenitoina; Fosfenitoina [INN-Spanish]; Fosphenytoin; Fosphenytoin (INN); Fosphenytoin [INN:BAN]; Fosphenytoine; Fosphenytoine [INN-French]; Fosphenytoinum; Fosphenytoinum [INN-Latin]; Prodilantin; (2,5-dioxo-4,4-diphenylimidazolidin-1-yl)methyl dihydrogen phosphate; (3-Phosphoryloxymethyl)phenytoin; 2,4-Imidazolidinedione, 5,5-diphenyl-3-((phosphonooxy)methyl)-; 2,4-Imidazolidinedione, 5,5-diphenyl-3-((phosphonooxy)methyl)-, (SP-4-2)-; 93390-81-9; B4SF212641; CHEBI:5165; HMPDP; UNII-B4SF212641; Fosphenytoin disodium salt; Fosphenytoin sodium; Fosphenytoin sodium [USAN]; Fosphenytoin_Sodium; Fostoin; Pro-Epanutin; fospenytoin; 2,4-Imidazolidinedione, 5,5-diphenyl-3-((phosphonooxy)methyl)-, disodium salt; 3-(Hydroxymethyl)-5,5-diphenylhydantoin, disodium phosphate (ester); 7VLR55452Z; 92134-98-0; ACC 9653; ACC 9653-010; ACC-9653-010; CI 982; CI-982; UNII-7VLR55452Z; disodium;(2,5-dioxo-4,4-diphenylimidazolidin-1-yl)methyl phosphate
Indication Epilepsy [ICD11: 8A60] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 406.24 Topological Polar Surface Area 122
Heavy Atom Count 27 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
56338
CAS Number
92134-98-0
TTD Drug ID
D0J5YC
Formula
C16H13N2Na2O6P
Canonical SMILES
C1=CC=C(C=C1)C2(C(=O)N(C(=O)N2)COP(=O)([O-])[O-])C3=CC=CC=C3.[Na+].[Na+]
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
InChIKey
GQPXYJNXTAFDLT-UHFFFAOYSA-L
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
3-hydroxymethylphenytoin DM002065
161366
Hydrolysis - Hydrolysis 1 [5]
Phenytoin DM003077
1775
Unclear 2 [5]
Phenytoin arene-oxide DM001248
101592230
Oxidation - Oxidation 3 [6]
Hydroxyphenytoin DM001249
17732
Unclear 4 [6]
Phenytoin dihydrodiol DM001254
152954
Oxidation - Dihydroxylation 4 [7]
Hydroxyphenytoin-O-glucuronide metabolite DM002067 N. A. Unclear 5 [8]
Phenytoin catechol DM001250
169703
Unclear 5 [7]
Phenytoin catechol DM001250
169703
Oxidation - Oxidation 5 [6]
Phenytoin methylcatechol DM001251
131769979
Conjugation - Methylation 6 [7]
Phenytoin quinone DM001252
131769980
Oxidation - Oxidation 6 [7]
Phenytoin quinone DM001252
131769980
Oxidation - Oxidation 7 [7]
⏷ Show the Full List of 11  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003171 Fosphenytoin sodium 3-hydroxymethylphenytoin Hydrolysis - Hydrolysis ALPL [5]
MR003170 3-hydroxymethylphenytoin Phenytoin Unclear Unclear [5]
MR003172 Phenytoin Phenytoin arene-oxide Oxidation - Oxidation CYP2C9 ... [6]
MR003162 Phenytoin arene-oxide Hydroxyphenytoin Unclear Unclear [6]
MR003163 Phenytoin arene-oxide Phenytoin dihydrodiol Oxidation - Dihydroxylation Unclear [7]
MR003164 Hydroxyphenytoin Phenytoin catechol Oxidation - Oxidation Unclear [6]
MR003165 Hydroxyphenytoin Hydroxyphenytoin-O-glucuronide metabolite Unclear UGT1A1 ... [8]
MR003169 Phenytoin dihydrodiol Phenytoin catechol Unclear Unclear [7]
MR003166 Phenytoin catechol Phenytoin methylcatechol Conjugation - Methylation COMT [7]
MR003167 Phenytoin catechol Phenytoin quinone Oxidation - Oxidation Unclear [7]
MR003168 Phenytoin methylcatechol Phenytoin quinone Oxidation - Oxidation Unclear [7]
⏷ Show the Full List of 11 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[4]
References
1 Phenytoin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
3 Basic review of the cytochrome p450 system. J Adv Pract Oncol. 2013 Jul;4(4):263-8.
4 CYP2C9, CYP2C19, and ABCB1 genotype and hospitalization for phenytoin toxicity. J Clin Pharmacol. 2009 Dec;49(12):1483-7.
5 Evaluation of in vitro models for screening alkaline phosphatase-mediated bioconversion of phosphate ester prodrugs Drug Metab Dispos. 2009 Jul;37(7):1443-7. doi: 10.1124/dmd.108.026245.
6 Pharmacogenomics knowledge for personalized medicine Clin Pharmacol Ther. 2012 Oct;92(4):414-7. doi: 10.1038/clpt.2012.96.
7 DrugBank(Pharmacology-Metabolism)Fosphenytoin sodium
8 U. S. FDA Label -Fosphenytoin sodium

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