Prodrug Information

Prodrug General Information

Prodrug ID

D5ERP2

Prodrug Name

Fosphenytoin

Synonyms

Cerebyx; 93390-81-9; (3-Phosphoryloxymethyl)phenytoin; Fosfenitoina [INN-Spanish]; Fosphenytoine [INN-French]; Fosphenytoinum [INN-Latin]; Fosphenytoin [INN:BAN]; UNII-B4SF212641; ACC-9653; CHEBI:5165; Prodilantin; B4SF212641; Fosfenitoina; Fosphenytoine; Fosphenytoinum; Fosphenytoin (INN); Sesquient; HSDB 7523; SCHEMBL94254; BIDD:GT0220; GTPL7190; CHEMBL1201336; DTXSID9044299; ZINC1530922; Tox21_113670; DB01320; NCGC00249894-01; K699; CAS-93390-81-9; LS-178209; LS-187339; FT-0738599; C07840; D07993; Q5473363

Click to Show/Hide

Indication

Seizure disorder [ICD-11: 8A6Z; ICD-9: 345.9, 780.3]

Approved outside US

[1]

Activation

Prodrug

Parent Drug

2D MOL 3D MOL

(1) Bioconversion Enzyme: Alkaline phosphatase (EC 3.1)

[1]

Prodrug Strategy

Classical prodrug strategy [Carrier linked prodrug]

Improved property

Increase solubility

[2]

Description

The aqueous solubility was incrreased from 20-25 microg/ml of phenytoin to 140 mg/ml of fosphenytoin.

[2]

Formula

C16H15N2O6P

Canonical SMILES

C1=CC=C(C=C1)C2(C(=O)N(C(=O)N2)COP(=O)(O)O)C3=CC=CC=C3

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

CAS Number

CAS 93390-81-9

PubChem Compound ID

56339

ChEBI ID

CHEBI:5165

Parent Drug General Information

Top

Parent Drug ID

DFMP49

Parent Drug Name

Phenytoin

Synonyms

Aladdin; Alepsin; Aleviatin; Antisacer; Auranile; CHEMBL16; Causoin; Citrullamon; Citrulliamon; Comital; Comitoina; Convul; D 4007; D0894; DILANTIN-30; DPH (VAN); Danten; Dantinal; Dantoinal; Dantoinal klinos; Dantoine; Denyl; Di-Hydan; Di-Lan; Di-Phetine; Didan TDC 250; Didan-tdc-250; Difenilhidantoina; Difenin; Difetoin; Difhydan; Dihycon; Dihydantoin; Dilabid; Dilantin; Dilantin acid; Dilantin,Phenytoin; Dilantin-125; Dilantine; Dillantin; Dintoin; Dintoina; Diphantoin; Diphedal; Diphedan; Diphenat; Diphenin; Diphenine; Diphentoin; Diphentyn; Diphenylan; Diphenylhydantoin; Diphenylhydantoine; Diphenylhydatanoin; Ditoinate; Ekko; Ekko capsules; Elepsindon; Enkelfel; Epamin; Epanutin; Epasmir 5; Epdantoin; Epelin; Epifenyl; Epihydan; Epilan D; Epilan-D; Epilantin; Epileptin; Epinat; Episar; Epised; Epsolin; Eptal; Eptoin; Fenantoin Mn Pharma; Fenigramon; Fenitoin; Fentoin; Fenylepsin; Fenytoin Dak; Fenytoine; Gerot-epilan-D; Hidan; Hidantal; Hidantilo; Hidantina; Hidantina senosian; Hidantina vitoria; Hidantomin; Hindatal; Hydantal; Hydantin; Hydantoinal; Hydantol; Idantoil; Idantoin; Iphenylhydantoin; Kessodanten; Labopal; Lehydan; Lepitoin; Lepsin; Minetoin; Neos-Hidantoina; Neosidantoina; Novantoina; Novophenytoin; Om-Hydantoine; PHENYTEK; Phanantin; Phanatine; Phenatoine; Phenhydan; Phenhydanin; Phenitoin; Phentoin; Phentytoin; Phenytex; Phenytoin; Phenytoin AWD; Phenytoin-Gerot; Ritmenal; Saceril; Sanepil; Silantin; Sinergina; Sodanthon; Sodantoin; Sodanton; Solantin; Solantoin; Solantyl; Sylantoic; TOIN; Tacosal; Thilophenyl; Toin unicelles; Zentronal; Zentropil; elepsi ndon; fen toin; phenat ine; taco sal

Click to Show/Hide

Formula

C15H12N2O2

Canonical SMILES

C1=CC=C(C=C1)C2(C(=O)NC(=O)N2)C3=CC=CC=C3

InChI

1S/C15H12N2O2/c18-13-15(17-14(19)16-13,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H,(H2,16,17,18,19)

InChIKey

CXOFVDLJLONNDW-UHFFFAOYSA-N

CAS Number

CAS 57-41-0

PubChem Compound ID

1775

ChEBI ID

CHEBI:8107

Target and Pathway

Top

Target(s)

Voltage-gated sodium channel (Nav)

Target Info

Modulator

[1]

References

Top

REF 1

Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2013

REF 2

Prodrugs: design and clinical applications. Nat Rev Drug Discov. 2008 Mar;7(3):255-70.

If You Find Any Error in Data or Bug in Web Service, Please Kindly Report It to Dr. Zhou and Dr. Zhang.

Prof. Feng ZHU

Prof. Yuzong CHEN