Prodrug Information
Prodrug General Information | Top | |||||
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Prodrug ID |
D5ERP2
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Prodrug Name |
Fosphenytoin
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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
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Indication | Seizure disorder [ICD-11: 8A6Z; ICD-9: 345.9, 780.3] | Approved outside US | [1] | |||
Activation |
Prodrug |
Parent Drug |
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2D MOL 3D MOL | 2D MOL 3D MOL | |||||
(1) Bioconversion Enzyme:
Alkaline phosphatase
(EC 3.1)
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[1] | |||||
Prodrug Strategy |
Classical prodrug strategy
[Carrier linked prodrug]
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Improved property |
Increase solubility
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[2] | ||||
Description |
The aqueous solubility was incrreased from 20-25 microg/ml of phenytoin to 140 mg/ml of fosphenytoin.
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[2] | ||||
Formula |
C16H15N2O6P
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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
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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)
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InChIKey |
XWLUWCNOOVRFPX-UHFFFAOYSA-N
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CAS Number |
CAS 93390-81-9
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PubChem Compound ID | ||||||
ChEBI ID |
CHEBI:5165
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Parent Drug General Information | Top | |||||
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Parent Drug ID |
DFMP49
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Parent Drug Name |
Phenytoin
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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
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Formula |
C15H12N2O2
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Canonical SMILES |
C1=CC=C(C=C1)C2(C(=O)NC(=O)N2)C3=CC=CC=C3
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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)
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InChIKey |
CXOFVDLJLONNDW-UHFFFAOYSA-N
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CAS Number |
CAS 57-41-0
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PubChem Compound ID | ||||||
ChEBI ID |
CHEBI:8107
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Target and Pathway | Top | |||||
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Target(s) | Voltage-gated sodium channel (Nav) | Target Info | Modulator | [1] |
References | Top | |||||
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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. |
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