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

General Information of Drug (ID: DR0684)
Drug Name
Felbamate
Synonyms
Felbamate [USAN:INN]; Felbamato; Felbamato [Spanish]; Felbamatum; Felbamatum [Latin]; Felbamyl; Felbatol; Taloxa; WKGXYQFOCVYPAC-UHFFFAOYSA-N; X72RBB02N8; felbamate; (3-carbamoyloxy-2-phenylpropyl) carbamate; 1,3-Propanediol, 2-phenyl-, dicarbamate; 2-Phenyl-1,3-propanediol dicarbamate; 2-Phenylpropane-1,3-diyl dicarbamate; 25451-15-4; 3-(carbamoyloxy)-2-phenylpropyl carbamate; ADD-03055; BRN 3345236; C11H14N2O4; CHEBI:4995; Carbamic acid, 2-phenyltrimethylene ester; EINECS 247-001-4; MLS000028465; UNII-X72RBB02N8; W 554; W-554
Indication Epilepsy [ICD11: 8A60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 238.24 Topological Polar Surface Area 105
Heavy Atom Count 17 Rotatable Bond Count 7
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
3331
PubChem SID
9704 ; 855835 ; 5299270 ; 7847602 ; 7979218 ; 8152115 ; 10515801 ; 11111171 ; 11113343 ; 11466947 ; 11528708 ; 12013710 ; 15196364 ; 17405087 ; 24277968 ; 26751526 ; 29222466 ; 46506375 ; 47589157 ; 47589158 ; 47662483 ; 48414310 ; 48416000 ; 50100240 ; 50104096 ; 50104097 ; 51299026 ; 53777630 ; 56422162 ; 57321729 ; 68530567 ; 81041130 ; 85231043 ; 85787789 ; 87350372 ; 90340922 ; 92304030 ; 92308149 ; 93166621 ; 99437094 ; 103158205 ; 103303660 ; 104171154 ; 104303197 ; 118317932 ; 121361313 ; 124749781 ; 124772217 ; 124800850 ; 124880084
ChEBI ID
CHEBI:4995
CAS Number
25451-15-4
TTD Drug ID
D05KON
Formula
C11H14N2O4
Canonical SMILES
C1=CC=C(C=C1)C(COC(=O)N)COC(=O)N
InChI
1S/C11H14N2O4/c12-10(14)16-6-9(7-17-11(13)15)8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H2,12,14)(H2,13,15)
InChIKey
WKGXYQFOCVYPAC-UHFFFAOYSA-N
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
2-hydroxyfelbamate DM000161
10400039
Oxidation - Oxidation 1 [5]
2-Phenyl-1,3-propanediol monocarbamate DM000154
213060
Hydrolysis - Esterase Hydrolysis 1 [6]
p-hydroxyfelbamate DM000160
9921310
Unclear 1 [2]
3-Carbamoyl-2-phenylpropionaldehyde DM000155
21350391
Unclear 2 [2]
3-Carbamoyl-2-phenylpropionic acid DM000158
3025746
Oxidation - Deamination 3 [2]
4-hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one DM000156
21350392
Unclear 3 [2]
Atropaldehyde DM000159
10312
Unclear 3 [2]
5-Phenyl-1,3-oxazinane-2,4-dione DM000157
21350393
Unclear 4 [2]
3-Carbamoyl-2-phenylpropionic acid DM000158
3025746
Unclear 5 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001018 Felbamate 2-Phenyl-1,3-propanediol monocarbamate Hydrolysis - Esterase Hydrolysis CYP2C19 [6]
MR001019 Felbamate p-hydroxyfelbamate Unclear CYP3A7 ... [2]
MR001020 Felbamate 2-hydroxyfelbamate Oxidation - Oxidation CYP3A7 ... [5]
MR001012 2-Phenyl-1,3-propanediol monocarbamate 3-Carbamoyl-2-phenylpropionaldehyde Unclear ADH1A [2]
MR001013 3-Carbamoyl-2-phenylpropionaldehyde 4-hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one Unclear ADH1A [2]
MR001014 3-Carbamoyl-2-phenylpropionaldehyde 3-Carbamoyl-2-phenylpropionic acid Oxidation - Deamination Unclear [2]
MR001015 3-Carbamoyl-2-phenylpropionaldehyde Atropaldehyde Unclear Unclear [2]
MR001016 4-hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one 5-Phenyl-1,3-oxazinane-2,4-dione Unclear ADH1A [2]
MR001017 5-Phenyl-1,3-oxazinane-2,4-dione 3-Carbamoyl-2-phenylpropionic acid Unclear Unclear [2]
⏷ Show the Full List of 9 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Alcohol dehydrogenase class-I alpha (ADH1A) DME0127 Homo sapiens
ADH1A_HUMAN
1.1.1.1
[2]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[3]
References
1 Felbamate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 DrugBank(Pharmacology-Metabolism)Felbamate
3 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
4 A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63.
5 LABEL:FELBAMATE suspension
6 Felbamate-induced apoptosis of hematopoietic cells is mediated by redox-sensitive and redox-independent pathways Epilepsy Res. 2002 Jan;48(1-2):57-69. doi: 10.1016/s0920-1211(01)00320-5.

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