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

General Information of Drug (ID: DR0911)
Drug Name
Lacosamide
Synonyms
Lacosamide; Lacosamide [USAN:INN:BAN]; SPM 927; SPM-927; Erlosamide; Erlosamide [INN]; Harkoseride; Vimpat; harkeroside; (2R)-2-(Acetylamino)-N-benzyl-3-methoxypropanamide; (2R)-2-acetamido-N-benzyl-3-methoxypropanamide; (2R)-N-benzyl-2-acetamido-3-methoxypropanamide; (R)-2-Acetylamino-N-benzyl-3-methoxy-propionamide; (R)-2-acetamido-N-benzyl-3-methoxypropanamide; 175481-36-4; 563KS2PQY5; ADD 234037; ADD 243037; CHEMBL58323; NCGC00253740-01; Propanamide, 2-(acetylamino)-3-methoxy-N-(phenylmethyl)-, (2R)-; UNII-563KS2PQY5
Indication Epilepsy [ICD11: 8A60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 250.29 Topological Polar Surface Area 67.4
Heavy Atom Count 18 Rotatable Bond Count 6
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
219078
PubChem SID
9374274 ; 12015335 ; 14847708 ; 15196715 ; 30422445 ; 50069298 ; 51091636 ; 53505872 ; 57399840 ; 58107206 ; 99218530 ; 99298399 ; 99437053 ; 103245465 ; 104154565 ; 109693474 ; 113468551 ; 123121578 ; 124757118 ; 125163922 ; 126575044 ; 126624062 ; 126644682 ; 126667072 ; 126733504 ; 129508865 ; 134339319 ; 135141960 ; 135367753 ; 135697647 ; 135707761 ; 136895303 ; 136991060 ; 137237313 ; 137237672 ; 139113413 ; 152258417 ; 160647253 ; 160660621 ; 160826045 ; 162037520 ; 162188094 ; 163092695 ; 163589394 ; 164824528 ; 170466190 ; 172086321 ; 174006177 ; 174527897 ; 175266112
ChEBI ID
CHEBI:135939
CAS Number
175481-36-4
TTD Drug ID
D05OFX
Formula
C13H18N2O3
Canonical SMILES
CC(=O)NC(COC)C(=O)NCC1=CC=CC=C1
InChI
1S/C13H18N2O3/c1-10(16)15-12(9-18-2)13(17)14-8-11-6-4-3-5-7-11/h3-7,12H,8-9H2,1-2H3,(H,14,17)(H,15,16)/t12-/m1/s1
InChIKey
VPPJLAIAVCUEMN-GFCCVEGCSA-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
Descarbonyl-lacosamide DM002844
10104501
Unclear 1 [4]
O-Desmethyl-lacosamide DM002843
10889901
Oxidation - Demethylation 1 [4]
Lacosamide-glucuronide DM002845
131769969
Conjugation - Glucuronidation 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001399 Lacosamide O-Desmethyl-lacosamide Oxidation - Demethylation CYP3A4 ... [4]
MR001400 Lacosamide Descarbonyl-lacosamide Unclear Unclear [4]
MR001398 Descarbonyl-lacosamide Lacosamide-glucuronide Conjugation - Glucuronidation Unclear [4]
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
[3]
References
1 Lacosamide was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Lacosamide: what can be expected from the next new antiepileptic drug? Epilepsy Curr. 2009 Sep-Oct;9(5):133-4.
3 Lacosamide therapeutic monitoring in patients with epilepsy: effect of concomitant antiepileptic drugs. Ther Drug Monit. 2013 Dec;35(6):849-52.
4 Absorption, disposition, metabolic fate and elimination of the anti-epileptic drug lacosamide in humans: mass balance following intravenous and oral administration Eur J Drug Metab Pharmacokinet. 2012 Dec;37(4):241-8. doi: 10.1007/s13318-012-0093-x.

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