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

General Information of Drug (ID: DR0967)
Drug Name
Lofexidine
Synonyms
Lofexidina; Lofexidina [INN-Spanish]; Lofexidine; Lofexidine [INN:BAN]; Lofexidinum; Lofexidinum [INN-Latin]; Britlofex; 1H-Imidazole, 2-[1-(2,6-dichlorophenoxy)ethyl]-4,5-dihydro-; 2-(1-(2,6-Dichlorophenoxy)ethyl)-4,5-dihydro-1H-imidazole; 2-(alpha-(2,6-Dichlorophenoxy)ethyl)2-imidazoline; 2-Imidazoline 2-(1-(2,6-dichlorophenoxy)ethyl)-; 2-[1-(2,6-dichlorophenoxy)ethyl]-2-imidazoline; 2-[1-(2,6-dichlorophenoxy)ethyl]-4,5-dihydro-1H-imidazole; 31036-80-3; CHEBI:51368; CHEMBL17860
Indication Opiate dependence [ICD11: 6C43] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 259.13 Topological Polar Surface Area 33.6
Heavy Atom Count 16 Rotatable Bond Count 3
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
30668
PubChem SID
4955007 ; 7979787 ; 8171702 ; 14774610 ; 34672885 ; 46508453 ; 48416180 ; 49980645 ; 56464309 ; 57310968 ; 77865548 ; 91614206 ; 92309039 ; 96024831 ; 103182297 ; 103930569 ; 104308830 ; 117466455 ; 128428177 ; 131309952 ; 134224363 ; 134337392 ; 134357768 ; 135023284 ; 137069359 ; 142970890 ; 152039684 ; 160967834 ; 164811810 ; 170466275 ; 172876170 ; 174560267 ; 175611898 ; 176484253 ; 179150300 ; 179499877 ; 184643900 ; 224374099 ; 226432808 ; 241060023 ; 252448593
ChEBI ID
ChEBI:51368
CAS Number
31036-80-3
TTD Drug ID
D0K0MW
Formula
C11H12Cl2N2O
Canonical SMILES
CC(C1=NCCN1)OC2=C(C=CC=C2Cl)Cl
InChI
1S/C11H12Cl2N2O/c1-7(11-14-5-6-15-11)16-10-8(12)3-2-4-9(10)13/h2-4,7H,5-6H2,1H3,(H,14,15)
InChIKey
KSMAGQUYOIHWFS-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
N-(2-aminoethyl)-2-(2,6-dichlorophenoxy)propanamide DM002599
13177851
Oxidation - Hydroxylation 1 [2]
2,6-dichlorophenol DM002600
6899
Oxidation - Oxidative Deamination 2 [2]
2-(2,6-dichlorophenoxy) propionic acid DM002601
91290
Oxidation - Oxidative Deamination 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001583 Lofexidine N-(2-aminoethyl)-2-(2,6-dichlorophenoxy)propanamide Oxidation - Hydroxylation CYP2C19 ... [2]
MR001581 N-(2-aminoethyl)-2-(2,6-dichlorophenoxy)propanamide 2,6-dichlorophenol Oxidation - Oxidative Deamination CYP2C19 ... [2]
MR001582 N-(2-aminoethyl)-2-(2,6-dichlorophenoxy)propanamide 2-(2,6-dichlorophenoxy) propionic acid Oxidation - Oxidative Deamination CYP2C19 ... [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [3]
References
1 ClinicalTrials.gov (NCT02363998) Open-Label, Safety Study of Lofexidine.
2 DrugBank(Pharmacology-Metabolism)Lofexidine
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.

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