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

General Information of Drug (ID: DR0974)
Drug Name
Loperamide hydrochloride
Synonyms
Loperamida; Loperamida [INN-Spanish]; Loperamide [INN:BAN]; Loperamidum; Loperamidum [INN-Latin]; Maalox Anti-Diarrheal; Nu-Loperamide; PMS-Loperamide; R-18553; Rho-Loperamide; loperamide; 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide; 53179-11-6; 6X9OC3H4II; BRN 1558273; C29H33ClN2O2; CHEMBL841; EINECS 258-416-5; UNII-6X9OC3H4II; Apo-Loperamide; Imodium A-D Caplets; Ioperamide; Kaopectate II; Loperacap; Dissenten; Fortasec; Imosec; Lopemid; Lopemin; Loperamide (hydrochloride); Loperamide HCl; Loperamide hydrochloride; Loperyl; Maalox Antidiarrheal; R 18553; Suprasec; Tebloc; 34552-83-5; 4-(4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl)-N,N-dimethyl-2,2-diphenylbutanamide hydrochloride; 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide hydrochloride; BLOX; BREK; CHEBI:6533; EINECS 252-082-4; MFCD00058581; MLS000069779; PJ185; UNII-77TI35393C
Indication Irritable bowel syndrome [ICD11: DD91] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 513.5 Topological Polar Surface Area 43.8
Heavy Atom Count 35 Rotatable Bond Count 7
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
71420
ChEBI ID
CHEBI:6533
CAS Number
34552-83-5
TTD Drug ID
D0CS2F
Formula
C29H34Cl2N2O2
Canonical SMILES
CN(C)C(=O)C(CCN1CCC(CC1)(C2=CC=C(C=C2)Cl)O)(C3=CC=CC=C3)C4=CC=CC=C4.Cl
InChI
1S/C29H33ClN2O2.ClH/c1-31(2)27(33)29(24-9-5-3-6-10-24,25-11-7-4-8-12-25)19-22-32-20-17-28(34,18-21-32)23-13-15-26(30)16-14-23;/h3-16,34H,17-22H2,1-2H3;1H
InChIKey
PGYPOBZJRVSMDS-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
Loperamide carbinolamide metabolite DM006418 N. A. Oxidation - C-hydroxylation 1 [2]
Loperamide oxide DM006417
71421
Oxidation - N-hydroxylation 1 [2]
N-demethyl loperamide DM006416
9805944
Oxidation - N-demethylation 1 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006895 Loperamide hydrochloride N-demethyl loperamide Oxidation - N-demethylation CYP3A4 ... [2]
MR006896 Loperamide hydrochloride Loperamide oxide Oxidation - N-hydroxylation Unclear [2]
MR006897 Loperamide hydrochloride Loperamide carbinolamide metabolite Oxidation - C-hydroxylation Unclear [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Oxygen-insensitive NADPH nitroreductase A (nfsA) DME1098 Escherichia coli
NFSA_ECOLI
1.5.1.38
[4]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1265 Escherichia coli Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1357 Alistipes indistinctus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1364 Bacteroides coprophilus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1366 Bacteroides eggerthii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1379 Bacteroides stercoris Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1404 Clostridium sporogenes Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1431 Holdemanella biformis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1445 Parabacteroides distasonis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1453 Providencia rettgeri Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1456 Roseburia intestinalis Not Available Not Available [5]
⏷ Show the Full List of 23  DME(s)
References
1 Loperamide Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Identification of cytochrome P450 isoforms involved in the metabolism of loperamide in human liver microsomes. Eur J Clin Pharmacol. 2004 Oct;60(8):575-81.
3 Loperamide: a pharmacological review. Rev Gastroenterol Disord. 2007;7 Suppl 3:S11-8.
4 Reduction of the prodrug loperamide oxide to its active drug loperamide in the gut of rats, dogs, and humans. Drug Metab Dispos. 1995 Mar;23(3):354-62.
5 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.

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