Loperamide

Loperamide is a synthetic piperidine derivative, effective against diarrhoea resulting from gastroenteritis or inflammatory bowel disease. It has a role as a mu-opioid receptor agonist, an antidiarrhoeal drug and an anticoronaviral agent

General

Type : Piperidine, Drug, Not A\/B H target, Opioid analgesic

Chemical_Nomenclature : 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide

Canonical SMILES : CN(C)C(=O)C(CCN1CCC(CC1)(C2=CC=C(C=C2)Cl)O)(C3=CC=CC=C3)C4=CC=CC=C4

InChI : InChI=1S\/C29H33ClN2O2\/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

InChIKey : RDOIQAHITMMDAJ-UHFFFAOYSA-N

Other name(s) : Imodium  ||  Loperamida  ||  Loperamidum  ||  CHEMBL841  ||  CHEBI:6532  ||  LPA


MW : 477.0

Formula : C29H33ClN2O2

CAS_number : 53179-11-6

PubChem : 3955

UniChem : RDOIQAHITMMDAJ-UHFFFAOYSA-N

Target

Families : Loperamide ligand of proteins in family
Carb_B_Chordata

Protein :
human-CES2 human-CES1

References (17)

Title : Rationally Engineered hCES2A Near-Infrared Fluorogenic Substrate for Functional Imaging and High-Throughput Inhibitor Screening - Fan_2023_Anal.Chem_95_15665
Author(s) : Fan Y , Zhang T , Song Y , Sang Z , Zeng H , Liu P , Wang P , Ge G
Ref : Analytical Chemistry , 95 :15665-15672 , 2023
Abstract :
PubMedSearch : Fan_2023_Anal.Chem_95_15665
PubMedID: 37782032
Gene_locus related to this paper: human-CES2

Title : Carboxylesterases and arylacetamide deacetylase comparison in human A549, H460, and H727 pulmonary cells - Gabriele_2021_Life.Sci__119486
Author(s) : Gabriele M , Puccini P , Gervasi PG , Longo V
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Abstract :
PubMedSearch : Gabriele_2021_Life.Sci__119486
PubMedID: 33864822

Title : Discovery and Characterization of the Biflavones From Ginkgo biloba as Highly Specific and Potent Inhibitors Against Human Carboxylesterase 2 - Song_2021_Front.Pharmacol_12_655659
Author(s) : Song YQ , He RJ , Pu D , Guan XQ , Shi JH , Li YG , Hou J , Jia SN , Qin WW , Fang SQ , Ge GB
Ref : Front Pharmacol , 12 :655659 , 2021
Abstract :
PubMedSearch : Song_2021_Front.Pharmacol_12_655659
PubMedID: 34084136
Gene_locus related to this paper: human-CES2

Title : Presence and inter-individual variability of carboxylesterases (CES1 and CES2) in human lung - Gabriele_2018_Biochem.Pharmacol_150_64
Author(s) : Gabriele M , Puccini P , Lucchi M , Vizziello A , Gervasi PG , Longo V
Ref : Biochemical Pharmacology , 150 :64 , 2018
Abstract :
PubMedSearch : Gabriele_2018_Biochem.Pharmacol_150_64
PubMedID: 29407485

Title : Development of an in vitro screening method of acute cytotoxicity of the pyrrolizidine alkaloid lasiocarpine in human and rodent hepatic cell lines by increasing susceptibility - Forsch_2018_J.Ethnopharmacol_217_134
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Ref : J Ethnopharmacol , 217 :134 , 2018
Abstract :
PubMedSearch : Forsch_2018_J.Ethnopharmacol_217_134
PubMedID: 29454024

Title : Comparative metabolism of DDAO benzoate in liver microsomes from various species - Ma_2017_Toxicol.In.Vitro_44_280
Author(s) : Ma HY , Yang JD , Hou J , Zou LW , Jin Q , Hao DC , Ning J , Ge GB , Yang L
Ref : Toxicol In Vitro , 44 :280 , 2017
Abstract :
PubMedSearch : Ma_2017_Toxicol.In.Vitro_44_280
PubMedID: 28647665

Title : Biotransformation Capacity of Carboxylesterase in Skin and Keratinocytes for the Penta-Ethyl Ester Prodrug of DTPA - Fu_2016_Drug.Metab.Dispos_44_1313
Author(s) : Fu J , Sadgrove M , Marson L , Jay M
Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 44 :1313 , 2016
Abstract :
PubMedSearch : Fu_2016_Drug.Metab.Dispos_44_1313
PubMedID: 27130352
Gene_locus related to this paper: human-CES1

Title : Urethane dimethacrylate induces cytotoxicity and regulates cyclooxygenase-2, hemeoxygenase and carboxylesterase expression in human dental pulp cells - Chang_2014_Acta.Biomater_10_722
Author(s) : Chang HH , Chang MC , Wang HH , Huang GF , Lee YL , Wang YL , Chan CP , Yeung SY , Tseng SK , Jeng JH
Ref : Acta Biomater , 10 :722 , 2014
Abstract :
PubMedSearch : Chang_2014_Acta.Biomater_10_722
PubMedID: 24140606

Title : Contributions of arylacetamide deacetylase and carboxylesterase 2 to flutamide hydrolysis in human liver - Kobayashi_2012_Drug.Metab.Dispos_40_1080
Author(s) : Kobayashi Y , Fukami T , Shimizu M , Nakajima M , Yokoi T
Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 40 :1080 , 2012
Abstract :
PubMedSearch : Kobayashi_2012_Drug.Metab.Dispos_40_1080
PubMedID: 22446520

Title : Conclusive identification of the oxybutynin-hydrolyzing enzyme in human liver - Sato_2012_Drug.Metab.Dispos_40_902
Author(s) : Sato Y , Miyashita A , Iwatsubo T , Usui T
Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 40 :902 , 2012
Abstract :
PubMedSearch : Sato_2012_Drug.Metab.Dispos_40_902
PubMedID: 22293119

Title : P-glycoprotein, multidrug-resistance associated protein 2, cyp3a, and carboxylesterase affect the oral availability and metabolism of vinorelbine - Lagas_2012_Mol.Pharmacol_82_636
Author(s) : Lagas JS , Damen CW , van Waterschoot RA , Iusuf D , Beijnen JH , Schinkel AH
Ref : Molecular Pharmacology , 82 :636 , 2012
Abstract :
PubMedSearch : Lagas_2012_Mol.Pharmacol_82_636
PubMedID: 22767610

Title : Carboxylesterase expression in human dental pulp cells: role in regulation of BisGMA-induced prostanoid production and cytotoxicity - Chang_2012_Acta.Biomater_8_1380
Author(s) : Chang MC , Lin LD , Chuang FH , Chan CP , Wang TM , Lee JJ , Jeng PY , Tseng WY , Lin HJ , Jeng JH
Ref : Acta Biomater , 8 :1380 , 2012
Abstract :
PubMedSearch : Chang_2012_Acta.Biomater_8_1380
PubMedID: 21951919

Title : Characterization of the expression and activity of carboxylesterases 1 and 2 from the beagle dog, cynomolgus monkey, and human - Williams_2011_Drug.Metab.Dispos_39_2305
Author(s) : Williams ET , Bacon JA , Bender DM , Lowinger JJ , Guo WK , Ehsani ME , Wang X , Wang H , Qian YW , Ruterbories KJ , Wrighton SA , Perkins EJ
Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 39 :2305 , 2011
Abstract :
PubMedSearch : Williams_2011_Drug.Metab.Dispos_39_2305
PubMedID: 21918037

Title : Detection and quantification of carboxylesterase 2 activity by capillary electrophoresis - Lamego_2011_Anal.Chem_83_881
Author(s) : Lamego J , Coroadinha AS , Simplicio AL
Ref : Analytical Chemistry , 83 :881 , 2011
Abstract :
PubMedSearch : Lamego_2011_Anal.Chem_83_881
PubMedID: 21207966

Title : Characterization of recombinant human carboxylesterases: fluorescein diacetate as a probe substrate for human carboxylesterase 2 - Wang_2011_Drug.Metab.Dispos_39_1329
Author(s) : Wang J , Williams ET , Bourgea J , Wong YN , Patten CJ
Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 39 :1329 , 2011
Abstract :
PubMedSearch : Wang_2011_Drug.Metab.Dispos_39_1329
PubMedID: 21540359
Gene_locus related to this paper: human-CES2

Title : Hydrolysis of a series of parabens by skin microsomes and cytosol from human and minipigs and in whole skin in short-term culture - Jewell_2007_Toxicol.Appl.Pharmacol_225_221
Author(s) : Jewell C , Prusakiewicz JJ , Ackermann C , Payne NA , Fate G , Voorman R , Williams FM
Ref : Toxicol Appl Pharmacol , 225 :221 , 2007
Abstract :
PubMedSearch : Jewell_2007_Toxicol.Appl.Pharmacol_225_221
PubMedID: 17889094

Title : Hydrolysis of capecitabine to 5'-deoxy-5-fluorocytidine by human carboxylesterases and inhibition by loperamide - Quinney_2005_J.Pharmacol.Exp.Ther_313_1011
Author(s) : Quinney SK , Sanghani SP , Davis WI , Hurley TD , Sun Z , Murry DJ , Bosron WF
Ref : Journal of Pharmacology & Experimental Therapeutics , 313 :1011 , 2005
Abstract :
PubMedSearch : Quinney_2005_J.Pharmacol.Exp.Ther_313_1011
PubMedID: 15687373
Gene_locus related to this paper: human-CES1 , human-CES2 , human-CES3