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 AlphaBeta Hydrolase 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 |
| Ref : Life Sciences , :119486 , 2021 |
| 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 |
| Author(s) : Forsch K , Schoning V , Disch L , Siewert B , Unger M , Drewe J |
| 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 |