Cocaine
General
Type : Natural || Drug || Alkaloid || Benzoate || Azabicyclo
Chemical_Nomenclature : methyl (1S,3S,4R,5R)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylate
Canonical SMILES : CN1C2CCC1C(C(C2)OC(=O)C3=CC=CC=C3)C(=O)OC
InChI : InChI=1S\/C17H21NO4\/c1-18-12-8-9-13(18)15(17(20)21-2)14(10-12)22-16(19)11-6-4-3-5-7-11\/h3-7,12-15H,8-10H2,1-2H3\/t12-,13+,14-,15+\/m0\/s1
InChIKey : ZPUCINDJVBIVPJ-LJISPDSOSA-N
Other name(s) : 2beta-carbomethoxy-3beta-benzoyloxytropane hydrochloride, (-)-Cocaine, 3-beta-Hydroxy-, Methyl Ester, Benzoate, Methylbenzoylepgonine, Cocaine Free Base, Benzoylmethylecgonine, Crack, L-Cocain, beta-Cocain, D-cocaine, Cocain, Kokain
Target
Families : BCHE, Carb_B_Chordata, Cocaine_esterase
References (64)
| Title : Long-lasting blocking of interoceptive effects of cocaine by a highly efficient cocaine hydrolase in rats - Wei_2024_Sci.Rep_14_927 |
| Author(s) : Wei H , LeSaint JE , Jin Z , Zhan CG , Zheng F |
| Ref : Sci Rep , 14 :927 , 2024 |
| PubMedID: 38195724 |
| Title : In vitro and in vivo stability of a highly efficient long-acting cocaine hydrolase - Shang_2024_Sci.Rep_14_10952 |
| Author(s) : Shang L , Wei H , Deng J , Stewart MJ , LeSaint JE , Kyomuhangi A , Park S , Maul EC , Zhan CG , Zheng F |
| Ref : Sci Rep , 14 :10952 , 2024 |
| PubMedID: 38740850 |
| Title : Human Butyrylcholinesterase Mutants for (-)-Cocaine Hydrolysis: A Correlation Relationship between Catalytic Efficiency and Total Hydrogen Bonding Energy with an Oxyanion Hole - Zheng_2023_J.Phys.Chem.B__ |
| Author(s) : Zheng F , Hou S , Xue L , Yang W , Zhan CG |
| Ref : J Phys Chem B , : , 2023 |
| PubMedID: 38063500 |
| Title : Efficient Cocaine Degradation by Cocaine Esterase-Loaded Red Blood Cells - Rossi_2020_Front.Physiol_11_573492 |
| Author(s) : Rossi L , Pierige F , Agostini M , Bigini N , Termopoli V , Cai Y , Zheng F , Zhan CG , Landry DW , Magnani M |
| Ref : Front Physiol , 11 :573492 , 2020 |
| PubMedID: 33013487 |
| Title : Development of a long-acting Fc-fused cocaine hydrolase with improved yield of protein expression - Chen_2019_Chem.Biol.Interact_13ChEPon_306_89 |
| Author(s) : Chen X , Deng J , Zheng X , Zhang J , Zhou Z , Wei H , Zhan CG , Zheng F |
| Ref : Chemico-Biological Interactions , 306 :89 , 2019 |
| PubMedID: 30986387 |
| Title : Catalytic Hydrolysis Mechanism of Cocaine by Human Carboxylesterase 1: An Orthoester Intermediate Slows Down the Reaction - Yan_2019_Molecules_24_ |
| Author(s) : Yan M , Zhang Z , Liu Z , Zhang C , Zhang J , Fan S , Yang Z |
| Ref : Molecules , 24 : , 2019 |
| PubMedID: 31717501 |
| Gene_locus related to this paper: human-CES1 |
| Title : Kinetic characterization of cholinesterases and a therapeutically valuable cocaine hydrolase for their catalytic activities against heroin and its metabolite 6-monoacetylmorphine - Kim_2018_Chem.Biol.Interact_293_107 |
| Author(s) : Kim K , Yao J , Jin Z , Zheng F , Zhan CG |
| Ref : Chemico-Biological Interactions , 293 :107 , 2018 |
| PubMedID: 30080993 |
| Title : Free energy profiles of cocaine esterase-cocaine binding process by molecular dynamics and potential of mean force simulations - Zhang_2016_Chem.Biol.Interact_259_142 |
| Author(s) : Zhang Y , Huang X , Han K , Zheng F , Zhan CG |
| Ref : Chemico-Biological Interactions , 259 :142 , 2016 |
| PubMedID: 27163853 |
| Title : Reward and Toxicity of Cocaine Metabolites Generated by Cocaine Hydrolase - Murthy_2015_Cell.Mol.Neurobiol_35_819 |
| Author(s) : Murthy V , Geng L , Gao Y , Zhang B , Miller JD , Reyes S , Brimijoin S |
| Ref : Cellular Molecular Neurobiology , 35 :819 , 2015 |
| PubMedID: 25814464 |
| Title : Kinetic characterization of a cocaine hydrolase engineered from mouse butyrylcholinesterase - Chen_2015_Biochem.J_466_243 |
| Author(s) : Chen X , Huang X , Geng L , Xue L , Hou S , Zheng X , Brimijoin S , Zheng F , Zhan CG |
| Ref : Biochemical Journal , 466 :243 , 2015 |
| PubMedID: 25486543 |
| Gene_locus related to this paper: human-BCHE |
| Title : Contribution of human esterases to the metabolism of selected drugs of abuse - Meyer_2014_Toxicol.Lett_232_159 |
| Author(s) : Meyer MR , Schutz A , Maurer HH |
| Ref : Toxicol Lett , 232 :159 , 2014 |
| PubMedID: 25445008 |
| Title : Rational design, preparation, and characterization of a therapeutic enzyme mutant with improved stability and function for cocaine detoxification - Fang_2014_ACS.Chem.Biol_9_1764 |
| Author(s) : Fang L , Chow KM , Hou S , Xue L , Chen X , Rodgers DW , Zheng F , Zhan CG |
| Ref : ACS Chemical Biology , 9 :1764 , 2014 |
| PubMedID: 24919140 |
| Gene_locus related to this paper: rhosm-cocE |
| Title : Preclinical studies on neurobehavioral and neuromuscular effects of cocaine hydrolase gene therapy in mice - Murthy_2014_J.Mol.Neurosci_53_409 |
| Author(s) : Murthy V , Gao Y , Geng L , LeBrasseur NK , White TA , Brimijoin S |
| Ref : Journal of Molecular Neuroscience , 53 :409 , 2014 |
| PubMedID: 24085526 |
| Title : The future potential for cocaine vaccines - Orson_2014_Expert.Opin.Biol.Ther_14_1271 |
| Author(s) : Orson FM , Wang R , Brimijoin S , Kinsey BM , Singh RA , Ramakrishnan M , Wang HY , Kosten TR |
| Ref : Expert Opin Biol Ther , 14 :1271 , 2014 |
| PubMedID: 24835496 |
| Title : A highly efficient cocaine-detoxifying enzyme obtained by computational design - Zheng_2014_Nat.Commun_5_3457 |
| Author(s) : Zheng F , Xue L , Hou S , Liu J , Zhan M , Yang W , Zhan CG |
| Ref : Nat Commun , 5 :3457 , 2014 |
| PubMedID: 24643289 |
| Gene_locus related to this paper: human-BCHE |
| Title : Amino-acid mutations to extend the biological half-life of a therapeutically valuable mutant of human butyrylcholinesterase - Fang_2014_Chem.Biol.Interact_214C_18 |
| Author(s) : Fang L , Hou S , Xue L , Zheng F , Zhan CG |
| Ref : Chemico-Biological Interactions , 214C :18 , 2014 |
| PubMedID: 24582612 |
| Gene_locus related to this paper: human-BCHE |
| Title : Plants as a source of butyrylcholinesterase variants designed for enhanced cocaine hydrolase activity - Larrimore_2013_Chem.Biol.Interact_203_217 |
| Author(s) : Larrimore KE , Barcus M , Kannan L , Gao Y , Zhan CG , Brimijoin S , Mor TS |
| Ref : Chemico-Biological Interactions , 203 :217 , 2013 |
| PubMedID: 23000451 |
| Title : Preparation and in vivo characterization of a cocaine hydrolase engineered from human butyrylcholinesterase for metabolizing cocaine - Xue_2013_Biochem.J_453_447 |
| Author(s) : Xue L , Hou S , Tong M , Fang L , Chen X , Jin Z , Tai HH , Zheng F , Zhan CG |
| Ref : Biochemical Journal , 453 :447 , 2013 |
| PubMedID: 23849058 |
| Title : Modeling of pharmacokinetics of cocaine in human reveals the feasibility for development of enzyme therapies for drugs of abuse - Zheng_2012_PLoS.Comput.Biol_8_e1002610 |
| Author(s) : Zheng F , Zhan CG |
| Ref : PLoS Comput Biol , 8 :e1002610 , 2012 |
| PubMedID: 22844238 |
| Title : Human butyrylcholinesterase-cocaine binding pathway and free energy profiles by molecular dynamics and potential of mean force simulations - Huang_2011_J.Phys.Chem.B_115_11254 |
| Author(s) : Huang X , Zheng F , Zhan CG |
| Ref : J Phys Chem B , 115 :11254 , 2011 |
| PubMedID: 21902185 |
| Title : Design, preparation, and characterization of high-activity mutants of human butyrylcholinesterase specific for detoxification of cocaine - Xue_2011_Mol.Pharmacol_79_290 |
| Author(s) : Xue L , Ko MC , Tong M , Yang W , Hou S , Fang L , Liu J , Zheng F , Woods JH , Tai HH , Zhan CG |
| Ref : Molecular Pharmacology , 79 :290 , 2011 |
| PubMedID: 20971807 |
| Title : Free energy perturbation simulation on transition states and high-activity mutants of human butyrylcholinesterase for (-)-cocaine hydrolysis - Yang_2010_J.Phys.Chem.B_114_10889 |
| Author(s) : Yang W , Pan Y , Fang L , Gao D , Zheng F , Zhan CG |
| Ref : J Phys Chem B , 114 :10889 , 2010 |
| PubMedID: 20677742 |
| Title : Design of high-activity mutants of human butyrylcholinesterase against (-)-cocaine: structural and energetic factors affecting the catalytic efficiency - Zheng_2010_Biochemistry_49_9113 |
| Author(s) : Zheng F , Yang W , Xue L , Hou S , Liu J , Zhan CG |
| Ref : Biochemistry , 49 :9113 , 2010 |
| PubMedID: 20886866 |
| Title : Reaction pathway and free energy profile for prechemical reaction step of human butyrylcholinesterase-catalyzed hydrolysis of (-)-cocaine by combined targeted molecular dynamics and potential of mean force simulations - Huang_2010_J.Phys.Chem.B_114_13545 |
| Author(s) : Huang X , Pan Y , Zheng F , Zhan CG |
| Ref : J Phys Chem B , 114 :13545 , 2010 |
| PubMedID: 20883001 |
| Title : Biochemical and molecular analysis of carboxylesterase-mediated hydrolysis of cocaine and heroin - Hatfield_2010_Br.J.Pharmacol_160_1916 |
| Author(s) : Hatfield MJ , Tsurkan LG , Hyatt JL , Yu X , Edwards CC , Hicks LD , Wadkins RM , Potter PM |
| Ref : British Journal of Pharmacology , 160 :1916 , 2010 |
| PubMedID: 20649590 |
| Gene_locus related to this paper: human-CES1 |
| Title : Recent progress in protein drug design and discovery with a focus on novel approaches to the development of anti-cocaine medications - Zheng_2009_Future.Med.Chem_1_515 |
| Author(s) : Zheng F , Zhan CG |
| Ref : Future Med Chem , 1 :515 , 2009 |
| PubMedID: 20161378 |
| Title : Structure-and-mechanism-based design and discovery of therapeutics for cocaine overdose and addiction - Zheng_2008_Org.Biomol.Chem_6_836 |
| Author(s) : Zheng F , Zhan CG |
| Ref : Org Biomol Chem , 6 :836 , 2008 |
| PubMedID: 18292872 |
| Title : Rational design of an enzyme mutant for anti-cocaine therapeutics - Zheng_2008_J.Comput.Aided.Mol.Des_22_661 |
| Author(s) : Zheng F , Zhan CG |
| Ref : J Comput Aided Mol Des , 22 :661 , 2008 |
| PubMedID: 17989928 |
| Title : Most efficient cocaine hydrolase designed by virtual screening of transition states - Zheng_2008_J.Am.Chem.Soc_130_12148 |
| Author(s) : Zheng F , Yang W , Ko MC , Liu J , Cho H , Gao D , Tong M , Tai HH , Woods JH , Zhan CG |
| Ref : Journal of the American Chemical Society , 130 :12148 , 2008 |
| PubMedID: 18710224 |
| Title : Fundamental reaction mechanism for cocaine hydrolysis in human butyrylcholinesterase - Zhan_2003_J.Am.Chem.Soc_125_2462 |
| Author(s) : Zhan CG , Zheng F , Landry DW |
| Ref : Journal of the American Chemical Society , 125 :2462 , 2003 |
| PubMedID: 12603134 |
| Title : Cocaine metabolism accelerated by a re-engineered human butyrylcholinesterase - Sun_2002_J.Pharmacol.Exp.Ther_302_710 |
| Author(s) : Sun H , Shen ML , Pang YP , Lockridge O , Brimijoin S |
| Ref : Journal of Pharmacology & Experimental Therapeutics , 302 :710 , 2002 |
| PubMedID: 12130735 |
| Gene_locus related to this paper: human-BCHE |
| Title : Re-engineering butyrylcholinesterase as a cocaine hydrolase - Sun_2002_Mol.Pharmacol_62_220 |
| Author(s) : Sun H , Pang YP , Lockridge O , Brimijoin S |
| Ref : Molecular Pharmacology , 62 :220 , 2002 |
| PubMedID: 12130672 |
| Gene_locus related to this paper: human-BCHE |
| Title : Crystal structure of a cocaine-binding antibody - Larsen_2001_J.Mol.Biol_311_9 |
| Author(s) : Larsen NA , Zhou B , Heine A , Wirsching P , Janda KD , Wilson IA |
| Ref : Journal of Molecular Biology , 311 :9 , 2001 |
| PubMedID: 11469854 |
| Title : Predicted Michaelis-Menten complexes of cocaine-butyrylcholinesterase. Engineering effective butyrylcholinesterase mutants for cocaine detoxication. - Sun_2001_J.Biol.Chem_276_9330 |
| Author(s) : Sun H , El Yazal J , Lockridge O , Schopfer LM , Brimijoin S , Pang YP |
| Ref : Journal of Biological Chemistry , 276 :9330 , 2001 |
| PubMedID: 11104759 |
| Title : An improved cocaine hydrolase: the A328Y mutant of human butyrylcholinesterase is 4-fold more efficient - Xie_1999_Mol.Pharmacol_55_83 |
| Author(s) : Xie W , Altamirano CV , Bartels CF , Speirs RJ , Cashman JR , Lockridge O |
| Ref : Molecular Pharmacology , 55 :83 , 1999 |
| PubMedID: 9882701 |
| Title : Role of cholinergic receptors and cholinesterase activity in hemodynamic responses to cocaine in conscious rats - Knuepfer_1999_Am.J.Physiol_276_R103 |
| Author(s) : Knuepfer MM , Gan Q |
| Ref : American Journal of Physiology , 276 :R103 , 1999 |
| PubMedID: 9887183 |
| Title : The influence of plasma butyrylcholinesterase concentration on the in vitro hydrolysis of cocaine in human plasma - Browne_1998_Biopharm.Drug.Dispos_19_309 |
| Author(s) : Browne SP , Slaughter EA , Couch RA , Rudnic EM , McLean AM |
| Ref : Biopharmaceutics & Drug Disposition , 19 :309 , 1998 |
| PubMedID: 9673783 |
| Title : Cocaine benzoyl thioester: synthesis, kinetics of base hydrolysis, and application to the assay of cocaine esterases - Cashman_1998_Chem.Res.Toxicol_11_895 |
| Author(s) : Cashman JR , Berkman CE , Underiner G , Kolly CA , Hunter AD |
| Ref : Chemical Research in Toxicology , 11 :895 , 1998 |
| PubMedID: 9705751 |
| Title : Normal and atypical butyrylcholinesterases in placental development, function, and malfunction - Sternfeld_1997_Cell.Mol.Neurobiol_17_315 |
| Author(s) : Sternfeld M , Rachmilewitz J , Loewenstein-Lichtenstein Y , Andres C , Timberg R , Ben-Ari S , Glick C , Soreq H , Zakut H |
| Ref : Cellular Molecular Neurobiology , 17 :315 , 1997 |
| PubMedID: 9187488 |
| Title : Enhancing cocaine metabolism with butyrylcholinesterase as a treatment strategy - Gorelick_1997_Drug.Alcohol.Depend_48_159 |
| Author(s) : Gorelick DA |
| Ref : Drug Alcohol Depend , 48 :159 , 1997 |
| PubMedID: 9449014 |
| Title : Cocaine detoxification by human plasma butyrylcholinesterase - Lynch_1997_Toxicol.Appl.Pharmacol_145_363 |
| Author(s) : Lynch TJ , Mattes CE , Singh A , Bradley RM , Brady RO , Dretchen KL |
| Ref : Toxicol Appl Pharmacol , 145 :363 , 1997 |
| PubMedID: 9266810 |
| Title : Therapeutic use of butyrylcholinesterase for cocaine intoxication - Mattes_1997_Toxicol.Appl.Pharmacol_145_372 |
| Author(s) : Mattes CE , Lynch TJ , Singh A , Bradley RM , Kellaris PA , Brady RO , Dretchen KL |
| Ref : Toxicol Appl Pharmacol , 145 :372 , 1997 |
| PubMedID: 9266811 |
| Title : Overlapping drug interaction sites of human butyrylcholinesterase dissected by site-directed mutagenesis - Loewenstein-Lichtenstein_1996_Mol.Pharmacol_50_1423 |
| Author(s) : Loewenstein-Lichtenstein Y , Glick D , Gluzman N , Sternfeld M , Zakut H , Soreq H |
| Ref : Molecular Pharmacology , 50 :1423 , 1996 |
| PubMedID: 8967962 |
| Gene_locus related to this paper: human-BCHE |
| Title : Acetylcholinesterase and butyrylcholinesterase activity in the human term placenta: implications for fetal cocaine exposure - Simone_1994_J.Lab.Clin.Med_123_400 |
| Author(s) : Simone C , Derewlany LO , Oskamp M , Johnson D , Knie B , Koren G |
| Ref : Journal of Laboratory & Clinical Medicine , 123 :400 , 1994 |
| PubMedID: 8133152 |
| Title : Differential toxicity of cocaine and its isomers, (+)-cocaine and (-)-psi-cocaine, is associated with stereoselective hydrolysis by hepatic carboxylesterases in cultured rat hepatocytes - Melchert_1992_Chem.Biol.Interact_84_243 |
| Author(s) : Melchert RB , Goldlin C , Zweifel U , Welder AA , Boelsterli UA |
| Ref : Chemico-Biological Interactions , 84 :243 , 1992 |
| PubMedID: 1423743 |
| Title : Activities of the enantiomers of cocaine and some related compounds as substrates and inhibitors of plasma butyrylcholinesterase - Gatley_1991_Biochem.Pharmacol_41_1249 |
| Author(s) : Gatley SJ |
| Ref : Biochemical Pharmacology , 41 :1249 , 1991 |
| PubMedID: 2009099 |
| Title : Genetic variants of human serum cholinesterase influence metabolism of the muscle relaxant succinylcholine. - Lockridge_1990_Pharmacol.Ther_47_35 |
| Author(s) : Lockridge O |
| Ref : Pharmacol Ther , 47 :35 , 1990 |
| PubMedID: 2195556 |
| Gene_locus related to this paper: human-BCHE |
| Title : Metabolism of cocaine in man - Inaba_1978_Clin.Pharmacol.Ther_23_547 |
| Author(s) : Inaba T , Stewart DJ , Kalow W |
| Ref : Clinical Pharmacology & Therapeutics , 23 :547 , 1978 |
| PubMedID: 639429 |