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Substrate Report for: Cocaine

Cocaine is a tropane alkaloid ester extracted from the leaves of plants including coca. It is a local anesthetic and vasoconstrictor and is clinically used for that purpose, particularly in the eye, ear, nose, and throat. It also has powerful central nervous system effects similar to the amphetamines and is a drug of abuse. Cocaine, like amphetamines, acts by multiple mechanisms on brain catecholaminergic neurons. Cocaine binds to the dopamine, serotonin, and norepinephrine transport proteins and inhibits the re-uptake of dopamine, serotonin, and norepinephrine into pre-synaptic neurons. This leads to an accumulation of the respective neurotransmitters in the synaptic cleft and may result in increased postsynaptic receptor activation. The mechanism of action through which cocaine exerts its local anesthetic effects is by binding to and blocking the voltage-gated sodium channels in the neuronal cell membrane. By stabilizing neuronal membranes, cocaine inhibits the initiation and conduction of nerve impulses and produces a reversible loss of sensation. (from PubChem). Cocaine is metabolized by three human enzymes: hCE1 (CE1), intestinal CE (CE2) and serum butyrylcholinesterase (BChE). Cocaine is hydrolized very efficiently by some designed mutants of BChE



General
Type: Natural, Drug, Alkaloid, Benzoate
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
MW: 303.35
Formula: C17H21NO4
CAS_number: 53-21-4
IUPHAR:
Wikipedia: Cocaine

Target families
Cocaine ligand of proteins in family: BCHE, Carb_B_Chordata, Cocaine_esterase
No structure

Protein target

References
Search PubMed for references concerning: Cocaine

22 more
    Title: Catalytic Reaction Mechanism for Drug Metabolism in Human Carboxylesterase-1: Cocaine Hydrolysis Pathway
    Yao J, Chen X, Zheng F, Zhan CG
    Ref: Mol Pharm, 15:3871, 2018 : PubMed

            

    Title: Kinetic characterization of a cocaine hydrolase engineered from mouse butyrylcholinesterase
    Chen X, Huang X, Geng L, Xue L, Hou S, Zheng X, Brimijoin S, Zheng F, Zhan CG
    Ref: Biochemical Journal, 466:243, 2015 : PubMed

            

    Title: Amino-acid mutations to extend the biological half-life of a therapeutically valuable mutant of human butyrylcholinesterase
    Fang L, Hou S, Xue L, Zheng F, Zhan CG
    Ref: Chemico-Biological Interactions, 214C:18, 2014 : PubMed