cocaine   Click here for help

GtoPdb Ligand ID: 2286

Approved drug PDB Ligand
cocaine is an approved drug
Comment: Cocaine is a tropane alkaloid obtained from leaves of the South American shrub Erythroxylon coca. Topically applied cocaine has local anesthetic effects, causing loss of feeling or numbness. It also causes vasoconstriction.
There is no information on the US Drugs@FDA website regarding marketing approval for formulations of this drug.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 0
Rotatable bonds 5
Topological polar surface area 55.84
Molecular weight 303.15
XLogP 2.31
No. Lipinski's rules broken 0
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Canonical SMILES COC(=O)C1C(CC2N(C1CC2)C)OC(=O)c1ccccc1
Isomeric SMILES COC(=O)[C@H]1[C@H](C[C@H]2N([C@@H]1CC2)C)OC(=O)c1ccccc1
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
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Summary of Clinical Use Click here for help
Used as a local anaesthetic in nasal, oral and laryngeal surgery.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The local anaesthetic action of cocaine is a result of its inhibition of sodium channels which results in inhibition of excitation at nerve endings and inhibition of peripheral nerve conductance. Vasoconstriction results from inhibition of noradrenaline reuptake. In pre-synaptic neurons cocaine prevents the re-uptake of dopamine, serotonin, and noradrenaline. Inhibiting dopamine re-uptake likely accounts for the development of cocaine addiction.