cocaine   

GtoPdb Ligand ID: 2286

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.
2D Structure
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Physico-chemical Properties
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
SMILES / InChI / InChIKey
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
InChI Key ZPUCINDJVBIVPJ-LJISPDSOSA-N
Selectivity at ion channels
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
5-HT3A Hs Antagonist Antagonist 5.1 – 5.4 pKi - 1,3
pKi 5.1 – 5.4 [1,3]
5-HT3AB Hs Antagonist Antagonist 4.8 pKi - 1
pKi 4.8 [1]
Selectivity at transporters
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
DAT Rn Inhibitor Inhibition 7.1 pIC50 - 2
pIC50 7.1 (IC50 8.91x10-8 M) [2]
Ligand mentioned in the following text fields