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
1. Brady CA, Stanford IM, Ali I, Lin L, Williams JM, Dubin AE, Hope AG, Barnes NM. (2001)
Pharmacological comparison of human homomeric 5-HT3A receptors versus heteromeric 5-HT3A/3B receptors.
Neuropharmacology, 41 (2): 282-4. [PMID:11489465]
2. Carroll FI, Runyon SP, Abraham P, Navarro H, Kuhar MJ, Pollard GT, Howard JL. (2004)
Monoamine transporter binding, locomotor activity, and drug discrimination properties of 3-(4-substituted-phenyl)tropane-2-carboxylic acid methyl ester isomers.
J Med Chem, 47 (25): 6401-9. [PMID:15566309]
3. Hope AG, Peters JA, Brown AM, Lambert JJ, Blackburn TP. (1996)
Characterization of a human 5-hydroxytryptamine3 receptor type A (h5-HT3R-AS) subunit stably expressed in HEK 293 cells.
Br J Pharmacol, 118 (5): 1237-45. [PMID:8818349]