paroxetine   Click here for help

GtoPdb Ligand ID: 4790

Synonyms: paroxetine hydrochloride (anhydrous or hemihydrate) | Paxil® | Seroxat®
Approved drug PDB Ligand
paroxetine is an approved drug (FDA (1992))
Compound class: Synthetic organic
Comment: Paroxetine is a selective serotonin-reuptake inhibitor (SSRI) antidepressant. An X-ray structure of crystals of paroxetine bound SERT, shows a single central binding site [1] (see PDB entry 5I6X)..
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 39.72
Molecular weight 329.14
XLogP 3.32
No. Lipinski's rules broken 0
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Canonical SMILES Fc1ccc(cc1)C1CCNCC1COc1ccc2c(c1)OCO2
Isomeric SMILES Fc1ccc(cc1)[C@@H]1CCNC[C@H]1COc1ccc2c(c1)OCO2
InChI InChI=1S/C19H20FNO3/c20-15-3-1-13(2-4-15)17-7-8-21-10-14(17)11-22-16-5-6-18-19(9-16)24-12-23-18/h1-6,9,14,17,21H,7-8,10-12H2/t14-,17-/m0/s1
1. Coleman JA, Green EM, Gouaux E. (2016)
X-ray structures and mechanism of the human serotonin transporter.
Nature, 532 (7599): 334-9. [PMID:27049939]
2. Jacobson KA, Müller CE. (2016)
Medicinal chemistry of adenosine, P2Y and P2X receptors.
Neuropharmacology, 104: 31-49. [PMID:26686393]
3. North RA, Jarvis MF. (2013)
P2X receptors as drug targets.
Mol Pharmacol, 83 (4): 759-69. [PMID:23253448]
4. Tatsumi M, Groshan K, Blakely RD, Richelson E. (1997)
Pharmacological profile of antidepressants and related compounds at human monoamine transporters.
Eur J Pharmacol, 340 (2-3): 249-58. [PMID:9537821]