norfluoxetine   Click here for help

GtoPdb Ligand ID: 208

Compound class: Synthetic organic
Comment: Active metabolite of fluoxetine. Norfluoxetine is a mixture of two stereoisomers, an R-form and an S-form, and the PDB links above each represent one of these stereoisomers.
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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 6
Topological polar surface area 35.25
Molecular weight 295.12
XLogP 4.26
No. Lipinski's rules broken 0
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Canonical SMILES NCCC(c1ccccc1)Oc1ccc(cc1)C(F)(F)F
Isomeric SMILES NCCC(c1ccccc1)Oc1ccc(cc1)C(F)(F)F
InChI InChI=1S/C16H16F3NO/c17-16(18,19)13-6-8-14(9-7-13)21-15(10-11-20)12-4-2-1-3-5-12/h1-9,15H,10-11,20H2
1. Choi BH, Choi JS, Yoon SH, Rhie DJ, Min DS, Jo YH, Kim MS, Hahn SJ. (2001)
Effects of norfluoxetine, the major metabolite of fluoxetine, on the cloned neuronal potassium channel Kv3.1.
Neuropharmacology, 41 (4): 443-53. [PMID:11543764]
2. Kennard LE, Chumbley JR, Ranatunga KM, Armstrong SJ, Veale EL, Mathie A. (2005)
Inhibition of the human two-pore domain potassium channel, TREK-1, by fluoxetine and its metabolite norfluoxetine.
Br J Pharmacol, 144 (6): 821-9. [PMID:15685212]
3. Rothman RB, Baumann MH, Savage JE, Rauser L, McBride A, Hufeisen SJ, Roth BL. (2000)
Evidence for possible involvement of 5-HT(2B) receptors in the cardiac valvulopathy associated with fenfluramine and other serotonergic medications.
Circulation, 102 (23): 2836-41. [PMID:11104741]