oxymetazoline   Click here for help

GtoPdb Ligand ID: 124

Synonyms: Afrin® | oxymethazoline | SCH-9384 | Upneeq® (opthalmic solution) | Vicks Sinex®
Approved drug PDB Ligand
oxymetazoline is an approved drug (FDA (1986))
Compound class: Synthetic organic
Comment: Oxymetazoline is a selective α1-adrenoceptor agonist and α2-adrenoceptor partial agonist with vasoconstricting properties.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 44.62
Molecular weight 260.19
XLogP 3.36
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES Cc1cc(c(c(c1CC1=NCCN1)C)O)C(C)(C)C
Isomeric SMILES Cc1cc(c(c(c1CC1=NCCN1)C)O)C(C)(C)C
InChI InChI=1S/C16H24N2O/c1-10-8-13(16(3,4)5)15(19)11(2)12(10)9-14-17-6-7-18-14/h8,19H,6-7,9H2,1-5H3,(H,17,18)
InChI Key WYWIFABBXFUGLM-UHFFFAOYSA-N
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
5-HT1B receptor Hs Agonist Full agonist 9.5 pKi - 4
pKi 9.5 [4]
5-HT1D receptor Hs Agonist Partial agonist 9.4 pKi - 4
pKi 9.4 [4]
α2A-adrenoceptor Primary target of this compound Hs Agonist Partial agonist 8.0 – 8.6 pKi - 3,5,10
pKi 8.0 – 8.6 (Ki 1x10-8 – 2.8x10-9 M) [3,5,10]
α1A-adrenoceptor Primary target of this compound Hs Agonist Full agonist 8.0 – 8.2 pKi - 2,7-9
pKi 8.0 – 8.2 [2,7-9]
α2C-adrenoceptor Hs Agonist Partial agonist 6.7 pKi - 3,10
pKi 6.7 [3,10]
5-HT2C receptor Hs Agonist Full agonist 6.3 – 6.8 pKi - 1
pKi 6.3 – 6.8 [1]
α1B-adrenoceptor Hs Agonist Full agonist 6.5 pKi - 7-8
pKi 6.5 [7-8]
α1D-adrenoceptor Hs Agonist Partial agonist 6.4 pKi - 7-8
pKi 6.4 [7-8]
α1D-adrenoceptor Rn Agonist Partial agonist 6.2 pKi - 6
pKi 6.2 [6]
α2B-adrenoceptor Hs Agonist Partial agonist 5.5 – 6.2 pKi - 3,10
pKi 5.5 – 6.2 [3,10]
Ligand mentioned in the following text fields