clonidine   Click here for help

GtoPdb Ligand ID: 516

Synonyms: Catapres® | Kapvay®
Approved drug PDB Ligand
clonidine is an approved drug (FDA (1974))
Compound class: Synthetic organic
Comment: Clonidine is an α2 adrenoceptor agonist.
The structure shown here is in the amino form. A tautomeric imino form, represented by CHEBI:3757 also exists.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 36.42
Molecular weight 229.02
XLogP 2.68
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES Clc1cccc(c1NC1=NCCN1)Cl
Isomeric SMILES Clc1cccc(c1NC1=NCCN1)Cl
InChI InChI=1S/C9H9Cl2N3/c10-6-2-1-3-7(11)8(6)14-9-12-4-5-13-9/h1-3H,4-5H2,(H2,12,13,14)
InChI Key GJSURZIOUXUGAL-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
α2A-adrenoceptor Primary target of this compound Hs Agonist Agonist 6.7 – 9.2 pKi - 1,5-7
pKi 6.7 – 9.2 [1,5-7]
α2B-adrenoceptor Primary target of this compound Hs Agonist Partial agonist 6.3 – 9.5 pKi - 1,5-7
pKi 6.3 – 9.5 [1,5-7]
α1D-adrenoceptor Rn Agonist Full agonist 6.9 pKi - 4
pKi 6.9 [4]
α2C-adrenoceptor Hs Agonist Agonist 6.0 – 7.8 pKi - 1,5-7
pKi 6.0 – 7.8 [1,5-7]
α1D-adrenoceptor Hs Agonist Agonist 5.6 pKi - 8
pKi 5.6 [8]
α2A-adrenoceptor Hs Agonist Agonist 6.4 – 9.0 pEC50 - 1,7
pEC50 9.0 [7]
Description: increased ERK1/2 phosphorylation
pEC50 7.6 [1]
Description: GTPγs binding
pEC50 6.4 [7]
Description: increased cAMP generation
α2B-adrenoceptor Hs Agonist Agonist 7.4 – 8.0 pEC50 - 7
pEC50 8.0 [7]
Description: ERK1/2 phosphorylation
pEC50 7.4 [7]
Description: cAMP generation
α2C-adrenoceptor Hs Agonist Agonist 4.6 – 7.8 pEC50 - 3,7
pEC50 7.8 [7]
Description: ERK1/2 phosphorylation
pEC50 4.6 – 6.7 [3]
Description: 4.64 =value for β-arrestin recruitment and internalization
α2B-adrenoceptor Hs Agonist Agonist 8.6 pIC50 - 7
pIC50 8.6 [7]
Description: inhibition of forskolin stimulated cAMP generation
α2A-adrenoceptor Hs Agonist Agonist 8.2 pIC50 - 7
pIC50 8.2 [7]
Description: inhibition of forskolin stimulated cAMP generation
α2C-adrenoceptor Hs Agonist Agonist 7.5 – 7.7 pIC50 - 3,7
pIC50 7.5 – 7.7 [3,7]
Description: inhibition of cAMP production
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
HCN2 Mm Channel blocker Antagonist 5.1 pIC50 - 2
pIC50 5.1 (IC50 8.09x10-6 M) [2]
Voltage: -40.0 mV
HCN4 Mm Channel blocker Antagonist 5.0 pIC50 - 2
pIC50 5.0 (IC50 9.68x10-6 M) [2]
Voltage: -40.0 mV
HCN1 Mm Channel blocker Antagonist 4.4 pIC50 - 2
pIC50 4.4 [2]
Voltage: -40.0 mV
Selectivity at transporters
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Organic cation transporter 1 Hs Inhibitor Inhibition 6.3 pKi - 9
pKi 6.3 (Ki 5.5x10-7 M) [9]
Ligand mentioned in the following text fields