asenapine   Click here for help

GtoPdb Ligand ID: 22

Synonyms: ORG-5222 | ORG5222 | Saphris® | Secuado® (transdermal asenapine) | Sycrest®
Approved drug
asenapine is an approved drug (FDA (2009), EMA (2010))
Compound class: Synthetic organic
Comment: Asenapine is an atypical antipsychotic. The drug is an enantiomeric mixture, and we show one enantioner here. Alternative enantiomers include CHEMBL1201756.
Marketed formulations may contain asenapine maleate (PubChem CID 6917875).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 0
Rotatable bonds 0
Topological polar surface area 12.47
Molecular weight 285.09
XLogP 3.41
No. Lipinski's rules broken 0
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Canonical SMILES Clc1ccc2c(c1)C1CN(CC1c1c(O2)cccc1)C
Isomeric SMILES Clc1ccc2c(c1)[C@H]1CN(C[C@@H]1c1c(O2)cccc1)C
InChI InChI=1S/C17H16ClNO/c1-19-9-14-12-4-2-3-5-16(12)20-17-7-6-11(18)8-13(17)15(14)10-19/h2-8,14-15H,9-10H2,1H3/t14-,15-/m1/s1
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
5-HT2A receptor Primary target of this compound Hs Antagonist Antagonist 10.2 pKi - 6
pKi 10.2 (Ki 6x10-11 M) [6]
H1 receptor Hs Antagonist Antagonist 9.8 pKi - 5
pKi 9.8 [5]
D2 receptor Primary target of this compound Hs Antagonist Antagonist 8.9 pKi - 6
pKi 8.9 (Ki 1.2x10-9 M) [6]
5-HT1D receptor Hs Agonist Full agonist 8.4 pKi - 5
pKi 8.4 [5]
5-HT1A receptor Hs Agonist Full agonist 8.0 – 8.3 pKi - 3,5
pKi 8.0 – 8.3 [3,5]
5-HT1B receptor Hs Agonist Full agonist 8.1 pKi - 5
pKi 8.1 [5]
5-ht1e receptor Hs Agonist Full agonist 8.0 pKi - 5
pKi 8.0 [5]