asenapine   

GtoPdb Ligand ID: 22

Synonyms: ORG-5222 | ORG5222 | Saphris® | Secuado® (transdermal asenapine) | Sycrest®
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
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
SMILES / InChI / InChIKey
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
InChI Key VSWBSWWIRNCQIJ-HUUCEWRRSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (2009), EMA (2010))
IUPAC Name
(2S,6S)-9-chloro-4-methyl-13-oxa-4-azatetracyclo[12.4.0.0^{2,6}.0^{7,12}]octadeca-1(18),7,9,11,14,16-hexaene
International Nonproprietary Names
INN number INN
8278 asenapine
Synonyms
ORG-5222 | ORG5222 | Saphris® | Secuado® (transdermal asenapine) | Sycrest®
Database Links
CAS Registry No. 65576-45-6 (source: Scifinder)
ChEBI CHEBI:71257
ChEMBL Ligand CHEMBL504548
GtoPdb PubChem SID 135650779
PubChem CID 163091
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Wikipedia Asenapine