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).
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: asenapine

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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 Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2009), EMA (2010))
IUPAC Name Click here for help
(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 Click here for help
INN number INN
8278 asenapine
Synonyms Click here for help
ORG-5222 | ORG5222 | Saphris® | Secuado® (transdermal asenapine) | Sycrest®
Database Links Click here for help
CAS Registry No. 65576-45-6 (source: Scifinder)
ChEBI CHEBI:71257
ChEMBL Ligand CHEMBL504548
GtoPdb PubChem SID 135650779
PubChem CID 163091
Search Google for chemical match using the InChIKey VSWBSWWIRNCQIJ-HUUCEWRRSA-N
Search Google for chemicals with the same backbone VSWBSWWIRNCQIJ
Search PubMed clinical trials asenapine
Search PubMed titles asenapine
Search PubMed titles/abstracts asenapine
Search UniChem for chemical match using the InChIKey VSWBSWWIRNCQIJ-HUUCEWRRSA-N
Search UniChem for chemicals with the same backbone VSWBSWWIRNCQIJ
Wikipedia Asenapine