Asenapine

Asenapine
Clinical data
Trade names	Saphris, Sycrest, Secuado
Other names	ORG-5222
AHFS/Drugs.com	Monograph
MedlinePlus	a610015
License data	EU EMA: by INN; US DailyMed: Asenapine; US FDA: Asenapine;
Pregnancy; category	AU: C;
Routes of; administration	Sublingual, transdermal
Drug class	Atypical antipsychotic
ATC code	N05AH05 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); UK: POM (Prescription only); US: WARNINGRx-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	35% (sublingual), <2% (Oral)
Protein binding	95%
Metabolism	hepatic (glucurinodation by UGT1A4 and oxidative metabolism by CYP1A2)
Elimination half-life	24 hours
Excretion	Kidney (50%), Faecal (40%; ~5–16% as unchanged drug in faeces)
Identifiers
	IUPAC name (3aRS,12bRS)-rel-5-Chloro-2,3,3a,12b-tetrahydro-; 2-methyl-1H-dibenz[2,3:6,7]oxepino[4,5-c]pyrrole;
CAS Number	65576-45-6 ; as salt: 85650-56-2;
PubChem CID	163091; as salt: 6917875;
IUPHAR/BPS	22;
DrugBank	DB06216; as salt: DBSALT000010;
ChemSpider	2300725 ; as salt: 5293095;
UNII	JKZ19V908O; as salt: CU9463U2E2;
KEGG	D11769; as salt: D02995;
ChEBI	CHEBI:71253 ; as salt: CHEBI:71245;
ChEMBL	ChEMBL1201756 ; as salt: ChEMBL2040684;
ECHA InfoCard	100.059.828
Chemical and physical data
Formula	C17H16ClNO
Molar mass	285.77 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc4cc2c(Oc1c(cccc1)[C@@H]3CN(C[C@@H]23)C)cc4;
	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-/m0/s1 ; Key:VSWBSWWIRNCQIJ-GJZGRUSLSA-N ; ; as salt: InChI=1S/C17H16ClNO.C4H4O4/c1-19-9-14-12-4-2-3-5-16(12)20-17-7-6-11(18)8-13(17)15(14)10-19;5-3(6)1-2-4(7)8/h2-8,14-15H,9-10H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t14-,15-;/m1./s1; Key:GMDCDXMAFMEDAG-CHHFXETESA-N;
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Asenapine, sold under the brand name Saphris among others, is an atypical antipsychotic medication used to treat schizophrenia and acute mania associated with bipolar disorder as well as the medium to long-term management of bipolar disorder.

It was chemically derived via altering the chemical structure of the tetracyclic (atypical) antidepressant, mianserin.

It was initially approved in the United States in 2009 and approved as a generic medication in 2020.

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