Asenapine

Asenapine

Clinical data
Trade names	Saphris, Sycrest
AHFS/Drugs.com	Monograph
MedlinePlus	a610015
License data	EU EMA: Sycrest US FDA: Asenapine
Pregnancy category	AU: C US: C (Risk not ruled out)
Routes of administration	sublingual
ATC code	N05AH05 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	35% (sublingual), <2% (Oral)
Protein binding	95%
Metabolism	hepatic (glucurinodation by UGT1A4 and oxidative metabolism by CYP1A2)
Biological half-life	24 hours
Excretion	Renal (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 N
PubChem (CID)	163091
IUPHAR/BPS	22
ChemSpider	2300725 Y
UNII	JKZ19V908O Y
ChEBI	CHEBI:71253 N
ChEMBL	CHEMBL1201756 N
ECHA InfoCard	100.059.828
Chemical and physical data
Formula	C17H16ClNO
Molar mass	285.77 g/mol
3D model (Jmol)	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 Y Key:VSWBSWWIRNCQIJ-GJZGRUSLSA-N Y
NY (what is this?)

Asenapine, sold under the trade names Saphrisand Sycrest, is an atypical antipsychotic developed for the treatment of schizophrenia and acute mania associated with bipolar disorder.

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

Asenapine has been approved by the FDA for the acute treatment of adults with schizophrenia and acute treatment of manic or mixed episodes associated with bipolar I disorder with or without psychotic features in adults. In Australia asenapine's approved (and also listed on the PBS) indications include the following:

In the European Union and the UK asenapine is only licensed for use as a treatment for acute mania in bipolar I disorder.

Absorbed readily if administered sublingually, asenapine is poorly absorbed when swallowed. It appears to be less efficacious than other antipsychotics in the treatment of schizophrenia, although its all-cause discontinuation rate is moderate. As for its efficacy in the treatment of acute mania, a recent meta-analysis showed that it produces comparatively small improvements in manic symptoms in patients with acute mania and mixed episodes than most other antipsychotic drugs (with the exception of ziprasidone) such as risperidone and olanzapine. Drop-out rates (in clinical trials) were also unusually high with asenapine. According to a post-hoc analysis of two 3-week clinical trials it may possess some antidepressant effects in patients with acute mania or mixed episodes.

Adverse effect incidence
Note: The discussion below these lists provides some more context into the frequency and severity of these adverse effects.

Very common (>10% incidence) adverse effects include:

Common (1-10% incidence) adverse effects include: