Sertindole

Sertindole

Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy category	AU: C
Routes of administration	Oral
ATC code	N05AE03 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) Approved for marketing in approximately 20 countries
Pharmacokinetic data
Bioavailability	75%
Protein binding	99.5%
Metabolism	Hepatic (mostly via CYP2D6 and CYP3A4)
Biological half-life	3 days
Excretion	Faecal (the majority), Renal (4% metabolites; 1% unchanged)
Identifiers
IUPAC name 1-[2-[4-[5-chloro-1-(4-fluorophenyl)-indol-3-yl]-1-piperidyl]ethyl]imidazolidin-2-one
CAS Number	106516-24-9 Y
PubChem CID	60149
IUPHAR/BPS	98
DrugBank	DB06144 Y
ChemSpider	54229 Y
UNII	GVV4Z879SP
KEGG	D00561 Y
ChEBI	CHEBI:9122 Y
ChEMBL	CHEMBL12713 Y
ECHA InfoCard	100.162.562
Chemical and physical data
Formula	C24H26ClFN4O
Molar mass	440.941 g/mol
3D model (Jmol)	Interactive image
SMILES Fc1ccc(cc1)n3c2ccc(Cl)cc2c(c3)C5CCN(CCN4C(=O)NCC4)CC5
InChI InChI=1S/C24H26ClFN4O/c25-18-1-6-23-21(15-18)22(16-30(23)20-4-2-19(26)3-5-20)17-7-10-28(11-8-17)13-14-29-12-9-27-24(29)31/h1-6,15-17H,7-14H2,(H,27,31) Y Key:GZKLJWGUPQBVJQ-UHFFFAOYSA-N Y

Sertindole (brand names: Serdolect and Serlect) is an antipsychotic medication. Sertindole was developed by the Danish pharmaceutical company Lundbeck and marketed under license by Abbott Labs. Like other atypical antipsychotics, it has activity at dopamine and serotonin receptors in the brain. It is used in the treatment of schizophrenia. It is classified chemically as a phenylindole derivative.

Sertindole is not approved for use in the United States and was discontinued in Australia in January 2014.

Sertindole appears effective as an antipsychotic in schizophrenia. It may have a favorable side effect profile, and efficacy similar to risperidone.

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

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

Uncommon (0.1–1% incidence) adverse effects include:

Rare (<0.1% incidence) adverse effects include:

Unknown frequency adverse events include:

Sertindole is metabolized in the body to dehydrosertindole.

Abbott Labs first applied for U.S. Food and Drug Administration (FDA) approval for sertindole in 1996, but withdrew this application in 1998 following concerns over the increased risk of sudden death from QTc prolongation. In a trial of 2000 patients on taking sertindole, 27 patients died unexpectedly, including 13 sudden deaths. Lundbeck cites the results of the Sertindole Cohort Prospective (SCoP) study of 10,000 patients to support its claim that although sertindole does increase the QTc interval, this is not associated with increased rates of cardiac arrhythmias, and that patients on sertindole had the same overall mortality rate as those on risperidone. Nevertheless, in April 2009 an FDA advisory panel voted 13-0 that sertindole was effective in the treatment of schizophrenia but 12-1 that it had not been shown to be acceptably safe. As of October 2010^[update], the drug has not been approved by the FDA for use in the USA.