Zotepine

Title: Zotepine
CAS Registry Number: 26615-21-4
CAS Name: 2-[(8-Chlorodibenzo[b,f]thiepin-10-yl)oxy]-N,N-dimethylethanamine
Additional Names: 2-chloro-11-(2-dimethylaminoethoxy)dibenzo[b,f]thiepine
Trademarks: Lodopin (Fujisawa); Nipolept (Aventis); Setous (Shionogi); Zoleptil (Abbott)
Molecular Formula: C18H18ClNOS
Molecular Weight: 331.86
Percent Composition: C 65.15%, H 5.47%, Cl 10.68%, N 4.22%, O 4.82%, S 9.66%
Literature References: Combined dopamine (D2) and serotonin (5-HT2) receptor antagonist. Prepn: S. Umio et al., DE 1907670; eidem, US 3704245 (1969, 1972 both to Fujisawa); I. Ueda et al., Chem. Pharm. Bull. 26, 3058 (1978). Pharmacology: S. Uchida et al., Arzneim.-Forsch. 29, 1588 (1979). Pharmacokinetics and metabolism: K. Noda et al., ibid. 1595. Toxicology: K. Fukuhara et al., ibid. 1600. Effects on serotonin receptors: A. Czyrak et al., Pharmacopsychiatry 26, 53 (1993). GC-MS determn in plasma: O. Tanaka et al., Ther. Drug Monit. 18, 294 (1996). Clinical trials in schizophrenia: C. Barnas et al., Int. Clin. Psychopharmacol. 7, 23 (1992); A. Meyer-Lindenberg et al., Pharmacopsychiatry 30, 35 (1997).
Properties: Crystals from cyclohexane, mp 90-91°. uv max (95% ethanol): 266 nm. LD50 in male mice, rats (mg/kg): 108, 458 orally; 43.3, 39.7 i.v.; 40.0, 97.0 i.p.; 84.9, 2080 s.c. (Fukuhara).
Melting point: mp 90-91°
Absorption maximum: uv max (95% ethanol): 266 nm
Toxicity data: LD50 in male mice, rats (mg/kg): 108, 458 orally; 43.3, 39.7 i.v.; 40.0, 97.0 i.p.; 84.9, 2080 s.c. (Fukuhara)
Therap-Cat: Antipsychotic.
Keywords: Antipsychotic; Other Tricyclics; Serotonin-Dopamine Antagonist.
Zoxamide Zoxazolamine Zygadenine

Zotepine
Zotepine2D1.svg
Zotepine3Dan3.gif
Systematic (IUPAC) name
2-[(8-​chlorodibenzo(b,f)​thiepin-​10-​yl)oxy]-​N,N-​dimethylethanamine
Clinical data
Trade names Zoleptil
AHFS/Drugs.com International Drug Names
Legal status Prescription only
Routes Oral
Pharmacokinetic data
Bioavailability 7-13% (Oral)[1]
Metabolism N-desmethylation to norzotepine (30-40%)[1]
Half-life 13.7-15.9 hours, 12 hours (Norzotepine)[1]
Excretion 17% (Urine)[1]
Identifiers
CAS number 26615-21-4 N
ATC code N05AX11
PubChem CID 5736
IUPHAR ligand 103
DrugBank none
ChemSpider 5534 YesY
UNII U29O83JAZW YesY
KEGG D01321 YesY
ChEBI CHEBI:32316 YesY
ChEMBL CHEMBL285802 YesY
Chemical data
Formula C18H18ClNOS 
Mol. mass 331.86
 N (what is this?)  (verify)

Zotepine (brand names: Losizopilon (JP), Lodopin (ID, JP), Setous (JP), Zoleptil (CZ, PT, TR, UK†); where † indicates a formulation that has been discontinued) is an atypical antipsychotic drug indicated for acute and chronic schizophrenia. It has been used in Germany since 1990 (although it has been discontinued in Germany) and Japan since 1982.

Zotepine is not approved for use in the United States, United Kingdom, Australia, Canada or New Zealand.[2]