Chlorprothixene

Title: Chlorprothixene
CAS Registry Number: 113-59-7
CAS Name: (Z)-3-(2-Chloro-9H-thioxanthen-9-ylidene)-N,N-dimethyl-1-propanamine
Additional Names: (Z)-2-chloro-N,N-dimethylthioxanthene-D9,g-propylamine; cis-2-chloro-N,N-dimethyl-3-thioxanthen-9-ylidenepropylamine; a-2-chloro-10-(3-dimethylaminopropylidene)thiaxanthene
Manufacturers' Codes: N-714
Trademarks: Taractan (Roche); Tarasan (Roche); Truxal (Lundbeck); Truxaletten (Lundbeck)
Molecular Formula: C18H18ClNS
Molecular Weight: 315.86
Percent Composition: C 68.45%, H 5.74%, Cl 11.22%, N 4.43%, S 10.15%
Literature References: Prepn: GB 829763; E. L. Engelhardt, US 3046283 (1960, 1962 both to Merck & Co.). Structure-activity study: G. E. Bonvicino et al., J. Org. Chem. 26, 2383 (1961). Comprehensive description: B. C. Rudy, B. Z. Senkowski, Anal. Profiles Drug Subs. 2, 63-84 (1973). HPLC determn in serum: M. Bagli et al., J. Chromatogr. B 657, 141 (1994). Clinical pharmacokinetics: idem et al., Arzneim.-Forsch. 46, 247 (1996).
Properties: Pale yellow crystals, mp 97-98°. Practically insol in water; sol in alcohol, ether, chloroform. Incompatible with acids, alkalies, phenobarbital, thiopental sodium, mepazine.
Melting point: mp 97-98°
Derivative Type: Hydrochloride
CAS Registry Number: 6469-93-8
Molecular Formula: C18H18ClNS.HCl
Molecular Weight: 352.32
Percent Composition: C 61.36%, H 5.44%, Cl 20.13%, N 3.98%, S 9.10%
Properties: Crystals, mp 221°. Freely sol in water at pH 6 to 6.5.
Melting point: mp 221°
Therap-Cat: Antipsychotic.
Keywords: Antipsychotic; Thioxanthenes.
Chlorpyrifos Chlorquinaldol Chlorsulfuron Chlortetracycline Chlorthalidone

Chlorprothixene
Chlorprothixene structure.svg
Chlorprothixene3Dan.gif
Systematic (IUPAC) name
(Z)-3-(2-chlorothioxanthen-9-ylidene)-N,N-dimethyl-propan-1-amine
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
Legal status Legend drug (US), ℞
Routes Oral, IM
Pharmacokinetic data
Metabolism Hepatic
Half-life 8–12 hours
Excretion Feces, urine
Identifiers
CAS number 113-59-7 YesY
ATC code N05AF03
PubChem CID 667467
DrugBank DB01239
ChemSpider 580849 YesY
UNII 9S7OD60EWP YesY
KEGG D00790 YesY
ChEBI CHEBI:50931 YesY
ChEMBL CHEMBL908 YesY
Chemical data
Formula C18H18ClNS 
Mol. mass 315.861 g/mol
 YesY (what is this?)  (verify)

Chlorprothixene (Cloxan, Taractan, Truxal) is a typical antipsychotic drug of the thioxanthene class and was the first of the series to be synthesized.[1] It was introduced in 1959 by Lundbeck.[2]

Chlorprothixene is not approved for use in the United States.