5910. Mesoridazine

Nomenclature

CAS number: 5588-33-0
10-[2-(1-Methyl-2-piperidinyl)ethyl]-2-(methylsulfinyl)-10H-phenothiazine; thioridazine-2-sulfoxide; TPS-23.
C21H26N2OS2; mol wt 386.57.
C 65.25%, H 6.78%, N 7.25%, O 4.14%, S 16.59%.

Description and references

Dopamine receptor blocking agent; analog of thioridazine. Prepn: Renz et al., US 3084161 (1963 to Sandoz). Pharmacology and toxicology: Loew et al., Boll. Chim. Farm. 106, 332-371 (1967). Effects on dopaminergic function in comparison with sulforidazine and thioridazine, q.q.v.: D. M. Niedzwiecki et al., J. Pharmacol. Exp. Ther. 228, 636 (1984); C. D. Kilts et al., ibid. 231, 334 (1984). GLC determn in plasma: E. C. Dinovo et al., J. Pharm. Sci. 65, 667 (1976). Clinical evaluation in sleep disorders: K. Adam et al., Br. J. Clin. Pharmacol. 3, 157 (1976); as antipsychotic: R. Axelsson, Curr. Ther. Res. 21, 587 (1977). Toxicity studies: S. Maruyama et al., Niigata Igakkai Zasshi 81, 611 (1967), C.A. 68, 76856h (1968). Brief description: J. Am. Med. Assoc. 216, 313 (1971).

Chemical structure

Properties

Oily product.

Derivative

Benzenesulfonate.

Nomenclature

CAS number: 32672-69-8
Mesoridazine besylate; NC-123; Lidanar (Sandoz); Lidanil (Sandoz); Serentil (Boehringer, Ing.).
C27H32N2O4S3; mol wt 544.75.
C 59.53%, H 5.92%, N 5.14%, O 11.75%, S 17.66%.

Properties

LD50 in mice (mg/kg): 33 i.v.; 611 s.c.; 346 orally (Maruyama).

Derivative

Tartrate.
C25H32N2O7S2; mol wt 536.66.
C 55.95%, H 6.01%, N 5.22%, O 20.87%, S 11.95%.

Properties

Crystals from ethyl acetate, mp 115-120°.

Therapeutic Category

Antipsychotic.

Keywords

Antipsychotic; Phenothiazines