4598. Haloperidol

Nomenclature

CAS number: 52-86-8
4-[4-(4-Chlorophenyl)-4-hydroxy-1-piperidinyl]-1-(4-fluorophenyl)-1-butanone; 4-[4-(p-chlorophenyl)-4-hydroxypiperidino]-4′-fluorobutyrophenone; 4′-fluoro-4-(4-hydroxy-4-p-chlorophenylpiperidino)butyrophenone; 1-(3-p-fluorobenzoylpropyl)-4-p-chlorophenyl-4-hydroxypiperidine; R-1625; Aloperidin; Bioperidolo (Firma); Brotopon (Pfizer Taito); Dozic (Rosemont); Einalon S (Kodama); Eukystol (Merckle); Haldol (McNeil); Halosten (Shionogi); Keselan (Sumitomo); Linton (Yoshitomi); Peluces (Isei); Serenace (Searle); Serenase (Lusofarmaco); Sigaperidol (Dumex).
C21H23ClFNO2; mol wt 375.86.
C 67.11%, H 6.17%, Cl 9.43%, F 5.05%, N 3.73%, O 8.51%.

Description and references

Prepn: P. A. J. Janssen et al., J. Med. Pharm. Chem. 1, 281 (1959); P. A. J. Janssen, BE 577977 (1959), C.A. 54, 4630c (1960); idem, GB 895309; idem, US 3438991 (1962, 1969 both to Janssen). Toxicity: E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971); A. J. Collins, M. Horlington, Br. J. Pharmacol. 37, 140 (1969). Metabolism in man: A. Forsman et al., Curr. Ther. Res. 21, 606 (1977). Comprehensive description: C. A. Janicki, C. Y. Ko, Anal. Profiles Drug Subs. 9, 341-369 (1980). Review of pharmacology and therapeutic efficacy of decanoate in psychosis: R. Beresford, A. Ward, Drugs 33, 31-49 (1987).

Chemical structure

Properties

Crystals, mp 148.0-149.4°. uv max (9:1 0.1M HCl:methanol): 247, 221 nm (ε 13300, 15000). pKa 8.3. Soly in water: 1.4 mg/100 ml. Freely sol in chloroform, methanol, acetone, benzene, dil acids. LD50 orally in rats: 165 mg/kg (Goldenthal); i.p. in mice: 60 mg/kg (Collins, Horlington).

Derivative

Hydrochloride.

Nomenclature

CAS number: 1511-16-6
C21H23ClFNO2.HCl; mol wt 412.33.
C 61.17%, H 5.87%, Cl 17.20%, F 4.61%, N 3.40%, O 7.76%.

Properties

Crystals, mp 226-227.5°. Soly in water: 300 mg/100 ml.

Derivative

Decanoate.

Nomenclature

CAS number: 74050-97-8
KD-136; Haldol Decanoate (Janssen); Halomonth (Dainippon); Neoperidole (Kyowa Hakko).
C31H41ClFNO3; mol wt 530.11.
C 70.24%, H 7.80%, Cl 6.69%, F 3.58%, N 2.64%, O 9.05%.

Therapeutic Category

Antidyskinetic (in Gilles de la Tourette's disease); antipsychotic.

Keywords

Antidyskinetic; Antipsychotic; Butyrophenones