Haloperidol
Structural Formula Vector Image
Title: Haloperidol
CAS Registry Number: 52-86-8
CAS Name: 4-[4-(4-Chlorophenyl)-4-hydroxy-1-piperidinyl]-1-(4-fluorophenyl)-1-butanone
Additional Names: 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
Manufacturers' Codes: R-1625
Trademarks: 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)
Molecular Formula: C21H23ClFNO2
Molecular Weight: 375.86
Percent Composition: C 67.11%, H 6.17%, Cl 9.43%, F 5.05%, N 3.73%, O 8.51%
Literature 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).
Properties: Crystals, mp 148.0-149.4°. uv max (9:1 0.1M HCl:methanol): 247, 221 nm (e 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).
Melting point: mp 148.0-149.4°
pKa: pKa 8.3
Absorption maximum: uv max (9:1 0.1M HCl:methanol): 247, 221 nm (e 13300, 15000)
Toxicity data: LD50 orally in rats: 165 mg/kg (Goldenthal); i.p. in mice: 60 mg/kg (Collins, Horlington)
 
Derivative Type: Hydrochloride
CAS Registry Number: 1511-16-6
Molecular Formula: C21H23ClFNO2.HCl
Molecular Weight: 412.33
Percent Composition: 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.
Melting point: mp 226-227.5°
 
Derivative Type: Decanoate
CAS Registry Number: 74050-97-8
Manufacturers' Codes: KD-136
Trademarks: Haldol Decanoate (Janssen); Halomonth (Dainippon); Neoperidole (Kyowa Hakko)
Molecular Formula: C31H41ClFNO3
Molecular Weight: 530.11
Percent Composition: C 70.24%, H 7.80%, Cl 6.69%, F 3.58%, N 2.64%, O 9.05%
 
Therap-Cat: Antidyskinetic (in Gilles de la Tourette's disease); antipsychotic.
Keywords: Antidyskinetic; Antipsychotic; Butyrophenones.

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