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Substance Name: Haloperidol [USAN:USP:INN:BAN:JAN]
RN: 52-86-8
UNII: J6292F8L3D
InChIKey: LNEPOXFFQSENCJ-UHFFFAOYSA-N

Note

  • A phenyl-piperidinyl-butyrophenone that is used primarily to treat SCHIZOPHRENIA and other PSYCHOSES. It is also used in schizoaffective disorder, DELUSIONAL DISORDERS, ballism, and TOURETTE SYNDROME (a drug of choice) and occasionally as adjunctive therapy in INTELLECTUAL DISABILITY and the chorea of HUNTINGTON DISEASE. It is a potent antiemetic and is used in the treatment of intractable HICCUPS. (From AMA Drug Evaluations Annual, 1994, p279)

Molecular Formula

  • C21-H23-Cl-F-N-O2

Molecular Weight

  • 375.8687
 

Classification Codes

  • Anti-Dyskinesia Agents
  • Antidyskinetic (in Gilles De La Tourette's Disease)
  • Antiemetics
  • Antipsychotic
  • Antipsychotic Agents
  • Autonomic Agents
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Dopamine Agents
  • Dopamine Antagonists
  • Drug / Therapeutic Agent
  • Gastrointestinal Agents
  • Human Data
  • Mutation Data
  • Neurotransmitter Agents
  • Peripheral Nervous System Agents
  • Psychotropic Drugs
  • Reproductive Effect
  • Tranquilizing Agents
  • Tumor Data

Names and Synonyms

Name of Substance

  • Haloperidol
  • Haloperidol [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Haloperidol

Synonyms

  • 1-(3-p-Fluorobenzoylpropyl)-4-p-chlorophenyl-4-hydroxypiperidine
  • 1-Butanone, 4-(4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl)-1-(4-fluorophenyl)-
  • 4'-Fluoro-4-(4-(p-chlorophenyl)-4-hydroxypiperidinyl)butyrophenone
  • 4'-Fluoro-4-(4-hydroxy-4-(4'-chlorophenyl)piperidino)butyrophenone
  • 4'-Fluoro-4-(4-hydroxy-4-p-chlorophenylpiperidino)butyrophenone
  • 4-(4-(4-Chlorophenyl)-4-hydroxy-1-piperidinyl)-1-(4-fluorophenyl)-1-butanone
  • 4-(4-(p-Chlorophenyl)-4-hydroxypiperidino)-4'-fluorobutyrophenone
  • 4-(4-Hydroxy-4'-chloro-4-phenylpiperidino)-4'-fluorobutyrophenone
  • 5-21-02-00377 (Beilstein Handbook Reference)
  • Aldo
  • Aloperidin
  • Aloperidol
  • Aloperidolo
  • Aloperidolo [DCIT]
  • Aloperidolo [Italian]
  • BRN 0331267
  • Brotopon
  • Butyrophenone, 4'-fluoro-4-(4-(p-chlorophenyl)-4-hydroxypiperidino)-
  • Butyrophenone, 4-(4-(p-chlorophenyl)-4-hydroxypiperidino)-4'-fluoro-
  • CCRIS 1630
  • Dozic
  • Einalon S
  • EINECS 200-155-6
  • Eukystol
  • Fortunan
  • Galoperidol
  • gamma-(4-(p-Chlorophenyl)-4-hydroxypiperidino)-p-fluorbutyrophenone
  • gamma-(4-(p-Chlorophenyl)-4-hydroxypiperidino)-p-fluorobutyrophenone
  • Haldol
  • Haldol Solutab
  • Halojust
  • Halopal
  • Haloperidol
  • Haloperidolum
  • Haloperidolum [INN-Latin]
  • Halopoidol
  • HSDB 3093
  • Keselan
  • Lealgin compositum
  • Linton
  • McN-JR-1625
  • Mixidol
  • NSC 170973
  • NSC 615296
  • Peluces
  • Pernox
  • R 1625
  • R-1625
  • Serenace
  • Serenase
  • Serenelfi
  • Sernas
  • Sernel
  • Ulcolind
  • Uliolind
  • UNII-J6292F8L3D
  • Vesalium

Systematic Names

  • 1-Butanone, 4-(4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl)-1-(4-fluorophenyl)-
  • Butyrophenone, 4-(4-(p-chlorophenyl)-4-hydroxypiperidino)-4'-fluoro-
  • Haloperidol

Superlist Name

  • Haloperidol

Registry Numbers

CAS Registry Number

  • 52-86-8

FDA UNII

  • J6292F8L3D

System Generated Number

  • 0000052868

Structure Descriptors

InChI

1S/C21H23ClFNO2/c22-18-7-5-17(6-8-18)21(26)11-14-24(15-12-21)13-1-2-20(25)16-3-9-19(23)10-4-16/h3-10,26H,1-2,11-15H2

InChIKey

LNEPOXFFQSENCJ-UHFFFAOYSA-N

Smiles

c1cc(ccc1C(=O)CCCN2CCC(CC2)(c3ccc(cc3)Cl)O)F

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 subcutaneous > 2500ug/kg (2.5mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961.
child TDLo oral 72ug/kg (0.072mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) American Journal of Psychiatry. Vol. 143, Pg. 1176, 1985.
child TDLo unreported 375ug/kg/3D (0.375mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Lancet. Vol. 2, Pg. 479, 1980.
dog LD50 intravenous 18mg/kg (18mg/kg)   Clinical Pharmacology and Therapeutics Vol. 8, Pg. 770, 1967.
dog LD50 oral 90mg/kg (90mg/kg)   Clinical Pharmacology and Therapeutics Vol. 8, Pg. 770, 1967.
dog LD50 subcutaneous > 80mg/kg (80mg/kg)   Clinical Pharmacology and Therapeutics Vol. 8, Pg. 770, 1967.
human TDLo oral 71ug/kg (0.071mg/kg) BEHAVIORAL: EXCITEMENT Journal of Clinical Pyschopharmacology. Vol. 5, Pg. 120, 1985.
human TDLo unreported 9800ug/kg/28D (9.8mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA
Arzneimittel-Forschung. Drug Research. Vol. 32, Pg. 911, 1982.
infant TDLo unreported 280ug/kg (0.28mg/kg) BEHAVIORAL: IRRITABILITY

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: AGGRESSION
Acta Paediatrica. Vol. 82, Pg. 877, 1993.
mammal (species unspecified) LD50 oral 80mg/kg (80mg/kg)   Doklady Akademii Nauk SSSR. Proceedings of the Academy of Sciences of the USSR. For English translation, see DBIOAM and DKBSAS. Vol. 320, Pg. 242, 1991.
mammal (species unspecified) LD50 unreported 80mg/kg (80mg/kg)   Khimiko-Farmatsevticheskii Zhurnal. Chemical Pharmaceutical Journal. For English translation, see PCJOAU. Vol. 24(7), Pg. 27, 1990.
man TDLo multiple routes 343ug/kg (0.343mg/kg) BEHAVIORAL: TREMOR Southern Medical Journal. Vol. 76, Pg. 546, 1983.
man TDLo multiple routes 1mg/kg/1D-I (1mg/kg) BEHAVIORAL: MUSCLE WEAKNESS Journal of Clinical Pyschopharmacology. Vol. 3, Pg. 338, 1983.
man TDLo oral 480ug/kg/6D-I (0.48mg/kg) BEHAVIORAL: REGIDITY

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
American Journal of Psychiatry. Vol. 142, Pg. 389, 1985.
man TDLo oral 9mg/kg/30W-I (9mg/kg) PERIPHERAL NERVE AND SENSATION: FASCICULATIONS Biological Psychiatry. Vol. 22, Pg. 111, 1987.
man TDLo unreported 500ug/kg/5D-I (0.5mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) JAMA, Journal of the American Medical Association. Vol. 250, Pg. 485, 1983.
monkey LD50 subcutaneous > 1250ug/kg (1.25mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961.
mouse LD50 intraperitoneal 30mg/kg (30mg/kg)   Bollettino Chimico Farmaceutico. Vol. 111, Pg. 293, 1972.
mouse LD50 intravenous 13mg/kg (13mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: REGIDITY
Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961.
mouse LD50 oral 71mg/kg (71mg/kg)   Farmaco, Edizione Scientifica. Vol. 31, Pg. 442, 1976.
mouse LD50 subcutaneous 41mg/kg (41mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 1, Pg. 74, 1967.
mouse LD50 unreported 18mg/kg (18mg/kg)   Clinical Pharmacology and Therapeutics Vol. 3, Pg. 432, 1962.
rabbit LD50 intravenous 8mg/kg (8mg/kg)   Clinical Pharmacology and Therapeutics Vol. 8, Pg. 770, 1967.
rat LD50 intraperitoneal 27mg/kg (27mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 190, 1972.
rat LD50 intravenous 15mg/kg (15mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 45, 1974.
rat LD50 oral 128mg/kg (128mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 45, 1974.
rat LD50 subcutaneous 60mg/kg (60mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 45, 1974.
women TDLo intravenous 18300ug/kg/7D (18.3mg/kg) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)
Annals of Pharmacotherpy. Vol. 33, Pg. 1046, 1999.
women TDLo oral 100ug/kg/10D- (0.1mg/kg) BLOOD: AGRANULOCYTOSIS Journal of the American Geriatrics Society. Vol. 35, Pg. 248, 1987.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 151.5 deg C   EXP
pKa Dissociation Constant 8.66 (none)   EXP
log P (octanol-water) 4.3 (none)   EXP
Water Solubility 14 mg/L 25 EXP
Vapor Pressure 4.85E-11 mm Hg 25 EST
Henry's Law Constant 2.26E-14 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.16E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.