AUTHOR OF THIS BLOG

DR ANTHONY MELVIN CRASTO, WORLDDRUGTRACKER

HALOPERIDOL

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Aug 152014
 

Haloperidol3DanJ.gif

 

 

Haloperidol /hæloʊpɛridɒl/ (INN, BAN, USAN, AAN; most common brand names: Haldol, Serenace) is an antipsychotic medication used in the treatment of schizophrenia, acute psychosis, mania, delirium, tics in Tourette syndrome, choreas, nausea and vomiting inpalliative care, intractable hiccups, agitation and severe anxiety.[3][4][5] Haloperidol is a butyrophenone derivative and functions as aninverse agonist of dopamine. It is classified as a typical antipsychotic and has pharmacological effects similar to the phenothiazines.[4]

A long-acting decanoate ester of haloperidol is used as an injection given every four weeks to people with schizophrenia or related illnesses who have poor adherence to medication regimens (most commonly due to them forgetting to take their medication, or due to poor insight into their illness) and suffer frequent relapses of illness, or to overcome the drawbacks inherent to its orally administered counterpart.[6] Such long acting injections are controversial because it can be seen as denying people their right to stop taking their medication.

It is on the World Health Organization’s List of Essential Medicines, a list of the most important medication needed in a basic health system.[7]

Skeletal formula of haloperidol decanoate: The decanoate group is highlighted in blue.

 

Brief background information

Salt ATC Formula MM CAS
– N05AD01 C 21 H 23 ClFNO 2 375.87 g / mol 52-86-8

Application

  • neuroleptic
  • antidiskinetik
  • antipsychotic
  • dopamine antagonists

Classes of substances

  • Chloro alcohols
    • p-Ftorbutirofenony 4-piperidinyl derivatives
      • Piperidinol

Synthesis pathway

Synthesis a)


Trade Names

Country Trade name Manufacturer
Germany Haldol-Janssen Janssen-Cilag
various generic drugs
France Haldol Janssen-Cilag
United Kingdom – “- – “-
Serenak Ivax
Italy Haldol Janssen-Cilag
Serenas Lusofarmaco
Japan Galomont Janssen – Dainippon Sumitomo
Neoperidol Janssen
Serenak Dainippon Sumitomo
USA various generic drugs
Ukraine Haloperidol Ltd. “Gedeon Richter”, Hungary
various generic drugs

Formulations

  • ampoules of 5 mg / 1 ml, 100 mg / ml, 50 mg / ml;
  • drops of 2 mg to 20 mg / ml, 2 mg / ml, 0.5 mg / ml;
  • garnuly 1%;
  • Powder 1%;
  • 0.2% solution, 10 mg;
  • oral solution 2 mg / ml, 10 mg / ml;
  • Tablets of 0.75 mg, 1 mg, 1.5 mg, 2 mg, 3 mg, 5 mg, 10 mg, 20 mg

Links

  • Janssen, PAJ et al .: J. Med. Pharm. Chem. (JMPCAS) 1, 281 (1959).
  • DE 1289845 (Janssen; appl. 18/4/1959; GB -prior. 4.22.1958).
  • US 3,438,991 (Janssen; 4.15.1969; GB -prior. 18.11.1959).

 

1H NMR

13 C NMR

IR

 

 

 

MASS

http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422012000200028

Systematic (IUPAC) name
4-[4-(4-Chlorophenyl)-4-hydroxy-1-piperidyl]-1-(4-fluorophenyl)-butan-1-one
Clinical data
Trade names Haldol
AHFS/Drugs.com monograph
MedlinePlus a682180
Pregnancy cat. C (AU) C (US)
Legal status Prescription Only (S4) (AU) ℞-only (CA) POM (UK) ℞-only (US)
Routes Oral, IM, IV, depot (asdecanoate ester)
Pharmacokinetic data
Bioavailability 60-70% (Oral)[1]
Protein binding ~90%[1]
Metabolism Liver-mediated[1]
Half-life 14-26 hours (IV), 20.7 hours (IM), 14-37 hours (oral)[1]
Excretion Biliary (hence in faeces) and in urine[1][2]
Identifiers
CAS number 52-86-8 Yes
ATC code N05AD01
PubChem CID 3559
IUPHAR ligand 86
DrugBank DB00502
ChemSpider 3438 Yes
UNII J6292F8L3D Yes
KEGG D00136 Yes
ChEBI CHEBI:5613 Yes
ChEMBL CHEMBL54 Yes
Chemical data
Formula C21H23ClFNO2 
Mol. mass 375.9 g/mol

History

Haloperidol was discovered by Paul Janssen.[70] It was developed in 1958 at the Belgian company Janssen Pharmaceutica and submitted to the first of clinical trials in Belgiumlater that year.[71]

Haloperidol was approved by the U.S. Food and Drug Administration (FDA) on April 12, 1967; it was later marketed in the U.S. and other countries under the brand name Haldol byMcNeil Laboratories.[citation needed]

Society and culture

Coincident with civil unrest in the United States in the 1960s and 1970s, schizophrenia was racialized to match the behavior of angry/violent black men. Haldol was promoted as a way to pacify them, and was marketed to appeal to feelings of racial unease. (cf. Metzl 2010. The Protest Psychosis)

Soviet dissidents, including medical staff, have reported several times on the use of haloperidol in the Soviet Union for punitive purposes or simply to break the prisoners’ will.[72][73][74] Notable dissidents who were administered haloperidol as part of their court-ordered treatment were Sergei Kovalev and Leonid Plyushch.[75] The accounts Plyushch gave in the West, after he was allowed to leave the Soviet Union in 1976, were instrumental in triggering Western condemnation of Soviet practices at the World Psychiatric Association‘s 1977 meeting.[76] The use of haloperidol in the Soviet Union’s psychiatric system was prevalent because it was one of the few psychotropic drugs produced in quantity in the USSR.[77]

Haloperidol has been used for its sedating effects during the deportations of immigrants by the United States Immigration and Customs Enforcement (ICE). During 2002-2008, federal immigration personnel used haloperidol to sedate 356 deportees. By 2008, following court challenges over the practice, it was given to only three detainees. Following lawsuits, U.S. officials changed the procedure so the drug is administered only by the recommendation of medical personnel and under court order.[78][79]

Brand names

Haloperidol is sold under the tradenames Aloperidin, Bioperidolo, Brotopon, Dozic, Duraperidol (Germany), Einalon S, Eukystol, Haldol (common tradename in the US and UK), Halosten, Keselan, Linton, Peluces, Serenace and Sigaperidol.

Veterinary use

Haloperidol is also used on many different kinds of animals. It appears to be particularly successful when given to birds, e.g., a parrot that will otherwise continuously pluck its feathers out.[80]

References

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