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Friday, 15 August 2014

HALOPERIDOL 1/2

Haloperidol3DanJ.gif


See part 2 athttp://orgspectroscopyint.blogspot.in/2016/02/haloperidol-22.html

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

SaltATCFormulaMMCAS
-N05AD01C 21 H 23 ClFNO 2375.87 g / mol52-86-8

Application

  • neuroleptic
  • antidiskinetik
  • antipsychotic
  • dopamine antagonists

Classes of substances

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

Synthesis pathway

Synthesis a)


Trade Names

CountryTrade nameManufacturer
GermanyHaldol-JanssenJanssen-Cilag
various generic drugs
FranceHaldolJanssen-Cilag
United Kingdom- "-- "-
SerenakIvax
ItalyHaldolJanssen-Cilag
SerenasLusofarmaco
JapanGalomontJanssen - Dainippon Sumitomo
NeoperidolJanssen
SerenakDainippon Sumitomo
USAvarious generic drugs
UkraineHaloperidolLtd. "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
Systematic (IUPAC) name
4-[4-(4-Chlorophenyl)-4-hydroxy-1-piperidyl]-1-(4-fluorophenyl)-butan-1-one
Clinical data
Trade namesHaldol
AHFS/Drugs.commonograph
MedlinePlusa682180
Pregnancy cat.C (AU) C (US)
Legal statusPrescription Only (S4) (AU) ℞-only (CA) POM (UK) ℞-only (US)
RoutesOral, IM, IV, depot (asdecanoate ester)
Pharmacokinetic data
Bioavailability60-70% (Oral)[1]
Protein binding~90%[1]
MetabolismLiver-mediated[1]
Half-life14-26 hours (IV), 20.7 hours (IM), 14-37 hours (oral)[1]
ExcretionBiliary (hence in faeces) and in urine[1][2]
Identifiers
CAS number52-86-8 Yes
ATC codeN05AD01
PubChemCID 3559
IUPHAR ligand86
DrugBankDB00502
ChemSpider3438 Yes
UNIIJ6292F8L3D Yes
KEGGD00136 Yes
ChEBICHEBI:5613 Yes
ChEMBLCHEMBL54 Yes
Chemical data
FormulaC21H23ClFNO2 
Mol. mass375.9 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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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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Khajuraho Group of Monuments is located in India
Khajuraho Group of Monuments
Location of Khajuraho Group of Monuments in India.

Location in Madhya PradeshLocation in Madhya Pradesh

  1. Khajuraho Group of Monuments - Wikipedia, the free ...

    en.wikipedia.org/wiki/Khajuraho_Group_of_Monuments

    The Khajuraho Group of Monuments are a group of Hindu and Jain temples in Madhya Pradesh, India. About 620 kilometres (385 mi) southeast of New Delhi, ...























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