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52-86-8 molecular structure
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4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-1-(4-fluorophenyl)butan-1-one

ChemBase ID: 385
Molecular Formular: C21H23ClFNO2
Molecular Mass: 375.8642232
Monoisotopic Mass: 375.14013488
SMILES and InChIs

SMILES:
Clc1ccc(C2(O)CCN(CC2)CCCC(=O)c2ccc(F)cc2)cc1
Canonical SMILES:
Fc1ccc(cc1)C(=O)CCCN1CCC(CC1)(O)c1ccc(cc1)Cl
InChI:
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

Cite this record

CBID:385 http://www.chembase.cn/molecule-385.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-1-(4-fluorophenyl)butan-1-one
IUPAC Traditional name
haloperidol
4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-1-(4-fluorophenyl)butan-1-one
Brand Name
Serenase
Serenelfi
Sernas
Sernel
Sigaperidol
Ulcolind
Uliolind
Vesalium
ALDO
Aloperidin
Aloperidol
Aloperidolo
Aloperidon
Apo-Haloperidol
Bioperidolo
Brotopon
Dozic
Dozix
Einalon S
Eukystol
Galoperidol
Haldol
Haldol Decanoate
Haldol La
Haldol Solutab
Halidol
Halojust
Halol
Halopal
Haloperido
Haloperidol Decanoate
Haloperidol Intensol
Haloperidol Lactate
Halopidol
Halopoidol
Halosten
Keselan
Lealgin Compositum
Linton
Mixidol
Novo-Peridol
Pekuces
Peluces
Peridol
Pernox
Pms Haloperidol
Serenace
Synonyms
Haloperidol
Aloperidin
Bioperidolo
Brotopon
Dozic
4-[4-(4-Chlorophenyl)-4-hydroxypiperidino]-4′-fluorobutyrophenone
4-[4-(p-Chlorophenyl)-4-hydroxypiperidino]-4′-fluorobutyrophenone
Haloperidol
Fortunan
Haldol
Serenace
4-[4-(4-Chlorophenyl)-4-hydroxy-1-piperidinyl]-1-(4-fluorophenyl)-1-butanone
4-[4-(4-Chlorophenyl)-4-hydroxypiperidino]-4'-fluorobutyrophenone
4-[4-(p-Chlorophenyl)-4-hydroxypiperidino]-4'-fluorobutyrophenone
CAS Number
52-86-8
EC Number
200-155-6
MDL Number
MFCD00051423
PubChem SID
160963848
24277917
46508794
PubChem CID
3559
CHEBI ID
5613
ATC CODE
N05AD01
CHEMBL
54
Chemspider ID
3438
DrugBank ID
DB00502
IUPHAR ligand ID
86
KEGG ID
D00136
Unique Ingredient Identifier
J6292F8L3D
Wikipedia Title
Haloperidol
Medline Plus
a682180

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
LogD (pH = 7.4) 2.9278276  Log P 3.6611137 
Molar Refractivity 102.5919 cm3 Polarizability 39.481518 Å3
Polar Surface Area 40.54 Å2 Rotatable Bonds
Lipinski's Rule of Five true  Acid pKa 13.963255 
H Acceptors H Donor
LogD (pH = 5.5) 1.160161 
Log P 3.7  LOG S -4.93 
Solubility (Water) 4.46e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
0.1 M HCl: soluble3 mg/mL expand Show data source
14 mg/L expand Show data source
45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble0.39 mg/mL expand Show data source
DMSO: soluble expand Show data source
ethanol: soluble expand Show data source
H2O: insoluble expand Show data source
Apperance
white powder expand Show data source
Melting Point
148.0-149.4 °C expand Show data source
Vapor Pressure
2.48 x 10-10 mm Hg at 25 °C (estimated). expand Show data source
Hydrophobicity(logP)
4 expand Show data source
Storage Condition
-20°C expand Show data source
Room Temperature (15-30°C) expand Show data source
RTECS
EU1575000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
UN Number
2811 expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
3 expand Show data source
III expand Show data source
Australian Hazchem
2X expand Show data source
Risk Statements
60-61-25-36/37/38-43 expand Show data source
R:25 expand Show data source
Safety Statements
53-26-36/37/39-45 expand Show data source
S:28-29-36/37/39-45 expand Show data source
EU Classification
T2 expand Show data source
EU Hazard Identification Number
6.1B expand Show data source
Emergency Response Guidebook(ERG) Number
154 expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H301-H315-H317-H319-H335-H361 expand Show data source
GHS Precautionary statements
P261-P280-P301 + P310-P305 + P351 + P338 expand Show data source
RID/ADR
UN 2811 6.1/PG 3 expand Show data source
Admin Routes
Oral, IM, IV, depot (as decanoate ester) expand Show data source
Bioavailability
Approx. 50–60% (tablets and liquid) expand Show data source
Excretion
Biliary and renal expand Show data source
Half Life
10–30 hours expand Show data source
Metabolism
hepatic expand Show data source
Legal Status
Rx-only expand Show data source
Pregnancy Category
C expand Show data source
Gene Information
human ... ABCB1(5243), ADRA1A(148), ADRA2A(150), ADRA2C(152), CHRM1(1128), DRD2(1813), DRD3(1814), DRD4(1815), EBP(10682), HRH1(3269), HTR2A(3356), HTR2C(3358), HTR7(3363), KCNH1(3756), KCNH2(3757), PRNP(5621)rat ... Adra1a(29412), Adra2a(25083), Chrm1(25229), Chrm2(81645), Drd1a(24316), Drd2(24318), Drd3(29238), Drd4(25432), Hrh1(24448), Htr1a(24473), Htr1b(25075), Htr2a(29595), Htr2c(25187), Oprs1(29336), Slc6a3(24898), Slc6a4(25553) expand Show data source
Mechanism of Action
Dopaminergic antagonist with activity at sigma and NMDA receptors.Also reported to be a potassium channel (IK Ca ) blocker expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Application(s)
Antipsychotic expand Show data source
Tranquilliser expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
MP Biomedicals - 02153696 external link
Dopamine antagonist
DrugBank - DB00502 external link
Item Information
Drug Groups approved
Description 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 mental retardation 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)
Indication For the management of psychotic disorders (eg. schizophrenia) and delirium, as well as to control tics and vocal utterances of Tourette's syndrome (Gilles de la Tourette's syndrome). Also used for the treatment of severe behavioural problems in children with disrubtive behaviour disorder or ADHD (attention-deficit hyperactivity disorder). Haloperidol has been used in the prevention and control of severe nausea and vomiting.
Pharmacology Haloperidol is a psychotropic agent indicated for the treatment of schizophrenia. It also exerts sedative and antiemetic activity. Haloperidol principal pharmacological effects are similar to those of piperazine-derivative phenothiazines. The drug has action at all levels of the central nervous system-primarily at subcortical levels-as well as on multiple organ systems. Haloperidol has strong antiadrenergic and weaker peripheral anticholinergic activity; ganglionic blocking action is relatively slight. It also possesses slight antihistaminic and antiserotonin activity.
Toxicity LD50=165 mg/kg (rats, oral)
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Absorption Oral-60%
Half Life 3 weeks
Protein Binding 92%
References
Niemegeers CJ, Laduron PM: Pharmacology and biochemistry of haloperidol. Proc R Soc Med. 1976;69 suppl 1:3-8. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals - S1920 external link
Research Area: Neurological Disease
Biological Activity:
Haloperidol (Haldol) is an antipsychotic and butyrophenone. It is in the butyrophenone class of antipsychotic medications and has pharmacological effects similar to the phenothiazines. Haloperidol is an older antipsychotic used in the treatment of schizophrenia and, more acutely, in the treatment of acute psychotic states and delirium. A long-acting decanoate ester is used as a long acting injection given every 4 weeks to people with schizophrenia or related illnesses who have a poor compliance with medication and suffer frequent relapses of illness, or to overcome the drawbacks inherent to its orally administered counterpart that burst dosage increases risk or intensity of side effects. [1]
Sigma Aldrich - H1512 external link
Biochem/physiol Actions
Butyrophenone antipsychotic; D2, D3, and D4 dopamine receptor antagonist.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. H1512.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Niemegeers CJ, Laduron PM: Pharmacology and biochemistry of haloperidol. Proc R Soc Med. 1976;69 suppl 1:3-8. Pubmed
  • • Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 868B, (nmr)
  • • Janssen, P.A.J. et al., J. Med. Chem., 1959, 1, 281, (synth, pharmacol)
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  • • Janicki, C.A. et al., Anal. Profiles Drug Subst., 1980, 9, 341, (rev)
  • • Haloperidol Update 1958-1980, (ed. Ayd, F.J.), Ayd Medical Communications, 1980, (book)
  • • Janssen, P.A.J. et al., Handb. Exp. Pharmacol., (Part 1), 1980, 55, 25-41, (pharmacol, rev)
  • • Settle, E.C. et al., J. Clin. Psychiatry, 1983, 44, 440, (rev, pharmacol)
  • • Azibi, M. et al., J. Pharm. Sci., 1984, 73, 512, (cryst struct, ir)
  • • Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6089, (synonyms)
  • • Froemming, J.S. et al., Clin. Pharmacokinet., 1989, 17, 396, (rev)
  • • Park, K.H. et al., J. Chromatogr., 1991, 572, 259, (hplc)
  • • Aravagiri, M. et al., J. Chromatogr., B: Biomed. Appl., 1994, 656, 373, (hplc)
  • • Ulrich, S. et al., J. Chromatogr., B: Biomed. Appl., 1995, 663, 289, (gc)
  • • Fang, J. et al., Psychopharmacology, 1995, 121, 373, (tox)
  • • Usuki, E. et al., Chem. Res. Technol., 1996, 9, 800, (metab)
  • • Lynch, D.R. et al., J. Pharmacol. Exp. Ther., 1996, 279, 154, (pharmacol)
  • • Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 714
  • • Hoja, H. et al., J. Chromatogr., B: Biomed. Appl., 1997, 688, 275, (hplc-ms)
  • • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CLY500; HAG300
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PATENTS

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