Prochlorperazine (CHEM002194)

Record Information
Version1.0
Creation Date2009-07-21 20:26:53 UTC
Update Date2026-05-14 16:38:36 UTC
Accession NumberCHEM002194
Identification
Common NameProchlorperazine
ClassSmall Molecule
Description
Prochlorperazine is only found in individuals that have used or taken this drug. It is a phenothiazine antipsychotic used principally in the treatment of nausea; vomiting; and vertigo. It is more likely than chlorpromazine to cause extrapyramidal disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p612) The mechanism of action of prochlorperazine has not been fully determined, but may be primarily related to its antidopaminergic effects. Prochlorperazine blocks the D2 somatodendritic autoreceptor, resulting in the blockade of postsynaptic dopamine receptors in the mesolimbic system and an increased dopamine turnover. Prochlorperazine also has anti-emetic effects, which can be attributed to dopamine blockade in the chemoreceptor trigger zone. Prochlorperazine also blocks anticholinergic and alpha-adrenergic receptors, the blockade of alpha(1)-adrenergic receptors resulting in sedation, muscle relaxation, and hypotension.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amine
  • Antiemetic
  • Antipsychotic Agent
  • Dopamine Antagonist
  • Drug
  • Ether
  • Metabolite
  • Organic Compound
  • Organochloride
  • Phenothiazine
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Chloro-10-(3-(1-methyl-4-piperazinyl)propyl)-phenothiazineChEBI
2-Chloro-10-(3-(4-methyl-1-piperazinyl)propyl)phenothiazineChEBI
3-Chloro-10-(3-(1-methyl-4-piperazinyl)propyl)phenothiazineChEBI
3-Chloro-10-(3-(4-methyl-1-piperazinyl)propyl)phenothiazineChEBI
Chloro-3 (N-methylpiperazinyl-3 propyl)-10 phenothiazineChEBI
N-(gamma-(4'-Methylpiperazinyl-1')propyl)-3-chlorophenothiazineChEBI
ProchlorperazinChEBI
ProchlorperazinumChEBI
ProchlorpermazineChEBI
ProchlorpromazineChEBI
ProcloperazineChEBI
ProclorperazinaChEBI
ComproKegg
N-(g-(4'-Methylpiperazinyl-1')propyl)-3-chlorophenothiazineGenerator
N-(Γ-(4'-methylpiperazinyl-1')propyl)-3-chlorophenothiazineGenerator
ChlormeprazineHMDB
ChlorperazineHMDB
ProchloroperazineHMDB
ProchlorpemazineHMDB
Prochlorperazine edisylateHMDB
Prochlorperazine maleateHMDB
ProclorperazineHMDB
CompazineHMDB
Edisylate salt, prochlorperazineHMDB
Prochlorperazine edisylate saltHMDB
Salt, prochlorperazine edisylateHMDB
Edisylate, prochlorperazineHMDB
Maleate, prochlorperazineHMDB
Chemical FormulaC20H24ClN3S
Average Molecular Mass373.943 g/mol
Monoisotopic Mass373.138 g/mol
CAS Registry Number58-38-8
IUPAC Name2-chloro-10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine
Traditional Namecompro
SMILESCN1CCN(CCCN2C3=CC=CC=C3SC3=C2C=C(Cl)C=C3)CC1
InChI IdentifierInChI=1S/C20H24ClN3S/c1-22-11-13-23(14-12-22)9-4-10-24-17-5-2-3-6-19(17)25-20-8-7-16(21)15-18(20)24/h2-3,5-8,15H,4,9-14H2,1H3
InChI KeyWIKYUJGCLQQFNW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazines
Sub ClassPhenothiazines
Direct ParentPhenothiazines
Alternative Parents
Substituents
  • Phenothiazine
  • Alkyldiarylamine
  • Diarylthioether
  • Aryl thioether
  • Tertiary aliphatic/aromatic amine
  • N-alkylpiperazine
  • N-methylpiperazine
  • Para-thiazine
  • Aryl chloride
  • Aryl halide
  • 1,4-diazinane
  • Benzenoid
  • Piperazine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Thioether
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point228°C
Boiling PointNot Available
Solubility15 mg/L (at 24°C)
Predicted Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP4.67ALOGPS
logP4.38ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)8.39ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.72 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity109.81 m³·mol⁻¹ChemAxon
Polarizability41.77 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureIntravenous, Oral, Rectal. Rapidly absorbed following oral administration.
Mechanism of ToxicityThe mechanism of action of prochlorperazine has not been fully determined, but may be primarily related to its antidopaminergic effects. Prochlorperazine blocks the D2 somatodendritic autoreceptor, resulting in the blockade of postsynaptic dopamine receptors in the mesolimbic system and an increased dopamine turnover. Prochlorperazine also has anti-emetic effects, which can be attributed to dopamine blockade in the chemoreceptor trigger zone. Prochlorperazine also blocks anticholinergic and alpha-adrenergic receptors, the blockade of alpha(1)-adrenergic receptors resulting in sedation, muscle relaxation, and hypotension.
MetabolismHepatic. Undergoes metabolism in the gastric mucosa and on first pass through the liver, CYP2D6 and/or CYP3A4. Half Life: 6 to 8 hours
Toxicity ValuesLD50=400mg/kg (orally in mice)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the symptomatic management of psychotic disorders, short term management of nonpsychotic anxiety in patients with generalized anxiety disorder, and for the control of severe nausea and vomiting of various causes.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSymptoms of central nervous system depression to the point of somnolence or coma. Agitation and restlessness may also occur. Other possible manifestations include convulsions, EKG changes and cardiac arrhythmias, fever and autonomic reactions such as hypotension, dry mouth and ileus; LD50=400mg/kg (orally in mice)
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB00433
HMDB IDHMDB0014577
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDP77
Wikipedia LinkProchlorperazine
Chemspider ID4748
ChEBI ID8435
PubChem Compound ID4917
Kegg Compound IDC07403
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

DrugSyn.org

MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=13808146
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1650428
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20825390
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=4891872