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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:55 UTC
HMDB IDHMDB0014577
Secondary Accession Numbers
  • HMDB14577
Metabolite Identification
Common NameProchlorperazine
DescriptionProchlorperazine 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.
Structure
Data?1582753195
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 Weight373.943
Monoisotopic Molecular Weight373.13794618
IUPAC Name2-chloro-10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine
Traditional Namecompro
CAS Registry Number58-38-8
SMILES
CN1CCN(CCCN2C3=CC=CC=C3SC3=C2C=C(Cl)C=C3)CC1
InChI Identifier
InChI=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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point228 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.011 g/LNot Available
LogP4.6Not Available
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
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01vo-9853000000-ba88fedd94e150c34e1aSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0229-7933000000-4e14a9a9728c361941d3Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01vo-9853000000-ba88fedd94e150c34e1aSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0229-7933000000-4e14a9a9728c361941d3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06xt-9553000000-7c5cfdffb1424ab9b4c3Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00fr-0219000000-abf2f9a1f6a1efb497b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0119000000-c5080d81978309713b43Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-3759000000-27beb72c9655a5a10292Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-9641000000-e1d8ff01b979f368bc22Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-237f2504c3b8b858f420Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03k9-0093000000-596171d19953284e7c67Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001j-6790000000-18250cf634dd842e2d16Spectrum
MSMass Spectrum (Electron Ionization)splash10-022c-9752000000-533ac31876b44d82f2aaSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00433 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00433 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00433
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4748
KEGG Compound IDC07403
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkProchlorperazine
METLIN IDNot Available
PubChem Compound4917
PDB IDP77
ChEBI ID8435
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:
DRD2
Uniprot ID:
P14416
Molecular weight:
50618.9
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Roberge RJ: Antiemetic-related dystonic reaction unmasked by removal of a scopolamine transdermal patch. J Emerg Med. 2006 Apr;30(3):299-302. [PubMed:16677982 ]
  3. Hamik A, Peroutka SJ: Differential interactions of traditional and novel antiemetics with dopamine D2 and 5-hydroxytryptamine3 receptors. Cancer Chemother Pharmacol. 1989;24(5):307-10. [PubMed:2527092 ]
  4. Vinson DR: Development of a simplified instrument for the diagnosis and grading of akathisia in a cohort of patients receiving prochlorperazine. J Emerg Med. 2006 Aug;31(2):139-45. [PubMed:17044574 ]
  5. Callan JE, Kostic MA, Bachrach EA, Rieg TS: Prochlorperazine vs. promethazine for headache treatment in the emergency department: a randomized controlled trial. J Emerg Med. 2008 Oct;35(3):247-53. doi: 10.1016/j.jemermed.2007.09.047. Epub 2008 Jun 5. [PubMed:18534808 ]
  6. Narita M, Takei D, Shiokawa M, Tsurukawa Y, Matsushima Y, Nakamura A, Takagi S, Asato M, Ikegami D, Narita M, Amano T, Niikura K, Hashimoto K, Kuzumaki N, Suzuki T: Suppression of dopamine-related side effects of morphine by aripiprazole, a dopamine system stabilizer. Eur J Pharmacol. 2008 Dec 14;600(1-3):105-9. doi: 10.1016/j.ejphar.2008.10.030. Epub 2008 Oct 21. [PubMed:18955042 ]
  7. Golembiewski J, Tokumaru S: Pharmacological prophylaxis and management of adult postoperative/postdischarge nausea and vomiting. J Perianesth Nurs. 2006 Dec;21(6):385-97. [PubMed:17169748 ]