Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:49 UTC |
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Update Date | 2022-03-07 02:51:40 UTC |
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HMDB ID | HMDB0014577 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Prochlorperazine |
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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. |
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Structure | CN1CCN(CCCN2C3=CC=CC=C3SC3=C2C=C(Cl)C=C3)CC1 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 |
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Synonyms | Value | Source |
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2-Chloro-10-(3-(1-methyl-4-piperazinyl)propyl)-phenothiazine | ChEBI | 2-Chloro-10-(3-(4-methyl-1-piperazinyl)propyl)phenothiazine | ChEBI | 3-Chloro-10-(3-(1-methyl-4-piperazinyl)propyl)phenothiazine | ChEBI | 3-Chloro-10-(3-(4-methyl-1-piperazinyl)propyl)phenothiazine | ChEBI | Chloro-3 (N-methylpiperazinyl-3 propyl)-10 phenothiazine | ChEBI | N-(gamma-(4'-Methylpiperazinyl-1')propyl)-3-chlorophenothiazine | ChEBI | Prochlorperazin | ChEBI | Prochlorperazinum | ChEBI | Prochlorpermazine | ChEBI | Prochlorpromazine | ChEBI | Procloperazine | ChEBI | Proclorperazina | ChEBI | Compro | Kegg | N-(g-(4'-Methylpiperazinyl-1')propyl)-3-chlorophenothiazine | Generator | N-(Γ-(4'-methylpiperazinyl-1')propyl)-3-chlorophenothiazine | Generator | Chlormeprazine | HMDB | Chlorperazine | HMDB | Prochloroperazine | HMDB | Prochlorpemazine | HMDB | Prochlorperazine edisylate | HMDB | Prochlorperazine maleate | HMDB | Proclorperazine | HMDB | Compazine | HMDB | Edisylate salt, prochlorperazine | HMDB | Prochlorperazine edisylate salt | HMDB | Salt, prochlorperazine edisylate | HMDB | Edisylate, prochlorperazine | HMDB | Maleate, prochlorperazine | HMDB |
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Chemical Formula | C20H24ClN3S |
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Average Molecular Weight | 373.943 |
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Monoisotopic Molecular Weight | 373.13794618 |
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IUPAC Name | 2-chloro-10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine |
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Traditional Name | compro |
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CAS Registry Number | 58-38-8 |
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SMILES | CN1CCN(CCCN2C3=CC=CC=C3SC3=C2C=C(Cl)C=C3)CC1 |
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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 |
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InChI Key | WIKYUJGCLQQFNW-UHFFFAOYSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Benzothiazines |
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Sub Class | Phenothiazines |
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Direct Parent | Phenothiazines |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 228 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.011 g/L | Not Available | LogP | 4.6 | Not Available |
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Experimental Chromatographic Properties | Experimental Collision Cross SectionsAdduct Type | Data Source | CCS Value (Å2) | Reference |
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[M+H]+ | CBM | 183.7 | 30932474 |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized | Show more...
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Prochlorperazine EI-B (Non-derivatized) | splash10-01vo-9853000000-ba88fedd94e150c34e1a | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Prochlorperazine EI-B (Non-derivatized) | splash10-0229-7933000000-4e14a9a9728c361941d3 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Prochlorperazine EI-B (Non-derivatized) | splash10-01vo-9853000000-ba88fedd94e150c34e1a | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Prochlorperazine EI-B (Non-derivatized) | splash10-0229-7933000000-4e14a9a9728c361941d3 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Prochlorperazine GC-MS (Non-derivatized) - 70eV, Positive | splash10-06xt-9553000000-7c5cfdffb1424ab9b4c3 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Prochlorperazine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-022c-9752000000-533ac31876b44d82f2aa | 2014-09-20 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Prochlorperazine , positive-QTOF | splash10-00fr-0219000000-abf2f9a1f6a1efb497b8 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Prochlorperazine 35V, Positive-QTOF | splash10-01vo-1913000000-18dc04b2a841732cef46 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prochlorperazine 10V, Positive-QTOF | splash10-00di-0119000000-c5080d81978309713b43 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prochlorperazine 20V, Positive-QTOF | splash10-00dl-3759000000-27beb72c9655a5a10292 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prochlorperazine 40V, Positive-QTOF | splash10-05fr-9641000000-e1d8ff01b979f368bc22 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prochlorperazine 10V, Negative-QTOF | splash10-00di-0009000000-237f2504c3b8b858f420 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prochlorperazine 20V, Negative-QTOF | splash10-03k9-0093000000-596171d19953284e7c67 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prochlorperazine 40V, Negative-QTOF | splash10-001j-6790000000-18250cf634dd842e2d16 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prochlorperazine 10V, Negative-QTOF | splash10-00di-0009000000-b7096763c7649cee6320 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prochlorperazine 20V, Negative-QTOF | splash10-00di-0019000000-a9bd62cc7ad7a33ce8ea | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prochlorperazine 40V, Negative-QTOF | splash10-001i-9073000000-a0220d70775ae8155309 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prochlorperazine 10V, Positive-QTOF | splash10-00di-0009000000-2aca52d377070d2c9d91 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prochlorperazine 20V, Positive-QTOF | splash10-00dl-0908000000-0cbc070d6e31e1a308b0 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prochlorperazine 40V, Positive-QTOF | splash10-08n9-9621000000-82835cd472af493a67f3 | 2021-09-24 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00433 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00433 | | details |
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Abnormal Concentrations |
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| Not Available |
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Predicted Concentrations |
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Blood | 0.000 uM | Adult (>18 years old) | Both | Normal | Predicted based on drug qualities | Blood | 0.000 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | Predicted based on drug qualities |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB00433 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 4748 |
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KEGG Compound ID | C07403 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Prochlorperazine |
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METLIN ID | Not Available |
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PubChem Compound | 4917 |
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PDB ID | P77 |
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ChEBI ID | 8435 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | Not Available |
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