Record Information |
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Version | 1.0 |
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Creation Date | 2016-05-25 18:28:32 UTC |
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Update Date | 2016-11-09 01:17:28 UTC |
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Accession Number | CHEM022332 |
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Identification |
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Common Name | Zuclopenthixol |
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Class | Small Molecule |
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Description | Zuclopenthixol, also known as Zuclopentixol or Zuclopenthixolum, is an antipsychotic agent. Zuclopenthixol is a thioxanthene-based neuroleptic with therapeutic actions similar to the phenothiazine antipsychotics. It is an antagonist at D1 and D2 dopamine receptors. Major brands of zuclopenthixol are Cisordinol, Acuphase, and Clopixol. This drug is a liquid. This compound belongs to the thioxanthenes. These are organic polycyclic compounds containing a thioxanthene moiety, which is an aromatic tricycle derived from xanthene by replacing the oxygen atom with a sulfur atom. Known drug targets of zuclopenthixol include 5-hydroxytryptamine receptor 2A, D(1B) dopamine receptor, D(2) dopamine receptor, D(1A) dopamine receptor, and alpha-1A adrenergic receptor. It is known that zuclopenthixol is metabolized by Cytochrome P450 2D6. Zuclopenthixol was approved for use in Canada in 2011, but is not approved for use in the United States. |
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Contaminant Sources | - HMDB Contaminants - Urine
- STOFF IDENT Compounds
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Contaminant Type | Not Available |
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Chemical Structure | |
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Synonyms | Value | Source |
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(Z)-4-(3-(2-Chlorothioxanthen-9-ylidene)propyl)-1-piperazineethanol | ChEBI | Zuclopenthixolum | ChEBI | Zuclopentixol | ChEBI | Clopixol | Kegg | Zuclopenthixol acetate | HMDB | Zuclopenthixol decanoate | HMDB | Zuclopenthixol dihydrochloride | HMDB | alpha Clopenthixol | HMDB | alpha-Clopenthixol | HMDB | Clopenthixol | HMDB | Cisordinol | HMDB |
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Chemical Formula | C22H25ClN2OS |
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Average Molecular Mass | 400.965 g/mol |
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Monoisotopic Mass | 400.138 g/mol |
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CAS Registry Number | 53772-83-1 |
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IUPAC Name | 2-(4-{3-[(9Z)-2-chloro-9H-thioxanthen-9-ylidene]propyl}piperazin-1-yl)ethan-1-ol |
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Traditional Name | zuclopenthixol |
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SMILES | OCCN1CCN(CC\C=C2\C3=CC=CC=C3SC3=C2C=C(Cl)C=C3)CC1 |
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InChI Identifier | InChI=1S/C22H25ClN2OS/c23-17-7-8-22-20(16-17)18(19-4-1-2-6-21(19)27-22)5-3-9-24-10-12-25(13-11-24)14-15-26/h1-2,4-8,16,26H,3,9-15H2/b18-5- |
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InChI Key | WFPIAZLQTJBIFN-DVZOWYKESA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as thioxanthenes. These are organic polycyclic compounds containing a thioxanthene moiety, which is an aromatic tricycle derived from xanthene by replacing the oxygen atom with a sulfur atom. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Benzothiopyrans |
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Sub Class | 1-benzothiopyrans |
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Direct Parent | Thioxanthenes |
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Alternative Parents | |
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Substituents | - Thioxanthene
- Diarylthioether
- Aryl thioether
- N-alkylpiperazine
- Aryl chloride
- Aryl halide
- 1,4-diazinane
- Piperazine
- Benzenoid
- Tertiary aliphatic amine
- Tertiary amine
- 1,2-aminoalcohol
- Azacycle
- Thioether
- Alkanolamine
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Organochloride
- Organohalogen compound
- Amine
- Alcohol
- Primary alcohol
- Organic oxygen compound
- Organopnictogen compound
- Organic nitrogen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Not Available |
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Cellular Locations | Not Available |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Not Available |
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Appearance | Not Available |
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Experimental Properties | Property | Value |
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Melting Point | Not Available | Boiling Point | Not Available | Solubility | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0007-9634000000-725d867abc3a21a8367b | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-0gi0-9344200000-75820d187d1501e996b0 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0122900000-b0c208380aecf467bf42 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0fl0-3797300000-6a0d6b81802987061025 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-022j-9742000000-32dbb76748579ce3b574 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0009000000-111f43ef21dddab4b92a | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-1309000000-5ad402c11e1d57ff2c3e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9200000000-4957e4a977f2522244e6 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0000900000-c8fc2efcbee8e9787417 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0uk9-0173900000-88227a1c47ee94c13262 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0c00-1498000000-7582c437e09f5a3c3e63 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0009000000-f42087d0e1f36c98fd92 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00kb-0009000000-de6822a024bc2597f5b7 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0pb9-1059000000-01d717517b320d6b747f | Spectrum |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | Not Available |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | Not Available |
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Uses/Sources | Not Available |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB01624 |
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HMDB ID | HMDB0015561 |
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FooDB ID | Not Available |
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Phenol Explorer ID | Not Available |
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KNApSAcK ID | Not Available |
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BiGG ID | Not Available |
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BioCyc ID | Not Available |
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METLIN ID | Not Available |
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PDB ID | Not Available |
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Wikipedia Link | Zuclopenthixol |
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Chemspider ID | 4470984 |
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ChEBI ID | 51364 |
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PubChem Compound ID | 5311507 |
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Kegg Compound ID | Not Available |
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YMDB ID | Not Available |
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ECMDB ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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MSDS | Not Available |
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General References | 1. Khalifa AE: Zuclopenthixol facilitates memory retrieval in rats: possible involvement of noradrenergic and serotonergic mechanisms. Pharmacol Biochem Behav. 2003 Jul;75(4):755-62. | 2. Khalifa AE: Pro-oxidant activity of zuclopenthixol in vivo: differential effect of the drug on brain oxidative status of scopolamine-treated rats. Hum Exp Toxicol. 2004 Aug;23(9):439-45. | 3. Jayakody K, Gibson RC, Kumar A, Gunadasa S: Zuclopenthixol acetate for acute schizophrenia and similar serious mental illnesses. Cochrane Database Syst Rev. 2012 Apr 18;(4):CD000525. doi: 10.1002/14651858.CD000525.pub3. | 4. Nielsen MK, Johansen SS: Simultaneous determination of 25 common pharmaceuticals in whole blood using ultra-performance liquid chromatography-tandem mass spectrometry. J Anal Toxicol. 2012 Sep;36(7):497-506. doi: 10.1093/jat/bks054. Epub 2012 Jun 19. | 5. Fond G, Macgregor A, Tamouza R, Hamdani N, Meary A, Leboyer M, Dubremetz JF: Comparative analysis of anti-toxoplasmic activity of antipsychotic drugs and valproate. Eur Arch Psychiatry Clin Neurosci. 2014 Mar;264(2):179-83. doi: 10.1007/s00406-013-0413-4. Epub 2013 Jun 15. | 6. Internet Mental Health: http://www.mentalhealth.com/drug/p30-z03.html#Head_7 |
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