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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:51 UTC
HMDB IDHMDB0015068
Secondary Accession Numbers
  • HMDB15068
Metabolite Identification
Common NameMesoridazine
DescriptionMesoridazine is only found in individuals that have used or taken this drug. It is a phenothiazine antipsychotic with effects similar to chlorpromazine. [PubChem]Based upon animal studies, mesoridazine, as with other phenothiazines, acts indirectly on reticular formation, whereby neuronal activity into reticular formation is reduced without affecting its intrinsic ability to activate the cerebral cortex. In addition, the phenothiazines exhibit at least part of their activities through depression of hypothalamic centers. Neurochemically, the phenothiazines are thought to exert their effects by a central adrenergic blocking action.
Structure
Data?1582753255
Synonyms
ValueSource
10-(2(1-Methyl-2-piperidyl)ethyl)-2-(methylsulfinyl)phenothiazineChEBI
10-(2-(1-Methyl-2-piperidyl)ethyl)-2-methylsulfinyl phenothiazineChEBI
2-Methanesulfinyl-10-[2-(1-methyl-piperidin-2-yl)-ethyl]-10H-phenothiazineChEBI
MesoridazinaChEBI
MesoridazinumChEBI
Thioridazine thiomethyl sulfoxideChEBI
Thioridazine-2-sulfoxideChEBI
TPS-23ChEBI
LidanarKegg
10-(2(1-Methyl-2-piperidyl)ethyl)-2-(methylsulphinyl)phenothiazineGenerator
10-(2-(1-Methyl-2-piperidyl)ethyl)-2-methylsulphinyl phenothiazineGenerator
2-Methanesulphinyl-10-[2-(1-methyl-piperidin-2-yl)-ethyl]-10H-phenothiazineGenerator
Thioridazine thiomethyl sulphoxideGenerator
Thioridazine-2-sulphoxideGenerator
Thioridazien thiomethyl sulfoxideHMDB
Thioridazine monosulfoxide analogHMDB
TPS23HMDB
SerentilHMDB
Chemical FormulaC21H26N2OS2
Average Molecular Weight386.574
Monoisotopic Molecular Weight386.148654844
IUPAC Name2-methanesulfinyl-10-[2-(1-methylpiperidin-2-yl)ethyl]-10H-phenothiazine
Traditional Namemesoridazine
CAS Registry Number5588-33-0
SMILES
CN1CCCCC1CCN1C2=CC=CC=C2SC2=C1C=C(C=C2)S(C)=O
InChI Identifier
InChI=1S/C21H26N2OS2/c1-22-13-6-5-7-16(22)12-14-23-18-8-3-4-9-20(18)25-21-11-10-17(26(2)24)15-19(21)23/h3-4,8-11,15-16H,5-7,12-14H2,1-2H3
InChI KeySLVMESMUVMCQIY-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
  • Para-thiazine
  • Piperidine
  • Benzenoid
  • Sulfoxide
  • Tertiary amine
  • Tertiary aliphatic amine
  • Thioether
  • Sulfinyl compound
  • Azacycle
  • Amine
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organosulfur compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.077 g/LNot Available
LogP3.9Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.077 g/LALOGPS
logP3.83ALOGPS
logP3.57ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)19.36ChemAxon
pKa (Strongest Basic)8.19ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.55 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity115.13 m³·mol⁻¹ChemAxon
Polarizability43.83 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+190.45831661259
DarkChem[M-H]-190.04331661259
DeepCCS[M+H]+183.20430932474
DeepCCS[M-H]-180.84630932474
DeepCCS[M-2H]-213.73130932474
DeepCCS[M+Na]+189.29730932474
AllCCS[M+H]+192.632859911
AllCCS[M+H-H2O]+190.032859911
AllCCS[M+NH4]+195.032859911
AllCCS[M+Na]+195.732859911
AllCCS[M-H]-189.432859911
AllCCS[M+Na-2H]-189.632859911
AllCCS[M+HCOO]-189.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MesoridazineCN1CCCCC1CCN1C2=CC=CC=C2SC2=C1C=C(C=C2)S(C)=O4376.4Standard polar33892256
MesoridazineCN1CCCCC1CCN1C2=CC=CC=C2SC2=C1C=C(C=C2)S(C)=O3396.1Standard non polar33892256
MesoridazineCN1CCCCC1CCN1C2=CC=CC=C2SC2=C1C=C(C=C2)S(C)=O3223.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Mesoridazine GC-MS (Non-derivatized) - 70eV, Positivesplash10-006t-9113000000-c43ca99a239d882aaec02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mesoridazine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-9331000000-8e14cb597ee411174c3e2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Mesoridazine , positive-QTOFsplash10-000i-0119000000-fffe496e2ff640e0c9352017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mesoridazine 35V, Positive-QTOFsplash10-009j-4409000000-1ac2768cf2aedf0c606d2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesoridazine 10V, Positive-QTOFsplash10-000i-0109000000-34ffca607374cc2d3dad2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesoridazine 20V, Positive-QTOFsplash10-002r-3419000000-8395b65edb5ff6d5cb3d2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesoridazine 40V, Positive-QTOFsplash10-002g-8912000000-af14b6ff98df3cb285e92016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesoridazine 10V, Negative-QTOFsplash10-000i-2009000000-a670d5fab14237f10c3c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesoridazine 20V, Negative-QTOFsplash10-03di-4195000000-c1fd7e13d41cc4d310642016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesoridazine 40V, Negative-QTOFsplash10-03di-9320000000-f0c0d591d683e00317972016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesoridazine 10V, Positive-QTOFsplash10-000i-0009000000-ea6eb7f211262d8b7c602021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesoridazine 20V, Positive-QTOFsplash10-000j-5419000000-67a5e726504808a7f1652021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesoridazine 40V, Positive-QTOFsplash10-0032-9342000000-55bdb60e5caa2bf4c40c2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesoridazine 10V, Negative-QTOFsplash10-000i-0009000000-ae73409bcb6436484a742021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesoridazine 20V, Negative-QTOFsplash10-000i-0039000000-5b62f5f508c6b499a5f32021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesoridazine 40V, Negative-QTOFsplash10-01ox-9082000000-3b94eddc2f178347c05e2021-10-11Wishart LabView Spectrum
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 DB00933 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00933 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 IDDB00933
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3936
KEGG Compound IDC07143
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMesoridazine
METLIN IDNot Available
PubChem Compound4078
PDB IDNot Available
ChEBI ID6780
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

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. Burstein ES, Ma J, Wong S, Gao Y, Pham E, Knapp AE, Nash NR, Olsson R, Davis RE, Hacksell U, Weiner DM, Brann MR: Intrinsic efficacy of antipsychotics at human D2, D3, and D4 dopamine receptors: identification of the clozapine metabolite N-desmethylclozapine as a D2/D3 partial agonist. J Pharmacol Exp Ther. 2005 Dec;315(3):1278-87. Epub 2005 Aug 31. [PubMed:16135699 ]
  3. Choi S, Haggart D, Toll L, Cuny GD: Synthesis, receptor binding and functional studies of mesoridazine stereoisomers. Bioorg Med Chem Lett. 2004 Sep 6;14(17):4379-82. [PubMed:15357957 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:
HTR2A
Uniprot ID:
P28223
Molecular weight:
52602.6
References
  1. Choi S, Haggart D, Toll L, Cuny GD: Synthesis, receptor binding and functional studies of mesoridazine stereoisomers. Bioorg Med Chem Lett. 2004 Sep 6;14(17):4379-82. [PubMed:15357957 ]
  2. Rauser L, Savage JE, Meltzer HY, Roth BL: Inverse agonist actions of typical and atypical antipsychotic drugs at the human 5-hydroxytryptamine(2C) receptor. J Pharmacol Exp Ther. 2001 Oct;299(1):83-9. [PubMed:11561066 ]
  3. Herrick-Davis K, Grinde E, Teitler M: Inverse agonist activity of atypical antipsychotic drugs at human 5-hydroxytryptamine2C receptors. J Pharmacol Exp Ther. 2000 Oct;295(1):226-32. [PubMed:10991983 ]