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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:50 UTC
HMDB IDHMDB0015038
Secondary Accession Numbers
  • HMDB15038
Metabolite Identification
Common NameMethdilazine
DescriptionMethdilazine is only found in individuals that have used or taken this drug. It is a phenothiazine compound with antihistaminic activity. It is used in the treatment of various dermatoses to relieve pruritus.Methdilazine binds to the histamine H1 receptor. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine.
Structure
Data?1582753250
Synonyms
ValueSource
10-[(1-Methyl-3-pyrrolidinyl)methyl]phenothiazineChEBI
DilosynChEBI
MetdilazinaChEBI
MethdilazinumChEBI
MJ 5022ChEBI
TacarylChEBI
TacazylChEBI
MDHMDB
Methdilazine monohydrochlorideHMDB
MethodilazineHMDB
Methdilazine hydrochlorideHMDB
Chemical FormulaC18H20N2S
Average Molecular Weight296.43
Monoisotopic Molecular Weight296.13471934
IUPAC Name10-[(1-methylpyrrolidin-3-yl)methyl]-10H-phenothiazine
Traditional Namemethdilazine
CAS Registry Number1982-37-2
SMILES
CN1CCC(CN2C3=CC=CC=C3SC3=CC=CC=C23)C1
InChI Identifier
InChI=1S/C18H20N2S/c1-19-11-10-14(12-19)13-20-15-6-2-4-8-17(15)21-18-9-5-3-7-16(18)20/h2-9,14H,10-13H2,1H3
InChI KeyHTMIBDQKFHUPSX-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
  • Benzenoid
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Thioether
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point87 - 88 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.015 g/LNot Available
LogP4.3Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.015 g/LALOGPS
logP4.56ALOGPS
logP3.94ChemAxon
logS-4.3ALOGPS
pKa (Strongest Basic)8.81ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity91.64 m³·mol⁻¹ChemAxon
Polarizability33.37 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]+170.3831661259
DarkChem[M-H]-167.83931661259
DeepCCS[M-2H]-200.40330932474
DeepCCS[M+Na]+175.65330932474
AllCCS[M+H]+169.632859911
AllCCS[M+H-H2O]+166.332859911
AllCCS[M+NH4]+172.632859911
AllCCS[M+Na]+173.532859911
AllCCS[M-H]-172.332859911
AllCCS[M+Na-2H]-171.632859911
AllCCS[M+HCOO]-171.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MethdilazineCN1CCC(CN2C3=CC=CC=C3SC3=CC=CC=C23)C13576.9Standard polar33892256
MethdilazineCN1CCC(CN2C3=CC=CC=C3SC3=CC=CC=C23)C12423.0Standard non polar33892256
MethdilazineCN1CCC(CN2C3=CC=CC=C3SC3=CC=CC=C23)C12466.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Methdilazine EI-B (Non-derivatized)splash10-0002-9310000000-08a0f77b83bac7e129ee2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methdilazine EI-B (Non-derivatized)splash10-0002-9310000000-08a0f77b83bac7e129ee2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methdilazine GC-MS (Non-derivatized) - 70eV, Positivesplash10-03e9-3190000000-f46571c32392cef178252017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methdilazine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-9630000000-8f3e969116ed3e70d7e52014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methdilazine 10V, Positive-QTOFsplash10-0002-4090000000-160b71afca5a22413d1b2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methdilazine 20V, Positive-QTOFsplash10-0002-9030000000-8d0d280a4305d9ee98b82016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methdilazine 40V, Positive-QTOFsplash10-0pwa-9000000000-9bf2c2541da751eb73d12016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methdilazine 10V, Negative-QTOFsplash10-0002-0090000000-1ab8cb488f1b6fbcfa892016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methdilazine 20V, Negative-QTOFsplash10-000b-0960000000-51823d86df854fd0b7c92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methdilazine 40V, Negative-QTOFsplash10-0002-2910000000-35bf29f0bae2eb02a6542016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methdilazine 10V, Positive-QTOFsplash10-0002-0090000000-9779fa04045a2c96d57f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methdilazine 20V, Positive-QTOFsplash10-0002-1090000000-789730aa3b37623adfc12021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methdilazine 40V, Positive-QTOFsplash10-0002-9230000000-cd9ffb7dec63f7fe8d122021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methdilazine 10V, Negative-QTOFsplash10-0002-0090000000-908c3cef276d5324ab632021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methdilazine 20V, Negative-QTOFsplash10-0002-0190000000-840a23c528d53f2591f22021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methdilazine 40V, Negative-QTOFsplash10-0002-0930000000-e8e7355d83e44f37c46e2021-10-11Wishart 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 DB00902 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00902 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 IDDB00902
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID14009
KEGG Compound IDC07175
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethdilazine
METLIN IDNot Available
PubChem Compound14677
PDB IDNot Available
ChEBI ID774910
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 References
  1. Chattopadhyay D, Mukherjee T, Pal P, Saha B, Bhadra R: Altered membrane permeability as the basis of bactericidal action of methdilazine. J Antimicrob Chemother. 1998 Jul;42(1):83-6. [PubMed:9700532 ]
  2. Chattopadhyay D, Dastidar SG, Chakrabarty AN: Antimicrobial properties of methdilazine and its synergism with antibiotics and some chemotherapeutic agents. Arzneimittelforschung. 1988 Jul;38(7):869-72. [PubMed:2905130 ]
  3. Rani Basu L, Mazumdar K, Dutta NK, Karak P, Dastidar SG: Antibacterial property of the antipsychotic agent prochlorperazine, and its synergism with methdilazine. Microbiol Res. 2005;160(1):95-100. [PubMed:15782943 ]

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:
HRH1
Uniprot ID:
P35367
Molecular weight:
55783.6
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  4. Chattopadhyay D, Mukherjee T, Pal P, Saha B, Bhadra R: Altered membrane permeability as the basis of bactericidal action of methdilazine. J Antimicrob Chemother. 1998 Jul;42(1):83-6. [PubMed:9700532 ]
  5. Dasgupta A, Chaki S, Mukherjee S, Lourduraja J, Mazumdar K, Dutta NK, Dastidar SG: Experimental analyses of synergistic combinations of antibiotics with a recently recognised antibacterial agent, lacidipine. Eur J Clin Microbiol Infect Dis. 2010 Feb;29(2):239-43. doi: 10.1007/s10096-009-0845-y. Epub 2009 Dec 13. [PubMed:20012879 ]