You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2021-09-14 15:45:46 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 effect

Health effect:

Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

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
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 Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available170.3831661259
DarkChem[M-H]-PredictedNot Available167.83931661259

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9310000000-08a0f77b83bac7e129ee2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9310000000-08a0f77b83bac7e129ee2018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03e9-3190000000-f46571c32392cef178252017-09-01View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-9630000000-8f3e969116ed3e70d7e52014-09-20View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-4090000000-160b71afca5a22413d1b2016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9030000000-8d0d280a4305d9ee98b82016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pwa-9000000000-9bf2c2541da751eb73d12016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-1ab8cb488f1b6fbcfa892016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000b-0960000000-51823d86df854fd0b7c92016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-2910000000-35bf29f0bae2eb02a6542016-08-03View 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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  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 ]