Methdilazine (T3D2924)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2009-07-21 20:27:54 UTC
Update Date2014-12-24 20:25:53 UTC
Accession NumberT3D2924
Identification
Common NameMethdilazine
ClassSmall Molecule
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.
Compound Type
  • Amine
  • Drug
  • Ether
  • Histamine Antagonist
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Synonym
Dilosyn
MD
Methdilazine Monohydrochloride
Methdilazinum
Methodilazine
Metodilazina
Tacaryl
Chemical FormulaC18H20N2S
Average Molecular Mass296.430 g/mol
Monoisotopic Mass296.135 g/mol
CAS Registry Number1982-37-2
IUPAC Name10-[(1-methylpyrrolidin-3-yl)methyl]-10H-phenothiazine
Traditional Namemethdilazine
SMILESCN1CCC(CN2C3=CC=CC=C3SC3=CC=CC=C23)C1
InChI IdentifierInChI=1/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 KeyInChIKey=HTMIBDQKFHUPSX-UHFFFAOYNA-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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point87-88°C
Boiling PointNot Available
Solubility0.348 mg/L
LogP5.23
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-9779fa04045a2c96d57f2021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1090000000-789730aa3b37623adfc12021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9230000000-cd9ffb7dec63f7fe8d122021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-908c3cef276d5324ab632021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0190000000-840a23c528d53f2591f22021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0930000000-e8e7355d83e44f37c46e2021-10-11View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-9630000000-8f3e969116ed3e70d7e52014-09-20View Spectrum
Toxicity Profile
Route of ExposureWell absorbed in the digestive tract.
Mechanism of ToxicityMethdilazine 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.
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed for the symptomatic relief of hypersensitivity reactions and particularly for the control of pruritic skin disorders
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSymptoms of overdose include clumsiness or unsteadiness, convulsions, drowsiness, dryness of mouth, nose, or throat, feeling faint, flushing or redness of face, hallucinations, muscle spasms (especially of neck and back), restlessness, shortness of breath or troubled breathing, shuffling walk, tic-like movements of head and face, trembling and shaking of hands, and trouble in sleeping.
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB00902
HMDB IDHMDB15038
PubChem Compound ID14677
ChEMBL IDCHEMBL1200959
ChemSpider ID14009
KEGG IDC07175
UniProt IDNot Available
OMIM ID
ChEBI ID774910
BioCyc IDNot Available
CTD IDNot Available
Stitch IDMethdilazine
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkMethdilazine
References
Synthesis ReferenceNot Available
MSDST3D2924.pdf
General References
  1. 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. [15782943 ]
  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. [9700532 ]
  3. 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. [2905130 ]
  4. Drugs.com [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Histamine H1 receptor
General Function:
Histamine receptor activity
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:
55783.61 Da
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. [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. [17016423 ]