Identification
- Generic Name
- Methdilazine
- DrugBank Accession Number
- DB00902
- Background
Methdilazine is a phenothiazine compound with antihistaminic activity. It is used in the treatment of various dermatoses to relieve pruritus.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Methdilazine (DB00902)
- Weight
- Average: 296.43
Monoisotopic: 296.13471934 - Chemical Formula
- C18H20N2S
- Synonyms
- Methdilazine
- Methdilazinum
- Metodilazina
Pharmacology
- Indication
Used for the symptomatic relief of hypersensitivity reactions and particularly for the control of pruritic skin disorders
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In allergic reactions an allergen interacts with and cross-links surface IgE antibodies on mast cells and basophils. Once the mast cell-antibody-antigen complex is formed, a complex series of events occurs that eventually leads to cell-degranulation and the release of histamine (and other chemical mediators) from the mast cell or basophil. Once released, histamine can react with local or widespread tissues through histamine receptors. Histamine, acting on H1-receptors, produces pruritis, vasodilatation, hypotension, flushing, headache, tachycardia, and bronchoconstriction. Histamine also increases vascular permeability and potentiates pain. Methdilazine is a histamine H1 antagonist. It competes with histamine for the normal H1-receptor sites on effector cells of the gastrointestinal tract, blood vessels and respiratory tract. It provides effective, temporary relief of sneezing, watery and itchy eyes, and runny nose due to hay fever and other upper respiratory allergies.
- Mechanism of action
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.
Target Actions Organism AHistamine H1 receptor antagonistHumans - Absorption
Well absorbed in the digestive tract.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Symptoms 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.
- Pathways
Pathway Category Methdilazine H1-Antihistamine Action Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcetazolamide The therapeutic efficacy of Acetazolamide can be decreased when used in combination with Methdilazine. Amifampridine The risk or severity of seizure can be increased when Methdilazine is combined with Amifampridine. Amobarbital The therapeutic efficacy of Amobarbital can be decreased when used in combination with Methdilazine. Amphetamine Amphetamine may decrease the sedative activities of Methdilazine. Benzphetamine Benzphetamine may decrease the sedative activities of Methdilazine. Benzylpenicilloyl polylysine Methdilazine may decrease effectiveness of Benzylpenicilloyl polylysine as a diagnostic agent. Betahistine The therapeutic efficacy of Betahistine can be decreased when used in combination with Methdilazine. Brexanolone The therapeutic efficacy of Brexanolone can be decreased when used in combination with Methdilazine. Brivaracetam The therapeutic efficacy of Brivaracetam can be decreased when used in combination with Methdilazine. Bupropion The risk or severity of seizure can be increased when Bupropion is combined with Methdilazine. 
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- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Methdilazine Hydrochloride T0GSO02UEZ 1229-35-2 IEISBKIVLDXSMZ-UHFFFAOYSA-N - International/Other Brands
- Dilosyn / Tacaryl
Categories
- ATC Codes
- R06AD04 — Methdilazine
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound 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.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzothiazines
- Sub Class
- Phenothiazines
- Direct Parent
- Phenothiazines
- Alternative Parents
- Alkyldiarylamines / Diarylthioethers / N-alkylpyrrolidines / Benzenoids / 1,4-thiazines / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Alkyldiarylamine / Amine / Aromatic heteropolycyclic compound / Aryl thioether / Azacycle / Benzenoid / Diarylthioether / Hydrocarbon derivative / N-alkylpyrrolidine / Organic nitrogen compound
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- phenothiazines (CHEBI:6823)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 4Q13LY9Z8X
- CAS number
- 1982-37-2
- InChI Key
- HTMIBDQKFHUPSX-UHFFFAOYSA-N
- InChI
- 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
- IUPAC Name
- 10-[(1-methylpyrrolidin-3-yl)methyl]-10H-phenothiazine
- SMILES
- CN1CCC(CN2C3=CC=CC=C3SC3=CC=CC=C23)C1
References
- General References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- External Links
- Human Metabolome Database
- HMDB0015038
- KEGG Drug
- D04979
- KEGG Compound
- C07175
- PubChem Compound
- 14677
- PubChem Substance
- 46505472
- ChemSpider
- 14009
- BindingDB
- 81470
- 29648
- ChEBI
- 6823
- ChEMBL
- CHEMBL1200959
- Therapeutic Targets Database
- DAP001070
- PharmGKB
- PA164743018
- Wikipedia
- Methdilazine
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Westwood squibb pharmaceuticals inc
- Alpharma us pharmaceuticals division
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 87-88 °C PhysProp water solubility 0.348 mg/L Not Available logP 5.23 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 0.0147 mg/mL ALOGPS logP 4.56 ALOGPS logP 3.94 Chemaxon logS -4.3 ALOGPS pKa (Strongest Basic) 8.81 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 6.48 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 91.64 m3·mol-1 Chemaxon Polarizability 33.37 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9901 Blood Brain Barrier + 0.9949 Caco-2 permeable + 0.7779 P-glycoprotein substrate Substrate 0.7768 P-glycoprotein inhibitor I Inhibitor 0.605 P-glycoprotein inhibitor II Inhibitor 0.864 Renal organic cation transporter Inhibitor 0.834 CYP450 2C9 substrate Non-substrate 0.7288 CYP450 2D6 substrate Substrate 0.7763 CYP450 3A4 substrate Non-substrate 0.526 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Non-inhibitor 0.9072 CYP450 2D6 inhibitor Inhibitor 0.9056 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.9346 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6238 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.9678 Biodegradation Not ready biodegradable 0.9972 Rat acute toxicity 3.2306 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8634 hERG inhibition (predictor II) Inhibitor 0.7305
Spectra
- Mass Spec (NIST)
- Download (11 KB)
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available GC-MS Spectrum - EI-B GC-MS splash10-0002-9310000000-08a0f77b83bac7e129ee Mass Spectrum (Electron Ionization) MS splash10-0002-9630000000-8f3e969116ed3e70d7e5 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- 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 catecholamin...
- Gene Name
- HRH1
- Uniprot ID
- P35367
- Uniprot Name
- Histamine H1 receptor
- Molecular Weight
- 55783.61 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- 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. [Article]
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at November 03, 2023 23:48