10-[(1-methylpyrrolidin-3-yl)methyl]-10H-phenothiazine

• ChemBase ID: 778
• Molecular Formular: C18H20N2S
• Molecular Mass: 296.4298
• Monoisotopic Mass: 296.13471965
• SMILES: S1c2c(N(CC3CCN(C3)C)c3c1cccc3)cccc2
• Canonical SMILES: CN1CCC(C1)CN1c2ccccc2Sc2c1cccc2
• 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
• InChIKey: HTMIBDQKFHUPSX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 10-[(1-methylpyrrolidin-3-yl)methyl]-10H-phenothiazine
• IUPAC Traditional name: @methdilazine; methdilazine
• Brand Name: Bristaline; Dilosyn; Disyncram; Disyncran; Tacaryl; Tacaryl hydrochloride; Tacazyl; Tacryl
• Synonyms: MD; Methdilazine Hcl; Methdilazine hydrochloride; Methdilazine Monohydrochloride; Methdilazinum [INN-Latin]; Methilazine hydrochloride; Methodilazine; Metodilazina [INN-Spanish]; Methdilazine

Database IDs

• CAS Number: 1982-37-2
• PubChem SID: 46505472; 160964241
• PubChem CID: 14677
• ATC CODE: R06AD04
• CHEMBL: 1200959
• Chemspider ID: 14009
• DrugBank ID: DB00902
• KEGG ID: D04979
• Unique Ingredient Identifier: 4Q13LY9Z8X
• Wikipedia Title: Methdilazine

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.8433999
• LogD (pH = 7.4): 2.5153599
• Log P: 3.9367464
• Molar Refractivity: 91.6363 cm^3
• Polarizability: 35.260246 Å^3
• Polar Surface Area: 6.48 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.56
• LOG S: -4.3
• Solubility (Water): 1.47e-02 g/l

PROPERTIES

Physical Property

• Solubility: 0.348 mg/L
• Hydrophobicity(logP): 4.3

DETAILS

DrugBank - DB00902

• Drug Groups: approved
• Description: Methdilazine is a phenothiazine compound with antihistaminic activity. It is used in the treatment of various dermatoses to relieve pruritus.
• Indication: Used for the symptomatic relief of hypersensitivity reactions and particularly for the control of pruritic skin disorders
• Pharmacology: 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.
• Toxicity: 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.
• Affected Organisms: Humans and other mammals
• Absorption: Well absorbed in the digestive tract.
• 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. [Pubmed] ; 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] ; 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]
• External Links: Wikipedia

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. Pubmed
• 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
• 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