[(3S)-3-(4-bromophenyl)-3-(pyridin-2-yl)propyl]dimethylamine

• ChemBase ID: 288
• Molecular Formular: C16H19BrN2
• Molecular Mass: 319.23946
• Monoisotopic Mass: 318.07316062
• SMILES: Brc1ccc([C@H](CCN(C)C)c2ncccc2)cc1
• Canonical SMILES: CN(CC[C@H](c1ccccn1)c1ccc(cc1)Br)C
• InChI: InChI=1S/C16H19BrN2/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13/h3-9,11,15H,10,12H2,1-2H3/t15-/m0/s1
• InChIKey: ZDIGNSYAACHWNL-HNNXBMFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(3S)-3-(4-bromophenyl)-3-(pyridin-2-yl)propyl]dimethylamine
• IUPAC Traditional name: dexbrompheniramine
• Brand Name: Ilvin
• Synonyms: D-Brompheniramine; Parabromdylamine; Parabromodylamine; Dexbrompheniramine

Database IDs

• CAS Number: 132-21-8
• PubChem SID: 46505186; 160963751
• PubChem CID: 16960

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.36835155
• LogD (pH = 7.4): 1.683695
• Log P: 3.7496588
• Molar Refractivity: 83.6683 cm^3
• Polarizability: 32.339294 Å^3
• Polar Surface Area: 16.13 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.63
• LOG S: -4.4
• Solubility (Water): 1.27e-02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 3.4

DETAILS

DrugBank - DB00405

• Drug Groups: approved
• Description: Dexbrompheniramine maleate is an antihistamine used to treat allergic conditions such as hay fever or urticaria.
• Indication: For treatment and relief of symptoms of allergies, hay fever, and colds
• 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. Dexbrompheniramine is a histamine H1 antagonist (or more correctly, an inverse histamine agonist) of the alkylamine class. It provides effective, temporary relief of sneezing, watery and itchy eyes, and runny nose due to hay fever and other upper respiratory allergies.
• Toxicity: Signs of an overdose include fast or irregular heartbeat, mental or mood changes, tightness in the chest, and unusual tiredness or weakness.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic (cytochrome P-450 system), some renal.
• Absorption: Antihistamines are well absorbed from the gastrointestinal tract after oral administration.
• Half Life: 25 hours
• External Links: Wikipedia