N-[(4-chlorophenyl)methyl]-N-[2-(dimethylamino)ethyl]pyridin-2-amine

• ChemBase ID: 5167
• Molecular Formular: C16H20ClN3
• Molecular Mass: 289.8031
• Monoisotopic Mass: 289.13457534
• SMILES: CN(C)CCN(c1ccccn1)Cc1ccc(cc1)Cl
• Canonical SMILES: CN(CCN(c1ccccn1)Cc1ccc(cc1)Cl)C
• InChI: InChI=1S/C16H20ClN3/c1-19(2)11-12-20(16-5-3-4-10-18-16)13-14-6-8-15(17)9-7-14/h3-10H,11-13H2,1-2H3
• InChIKey: ICKFFNBDFNZJSX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(4-chlorophenyl)methyl]-N-[2-(dimethylamino)ethyl]pyridin-2-amine
• IUPAC Traditional name: chloropyramine
• Brand Name: Suprastin; Avapena; Synopen; Synpen
• Synonyms: N-(4-chlorobenzyl)-N',N'-dimethyl-N-pyridin-2-ylethane-1,2-diamine; Chlorpyramine; Anaphylline; Halopyramine; Chlorpyraminum; Chloropyramine

Database IDs

• CAS Number: 59-32-5
• PubChem SID: 160968597
• PubChem CID: 25295
• ATC CODE: R06AC03; D04AA09
• Chemspider ID: 23628
• DrugBank ID: DB08800
• KEGG ID: D07195
• Unique Ingredient Identifier: 2K3L8O9SOV
• Wikipedia Title: Chloropyramine

CALCULATED PROPERTIES

JChem

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.5361275
• LogD (pH = 7.4): 2.4228516
• Log P: 3.805237
• Molar Refractivity: 86.0797 cm^3
• Polarizability: 32.760555 Å^3
• Polar Surface Area: 19.37 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.79
• LOG S: -2.82
• Solubility (Water): 4.41e-01 g/l

PROPERTIES

Physical Property

• Solubility: Insoluble [MSDS]

Pharmacology Properties

• Pregnancy Category: C

DETAILS

DrugBank - DB08800

• Drug Groups: approved
• Description: Chloropyramine is a first generation antihistamine drug approved in some Eastern European countries for the treatment of allergic conjunctivitis, allergic rhinitis, bronchial asthma, and other atopic (allergic) conditions. Related indications for clinical use include Quincke's edema, allergic reactions to insect bites, food and drug allergies, and anaphylactic shock.
• Indication: For the treatment of allergic conjunctivitis, allergic rhinitis, bronchial asthma, and other atopic (allergic) conditions.
• Pharmacology: Chloropyramine is known as a competitive reversible H1-receptor antagonist (also known as an H1 inverse agonist), meaning that it exerts its pharmacological action by competing with histamine for the H1 subtype histamine receptor. By blocking the effects of histamine, the drug inhibits the vasodilation, increased vascular permeability, and tissue edema associated with histamine release in the tissue. In addition, chloropyramine has some anticholinergic properties. Chloropyramine's anticholinergic properties and the fact that it can pass through the blood-brain barrier are linked to its clinical side effects: drowsiness, weakness, vertigo, fatigue, dryness in the mouth, constipation, and rarely - visual disturbances and increase of intraocular pressure.
• Toxicity: Oral (LD50): Acute: 142 mg/kg [Rat]. 135 mg/kg [Mouse]. DUST (LC50): Acute: 209 mg/m 2 hours [Rat].
• Affected Organisms: Humans and other mammals

DrugBank - DB07523

Drug information: experimental