1-(2-ethoxyethyl)-2-(4-methyl-1,4-diazepan-1-yl)-1H-1,3-benzodiazole

• ChemBase ID: 955
• Molecular Formular: C17H26N4O
• Molecular Mass: 302.41454
• Monoisotopic Mass: 302.21066147
• SMILES: O(CCn1c(N2CCCN(CC2)C)nc2c1cccc2)CC
• Canonical SMILES: CCOCCn1c(nc2c1cccc2)N1CCCN(CC1)C
• InChI: InChI=1S/C17H26N4O/c1-3-22-14-13-21-16-8-5-4-7-15(16)18-17(21)20-10-6-9-19(2)11-12-20/h4-5,7-8H,3,6,9-14H2,1-2H3
• InChIKey: KBUZBQVCBVDWKX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(2-ethoxyethyl)-2-(4-methyl-1,4-diazepan-1-yl)-1H-1,3-benzodiazole
• IUPAC Traditional name: emedastine
• Brand Name: Emadine
• Synonyms: Emedastina [INN-Spanish]; Emedastinum [INN-Latin]; Emedastine difumarate; Emedastine; 1-(2-ethoxyethyl)-2-(4-methyl-1,4-diazepan-1-yl)benzimidazole

Database IDs

• CAS Number: 87233-61-2
• PubChem SID: 46505109; 160964418
• PubChem CID: 3219

CALCULATED PROPERTIES

JChem

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -0.8740286
• LogD (pH = 7.4): 1.1855345
• Log P: 2.4923856
• Molar Refractivity: 90.4747 cm^3
• Polarizability: 35.620316 Å^3
• Polar Surface Area: 33.53 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.91
• LOG S: -2.32
• Solubility (Water): 1.44e+00 g/l

PROPERTIES

Physical Property

• Solubility: Soluble (difumarate formulation)
• Hydrophobicity(logP): 2.6

Product Information

• Purity: 97%

DETAILS

DrugBank - DB01084

• Drug Groups: approved
• Description: Emedastine is an antihistamine used in eye drops to treat allergic conjunctivitis. [Wikipedia]
• Indication: For the temporary relief of the signs and symptoms of allergic conjunctivitis.
• Pharmacology: Emedastine is a relatively selective H₁-receptor antagonist.
• Toxicity: Somnolence and malaise have been reported following daily oral administration.
• Affected Organisms: Humans and other mammals
• Biotransformation: Two primary metabolites, 5-hydroxyemedastine and 6-hydroxyemedastine, are excreted in the urine as both free and conjugated forms. The 5'-oxoanalogs of 5-hydroxyemedastine and 6-hydroxy-emedastine and the N-oxide are also formed as minor metabolites.
• Absorption: Ophthalmic use of emedastine usually does not produce measurable plasma concentrations.
• Half Life: The elimination half-life of oral emedastine in plasma is 3-4 hours.
• Elimination: Approximately 44% of the oral dose is recovered in the urine over 24 hours with only 3.6% of the dose excreted as parent drug. Two primary metabolites, 5- and 6-hydroxyemedastine, are excreted in the urine as both free and conjugated forms.
• External Links: Wikipedia; RxList; Drugs.com