4-{1-hydroxy-2-[(propan-2-yl)amino]butyl}benzene-1,2-diol

• ChemBase ID: 106
• Molecular Formular: C13H21NO3
• Molecular Mass: 239.31074
• Monoisotopic Mass: 239.15214354
• SMILES: OC(C(NC(C)C)CC)c1cc(O)c(O)cc1
• Canonical SMILES: CCC(C(c1ccc(c(c1)O)O)O)NC(C)C
• InChI: InChI=1S/C13H21NO3/c1-4-10(14-8(2)3)13(17)9-5-6-11(15)12(16)7-9/h5-8,10,13-17H,4H2,1-3H3
• InChIKey: HUYWAWARQUIQLE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{1-hydroxy-2-[(propan-2-yl)amino]butyl}benzene-1,2-diol
• IUPAC Traditional name: isoetarine
• Brand Name: Beta-2; Bronkometer; Bronkosol; Dey-Lute Isoetharine; Dilabron; Etyprenaline; Isoetarin; Isoetarine; Isoetharine HCl S/F; Neoisuprel
• Synonyms: Isoetarina [INN-Spanish]; Isoetarinum [INN-Latin]; Isoetharine Hcl; Isoetharine mesylate; Isoetharine

Database IDs

• CAS Number: 530-08-5
• PubChem SID: 46505384; 160963569
• PubChem CID: 3762

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.005785
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -1.1862651
• LogD (pH = 7.4): -0.22287796
• Log P: 1.0474801
• Molar Refractivity: 67.3405 cm^3
• Polarizability: 26.567184 Å^3
• Polar Surface Area: 72.72 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.63
• LOG S: -1.88
• Solubility (Water): 3.18e+00 g/l

PROPERTIES

Physical Property

• Solubility: Appreciable
• Hydrophobicity(logP): 2.2

DETAILS

DrugBank - DB00221

• Drug Groups: approved
• Description: Isoetharine is a selective adrenergic beta-2 agonist used as fast acting bronchodilator for emphysema, bronchitis and asthma. [PubChem]
• Indication: For the treatment of asthma, wheezing, and chronic asthmatic bronchitis.
• Pharmacology: Isoetharine is a relatively selective beta2-adrenergic bronchodilator. Isoetharine is indicated for the relief of bronchospasm associated with chronic obstructive pulmonary disease. Adrenergic bronchodilators are breathed in through the mouth to open up the bronchial tubes (air passages) of the lungs.
• Toxicity: Signs of overdose include tachycardia, palpitations, nausea, headache, and epinephrine-like side effects.
• Affected Organisms: Humans and other mammals
• References: Emerman CL, Cydulka RK, Effron D, Lukens TW, Gershman H, Boehm SP: A randomized, controlled comparison of isoetharine and albuterol in the treatment of acute asthma. Ann Emerg Med. 1991 Oct;20(10):1090-3. [Pubmed]
• External Links: Wikipedia; Drugs.com

REFERENCES

• Emerman CL, Cydulka RK, Effron D, Lukens TW, Gershman H, Boehm SP: A randomized, controlled comparison of isoetharine and albuterol in the treatment of acute asthma. Ann Emerg Med. 1991 Oct;20(10):1090-3. Pubmed