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

• ChemBase ID: 935
• Molecular Formular: C11H17NO3
• Molecular Mass: 211.25758
• Monoisotopic Mass: 211.12084341
• SMILES: OC(CNC(C)C)c1cc(O)c(O)cc1
• Canonical SMILES: CC(NCC(c1ccc(c(c1)O)O)O)C
• InChI: InChI=1S/C11H17NO3/c1-7(2)12-6-11(15)8-3-4-9(13)10(14)5-8/h3-5,7,11-15H,6H2,1-2H3
• InChIKey: JWZZKOKVBUJMES-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}benzene-1,2-diol
• IUPAC Traditional name: (+-)-isoproterenol; isoproterenol
• Brand Name: Aerolone; Aleudrin; Aleudrine; Aludrin; Aludrine; Asiprenol; Asmalar; Assiprenol; Bellasthman; Bronkephrine; Euspiran; Isadrine; Isonorene; Isonorin; Isorenin; Isuprel; Isuprel Mistometer; Isupren; Medihaler-Iso; Neo-Epinine; Neodrenal; Norisodrine; Norisodrine Aerotrol; Novodrin; Proternol; Respifral; Saventrine; Vapo-Iso
• Synonyms: IPA; Epinephrine Isopropyl Homolog; Isopropyladrenaline; Isopropylarterenol; Isopropylnoradrenaline; Isopropylnorepinephrine; Isoproterenol Chloride; Isoproterenol HCl; L-Isopropylnoradrenaline; L-Isoproterenol; N-Isopropylnoradrenaline; N-Isopropylnorepinephrine; Isopropydrin; Isoprenalin; Isoprenaline; Isoproterenol; Isoprenaline

Database IDs

• CAS Number: 7683-59-2
• PubChem SID: 46507323; 160964398
• PubChem CID: 3779
• ATC CODE: R03CB01; R03AB02; C01CA02
• CHEMBL: 434
• Chemspider ID: 3647
• DrugBank ID: DB01064
• IUPHAR ligand ID: 536
• KEGG ID: D08090
• Unique Ingredient Identifier: L628TT009W
• Wikipedia Title: Isoprenaline
• Medline Plus: a601236

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.814519
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -2.1009066
• LogD (pH = 7.4): -0.9903411
• Log P: 0.24020568
• Molar Refractivity: 58.3977 cm^3
• Polarizability: 22.887892 Å^3
• Polar Surface Area: 72.72 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.27
• LOG S: -1.56
• Solubility (Water): 5.86e+00 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 1.4

Pharmacology Properties

• Admin Routes: inhaled 80-120μg
• Legal Status: Rx-only
• Pregnancy Category: C

DETAILS

DrugBank - DB01064

• Drug Groups: approved
• Description: Isopropyl analog of epinephrine; beta-sympathomimetic that acts on the heart, bronchi, skeletal muscle, alimentary tract, etc. It is used mainly as bronchodilator and heart stimulant. [PubChem]
• Indication: For the treatment of mild or transient episodes of heart block that do not require electric shock or pacemaker therapy also used in management of asthma and chronic bronchitis
• Pharmacology: Isoproterenol is a relatively selective beta2-adrenergic bronchodilator. Isoproterenol is indicated for the relief of bronchospasm associated with chronic obstructive pulmonary disease. The pharmacologic effects of beta adrenergic agonist drugs, including Isoproterenol, are at least in part attributable to stimulation through beta adrenergic receptors of intracellular adenyl cyclase, the enzyme which catalyzes the conversion of adenosine triphosphate (ATP) to cyclic- 3',5'- adenosine monophosphate (c-AMP). Increased c-AMP levels are associated with relaxation of bronchial smooth muscle and inhibition of release of mediators of immediate hypersensitivity from cells, especially from mast cells.
• Affected Organisms: Humans and other mammals
• Elimination: Excretion following inhalation administration is primarily renal and the major metabolite is the sulfate conjugate of isoproterenol.
• External Links: Wikipedia; RxList; Drugs.com