8-hydroxy-5-[(1R,2S)-1-hydroxy-2-[(propan-2-yl)amino]butyl]-1,2-dihydroquinolin-2-one

• ChemBase ID: 1191
• Molecular Formular: C16H22N2O3
• Molecular Mass: 290.35748
• Monoisotopic Mass: 290.16304257
• SMILES: O[C@@H]([C@@H](NC(C)C)CC)c1c2c([nH]c(=O)cc2)c(O)cc1
• Canonical SMILES: CC[C@@H]([C@@H](c1ccc(c2c1ccc(=O)[nH]2)O)O)NC(C)C
• InChI: InChI=1S/C16H22N2O3/c1-4-12(17-9(2)3)16(21)11-5-7-13(19)15-10(11)6-8-14(20)18-15/h5-9,12,16-17,19,21H,4H2,1-3H3,(H,18,20)/t12-,16+/m0/s1
• InChIKey: FKNXQNWAXFXVNW-BLLLJJGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-hydroxy-5-[(1R,2S)-1-hydroxy-2-[(propan-2-yl)amino]butyl]-1,2-dihydroquinolin-2-one
• IUPAC Traditional name: procaterol
• Brand Name: Pro-Air
• Synonyms: Procaterol

Database IDs

• CAS Number: 72332-33-3
• PubChem SID: 46507907; 160964653
• PubChem CID: 688561

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.519182
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -1.2235061
• LogD (pH = 7.4): -0.0811332
• Log P: 0.88412946
• Molar Refractivity: 84.5808 cm^3
• Polarizability: 31.786533 Å^3
• Polar Surface Area: 81.59 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.28
• LOG S: -2.95
• Solubility (Water): 3.29e-01 g/l

DETAILS

DrugBank - DB01366

• Drug Groups: approved
• Description: A long-acting beta-2-adrenergic receptor agonist. It is a potent bronchodilator that may be administered orally or by aerosol inhalation. [PubChem]
• Indication: For the treatment of asthma and chronic obstructive pulmonary disease (COPD).
• Pharmacology: Procaterol is a long-acting beta-2-adrenergic receptor agonist. It is a potent bronchodilator that may be administered orally or by aerosol inhalation.
• Toxicity: Symptoms of overdose include angina (chest pain), dizziness, dry mouth, fatigue, flu-like symptoms, headache, heart irregularities, high or low blood pressure, high blood sugar, insomnia, muscle cramps, nausea, nervousness, rapid heartbeat, seizures, and tremor.
• Affected Organisms: Humans and other mammals
• Absorption: Because of the small therapeutic dose, systemic levels of salmeterol are low or undetectable after inhalation of recommended doses.