5-[2-(tert-butylamino)-1-hydroxyethyl]-2-(4-methylbenzoyloxy)phenyl 4-methylbenzoate

• ChemBase ID: 777
• Molecular Formular: C28H31NO5
• Molecular Mass: 461.54944
• Monoisotopic Mass: 461.2202231
• SMILES: OC(CNC(C)(C)C)c1cc(OC(=O)c2ccc(cc2)C)c(OC(=O)c2ccc(cc2)C)cc1
• Canonical SMILES: Cc1ccc(cc1)C(=O)Oc1cc(ccc1OC(=O)c1ccc(cc1)C)C(CNC(C)(C)C)O
• InChI: InChI=1S/C28H31NO5/c1-18-6-10-20(11-7-18)26(31)33-24-15-14-22(23(30)17-29-28(3,4)5)16-25(24)34-27(32)21-12-8-19(2)9-13-21/h6-16,23,29-30H,17H2,1-5H3
• InChIKey: FZGVEKPRDOIXJY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[2-(tert-butylamino)-1-hydroxyethyl]-2-(4-methylbenzoyloxy)phenyl 4-methylbenzoate
• IUPAC Traditional name: 5-[2-(tert-butylamino)-1-hydroxyethyl]-2-(4-methylbenzoyloxy)phenyl 4-methylbenzoate
• Brand Name: Tornalate
• Synonyms: Bitolterolum [INN-Latin]; Bitolterol Mesylate; Bitolterol

Database IDs

• CAS Number: 30392-40-6
• PubChem SID: 46506895; 160964240
• PubChem CID: 35330

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.996354
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.1208308
• LogD (pH = 7.4): 4.151406
• Log P: 6.304933
• Molar Refractivity: 132.7623 cm^3
• Polarizability: 51.34794 Å^3
• Polar Surface Area: 84.86 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 4.69
• LOG S: -5.98
• Solubility (Water): 4.80e-04 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 5.8

DETAILS

DrugBank - DB00901

• Drug Groups: withdrawn
• Description: Bitolterol mesylate is a beta-2-adrenergic receptor agonist used for the relief of bronchospasm in conditions such as asthma and COPD. Bitolterol was withdrawn from the market by Elan Pharmaceuticals in 2001. [Wikipedia]
• Indication: Used to dilate air passages in the lungs that have become narrowed as a result of disease or inflammation. It is used in the treatment of asthma and chronic obstructive pulmonary disease (COPD).
• Pharmacology: Bitolterol, an adrenergic bronchodilator, is a prodrug that widens constricted airways in the lungs by relaxing the smooth muscles that surround the bronchial passages. Bitolterol probably does not affect the inflammation in the lung, such as in bronchitis. Bitolterol is unique in that it is a prodrug because it must first be metabolized by the body before it becomes active.
• Affected Organisms: Humans and other mammals
• References: Bierman CW, Kemp JP, Nathan RA: Efficacy and safety of inhaled bitolterol mesylate via metered-dose inhaler in children with asthma. Ann Allergy Asthma Immunol. 1996 Jan;76(1):27-35. [Pubmed] ; Friedel HA, Brogden RN: Bitolterol. A preliminary review of its pharmacological properties and therapeutic efficacy in reversible obstructive airways disease. Drugs. 1988 Jan;35(1):22-41. [Pubmed] ; Nathan RA, Bronsky EA, Dockhorn RJ, Kemp JP: Multicenter dose-ranging study of bitolterol mesylate solution for nebulization in children with asthma. Ann Allergy. 1994 Mar;72(3):209-16. [Pubmed] ; Messina MS: Retrospective study of bitolterol mesylate in the treatment of conditions associated with reversible bronchospasm. Adv Ther. 1995 May-Jun;12(3):157-63. [Pubmed]
• External Links: Wikipedia; Drugs.com

REFERENCES

• Bierman CW, Kemp JP, Nathan RA: Efficacy and safety of inhaled bitolterol mesylate via metered-dose inhaler in children with asthma. Ann Allergy Asthma Immunol. 1996 Jan;76(1):27-35. Pubmed
• Friedel HA, Brogden RN: Bitolterol. A preliminary review of its pharmacological properties and therapeutic efficacy in reversible obstructive airways disease. Drugs. 1988 Jan;35(1):22-41. Pubmed
• Nathan RA, Bronsky EA, Dockhorn RJ, Kemp JP: Multicenter dose-ranging study of bitolterol mesylate solution for nebulization in children with asthma. Ann Allergy. 1994 Mar;72(3):209-16. Pubmed
• Messina MS: Retrospective study of bitolterol mesylate in the treatment of conditions associated with reversible bronchospasm. Adv Ther. 1995 May-Jun;12(3):157-63. Pubmed