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30392-40-6 molecular structure
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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 and InChIs

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

Cite this record

CBID:777 http://www.chembase.cn/molecule-777.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
30392-40-6
PubChem SID
160964240
46506895
PubChem CID
35330

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
DrugBank DB00901 external link
PubChem 35330 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 13.996354  H Acceptors
H Donor LogD (pH = 5.5) 3.1208308 
LogD (pH = 7.4) 4.151406  Log P 6.304933 
Molar Refractivity 132.7623 cm3 Polarizability 51.34794 Å3
Polar Surface Area 84.86 Å2 Rotatable Bonds 10 
Lipinski's Rule of Five false 
Log P 4.69  LOG S -5.98 
Solubility (Water) 4.80e-04 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Hydrophobicity(logP)
5.8 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00901 external link
Item Information
Drug Groups withdrawn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 Bitolterol was withdrawn from the market by Elan Pharmaceuticals in 2001.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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
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PATENTS

PATENTS

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INTERNET

INTERNET

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