CAS 30392-40-6|Bitolterol Mesylate|5-[2-(tert-butylamino)-1-hydroxyethyl]-2-(4-methylbenzoyloxy)phenyl 4-methylbenzoate|5-[2-(tert-butylamino)-1-hydroxyethyl]-2-(4-methylbenzoyloxy)phenyl 4-methylbe...

General Information

Structure

Molecular Formula

C₂₈H₃₁NO₅

Molecular Mass

461.54944

Exact Mass

461.2202231

Charge

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

Canonic Smiles

Cc1ccc(cc1)C(=O)Oc1cc(ccc1OC(=O)c1ccc(cc1)C)C(CNC(C)(C)C)O

Isomeric Smiles

OC(CNC(C)(C)C)c1cc(OC(=O)c2ccc(cc2)C)c(OC(=O)c2ccc(cc2)C)cc1

Calculated Properties

JChem

LogD (pH = 7.4)

4.15

LogD (pH = 5.5)

3.12

Log P

6.30

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

false

Acid pKa

9.59

Polar Surface Area

84.86

Polarizability

50.86

Molar Refractivity

132.76

LOG S

-6.83

Data Source

Academic Data

Data Source

Names and Identifiers

Synonyms

Bitolterol MesylateBitolterolBitolterolum [INN-Latin]bis(4-methylbenzoic acid) 4-[2-(tert-butylamino)-1-hydroxyethyl]-1,2-phenylene ester4-(2-(tert-butylamino)-1-hydroxyethyl)-o-phenylene di-p-toluatebitolterol4-[2-(tert-butylamino)-1-hydroxyethyl]-o-phenylene di-p-toluate

IUPAC Traditional name

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

IUPAC name

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

Brand Name

Tornalate

International Nonproprietary Name (INN)

bitolterolumbitolterol

Names and Identifiers

Registration numbers

PubChem CID

35330

PubChem SID

1609642404650689592740965

CAS Number

KEGG ID

ACToR Database

CHEBI ID

Patent number

Beilstein Number

PubMed Citation Links

4737923278878

CompTox Database

DTXSID1022683

MetaboLights Database

MTBLS2825

Drug Central Database

Reaxys Registry

SureChEMBL Database

DrugBank ID

KEGG DRUG Database

CHEMBL

Wikipedia Title

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

5.8

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule 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withdrawn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]

ChEBI

CHEBI:3133

The di-4-toluate ester of (+-)-N-tert-butylnoradrenaline (colterol). A pro-drug for colterol, a beta2-adrenergic receptor agonist, bitolterol is used as its methanesulfonate salt for relief of bronchospasm in conditions such as asthma, chronic bronchitis and emphysema.

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• 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

References

Bioactivity

PubChem BioAssay

Bioactivity

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General Information

Calculated Properties

• RDKit

• JChem

Data Source

• Academic Data

Names and Identifiers