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Identification
NameBitolterol
Accession NumberDB00901  (APRD00827)
TypeSmall Molecule
GroupsWithdrawn
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 Bitolterol was withdrawn from the market by Elan Pharmaceuticals in 2001.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]

Structure
Thumb
Synonyms
SynonymLanguageCode
Bitolterol MesylateNot AvailableNot Available
BitolterolumLatinINN
SaltsNot Available
Brand names
NameCompany
TornalateNot Available
Brand mixturesNot Available
Categories
CAS number30392-40-6
WeightAverage: 461.5494
Monoisotopic: 461.220223107
Chemical FormulaC28H31NO5
InChI KeyFZGVEKPRDOIXJY-UHFFFAOYSA-N
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
IUPAC Name
5-[2-(tert-butylamino)-1-hydroxyethyl]-2-[(4-methylphenyl)carbonyloxy]phenyl 4-methylbenzoate
SMILES
CC1=CC=C(C=C1)C(=O)OC1=C(OC(=O)C2=CC=C(C)C=C2)C=C(C=C1)C(O)CNC(C)(C)C
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassPhenylpropanoids and Polyketides
ClassDepsides and Depsidones
SubclassNot Available
Direct parentDepsides and Depsidones
Alternative parentsBenzoic Acid Esters; Phenol Esters; Benzylethers; Phenol Ethers; Benzoyl Derivatives; Alkyl Aryl Ethers; Toluenes; Dicarboxylic Acids and Derivatives; Carboxylic Acid Esters; Secondary Alcohols; 1,2-Aminoalcohols; Polyamines; Dialkylamines; Enolates
Substituentsphenol ester; benzoate ester; benzylether; benzoic acid or derivative; benzoyl; phenol ether; toluene; alkyl aryl ether; dicarboxylic acid derivative; benzene; 1,2-aminoalcohol; secondary alcohol; carboxylic acid ester; carboxylic acid derivative; secondary amine; polyamine; ether; secondary aliphatic amine; enolate; organonitrogen compound; alcohol; amine
Classification descriptionThis compound belongs to the depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound contaning the depsidone structure (depsidone).
Pharmacology
IndicationUsed 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).
PharmacodynamicsBitolterol, 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.
Mechanism of actionBitolterol is an adrenergic beta-2 agonist. Asthma results from a narrowing of the bronchial tubes. This narrowing is caused by muscle spasm and inflammation within the bronchial tubes. Agonism of the beta-2 adrenergic receptors by bitolterol leads to a relaxation of the smooth muscles surrounding these airway tubes which then increases the diameter and ease of air flow through the tubes.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.8753
Blood Brain Barrier - 0.9679
Caco-2 permeable - 0.7805
P-glycoprotein substrate Substrate 0.7533
P-glycoprotein inhibitor I Inhibitor 0.5438
P-glycoprotein inhibitor II Non-inhibitor 0.7643
Renal organic cation transporter Non-inhibitor 0.9069
CYP450 2C9 substrate Non-substrate 0.7406
CYP450 2D6 substrate Non-substrate 0.771
CYP450 3A4 substrate Non-substrate 0.5086
CYP450 1A2 substrate Non-inhibitor 0.8381
CYP450 2C9 substrate Non-inhibitor 0.8987
CYP450 2D6 substrate Non-inhibitor 0.8594
CYP450 2C19 substrate Non-inhibitor 0.9
CYP450 3A4 substrate Non-inhibitor 0.7754
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8853
Ames test Non AMES toxic 0.9151
Carcinogenicity Non-carcinogens 0.8648
Biodegradation Not ready biodegradable 0.9876
Rat acute toxicity 2.3906 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9912
hERG inhibition (predictor II) Non-inhibitor 0.7982
Pharmacoeconomics
Manufacturers
  • Sanofi aventis us llc
Packagers
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
logP5.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00048ALOGPS
logP4.69ALOGPS
logP6.3ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)14ChemAxon
pKa (Strongest Basic)9.59ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area84.86 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity132.76 m3·mol-1ChemAxon
Polarizability50.91 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. 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
  2. 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
  3. 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
  4. 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
ResourceLink
KEGG DrugD00684
KEGG CompoundC06853
PubChem Compound35330
PubChem Substance46506895
ChemSpider32525
ChEBI3133
ChEMBL
PharmGKBPA448644
Drugs.comhttp://www.drugs.com/mtm/bitolterol-inhalation.html
WikipediaBitolterol
ATC CodesR03AC17
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
EntacaponeEntacapone may increase the effect and toxicity of bitolterol.
Food InteractionsNot Available

Targets

1. Beta-2 adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Components

Name UniProt ID Details
Beta-2 adrenergic receptor P07550 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Wilson AJ, Gibson PG, Coughlan J: Long acting beta-agonists versus theophylline for maintenance treatment of asthma. Cochrane Database Syst Rev. 2000;(2):CD001281. Pubmed
  4. 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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:12