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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 Bitolterol was withdrawn from the market by Elan Pharmaceuticals in 2001.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
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
TornalateNot Available
Brand mixturesNot Available
SaltsNot 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
4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(4-methylbenzoyloxy)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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 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 containing the depsidone structure (depsidone).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassDepsides and depsidones
Sub ClassNot Available
Direct ParentDepsides and depsidones
Alternative Parents
Substituents
  • Depside backbone
  • Phenol ester
  • Benzoate ester
  • Benzoic acid or derivatives
  • Benzoyl
  • Aralkylamine
  • Toluene
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Carboxylic acid ester
  • 1,2-aminoalcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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
PropertyValueProbability
Human Intestinal Absorption+0.8753
Blood Brain Barrier-0.9679
Caco-2 permeable-0.7805
P-glycoprotein substrateSubstrate0.7533
P-glycoprotein inhibitor IInhibitor0.5438
P-glycoprotein inhibitor IINon-inhibitor0.7643
Renal organic cation transporterNon-inhibitor0.9069
CYP450 2C9 substrateNon-substrate0.7406
CYP450 2D6 substrateNon-substrate0.771
CYP450 3A4 substrateNon-substrate0.5086
CYP450 1A2 substrateNon-inhibitor0.8381
CYP450 2C9 substrateNon-inhibitor0.8987
CYP450 2D6 substrateNon-inhibitor0.8594
CYP450 2C19 substrateNon-inhibitor0.9
CYP450 3A4 substrateNon-inhibitor0.7754
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8853
Ames testNon AMES toxic0.9151
CarcinogenicityNon-carcinogens0.8648
BiodegradationNot ready biodegradable0.9876
Rat acute toxicity2.3906 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9912
hERG inhibition (predictor II)Non-inhibitor0.7982
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 Solubility0.00048 mg/mLALOGPS
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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
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
ATC CodesNot Available
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