Bitolterol

Identification

Generic Name
Bitolterol
DrugBank Accession Number
DB00901
Background

Bitolterol mesylate was used to treat bronchospasms in asthma and COPD. It is a beta-2-adrenergic receptor agonist. Bitolterol was withdrawn from the market by Elan Pharmaceuticals in 2001.

Type
Small Molecule
Groups
Withdrawn
Structure
Thumb
Weight
Average: 461.5494
Monoisotopic: 461.220223107
Chemical Formula
C28H31NO5
Synonyms
  • 4-(2-(tert-butylamino)-1-hydroxyethyl)-o-phenylene di-p-toluate
  • 4-[2-(tert-butylamino)-1-hydroxyethyl]-o-phenylene di-p-toluate
  • bis(4-methylbenzoic acid) 4-[2-(tert-butylamino)-1-hydroxyethyl]-1,2-phenylene ester
  • Bitolterol
  • Bitoltérol
  • Bitolterolum

Pharmacology

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
Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:
Machine Learning
Data Science
Drug Discovery
Accelerate your drug discovery research with our fully connected ADMET dataset
Learn more
Contraindications & Blackbox Warnings
Contraindications
Contraindications & Blackbox Warnings
With our commercial data, access important information on dangerous risks, contraindications, and adverse effects.
Learn more
Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects
Learn more
Pharmacodynamics

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.

Mechanism of action

Bitolterol 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.

TargetActionsOrganism
ABeta-2 adrenergic receptorNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Medicalerrors
Reduce medical errors
and improve treatment outcomes with our comprehensive & structured data on drug adverse effects.
Learn more
Reduce medical errors & improve treatment outcomes with our adverse effects data
Learn more
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcebutololThe therapeutic efficacy of Bitolterol can be decreased when used in combination with Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Bitolterol is combined with Aceclofenac.
AcemetacinThe risk or severity of hypertension can be increased when Bitolterol is combined with Acemetacin.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Bitolterol is combined with Acetylsalicylic acid.
AclidiniumThe risk or severity of Tachycardia can be increased when Bitolterol is combined with Aclidinium.
AdenosineThe risk or severity of Tachycardia can be increased when Adenosine is combined with Bitolterol.
AlclofenacThe risk or severity of hypertension can be increased when Bitolterol is combined with Alclofenac.
AlfentanilThe risk or severity of hypertension can be increased when Alfentanil is combined with Bitolterol.
AlfuzosinThe therapeutic efficacy of Bitolterol can be decreased when used in combination with Alfuzosin.
AliskirenBitolterol may decrease the antihypertensive activities of Aliskiren.
Interactions
Improve patient outcomes
Build effective decision support tools with the industry’s most comprehensive drug-drug interaction checker.
Learn more
Food Interactions
Not Available

Products

Products
Comprehensive & structured drug product info
From application numbers to product codes, connect different identifiers through our commercial datasets.
Learn more
Easily connect various identifiers back to our datasets
Learn more
Product Ingredients
IngredientUNIICASInChI Key
Bitolterol mesylate4E53T3611U30392-41-7HODFCFXCOMKRCG-UHFFFAOYSA-N
International/Other Brands
Tornalate

Categories

ATC Codes
R03AC17 — Bitolterol
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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).
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Depsides and depsidones
Sub Class
Not Available
Direct Parent
Depsides and depsidones
Alternative Parents
Benzoic acid esters / Phenol esters / Phenoxy compounds / Benzoyl derivatives / Aralkylamines / Toluenes / Dicarboxylic acids and derivatives / Amino acids and derivatives / Carboxylic acid esters / 1,2-aminoalcohols
show 6 more
Substituents
1,2-aminoalcohol / Alcohol / Amine / Amino acid or derivatives / Aralkylamine / Aromatic alcohol / Aromatic homomonocyclic compound / Benzenoid / Benzoate ester / Benzoic acid or derivatives
show 19 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
diester, carboxylic ester, secondary alcohol, secondary amino compound, ethanolamines (CHEBI:3133)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
9KY0QXD6LI
CAS number
30392-40-6
InChI Key
FZGVEKPRDOIXJY-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-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

References

General References
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
KEGG Drug
D07534
KEGG Compound
C06853
PubChem Compound
35330
PubChem Substance
46506895
ChemSpider
32525
RxNav
19499
ChEBI
3133
ChEMBL
CHEMBL1201295
PharmGKB
PA448644
Drugs.com
Drugs.com Drug Page
Wikipedia
Bitolterol

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
  • Sanofi aventis us llc
Packagers
  • Pharmedix
Dosage Forms
FormRouteStrength
AerosolRespiratory (inhalation)
Aerosol, meteredRespiratory (inhalation)
Prices
Not Available
Patents
Not Available

Properties

State
Solid
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
Polarizability52.07 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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 inhibitorNon-inhibitor0.8987
CYP450 2D6 inhibitorNon-inhibitor0.8594
CYP450 2C19 inhibitorNon-inhibitor0.9
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets
Accelerate your drug discovery research
with our fully connected ADMET & drug target dataset.
Learn more
Accelerate your drug discovery research with our ADMET & drug target dataset
Learn more
Kind
Protein
Organism
Humans
Pharmacological action
Yes
General Function
Protein homodimerization activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...
Gene Name
ADRB2
Uniprot ID
P07550
Uniprot Name
Beta-2 adrenergic receptor
Molecular Weight
46458.32 Da
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]

Drug created on June 13, 2005 13:24 / Updated on April 03, 2021 09:40