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 Bitolterol was withdrawn from the market by Elan Pharmaceuticals in 2001.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- Withdrawn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
Structure for Bitolterol (DB00901)
- 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).
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism ABeta-2 adrenergic receptor Not Available Humans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcebutolol The therapeutic efficacy of Bitolterol can be decreased when used in combination with Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Bitolterol is combined with Aceclofenac. Acemetacin The risk or severity of hypertension can be increased when Bitolterol is combined with Acemetacin. Acetylsalicylic acid The risk or severity of hypertension can be increased when Bitolterol is combined with Acetylsalicylic acid. Aclidinium The risk or severity of Tachycardia can be increased when Bitolterol is combined with Aclidinium. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Bitolterol mesylate 4E53T3611U 30392-41-7 HODFCFXCOMKRCG-UHFFFAOYSA-N - International/Other Brands
- Tornalate
Categories
- ATC Codes
- R03AC17 — Bitolterol
- Drug Categories
- Adrenergic Agents
- Adrenergic Agonists
- Adrenergic beta-2 Receptor Agonists
- Adrenergic beta-Agonists
- Adrenergics, Inhalants
- Agents producing tachycardia
- Agents that produce hypertension
- Alcohols
- Amines
- Amino Alcohols
- Anti-Asthmatic Agents
- Autonomic Agents
- Bronchodilator Agents
- Drugs for Obstructive Airway Diseases
- Neurotransmitter Agents
- Peripheral Nervous System Agents
- Respiratory System Agents
- Selective Beta 2-adrenergic Agonists
- 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
- 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]
- 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]
- 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]
- 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]
- External Links
- Human Metabolome Database
- HMDB0249279
- KEGG Drug
- D07534
- KEGG Compound
- C06853
- PubChem Compound
- 35330
- PubChem Substance
- 46506895
- ChemSpider
- 32525
- 19499
- ChEBI
- 3133
- ChEMBL
- CHEMBL1201295
- PharmGKB
- PA448644
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Bitolterol
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Sanofi aventis us llc
- Packagers
- Pharmedix
- Dosage Forms
Form Route Strength Aerosol Respiratory (inhalation) Aerosol, metered Respiratory (inhalation) - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 5.8 Not Available - Predicted Properties
Property Value Source Water Solubility 0.00048 mg/mL ALOGPS logP 4.69 ALOGPS logP 6.3 Chemaxon logS -6 ALOGPS pKa (Strongest Acidic) 14 Chemaxon pKa (Strongest Basic) 9.59 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 84.86 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 132.76 m3·mol-1 Chemaxon Polarizability 52.07 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - 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 inhibitor Non-inhibitor 0.8987 CYP450 2D6 inhibitor Non-inhibitor 0.8594 CYP450 2C19 inhibitor Non-inhibitor 0.9 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-014i-5900000000-b67f918d20fb5fd2f95f Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-022c-1104900000-98890a145cf4f288f713 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-0179300000-12a28945662f6adb6706 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00kr-3509000000-3d83ca661c68efae8908 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-00kf-9300000000-6a21ada65f33257bb15d Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00mo-9100000000-25693057fcc57c33a90e Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 206.81421 predictedDeepCCS 1.0 (2019) [M+H]+ 209.20976 predictedDeepCCS 1.0 (2019) [M+Na]+ 215.12228 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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]
- 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 at June 13, 2005 13:24 / Updated at February 02, 2024 22:46