Explore a selection of our essential drug information below, or:
Identification
- Summary
Bambuterol is a long acting beta2-adrenoceptor agonist for the management of lung diseases associated with bronchospasm.
- Generic Name
- Bambuterol
- DrugBank Accession Number
- DB01408
- Background
Bambuterol is a long acting beta-adrenoceptor agonist used in the treatment of asthma. It is a prodrug of terbutaline.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Bambuterol (DB01408)
- Weight
- Average: 367.44
Monoisotopic: 367.210721053 - Chemical Formula
- C18H29N3O5
- Synonyms
- (±)-5-(2-(tert-butylamino)-1-hydroxyethyl)-m-phenylene bis(dimethylcarbamate)
- Bambuterol
- bambutérol
- Bambuterolum
Pharmacology
- Indication
For the prevention and reversal of bronchospasm in patients 12 years of age and older with asthma and reversible bronchospasm associated with bronchitis and emphysema.
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.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Bronchial asthma •••••••••••• •••••• Treatment of Bronchospasm •••••••••••• •••••• Treatment of Chronic bronchitis •••••••••••• •••••• Treatment of Emphysema •••••••••••• •••••• - 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
Bambuterol is a long acting beta2-adrenoceptor agonist used in the treatment of asthma. It is a prodrug of terbutaline. Bambuterol causes smooth muscle relaxation, resulting in dilation of bronchial passages.
- Mechanism of action
The pharmacologic effects of bambuterol are at least in part attributable to stimulation through beta-adrenergic receptors (beta 2 receptors) of intracellular adenyl cyclase, the enzyme that catalyzes the conversion of adenosine triphosphate (ATP) to cyclic AMP. Increased cyclic AMP levels are associated with relaxation of bronchial smooth muscle and inhibition of release of mediators of immediate hypersensitivity from cells, especially from mast cells.
Target Actions Organism ABeta-2 adrenergic receptor agonistHumans UCholinesterase inhibitorHumans - Absorption
Bioavailability is 20% following oral administration.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hepatic, extensive. Further metabolized to terbutaline by plasma cholinesterase.
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- Route of elimination
Not Available
- Half-life
13 hours for bambuterol and 21 hours for the primary active metabolite terbutaline.
- 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
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcebutolol The therapeutic efficacy of Bambuterol can be decreased when used in combination with Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Bambuterol is combined with Aceclofenac. Acemetacin The risk or severity of hypertension can be increased when Bambuterol is combined with Acemetacin. Acetylcholine The risk or severity of adverse effects can be increased when Bambuterol is combined with Acetylcholine. Acetylsalicylic acid The risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Bambuterol. - Food Interactions
- Not Available
Products
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Ingredient UNII CAS InChI Key Bambuterol hydrochloride 786Q84QZ3F 81732-46-9 LBARATORRVNNQM-UHFFFAOYSA-N - Active Moieties
Name Kind UNII CAS InChI Key Terbutaline prodrug N8ONU3L3PG 23031-25-6 XWTYSIMOBUGWOL-UHFFFAOYSA-N - International/Other Brands
- Bambec / Oxeol
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image BAMBEC TABLET 10 mg Tablet 10 mg Oral Astrazeneca Ab 1997-03-06 Not applicable Singapore 
Categories
- ATC Codes
- R03CC12 — Bambuterol
- Drug Categories
- Adrenergic Agonists
- Adrenergic beta-2 Receptor Agonists
- Adrenergic beta-Agonists
- Adrenergics for Systemic Use
- Agents producing tachycardia
- Agents that produce hypertension
- Agents to Treat Airway Disease
- Alcohols
- Amines
- Amino Alcohols
- Anti-Asthmatic Agents
- Autonomic Agents
- Bronchodilator Agents
- Cholinesterase Inhibitors
- Cholinesterase substrates
- Delayed-Action Preparations
- Drugs for Obstructive Airway Diseases
- Ethanolamines
- Long-acting beta-adrenoceptor agonists
- Peripheral Nervous System Agents
- Prodrugs
- Respiratory System Agents
- Selective Beta 2-adrenergic Agonists
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenoxy compounds. These are aromatic compounds contaning a phenoxy group.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Phenoxy compounds
- Direct Parent
- Phenoxy compounds
- Alternative Parents
- Aralkylamines / Carbamate esters / Secondary alcohols / Organic carbonic acids and derivatives / 1,2-aminoalcohols / Dialkylamines / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds show 1 more
- Substituents
- 1,2-aminoalcohol / Alcohol / Amine / Aralkylamine / Aromatic alcohol / Aromatic homomonocyclic compound / Carbamic acid ester / Carbonic acid derivative / Carbonyl group / Hydrocarbon derivative show 10 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- carbamate ester, phenylethanolamines (CHEBI:553827)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- Y1850G1OVC
- CAS number
- 81732-65-2
- InChI Key
- ANZXOIAKUNOVQU-UHFFFAOYSA-N
- InChI
- InChI=1S/C18H29N3O5/c1-18(2,3)19-11-15(22)12-8-13(25-16(23)20(4)5)10-14(9-12)26-17(24)21(6)7/h8-10,15,19,22H,11H2,1-7H3
- IUPAC Name
- 3-[2-(tert-butylamino)-1-hydroxyethyl]-5-[(dimethylcarbamoyl)oxy]phenyl N,N-dimethylcarbamate
- SMILES
- CN(C)C(=O)OC1=CC(=CC(OC(=O)N(C)C)=C1)C(O)CNC(C)(C)C
References
- Synthesis Reference
Peter Jaksch, "Method of preparing an intermediate for the manufacture of bambuterol." U.S. Patent US5200551, issued May, 1986.
US5200551- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015478
- KEGG Drug
- D07377
- PubChem Compound
- 54766
- PubChem Substance
- 46505785
- ChemSpider
- 49466
- BindingDB
- 50235800
- 18751
- ChEBI
- 553827
- ChEMBL
- CHEMBL521589
- Therapeutic Targets Database
- DAP000250
- PharmGKB
- PA164743113
- Wikipedia
- Bambuterol
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data4 Completed Treatment Chronic Obstructive Pulmonary Disease (COPD) 1 somestatus stop reason just information to hide 4 Unknown Status Treatment Cough Variant Asthma / Eosinophilic Bronchitis 1 somestatus stop reason just information to hide 1 Completed Treatment High Altitude Pulmonary Hypertension 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral Tablet Oral 10 mg/1 Tablet Oral 10.000 mg Tablet Oral 20 mg Tablet Oral 10 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.469 mg/mL ALOGPS logP 1.69 ALOGPS logP 1.4 Chemaxon logS -2.9 ALOGPS pKa (Strongest Acidic) 13.91 Chemaxon pKa (Strongest Basic) 9.52 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 91.34 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 98.28 m3·mol-1 Chemaxon Polarizability 40.77 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.8638 Blood Brain Barrier - 0.761 Caco-2 permeable - 0.6746 P-glycoprotein substrate Substrate 0.7076 P-glycoprotein inhibitor I Non-inhibitor 0.8708 P-glycoprotein inhibitor II Non-inhibitor 0.8921 Renal organic cation transporter Non-inhibitor 0.9451 CYP450 2C9 substrate Non-substrate 0.7745 CYP450 2D6 substrate Non-substrate 0.8167 CYP450 3A4 substrate Non-substrate 0.5157 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9155 CYP450 2D6 inhibitor Inhibitor 0.8689 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.927 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9738 Ames test Non AMES toxic 0.7909 Carcinogenicity Non-carcinogens 0.762 Biodegradation Not ready biodegradable 0.9963 Rat acute toxicity 2.5730 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9727 hERG inhibition (predictor II) Non-inhibitor 0.937
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 204.173351 predictedDarkChem Lite v0.1.0 [M-H]- 186.4136 predictedDeepCCS 1.0 (2019) [M+H]+ 204.304451 predictedDarkChem Lite v0.1.0 [M+H]+ 188.8252 predictedDeepCCS 1.0 (2019) [M+Na]+ 204.300451 predictedDarkChem Lite v0.1.0 [M+Na]+ 195.98637 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.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General 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 30-fold greater affinity than it does norepinephrine
- Specific Function
- adenylate cyclase binding
- Gene Name
- ADRB2
- Uniprot ID
- P07550
- Uniprot Name
- Beta-2 adrenergic receptor
- Molecular Weight
- 46458.32 Da
References
- Rosberg B, Schroder C, Nyberg L, Rosenborg J, Wiren JE: Bambuterol and terbutaline in human cerebrospinal fluid and plasma. Eur J Clin Pharmacol. 1993;45(2):147-50. [Article]
- Svensson LA: Bambuterol, a bronchodilator prodrug with sustained action, enhances delivery of active drug to the lung. Agents Actions Suppl. 1988;23:271-6. [Article]
- Waldeck B: Beta-adrenoceptor agonists and asthma--100 years of development. Eur J Pharmacol. 2002 Jun 7;445(1-2):1-12. [Article]
- Coleman RA, Johnson M, Nials AT, Vardey CJ: Exosites: their current status, and their relevance to the duration of action of long-acting beta 2-adrenoceptor agonists. Trends Pharmacol Sci. 1996 Sep;17(9):324-30. [Article]
- Zhang D, Cheng M, Hyun MH, Xiong Z, Pan L, Li F: Enantiomeric separation of beta2-agonists on macrocyclic antibiotic chiral stationary phases in high performance liquid chromatography. Pharmazie. 2007 Nov;62(11):836-40. [Article]
- Chou YL, Wu CC, Wang HW: Effects of bambuterol and terbutaline on isolated rat's tracheal smooth muscle. Eur Arch Otorhinolaryngol. 2010 Aug;267(8):1305-11. doi: 10.1007/s00405-009-1173-7. Epub 2009 Dec 12. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters
- Specific Function
- acetylcholinesterase activity
- Gene Name
- BCHE
- Uniprot ID
- P06276
- Uniprot Name
- Cholinesterase
- Molecular Weight
- 68417.575 Da
References
- Li S, Li AJ, Travers J, Xu T, Sakamuru S, Klumpp-Thomas C, Huang R, Xia M: Identification of Compounds for Butyrylcholinesterase Inhibition. SLAS Discov. 2021 Dec;26(10):1355-1364. doi: 10.1177/24725552211030897. Epub 2021 Jul 16. [Article]
- Tunek A, Hjertberg E, Mogensen JV: Interactions of bambuterol with human serum cholinesterase of the genotypes EuEu (normal), EaEa (atypical) and EuEa. Biochem Pharmacol. 1991 Feb 1;41(3):345-8. doi: 10.1016/0006-2952(91)90530-i. [Article]
- Wu J, Tian Y, Wang S, Pistolozzi M, Jin Y, Zhou T, Roy G, Xu L, Tan W: Design, synthesis and biological evaluation of bambuterol analogues as novel inhibitors of butyrylcholinesterase. Eur J Med Chem. 2017 Jan 27;126:61-71. doi: 10.1016/j.ejmech.2016.08.061. Epub 2016 Aug 26. [Article]
- Feldman S, Karalliedde L: Drug interactions with neuromuscular blockers. Drug Saf. 1996 Oct;15(4):261-73. doi: 10.2165/00002018-199615040-00004. [Article]
- Ostergaard D, Rasmussen SN, Viby-Mogensen J, Pedersen NA, Boysen R: The influence of drug-induced low plasma cholinesterase activity on the pharmacokinetics and pharmacodynamics of mivacurium. Anesthesiology. 2000 Jun;92(6):1581-7. doi: 10.1097/00000542-200006000-00014. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters
- Specific Function
- acetylcholinesterase activity
- Gene Name
- BCHE
- Uniprot ID
- P06276
- Uniprot Name
- Cholinesterase
- Molecular Weight
- 68417.575 Da
References
- Gazic I, Bosak A, Sinko G, Vinkovic V, Kovarik Z: Preparative HPLC separation of bambuterol enantiomers and stereoselective inhibition of human cholinesterases. Anal Bioanal Chem. 2006 Aug;385(8):1513-9. Epub 2006 Jul 25. [Article]
- Bosak A, Gazic Smilovic I, Sinko G, Vinkovic V, Kovarik Z: Metaproterenol, isoproterenol, and their bisdimethylcarbamate derivatives as human cholinesterase inhibitors. J Med Chem. 2012 Aug 9;55(15):6716-23. doi: 10.1021/jm300289k. Epub 2012 Jul 27. [Article]
- Tunek A, Hjertberg E, Mogensen JV: Interactions of bambuterol with human serum cholinesterase of the genotypes EuEu (normal), EaEa (atypical) and EuEa. Biochem Pharmacol. 1991 Feb 1;41(3):345-8. doi: 10.1016/0006-2952(91)90530-i. [Article]
- Chen XY, Xu HY, Zhong DF, Yang HY, Zhang YF: [Determination of bambuterol in human plasma by liquid chromatography-electrospray tandem mass spectrometry: application to pharmacokinetic study]. Yao Xue Xue Bao. 2001 Oct;36(10):762-5. [Article]
- Tunek A, Levin E, Svensson LA: Hydrolysis of 3H-bambuterol, a carbamate prodrug of terbutaline, in blood from humans and laboratory animals in vitro. Biochem Pharmacol. 1988 Oct 15;37(20):3867-76. doi: 10.1016/0006-2952(88)90068-8. [Article]
- Nyberg L, Rosenborg J, Weibull E, Jonsson S, Kennedy BM, Nilsson M: Pharmacokinetics of bambuterol in healthy subjects. Br J Clin Pharmacol. 1998 May;45(5):471-8. doi: 10.1046/j.1365-2125.1998.00695.x. [Article]
- Staun P, Lennmarken C, Eriksson LI, Wiren JE: The influence of 10 mg and 20 mg of bambuterol on the duration of succinylcholine-induced neuromuscular blockade. Acta Anaesthesiol Scand. 1990 Aug;34(6):498-500. [Article]
Drug created at July 17, 2007 12:34 / Updated at October 14, 2024 09:58