Page last updated: 2024-12-05

pirbuterol

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Pirbuterol is a short-acting beta2-adrenergic agonist used as a bronchodilator to treat asthma and other respiratory conditions. It works by relaxing the muscles in the airways, making it easier to breathe. Pirbuterol is typically administered as an inhaler, which delivers the medication directly to the lungs. It is synthesized through a multi-step process involving reactions with various chemicals and intermediates. Pirbuterol is effective in relieving bronchospasm and improving lung function in patients with asthma and chronic obstructive pulmonary disease (COPD). However, it is not a long-term treatment for these conditions and may not be suitable for all patients. The drug has been studied extensively for its effects on the respiratory system, its safety, and its efficacy compared to other bronchodilators. It has been shown to be safe and effective in treating asthma and COPD when used appropriately. Pirbuterol is a widely studied compound due to its potential as a therapeutic agent for respiratory diseases.'

pirbuterol: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID4845
CHEMBL ID1094966
CHEBI ID8245
SCHEMBL ID4819
MeSH IDM0053542

Synonyms (43)

Synonym
NCI60_003197
2-tert-butylamino-1-(5-hydroxy-6-hydroxymethyl-2-pyridyl)ethanol
pirbuterol [inn:ban]
ethanol, 2-tert-butylamino-1-(5-hydroxy-6-hydroxymethyl-2-pyridyl)-
pirbuterolum [inn-latin]
6-(2-(tert-butylamino)-1-hydroxyethyl)-2-(hydroxymethyl)-3-pyridinol
38677-81-5
pirbuterol
C07807
DB01291
(+/-)-pirbuterol
L013424
D08387
pirbuterol (inn)
ara-211
CHEMBL1094966
chebi:8245 ,
6-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)pyridin-3-ol
og645j8rvw ,
unii-og645j8rvw
pirbuterolum
gtpl7272
cp-2431414
.alpha.6-(((1,1-dimethylethyl)amino)methyl)-3-hydroxy-2,6-pyridinedimethanol
pirbuterol [mi]
pirbuterol [inn]
(rs)-6-(2-(tert-butylamino)-1-hydroxyethyl)-2-(hydroxymethyl)pyridin-3-ol
pirbuterol [who-dd]
pirbuterol [mart.]
2,6-pyridinedimethanol, .alpha.6-(((1,1-dimethylethyl)amino)methyl)-3-hydroxy-
pirbuterol [vandf]
SCHEMBL4819
VQDBNKDJNJQRDG-UHFFFAOYSA-N
DTXSID0046937
38677-81-5 (free base)
64856-15-1
Q1236526
2-(hydroxymethyl)-6-(1-hydroxy-2-tert-butylaminoethyl)pyridin-3-ol
(+/-)-pirbuterol; ara 211
()-pirbuterol; ara 211
EN300-23818614
2,6-pyridinedimethanol,a6-[[(1,1-dimethylethyl)amino]methyl]-3-hydroxy-
AKOS040749215

Research Excerpts

Overview

Pirbuterol hydrochloride is a beta-adrenoceptor agonist. It differs structurally from salbutamol in the substitution of a pyridine ring for the benzene ring. It is a well tolerated bronchodilator which appears to be of clinical importance in inhalative treatment of bronchospastic disease.

ExcerptReferenceRelevance
"Pirbuterol acts as a vasodilator on the pulmonary circulation in these patients and may in addition improve right ventricular performance by an inotropic action."( Effects of pirbuterol and sodium nitroprusside on pulmonary haemodynamics in hypoxic cor pulmonale.
Flenley, DC; Hannan, WJ; MacNee, W; Muir, AL; Wathen, CG, 1983
)
1.38
"Pirbuterol hydrochloride is a beta 2 adrenergic agonist with a structure similar to that of albuterol, except for the substitution of a pyridine ring for the benzene ring. "( Pirbuterol hydrochloride: evaluation of beta adrenergic agonist activity in reversible obstructive pulmonary disease and congestive heart failure.
Nelson, HS; Weber, RW,
)
3.02
"Pirbuterol is a relatively selective beta 2-agonist with somewhat greater effects on CO than on LVFP."( Comparative pharmacology and clinical efficacy of newer agents in treatment of heart failure.
Baird, JR; Blackburn, KJ; Cambridge, D; Constantine, JW; Ghaly, MS; Hayden, ML; McIlhenny, HM; Moore, PF; Olukotun, AY; Pullman, LG; Salsburg, DS; Saxton, CA; Shevde, S; Taylor, CR, 1981
)
0.98
"Pirbuterol is a selective beta-2 adrenergic agonist that is indicated for the treatment of bronchospasm in patients with asthma. "( Double-blind, clinical efficacy study comparing 400 micrograms of pirbuterol versus placebo delivered by a breath-actuated aerosol inhaler.
Ekholm, BP; Tinkelman, DG; Vanden Burgt, JA, 1994
)
1.97
"Pirbuterol is a well-tolerated bronchodilator which appears to be of clinical importance in the long-term treatment of bronchospastic disease."( Pirbuterol in the treatment of bronchial asthma.
Beumer, HM, 1979
)
2.42
"Pirbuterol is a well tolerated bronchodilator which appears to be of clinical importance in inhalative treatment of bronchospastic disease."( Comparative investigations on pirbuterol, salbutamol and placebo aerosols in bronchial asthma.
Beumer, HM, 1979
)
1.27
"Pirbuterol is a beta-adrenoceptor agonist which differs structurally from salbutamol in the substitution of a pyridine ring for the benzene ring. "( Pirbuterol. A preliminary review of its pharmacological properties and therapeutic efficacy in reversible bronchospastic disease.
Brogden, RN; Richards, DM, 1985
)
3.15

Effects

Pirbuterol orally has a marked and prolonged salutary hemodynamic effect and offers promise in CHF treatment.

ExcerptReferenceRelevance
"Pirbuterol orally has a marked and prolonged salutary hemodynamic effect and offers promise in CHF treatment."( Pirbuterol: a new oral sympathomimetic amine for the treatment of congestive heart failure.
Asinger, RW; Cohn, JN; Francis, GS; Hoback, J; Hodges, M; Sharma, B; Taylor, CR, 1981
)
2.43
"Pirbuterol orally has a marked and prolonged salutary hemodynamic effect and offers promise in CHF treatment."( Pirbuterol: a new oral sympathomimetic amine for the treatment of congestive heart failure.
Asinger, RW; Cohn, JN; Francis, GS; Hoback, J; Hodges, M; Sharma, B; Taylor, CR, 1981
)
2.43
"Pirbuterol hydrochloride has been assayed in alkaline medium by using a fluorometric method to measure fluorescence intensity at 372 nm with excitation at 310 nm and by the delta A method at 242 nm. "( Fluorometric and spectrophotometric determination of pirbuterol hydrochloride in authentic and dosage forms.
Aboul-Enein, HY; Mohamed, ME,
)
1.82

Actions

Pirbuterol in a lower dosage (15 mg by mouth) in six further patients with hypoxic chronic bronchitis and emphysema produced similar changes in total pulmonary vascular resistance and right ventricular ejection fraction.

ExcerptReferenceRelevance
"Pirbuterol in a lower dosage (15 mg by mouth) in six further patients with hypoxic chronic bronchitis and emphysema produced similar changes in total pulmonary vascular resistance and right ventricular ejection fraction."( Effects of pirbuterol and sodium nitroprusside on pulmonary haemodynamics in hypoxic cor pulmonale.
Flenley, DC; Hannan, WJ; MacNee, W; Muir, AL; Wathen, CG, 1983
)
1.38
"Pirbuterol induced an increase in cardiac index (1.7 +/- 0.1 to 2.3 +/- 0.2 l/min/m2, p less than 0.05) and a fall in systemic vascular resistance (1884 +/- 118 to 1391 +/- 69 dyn-sec-cm-5, p less than 0.01) 2 hours after administration."( Acute effects of oral pirbuterol on myocardial oxygen metabolism and systemic hemodynamics in chronic congestive heart failure.
Brown, EJ; Colucci, WS; Grossman, W; Lorell, BH; Mudge, GH; Rude, RE; Taylor, CR; Turi, Z, 1981
)
1.3

Treatment

ExcerptReferenceRelevance
"Treatment with pirbuterol for 3 months was associated with sustained increases in stroke volume and fasting plasma glucose and insulin, but there was loss of all other acute metabolic effects."( Differences between acute and long-term metabolic and endocrine effects of oral beta-adrenoceptor agonist therapy with pirbuterol for cardiac failure.
Canepa-Anson, R; Cockrill, B; Dawson, JR; Kuan, P; Poole-Wilson, PA; Reuben, SR; Sutton, GC, 1987
)
0.82

Toxicity

ExcerptReferenceRelevance
" Our conclusion is that pirbuterol is at least as effective and safe under conditions of chronic administration to asthmatics as metaproterenol and therefore can be considered a suitable alternative for therapy."( Comparison of safety and efficacy of inhaled pirbuterol with metaproterenol.
Brandon, ML; Grieco, M; Hudson, L; Rosenthal, RR; Spector, SL; Tashkin, D; Tinkelman, DG; Votteri, B, 1990
)
0.85
"5 million adverse drug reaction (ADR) reports for 8620 drugs/biologics that are listed for 1191 Coding Symbols for Thesaurus of Adverse Reaction (COSTAR) terms of adverse effects."( Assessment of the health effects of chemicals in humans: II. Construction of an adverse effects database for QSAR modeling.
Benz, RD; Contrera, JF; Kruhlak, NL; Matthews, EJ; Weaver, JL, 2004
)
0.32

Bioavailability

ExcerptReferenceRelevance
" A convenient method for study of the bioavailability of sublingual formulations is described, and the potential usefulness of a sublingual dosage form of pirbuterol is discussed."( Pharmacokinetics and cardiopulmonary effects in dogs of sublingual pirbuterol, a new bronchodilator.
Constantine, JW; McIlhenny, HM; Moore, PF, 1979
)
0.69

Dosage Studied

Pirbuterol in a lower dosage (15 mg by mouth) in six further patients with hypoxic chronic bronchitis and emphysema produced similar changes in total pulmonary vascular resistance and right ventricular ejection fraction. A convenient method for study of the bioavailability of sublingual formulations is described, and the potential usefulness of a sublingually dosage form of pirbutersol is discussed.

ExcerptRelevanceReference
" A convenient method for study of the bioavailability of sublingual formulations is described, and the potential usefulness of a sublingual dosage form of pirbuterol is discussed."( Pharmacokinetics and cardiopulmonary effects in dogs of sublingual pirbuterol, a new bronchodilator.
Constantine, JW; McIlhenny, HM; Moore, PF, 1979
)
0.69
" Biotransformations are determined by environmental or genetic factors and by the associated therapy and can change dramatically from one patient to another (interindividual variability) or for the same patient by multiple dosing (intra-individual variability)."( [Metabolism of beta-adrenergic substances. Therapeutic implications].
Brès, J; Bressolle, F; Clauzel, AM; Pistre, MC; Rachmat, H,
)
0.13
" The characteristics of the oral route are easy usage, precise dosage and assured effects."( Oral beta 2-selective adrenergic bronchodilators.
Daniotti, S; Dottorini, M; Grassi, V; Schiassi, M; Tantucci, C, 1986
)
0.27
" To assess the adequacy of 20 mg of PB, the dose-response relations of cardiocirculatory effects to 10, 15, 20 and 30 mg of PB were compared in seven of the above patients and nine other patients."( Pirbuterol, an oral beta-adrenergic receptor agonist, in the treatment of chronic cardiac failure.
Andrews, V; Janicki, JS; Likoff, M; Reichek, N; Weber, KT, 1982
)
1.71
" Pirbuterol in a lower dosage (15 mg by mouth) in six further patients with hypoxic chronic bronchitis and emphysema produced similar changes in total pulmonary vascular resistance and right ventricular ejection fraction."( Effects of pirbuterol and sodium nitroprusside on pulmonary haemodynamics in hypoxic cor pulmonale.
Flenley, DC; Hannan, WJ; MacNee, W; Muir, AL; Wathen, CG, 1983
)
1.57
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
pyridinesAny organonitrogen heterocyclic compound based on a pyridine skeleton and its substituted derivatives.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (29)

Assay IDTitleYearJournalArticle
AID625287Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for hepatomegaly2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID625283Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for elevated liver function tests2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID625292Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) combined score2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID588218FDA HLAED, lactate dehydrogenase (LDH) increase2004Current drug discovery technologies, Dec, Volume: 1, Issue:4
Assessment of the health effects of chemicals in humans: II. Construction of an adverse effects database for QSAR modeling.
AID625280Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for cholecystitis2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID625290Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for liver fatty2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID625289Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for liver disease2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1146174Agonist activity at beta-adrenergic receptor in guinea pig tracheal tissue assessed as bronchodilator activity1977Journal of medicinal chemistry, Oct, Volume: 20, Issue:10
Adrenerigic agents. 7.1 Synthesis and beta-adrenergic agonist activity of several 2-pyridylethanolamines.
AID588214FDA HLAED, liver enzyme composite activity2004Current drug discovery technologies, Dec, Volume: 1, Issue:4
Assessment of the health effects of chemicals in humans: II. Construction of an adverse effects database for QSAR modeling.
AID1146178Intrinsic activity at beta-adrenergic receptor in guinea pig right atrial muscle assessed as rate of contraction of spontaneously beating atria relative to isoproterenol1977Journal of medicinal chemistry, Oct, Volume: 20, Issue:10
Adrenerigic agents. 7.1 Synthesis and beta-adrenergic agonist activity of several 2-pyridylethanolamines.
AID1864500Substrate activity at human OCT1 overexpressed in HEK293 cells at 2.5 uM incubated for 2 mins by LC-MS/MS analysis2022Journal of medicinal chemistry, 09-22, Volume: 65, Issue:18
Substrates and Inhibitors of the Organic Cation Transporter 3 and Comparison with OCT1 and OCT2.
AID1146175Agonist activity at beta-adrenergic receptor in guinea pig right atrial muscle assessed as rate of contraction of spontaneously beating atria1977Journal of medicinal chemistry, Oct, Volume: 20, Issue:10
Adrenerigic agents. 7.1 Synthesis and beta-adrenergic agonist activity of several 2-pyridylethanolamines.
AID588219FDA HLAED, gamma-glutamyl transferase (GGT) increase2004Current drug discovery technologies, Dec, Volume: 1, Issue:4
Assessment of the health effects of chemicals in humans: II. Construction of an adverse effects database for QSAR modeling.
AID1864498Substrate activity at human OCT3 overexpressed in HEK293 cells at 2.5 uM incubated for 2 mins by LC-MS/MS analysis2022Journal of medicinal chemistry, 09-22, Volume: 65, Issue:18
Substrates and Inhibitors of the Organic Cation Transporter 3 and Comparison with OCT1 and OCT2.
AID588217FDA HLAED, serum glutamic pyruvic transaminase (SGPT) increase2004Current drug discovery technologies, Dec, Volume: 1, Issue:4
Assessment of the health effects of chemicals in humans: II. Construction of an adverse effects database for QSAR modeling.
AID588216FDA HLAED, serum glutamic oxaloacetic transaminase (SGOT) increase2004Current drug discovery technologies, Dec, Volume: 1, Issue:4
Assessment of the health effects of chemicals in humans: II. Construction of an adverse effects database for QSAR modeling.
AID625282Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for cirrhosis2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID588215FDA HLAED, alkaline phosphatase increase2004Current drug discovery technologies, Dec, Volume: 1, Issue:4
Assessment of the health effects of chemicals in humans: II. Construction of an adverse effects database for QSAR modeling.
AID625279Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for bilirubinemia2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID625284Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for hepatic failure2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID625291Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for liver function tests abnormal2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1146179Selectivity ratio of ED25 for beta-adrenergic receptor in guinea pig right atrial muscle to ED50 for beta-adrenergic receptor in guinea pig tracheal tissue1977Journal of medicinal chemistry, Oct, Volume: 20, Issue:10
Adrenerigic agents. 7.1 Synthesis and beta-adrenergic agonist activity of several 2-pyridylethanolamines.
AID625285Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for hepatic necrosis2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1864499Substrate activity at human OCT2 overexpressed in HEK293 cells at 2.5 uM incubated for 2 mins by LC-MS/MS analysis2022Journal of medicinal chemistry, 09-22, Volume: 65, Issue:18
Substrates and Inhibitors of the Organic Cation Transporter 3 and Comparison with OCT1 and OCT2.
AID625286Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for hepatitis2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID625288Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for jaundice2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID567091Drug absorption in human assessed as human intestinal absorption rate2011European journal of medicinal chemistry, Jan, Volume: 46, Issue:1
Prediction of drug intestinal absorption by new linear and non-linear QSPR.
AID625281Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for cholelithiasis2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID476929Human intestinal absorption in po dosed human2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Neural computational prediction of oral drug absorption based on CODES 2D descriptors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (108)

TimeframeStudies, This Drug (%)All Drugs %
pre-199078 (72.22)18.7374
1990's18 (16.67)18.2507
2000's7 (6.48)29.6817
2010's4 (3.70)24.3611
2020's1 (0.93)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 43.72

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index43.72 (24.57)
Research Supply Index5.08 (2.92)
Research Growth Index4.22 (4.65)
Search Engine Demand Index66.73 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (43.72)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials41 (34.45%)5.53%
Reviews13 (10.92%)6.00%
Case Studies3 (2.52%)4.05%
Observational0 (0.00%)0.25%
Other62 (52.10%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]