DT-Web

DB01291 - Pirbuterol


Identification
Name Pirbuterol
Accession Number DB01291
Type small molecule
Description Pirbuterol is a beta-2 adrenergic bronchodilator. In vitro studies and in vivo pharmacologic studies have demonstrated that pirbuterol has a preferential effect on beta-2 Adrenergic receptors compared with isoproterenol. While it is recognized that beta-2 adrenergic receptors are the predominant receptors in bronchial smooth muscle, data indicate that there is a population of beta-2 receptors in the human heart, existing in a concentration between 10-50%. The precise function of these receptors has not been established. The pharmacologic effects of beta adrenergic agonist drugs, including pirbuterol, are at least in proof attributable to stimulation through beta adrenergic receptors of intracellular adenyl cyclase, the enzyme which catalyzes the conversion of adenosine triphosphate (AlP) to cyclic-3+ ,5+-adenosine monophosphate (c-AMP). Increased c-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.
Structure
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 240.2988
Groups approved
Monoisotopic Weight 240.147392516
Pharmacology
Indication For the prevention and reversal of bronchospasm in patients 12 years of age and older with reversible bronchospasm including asthma.
Mechanism of action The pharmacologic effects of beta adrenergic agonist drugs, including pirbuterol, are at least in proof attributable to stimulation through beta adrenergic receptors of intracellular adenyl cyclase, the enzyme which catalyzes the conversion of adenosine triphosphate (AlP) to cyclic-3† ,5†-adenosine monophosphate (c-AMP). Increased c-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.
Absorption Not Available
Protein binding Not Available
Biotransformation Not Available
Route of elimination Not Available
Toxicity As with all sympathomimetic aerosol medication, cardiac arrest and even death may be associated with abuse of pirbuterol.
Affected organisms
  • Humans and other mammals
Interactions
Drug Interactions
Drug Mechanism of interaction
Acebutolol Antagonism
Amitriptyline The tricyclic antidepressant, amitriptyline, increases the sympathomimetic effect of pirbuterol.
Amoxapine The tricyclic antidepressant, amoxapine, increases the sympathomimetic effect of pirbuterol.
Atenolol Antagonism
Bisoprolol Antagonism
Carvedilol Antagonism
Clomipramine The tricyclic antidepressant, clomipramine, increases the sympathomimetic effect of pirbuterol.
Desipramine The tricyclic antidepressant, desipramine, increases the sympathomimetic effect of pirbuterol.
Doxepin The tricyclic antidepressant, doxepin, increases the sympathomimetic effect of pirbuterol.
Esmolol Antagonism
Imipramine The tricyclic antidepressant, imipramine, increases the sympathomimetic effect of pirbuterol.
Isocarboxazid Increased arterial pressure
Labetalol Antagonism
Linezolid Possible increase of arterial pressure
Methyldopa Increased arterial pressure
Metoprolol Antagonism
Midodrine Increased arterial pressure
Moclobemide Moclobemide increases the sympathomimetic effect of pirbuterol.
Nadolol Antagonism
Nortriptyline The tricyclic antidepressant, nortriptyline, increases the sympathomimetic effect of pirbuterol.
Oxprenolol Antagonism
Phenelzine Increased arterial pressure
Pindolol Antagonism
Propranolol Antagonism
Rasagiline Increased arterial pressure
Reserpine Increased arterial pressure
Timolol Antagonism
Food Interactions Not Available

Targets


Beta-2 adrenergic receptor
Name Beta-2 adrenergic receptor
Gene Name ADRB2
Pharmacological action yes
Actions agonist
References
  • Carie AE, Sebti SM: A chemical biology approach identifies a beta-2 adrenergic receptor agonist that causes human tumor regression by blocking the Raf-1/Mek-1/Erk1/2 pathway. Oncogene. 2007 May 31;26(26):3777-88. Epub 2007 Jan 29. - Pubmed
  • Leier CV, Nelson S, Huss P, Bianchine JR, Olukotun AY, Taylor CR, Salzburg DS: Intravenous pirbuterol. Clin Pharmacol Ther. 1982 Jan;31(1):89-94. - Pubmed
  • Hamdad N, Ming Z, Parent R, Lavallee M: Beta 2-adrenergic dilation of conductance coronary arteries involves flow-dependent NO formation in conscious dogs. Am J Physiol. 1996 Nov;271(5 Pt 2):H1926-37. - Pubmed
  • Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. - Pubmed
DTHybrid score 0.6916
Beta-1 adrenergic receptor
Name Beta-1 adrenergic receptor
Gene Name ADRB1
Pharmacological action unknown
Actions agonist
References
  • van Zwieten PA: Receptor-mediated inotropic drugs. Eur Heart J. 1988 Jun;9 Suppl H:85-90. - Pubmed
  • Kenakin TP, Beek D: Relative efficacy of prenalterol and pirbuterol for beta-1 adrenoceptors: measurement of agonist affinity by alteration of receptor number. J Pharmacol Exp Ther. 1984 May;229(2):340-5. - Pubmed
DTHybrid score 0.6854

Predictions


Id Partner name Gene Name Score
1517 Beta-3 adrenergic receptor ADRB3 0.1348
4119 Cytochrome P450 2D6 CYP2D6 0.108
556 Alpha-1A adrenergic receptor ADRA1A 0.0576
320 5-hydroxytryptamine 1A receptor HTR1A 0.0509
1588 Multidrug resistance protein 1 ABCB1 0.0499
4512 Cytochrome P450 3A4 CYP3A4 0.0356
318 Alpha-2A adrenergic receptor ADRA2A 0.035
6144 Solute carrier family 22 member 2 SLC22A2 0.0326
4200 Cytochrome P450 1A2 CYP1A2 0.0304
885 5-hydroxytryptamine 1B receptor HTR1B 0.0284
3923 Cholinesterase BCHE 0.028
101 Potassium voltage-gated channel subfamily H member 2 KCNH2 0.0262
2300 Lysozyme E 0.0243
3633 Lysozyme R 0.0243
5597 Lysozyme 17 0.0243
6016 Cytochrome P450 2C19 CYP2C19 0.0243
632 Alpha-1B adrenergic receptor ADRA1B 0.022
629 Alpha-2B adrenergic receptor ADRA2B 0.022
3810 Catechol O-methyltransferase COMT 0.0211
540 Sodium-dependent noradrenaline transporter SLC6A2 0.0186
6145 Solute carrier family 22 member 1 SLC22A1 0.0185
6024 Cytochrome P450 1A1 CYP1A1 0.0184
378 Alpha-2C adrenergic receptor ADRA2C 0.0184
1181 Alpha-1-acid glycoprotein 1 ORM1 0.018
1820 Beta-nerve growth factor NGF 0.0166
6040 6-phosphogluconate dehydrogenase, decarboxylating PGD 0.016
3941 Amine oxidase [flavin-containing] A MAOA 0.0153
4146 Phosphatidylinositol 3-kinase regulatory subunit gamma PIK3R3 0.0151
4145 Phosphatidylinositol 3-kinase regulatory subunit beta PIK3R2 0.0151
828 Phenylalanine-4-hydroxylase PAH 0.0149
3109 Phenylalanine-4-hydroxylase phhA 0.0149
789 Alpha-1D adrenergic receptor ADRA1D 0.0131
1281 Phosphatidylinositol 3-kinase regulatory subunit alpha PIK3R1 0.0125
4292 Acyl-[acyl-carrier-protein]--UDP-N-acetylglucosamine O-acyltransferase lpxA 0.0124
4757 Cytochrome P450 2C9 CYP2C9 0.0123
3076 Antigen 85-C fbpC 0.0122
824 Sodium-dependent serotonin transporter SLC6A4 0.0118
777 Tumor necrosis factor TNF 0.0112
713 Sodium-dependent dopamine transporter SLC6A3 0.0107
5718 Cytochrome P450 2A6 CYP2A6 0.0103
6847 Lactase-phlorizin hydrolase LCT 0.0093
1176 Mitogen-activated protein kinase 1 MAPK1 0.0083
6107 Cytochrome P450 3A7 CYP3A7 0.008
118 Organic cation/carnitine transporter 2 SLC22A5 0.0078
6147 Solute carrier family 22 member 3 SLC22A3 0.0076
4118 Cytochrome P450 3A5 CYP3A5 0.0076
23 D(1A) dopamine receptor DRD1 0.0064
6022 UDP-glucuronosyltransferase 1-1 UGT1A1 0.0063
1374 Natriuretic peptides B NPPB 0.0061
1827 Gap junction alpha-1 protein GJA1 0.0061
1908 Vascular cell adhesion protein 1 VCAM1 0.0061
6164 POU domain, class 5, transcription factor 1 POU5F1 0.0061
131 Synaptic vesicular amine transporter SLC18A2 0.0058
3876 Aromatic-L-amino-acid decarboxylase DDC 0.0055
194 NADH dehydrogenase [ubiquinone] 1 subunit C2 NDUFC2 0.005
4924 Cytochrome P450 2C8 CYP2C8 0.005
183 Vascular endothelial growth factor A VEGFA 0.0045
3939 Amine oxidase [flavin-containing] B MAOB 0.0045
6151 Monocarboxylate transporter 10 SLC16A10 0.004
1360 Sphingomyelin phosphodiesterase SMPD1 0.0036
6013 Cytochrome P450 2E1 CYP2E1 0.0036
502 5-hydroxytryptamine 2A receptor HTR2A 0.0036
492 Histamine H1 receptor HRH1 0.0035
3947 Xanthine dehydrogenase/oxidase XDH 0.0032
1256 5-hydroxytryptamine 6 receptor HTR6 0.003
6025 UDP-glucuronosyltransferase 1-4 UGT1A4 0.0029
124 Histamine H2 receptor HRH2 0.0028
465 Calmodulin CALM1 0.0028
716 5-hydroxytryptamine 7 receptor HTR7 0.0028
6432 Transporter snf 0.0027
4160 Voltage-dependent calcium channel subunit alpha-2/delta-2 CACNA2D2 0.0027
436 5-hydroxytryptamine 2B receptor HTR2B 0.0026
432 D(4) dopamine receptor DRD4 0.0025
964 Voltage-dependent T-type calcium channel subunit alpha-1H CACNA1H 0.0025
638 D(3) dopamine receptor DRD3 0.0024
20 Prostaglandin G/H synthase 1 PTGS1 0.0024
233 Potassium channel subfamily K member 2 KCNK2 0.0023
590 5-hydroxytryptamine 2C receptor HTR2C 0.0023
831 D(2) dopamine receptor DRD2 0.002
4114 Voltage-dependent L-type calcium channel subunit beta-3 CACNB3 0.0019
4112 Voltage-dependent L-type calcium channel subunit beta-4 CACNB4 0.0019
6106 Cytochrome P450 2C18 CYP2C18 0.0019
274 Muscarinic acetylcholine receptor M5 CHRM5 0.0019
833 Organic cation/carnitine transporter 1 SLC22A4 0.0019
450 Muscarinic acetylcholine receptor M4 CHRM4 0.0018
4113 Voltage-dependent L-type calcium channel subunit alpha-1F CACNA1F 0.0018
333 Voltage-dependent L-type calcium channel subunit beta-1 CACNB1 0.0017
158 Sodium channel protein type 1 subunit alpha SCN1A 0.0017
51 Muscarinic acetylcholine receptor M3 CHRM3 0.0016
617 Muscarinic acetylcholine receptor M2 CHRM2 0.0016
103 Muscarinic acetylcholine receptor M1 CHRM1 0.0015
4110 Voltage-dependent L-type calcium channel subunit beta-2 CACNB2 0.0015
4115 Voltage-dependent L-type calcium channel subunit alpha-1D CACNA1D 0.0015
4111 Voltage-dependent L-type calcium channel subunit alpha-1S CACNA1S 0.0015
478 Voltage-dependent L-type calcium channel subunit alpha-1C CACNA1C 0.0014
6030 Cytochrome P450 2B6 CYP2B6 0.0014
587 Serum albumin ALB 0.0009
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