Details of the Drug

General Information of Drug (ID: DMI5678)

Drug Name

Pirbuterol

Synonyms

Maxair; Pirbuterolum; Pyrbuterol; Pirbuterol acetate salt; CP 24315-1; Maxair (TN); Pirbuterol (INN); Pirbuterol [INN:BAN]; Pirbuterolum [INN-Latin]; CP-24315-1; CP-24,314-1; CP-24,314-14; 2-hydroxymethyl-3-hydroxy-6-(1-hydroxy-2-tert-butylamino ethyl)pyridine, dihydrochloride; 2-tert-Butylamino-1-(5-hydroxy-6-hydroxymethyl-2-pyridyl)ethanol; 6-(2-(tert-butylamino)-1-hydroxyethyl)-2-(hydroxymethyl)-3-pyridinol; 6-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)pyridin-3-ol

Indication

Disease Entry	ICD 11	Status	REF
Asthma	CA23	Approved	[1], [2]

Therapeutic Class

Bronchodilator Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

240.3

Topological Polar Surface Area (xlogp)

-0.1

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Half-life: The concentration or amount of drug in body reduced by one-half in 2 hours [3]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.14268 micromolar/kg/day [4]

Chemical Identifiers

Formula: C12H20N2O3
IUPAC Name: 6-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)pyridin-3-ol
Canonical SMILES: CC(C)(C)NCC(C1=NC(=C(C=C1)O)CO)O
InChI: InChI=1S/C12H20N2O3/c1-12(2,3)13-6-11(17)8-4-5-10(16)9(7-15)14-8/h4-5,11,13,15-17H,6-7H2,1-3H3
InChIKey: VQDBNKDJNJQRDG-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 4845
ChEBI ID: CHEBI:8245
CAS Number: 38677-81-5
DrugBank ID: DB01291
TTD ID: D0SS4P

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Adrenergic receptor beta-2 (ADRB2)	TT2CJVK	ADRB2_HUMAN	Agonist	[5], [6]

------------------------------------------------------------------------------------

Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Asthma

ICD Disease Classification

CA23

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Adrenergic receptor beta-2 (ADRB2)	DTT	ADRB2	4.88E-01	-0.05	-0.12
Adrenergic receptor beta-2 (ADRB2)	DTT	ADRB2	7.10E-01	0.06	0.09

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Pirbuterol (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Methylene blue	DMJAPE7	Moderate	Additive hypertensive effects by the combination of Pirbuterol and Methylene blue.	Acquired methaemoglobinaemia [3A93]	[17]
Ivosidenib	DM8S6T7	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Ivosidenib.	Acute myeloid leukaemia [2A60]	[18]
Midostaurin	DMI6E0R	Moderate	Increased risk of prolong QT interval by the combination of Pirbuterol and Midostaurin.	Acute myeloid leukaemia [2A60]	[18]
Arn-509	DMT81LZ	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Arn-509.	Acute myeloid leukaemia [2A60]	[18]
Gilteritinib	DMWQ4MZ	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Gilteritinib.	Acute myeloid leukaemia [2A60]	[18]
Oliceridine	DM6MDCF	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Oliceridine.	Acute pain [MG31]	[19]
Ivabradine	DM0L594	Moderate	Increased risk of prolong QT interval by the combination of Pirbuterol and Ivabradine.	Angina pectoris [BA40]	[18]
Droxidopa	DM5YF4M	Moderate	Additive hypertensive effects by the combination of Pirbuterol and Droxidopa.	Autonomic nervous system disorder [8D87]	[20]
Retigabine	DMGNYIH	Moderate	Increased risk of prolong QT interval by the combination of Pirbuterol and Retigabine.	Behcet disease [4A62]	[19]
Eribulin	DM1DX4Q	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Eribulin.	Breast cancer [2C60-2C6Y]	[18]
Bosutinib	DMTI8YE	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Bosutinib.	Breast cancer [2C60-2C6Y]	[18]
Levomilnacipran	DMV26S8	Moderate	Increased risk of rapid heart rate by the combination of Pirbuterol and Levomilnacipran.	Chronic pain [MG30]	[21]
Probucol	DMVZQ2M	Moderate	Increased risk of prolong QT interval by the combination of Pirbuterol and Probucol.	Coronary atherosclerosis [BA80]	[19]
Pasireotide	DMHM7JS	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Pasireotide.	Cushing syndrome [5A70]	[18]
Milnacipran	DMBFE74	Moderate	Increased risk of rapid heart rate by the combination of Pirbuterol and Milnacipran.	Depression [6A70-6A7Z]	[21]
Desvenlafaxine	DMHD4PE	Moderate	Additive hypertensive effects by the combination of Pirbuterol and Desvenlafaxine.	Depression [6A70-6A7Z]	[21]
Tetrabenazine	DMYWQ0O	Moderate	Increased risk of prolong QT interval by the combination of Pirbuterol and Tetrabenazine.	Dissociative neurological symptom disorder [6B60]	[18]
Deutetrabenazine	DMUPFLI	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Deutetrabenazine.	Dystonic disorder [8A02]	[18]
Ingrezza	DMVPLNC	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Ingrezza.	Dystonic disorder [8A02]	[18]
Solifenacin	DMG592Q	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Solifenacin.	Functional bladder disorder [GC50]	[18]
Fostemsavir	DM50ILT	Moderate	Increased risk of prolong QT interval by the combination of Pirbuterol and Fostemsavir.	Human immunodeficiency virus disease [1C60-1C62]	[18]
Lopinavir	DMITQS0	Moderate	Increased risk of prolong QT interval by the combination of Pirbuterol and Lopinavir.	Human immunodeficiency virus disease [1C60-1C62]	[19]
Rilpivirine	DMJ0QOW	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Rilpivirine.	Human immunodeficiency virus disease [1C60-1C62]	[18]
Crizotinib	DM4F29C	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Crizotinib.	Lung cancer [2C25]	[18]
Ceritinib	DMB920Z	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Ceritinib.	Lung cancer [2C25]	[18]
Osimertinib	DMRJLAT	Moderate	Increased risk of prolong QT interval by the combination of Pirbuterol and Osimertinib.	Lung cancer [2C25]	[18]
Selpercatinib	DMZR15V	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Selpercatinib.	Lung cancer [2C25]	[19]
Lumefantrine	DM29GAD	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Lumefantrine.	Malaria [1F40-1F45]	[19]
Hydroxychloroquine	DMSIVND	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Hydroxychloroquine.	Malaria [1F40-1F45]	[18]
Inotuzumab ozogamicin	DMAC130	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Inotuzumab ozogamicin.	Malignant haematopoietic neoplasm [2B33]	[18]
Vemurafenib	DM62UG5	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Vemurafenib.	Melanoma [2C30]	[18]
LGX818	DMNQXV8	Moderate	Increased risk of prolong QT interval by the combination of Pirbuterol and LGX818.	Melanoma [2C30]	[18]
Panobinostat	DM58WKG	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Panobinostat.	Multiple myeloma [2A83]	[18]
Siponimod	DM2R86O	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Siponimod.	Multiple sclerosis [8A40]	[18]
Fingolimod	DM5JVAN	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Fingolimod.	Multiple sclerosis [8A40]	[18]
Ozanimod	DMT6AM2	Major	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Ozanimod.	Multiple sclerosis [8A40]	[22]
Romidepsin	DMT5GNL	Moderate	Increased risk of prolong QT interval by the combination of Pirbuterol and Romidepsin.	Mycosis fungoides [2B01]	[19]
Nilotinib	DM7HXWT	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Nilotinib.	Myeloproliferative neoplasm [2A20]	[18]
Entrectinib	DMMPTLH	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Entrectinib.	Non-small cell lung cancer [2C25]	[19]
Lofexidine	DM1WXA6	Moderate	Increased risk of prolong QT interval by the combination of Pirbuterol and Lofexidine.	Opioid use disorder [6C43]	[18]
Rucaparib	DM9PVX8	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Rucaparib.	Ovarian cancer [2C73]	[18]
Triclabendazole	DMPWGBR	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Triclabendazole.	Parasitic worm infestation [1F90]	[19]
Safinamide	DM0YWJC	Moderate	Additive hypertensive effects by the combination of Pirbuterol and Safinamide.	Parkinsonism [8A00]	[17]
Rasagiline	DM3WKQ4	Moderate	Additive hypertensive effects by the combination of Pirbuterol and Rasagiline.	Parkinsonism [8A00]	[17]
Pimavanserin	DMR7IVC	Moderate	Increased risk of prolong QT interval by the combination of Pirbuterol and Pimavanserin.	Parkinsonism [8A00]	[18]
Macimorelin	DMQYJIR	Major	Increased risk of prolong QT interval by the combination of Pirbuterol and Macimorelin.	Pituitary gland disorder [5A60-5A61]	[23]
Lefamulin	DME6G97	Moderate	Increased risk of prolong QT interval by the combination of Pirbuterol and Lefamulin.	Pneumonia [CA40]	[18]
Degarelix	DM3O8QY	Moderate	Increased risk of prolong QT interval by the combination of Pirbuterol and Degarelix.	Prostate cancer [2C82]	[18]
ABIRATERONE	DM8V75C	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and ABIRATERONE.	Prostate cancer [2C82]	[18]
Enzalutamide	DMGL19D	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Enzalutamide.	Prostate cancer [2C82]	[18]
Levomepromazine	DMIKFEL	Moderate	Increased risk of prolong QT interval by the combination of Pirbuterol and Levomepromazine.	Psychotic disorder [6A20-6A25]	[19]
Ciclesonide	DM2NA4K	Minor	Increased risk of hypokalemia by the combination of Pirbuterol and Ciclesonide.	Respiratory system disease [CB40-CB7Z]	[24]
Iloperidone	DM6AUFY	Moderate	Increased risk of prolong QT interval by the combination of Pirbuterol and Iloperidone.	Schizophrenia [6A20]	[18]
Amisulpride	DMSJVAM	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Amisulpride.	Schizophrenia [6A20]	[18]
Asenapine	DMSQZE2	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Asenapine.	Schizophrenia [6A20]	[18]
LEE011	DMMX75K	Major	Increased risk of prolong QT interval by the combination of Pirbuterol and LEE011.	Solid tumour/cancer [2A00-2F9Z]	[25]
Vandetanib	DMRICNP	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Vandetanib.	Solid tumour/cancer [2A00-2F9Z]	[18]
Triptorelin	DMTK4LS	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Triptorelin.	Solid tumour/cancer [2A00-2F9Z]	[18]
Pitolisant	DM8RFNJ	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Pitolisant.	Somnolence [MG42]	[18]
Telavancin	DM58VQX	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Telavancin.	Staphylococcal/streptococcal disease [1B5Y]	[18]
Lenvatinib	DMB1IU4	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Lenvatinib.	Thyroid cancer [2D10]	[18]
Cabozantinib	DMIYDT4	Moderate	Increased risk of ventricular arrhythmias by the combination of Pirbuterol and Cabozantinib.	Thyroid cancer [2D10]	[18]
Fluticasone	DMGCSVF	Minor	Increased risk of hypokalemia by the combination of Pirbuterol and Fluticasone.	Vasomotor/allergic rhinitis [CA08]	[24]
-----------


⏷ Show the Full List of 63 DDI Information of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7272).
2	Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
3	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
5	Inhaled beta agonists. Respir Care. 2007 Jul;52(7):820-32.
6	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 p... Oncogene. 2007 May 31;26(26):3777-88.
7	Emerging drugs in chronic obstructive pulmonary disease. Expert Opin Emerg Drugs. 2009 Mar;14(1):181-94.
8	Long-acting beta2-agonists for chronic obstructive pulmonary disease patients with poorly reversible airflow limitation. Cochrane Database Syst Rev. 2002;(3):CD001104.
9	Potential of beta2-adrenoceptor agonists as add-on therapy for multiple sclerosis: focus on salbutamol (albuterol). CNS Drugs. 2002;16(1):1-8.
10	Arformoterol tartrate in the treatment of bronchoconstriction in patients with chronic obstructive pulmonary disease. Drugs Today (Barc). 2009 Jan;45(1):3-9.
11	Current therapeutic uses and potential of beta-adrenoceptor agonists and antagonists. Eur J Clin Pharmacol. 1998 Feb;53(6):389-404.
12	Pharmacogenetic tests in asthma therapy. Clin Lab Med. 2008 Dec;28(4):645-65.
13	Postischemic brain injury is attenuated in mice lacking the beta2-adrenergic receptor. Anesth Analg. 2009 Jan;108(1):280-7.
14	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
15	2014 FDA drug approvals. Nat Rev Drug Discov. 2015 Feb;14(2):77-81.
16	Functional alpha1- and beta2-adrenergic receptors in human osteoblasts. J Cell Physiol. 2009 Jul;220(1):267-75.
17	Adverse effects and complications of treatment with beta-adrenergic agonist drugs. Committee on drugs, the American Academy of Allergy and Immunology. J Allergy Clin Immunol 75 (1985): 443-9. [PMID: 2858503]
18	Bengtsson B, Fagerstrom PO "Extrapulmonary effects of terbutaline during prolonged administration." Clin Pharmacol Ther 31 (1982): 726-32. [PMID: 7042176]
19	Product Information. Arcapta Neohaler (indacaterol). Novartis Pharmaceuticals, East Hanover, NJ.
20	Product Information. Northera (droxidopa). Chelsea Therapeutics Inc, Charlotte, NC.
21	Product Information. Cymbalta (duloxetine). Lilly, Eli and Company, Indianapolis, IN.
22	Product Information. Zeposia (ozanimod). Celgene Corporation, Summit, NJ.
23	Product Information. Macrilen (macimorelin). Aeterna Zentaris, Charleston, SC.
24	Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".
25	Canadian Pharmacists Association.