Synonym
Pirbuterol Acetate; Maxair; Pirbuterol acetate [USAN]; EINECS 265-862-4; Pirbuterol acetate (USAN); pirbuterol sulfate; pyrbuterol;pirbuterol acetate salt; pirbuterol dihydrochloride; 3M brand of pirbuterol acetate; CP 24315-1; CP-24,314-1; CP-24315-1;
IUPAC/Chemical Name
6-(2-(tert-butylamino)-1-hydroxyethyl)-2-(hydroxymethyl)pyridin-3-ol; acetic acid
InChi Key
QSXMZJGGEWYVCN-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H20N2O3.C2H4O2/c1-12(2,3)13-6-11(17)8-4-5-10(16)9(7-15)14-8;1-2(3)4/h4-5,11,13,15-17H,6-7H2,1-3H3;1H3,(H,3,4)
SMILES Code
CC(=O)O.CC(C)(C)NCC(C1=NC(=C(C=C1)O)CO)O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Pirbuterol Acetate is a short-acting β2 adrenoreceptor agonist.
In vitro activity:
A chemical biology approach identifies a beta 2 adrenergic receptor (beta2AR) agonist ARA-211 (Pirbuterol), which causes apoptosis and human tumor regression in animal models. ARA-211 inhibition of the Raf/Mek/Erk1/2 pathway is mediated by PKA and not exchange protein activated by cAMP (EPAC). ARA-211 is selective and suppresses P-Erk1/2 but not P-JNK, P-p38, P-Akt or P-STAT3 levels. beta2AR stimulation results in inhibition of anchorage-dependent and -independent growth, induction of apoptosis in vitro and tumor regression in vivo. beta2AR antagonists and constitutively active Mek-1 rescue from the effects of ARA-211, demonstrating that beta2AR stimulation and Mek kinase inhibition are required for ARA-211 antitumor activity. Furthermore, suppression of growth occurs only in human tumors where ARA-211 induces cAMP formation and decreases P-Erk1/2 levels.
Reference: Oncogene. 2007 May 31;26(26):3777-88. https://pubmed.ncbi.nlm.nih.gov/17260025/
In vivo activity:
A chemical biology approach identifies a beta 2 adrenergic receptor (beta2AR) agonist ARA-211 (Pirbuterol), which causes apoptosis and human tumor regression in animal models. ARA-211 inhibition of the Raf/Mek/Erk1/2 pathway is mediated by PKA and not exchange protein activated by cAMP (EPAC). ARA-211 is selective and suppresses P-Erk1/2 but not P-JNK, P-p38, P-Akt or P-STAT3 levels. beta2AR stimulation results in inhibition of anchorage-dependent and -independent growth, induction of apoptosis in vitro and tumor regression in vivo. beta2AR antagonists and constitutively active Mek-1 rescue from the effects of ARA-211, demonstrating that beta2AR stimulation and Mek kinase inhibition are required for ARA-211 antitumor activity. Furthermore, suppression of growth occurs only in human tumors where ARA-211 induces cAMP formation and decreases P-Erk1/2 levels.
Reference: Oncogene. 2007 May 31;26(26):3777-88. https://pubmed.ncbi.nlm.nih.gov/17260025/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
300.36
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
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. doi: 10.1038/sj.onc.1210172. Epub 2007 Jan 29. PMID: 17260025.
In vitro protocol:
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. doi: 10.1038/sj.onc.1210172. Epub 2007 Jan 29. PMID: 17260025.
In vivo protocol:
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. doi: 10.1038/sj.onc.1210172. Epub 2007 Jan 29. PMID: 17260025.
1: Langley PC. The technology of metered-dose inhalers and treatment costs in asthma: a retrospective study of breath actuation versus traditional press-and- breathe inhalers. Clin Ther. 1999 Jan;21(1):236-53. doi: 10.1016/S0149-2918(00)88281-8. PMID: 10090438.
2: Simon MR, Houser WL, Smith KA, Long PM. Esophageal candidiasis as a complication of inhaled corticosteroids. Ann Allergy Asthma Immunol. 1997 Oct;79(4):333-8. doi: 10.1016/S1081-1206(10)63024-4. PMID: 9357379.
3: Derksen FJ, Olszewski M, Robinson NE, Berney C, Lloyd JW, Hakala J, Matson C, Ruth D. Use of a hand-held, metered-dose aerosol delivery device to administer pirbuterol acetate to horses with 'heaves'. Equine Vet J. 1996 Jul;28(4):306-10. doi: 10.1111/j.2042-3306.1996.tb03094.x. PMID: 8818596.
4: Schecker MH, Wilson AF, Mukai DS, Hahn M, Crook D, Novey HS. A device for overcoming discoordination with metered-dose inhalers. J Allergy Clin Immunol. 1993 Dec;92(6):783-9. doi: 10.1016/0091-6749(93)90054-j. PMID: 7794289.
5: Bronsky EA, Debelic M, Pujet JC, Hahn M. Ease-of-use study of pirbuterol acetate in the Autohaler actuator in three countries: the United States, Germany, and France. J Asthma. 1993;30(6):439-43. doi: 10.3109/02770909309056752. PMID: 8244913.
6: Chodosh S, Crooks LA, Tuck J. Comparative effects of pirbuterol acetate, metaproterenol, and placebo aerosols on pulmonary function and incidence of cardiac ectopy. J Asthma. 1989;26(5):309-15. doi: 10.3109/02770908909073268. PMID: 2484663.
7: Littner MR, Tashkin DP, Calvarese B, Bautista M. Acute bronchial and cardiovascular effects of increasing doses of pirbuterol acetate aerosol in asthma. Ann Allergy. 1982 Jan;48(1):14-20. PMID: 7055342.
8: Levinsky HV, Breckenridge C, Lough R, Gonci DA, McIlhenny HM, Qureshi S. Six month inhalation studies of pirbuterol acetate aerosol in the beagle dog and squirrel monkey. Fundam Appl Toxicol. 1981 Nov-Dec;1(6):426-31. doi: 10.1016/s0272-0590(81)80022-x. PMID: 7185594.
