Synonym
Salmeterol free base; Astmerole; GR 33343 X; GR 33343X; GR33343X; GR-33343X; SN408D.
IUPAC/Chemical Name
4-Hydroxy-alpha1-[[[6-(4-phenylbutoxy)hexyl]amino]methyl]-1,3-benzenedimethanol
InChi Key
GIIZNNXWQWCKIB-UHFFFAOYSA-N
InChi Code
InChI=1S/C25H37NO4/c27-20-23-18-22(13-14-24(23)28)25(29)19-26-15-7-1-2-8-16-30-17-9-6-12-21-10-4-3-5-11-21/h3-5,10-11,13-14,18,25-29H,1-2,6-9,12,15-17,19-20H2
SMILES Code
OC(CNCCCCCCOCCCCC1=CC=CC=C1)C2=CC=C(O)C(CO)=C2
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
To be determined
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
More Info
Related CAS#
CAS#94749-08-3 (Salmeterol xinafoate salt)
CAS#89365-50-4 (Salmeterol free base).
Biological target:
Salmeterol shows potent stimulation of cAMP accumulation in CHO cells expressing human β2, β1 and β3 adrenoceptors with pEC50s of 9.6, 6.1, and 5.9, respectively.
In vitro activity:
This study investigated the anti-inflammatory effects of salmeterol on LPS-activated murine microglial BV2 cells. Salmeterol inhibited LPS-induced release of TNF-α, IL-1β, and NO in BV2 cells. Salmeterol suppressed nuclear translocation of NF-κB p65 by inhibiting the IκB-α degradation and TAK1 phosphorylation. Salmeterol increased the expression of β-arrestin2 and enhanced the interaction between β-arrestin2 and TAB1.
Reference: J Neuroimmunol. 2018 Dec 15;325:10-19. https://pubmed.ncbi.nlm.nih.gov/30352316/
In vivo activity:
Salmeterol shows promise in combating stress-related disruptions in adult hippocampal neurogenesis and depressive behavior. It enhances neuroplasticity in the hippocampus, fostering the development of neuroblasts with increased complexity. These benefits are primarily observed in the ventral hippocampus, which plays a role in emotional behavior and mood regulation.
Reference: Front Pharmacol. 2019 Sep 12;10:1000. https://pubmed.ncbi.nlm.nih.gov/31572182/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
415.57
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:
1. Sharma M, Flood PM. β-arrestin2 regulates the anti-inflammatory effects of Salmeterol in lipopolysaccharide-stimulated BV2 cells. J Neuroimmunol. 2018 Dec 15;325:10-19. doi: 10.1016/j.jneuroim.2018.10.001. Epub 2018 Oct 4. PMID: 30352316.
2. Haghi M, Traini D, Postma DS, Bebawy M, Young PM. Fluticasone uptake across Calu-3 cells is mediated by salmeterol when deposited as a combination powder inhaler. Respirology. 2013 Nov;18(8):1197-201. doi: 10.1111/resp.12146. PMID: 23796052.
3. Bortolotto V, Bondi H, Cuccurazzu B, Rinaldi M, Canonico PL, Grilli M. Salmeterol, a β2 Adrenergic Agonist, Promotes Adult Hippocampal Neurogenesis in a Region-Specific Manner. Front Pharmacol. 2019 Sep 12;10:1000. doi: 10.3389/fphar.2019.01000. PMID: 31572182; PMCID: PMC6751403.
4. Han SO, Li S, Koeberl DD. Salmeterol enhances the cardiac response to gene therapy in Pompe disease. Mol Genet Metab. 2016 May;118(1):35-40. doi: 10.1016/j.ymgme.2016.03.006. Epub 2016 Mar 18. PMID: 27017193; PMCID: PMC4833676.
In vitro protocol:
1. Sharma M, Flood PM. β-arrestin2 regulates the anti-inflammatory effects of Salmeterol in lipopolysaccharide-stimulated BV2 cells. J Neuroimmunol. 2018 Dec 15;325:10-19. doi: 10.1016/j.jneuroim.2018.10.001. Epub 2018 Oct 4. PMID: 30352316.
2. Haghi M, Traini D, Postma DS, Bebawy M, Young PM. Fluticasone uptake across Calu-3 cells is mediated by salmeterol when deposited as a combination powder inhaler. Respirology. 2013 Nov;18(8):1197-201. doi: 10.1111/resp.12146. PMID: 23796052.
In vivo protocol:
1. Bortolotto V, Bondi H, Cuccurazzu B, Rinaldi M, Canonico PL, Grilli M. Salmeterol, a β2 Adrenergic Agonist, Promotes Adult Hippocampal Neurogenesis in a Region-Specific Manner. Front Pharmacol. 2019 Sep 12;10:1000. doi: 10.3389/fphar.2019.01000. PMID: 31572182; PMCID: PMC6751403.
2. Han SO, Li S, Koeberl DD. Salmeterol enhances the cardiac response to gene therapy in Pompe disease. Mol Genet Metab. 2016 May;118(1):35-40. doi: 10.1016/j.ymgme.2016.03.006. Epub 2016 Mar 18. PMID: 27017193; PMCID: PMC4833676.
1: Liu S, Watts AB, Du J, Bui A, Hengsawas S, Williams RO 3rd. Formulation of a novel fixed dose combination of salmeterol xinafoate and mometasone furoate for inhaled drug delivery. Eur J Pharm Biopharm. 2015 Jul 26. pii: S0939-6411(15)00317-3. doi: 10.1016/j.ejpb.2015.07.017. [Epub ahead of print] PubMed PMID: 26220015.
2: Anwar MM, El-Haggar RS, Zaghary WA. Salmeterol Xinafoate. Profiles Drug Subst Excip Relat Methodol. 2015;40:321-69. doi: 10.1016/bs.podrm.2015.02.002. Epub 2015 Apr 1. Review. PubMed PMID: 26051688.
3: Hassoun M, Ho S, Muddle J, Buttini F, Parry M, Hammond M, Forbes B. Formulating powder-device combinations for salmeterol xinafoate dry powder inhalers. Int J Pharm. 2015 Jul 25;490(1-2):360-7. doi: 10.1016/j.ijpharm.2015.05.028. Epub 2015 May 15. PubMed PMID: 25987210.
4: Bi S, Wang T, Wang Y, Zhao T, Zhou H. Using gold nanoparticles as probe for detection of salmeterol xinafoate by resonance Rayleigh light scattering. Spectrochim Acta A Mol Biomol Spectrosc. 2015 Jan 25;135:1074-9. doi: 10.1016/j.saa.2014.08.010. Epub 2014 Aug 19. PubMed PMID: 25173524.
5: Zhao T, Bi S, Wang Y, Wang T, Pang B, Gu T. In vitro studies on the behavior of salmeterol xinafoate and its interaction with calf thymus DNA by multi-spectroscopic techniques. Spectrochim Acta A Mol Biomol Spectrosc. 2014 Nov 11;132:198-204. doi: 10.1016/j.saa.2014.04.158. Epub 2014 May 9. PubMed PMID: 24866086.
6: Restrepo RD, Tate A, Coquat J. Evaluation of salmeterol xinafoate plus fluticasone propionate for the treatment of chronic obstructive pulmonary disease. Expert Opin Pharmacother. 2013 Oct;14(14):1993-2002. doi: 10.1517/14656566.2013.823949. Epub 2013 Jul 31. Review. PubMed PMID: 23898819.
7: Dalal AA, Candrilli SD, Davis KL. Outcomes and costs associated with initial maintenance therapy with fluticasone propionate-salmeterol xinafoate 250 microg/50 microg combination versus tiotropium in commercially insured patients with COPD. Manag Care. 2011 Aug;20(8):46-50, 53-5. PubMed PMID: 21887993.
8: Harrison LI, Novak CC, Needham MJ, Ratner P. Comparative pulmonary function and pharmacokinetics of fluticasone propionate and salmeterol xinafoate delivered by two dry powder inhalers to patients with asthma. J Aerosol Med Pulm Drug Deliv. 2011 Oct;24(5):245-52. doi: 10.1089/jamp.2011.0884. Epub 2011 Jun 14. PubMed PMID: 21671752.
9: Kasaye L, Hymete A, Mohamed AM. HPTLC-densitometric method for simultaneous determination of salmeterol xinafoate and fluticasone propionate in dry powder inhalers. Saudi Pharm J. 2010 Jul;18(3):153-9. doi: 10.1016/j.jsps.2010.05.001. Epub 2010 May 31. PubMed PMID: 23964174; PubMed Central PMCID: PMC3731032.
10: Mostafapour E, Mousavi SA, Shahmiri SS, Fereshtehnejad SM. Effects of combination of fluticasone propionate and salmeterol xinafoate on lung function improvement in patients with bronchiectasis. Lijec Vjesn. 2009 Nov;131 Suppl 6:8-11. PubMed PMID: 22046624.
