Salmeterol xinafoate| CAS#18910-65-1 | 94749-08-3 | beta2-adrenoceptor agonist

MedKoo Cat#: 326763 | Name: Salmeterol xinafoate

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Salmeterol is a long-acting beta2-adrenergic receptor agonist drug used in the maintenance and prevention of asthma symptoms and maintenance of chronic obstructive pulmonary disease (COPD) symptoms. Salmeterol is also used to prevent breathing difficulties during exercise (exercise induced bronchospasm). It is marketed as Serevent in the US.

Chemical Structure

Salmeterol xinafoate

CAS#94749-08-3 (xinafoate)

Theoretical Analysis

MedKoo Cat#: 326763

Name: Salmeterol xinafoate

CAS#: 94749-08-3 (xinafoate)

Chemical Formula: C36H45NO7

Exact Mass: 0.0000

Molecular Weight: 603.76

Elemental Analysis: C, 71.62; H, 7.51; N, 2.32; O, 18.55

Price and Availability

Size	Price	Availability
10mg	USD 425.00	2 weeks
25mg	USD 715.00	2 weeks
50mg	USD 1,100.00	2 weeks
100mg	USD 1,650.00	2 Weeks

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Related CAS #

89365-50-4 (free base) 94749-08-3 (xinafoate)

Synonym

AH 3923; AH-3923; AH3923; AHR 3929; AHR-3929; AHR3929; Salmefamol; Salmeterol xinafoate; GR-33343G, Salmetedur, Serevent®

IUPAC/Chemical Name

1-(4-Hydroxy-3-hydroxymethylphenyl)-2-(4-methoxy-alpha-methylphenethylamino)ethanol 1-hydroxy-2-naphthalenecarboxylic acid

InChi Key

WKLZKCJBRYIIHQ-UHFFFAOYSA-N

InChi Code

InChI=1S/C19H25NO4.C11H8O3/c1-13(9-14-3-6-17(24-2)7-4-14)20-11-19(23)15-5-8-18(22)16(10-15)12-21;12-10-8-4-2-1-3-7(8)5-6-9(10)11(13)14/h3-8,10,13,19-23H,9,11-12H2,1-2H3;1-6,12H,(H,13,14)

SMILES Code

CC(NCC(O)C1=CC=C(O)C(CO)=C1)CC2=CC=C(OC)C=C2.O=C(C3=CC=C4C=CC=CC4=C3O)O

Appearance

Solid powder

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 and ethanol

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

Product Data

Product Data

Instruction

View handling instruction

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/

	Solvent	mg/mL	mM
Solubility
	DMSO	60.4	100.00
	Ethanol	12.1	20.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 603.76 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:

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: Farias G, Ganley WJ, Price R, Conti DS, Mangal S, Bielski E, Newman B, Shur J. Microstructural Characterization of Dry Powder Inhaler Formulations Using Orthogonal Analytical Techniques. Pharm Res. 2024 Oct;41(10):2015-2029. doi: 10.1007/s11095-024-03776-1. Epub 2024 Oct 7. PMID: 39375241; PMCID: PMC11530509. 2: Yin Y, Ruan G, Su Q, Li L, Hong Y. Effect of Small Doses of Azithromycin on Pulmonary Ventilation Function and Inflammatory Factors IL-6, IL-13 in Children with Bronchial Asthma. Ann Clin Lab Sci. 2024 Jul;54(4):452-456. PMID: 39293830. 3: Dupont J, Mignini B, Salciccia A, Serteyn D, Sandersen C. Comparison of inhaled salbutamol and salmeterol for the treatment of arterial hypoxaemia in anaesthetized horses: a randomized clinical trial. Vet Anaesth Analg. 2024 Sep- Oct;51(5):426-432. doi: 10.1016/j.vaa.2024.05.009. Epub 2024 May 29. PMID: 39138052. 4: Singh GJP, Hickey AJ. Pharmacokinetic Bioequivalence between Generic and Originator Orally Inhaled Drug Products: Validity of Administration of Doses above the Approved Single Maximum Dose. Mol Pharm. 2024 Sep 2;21(9):4191-4198. doi: 10.1021/acs.molpharmaceut.4c00479. Epub 2024 Aug 12. PMID: 39133824. 5: Dahmash EZ, Achkar NR, Ali DK, Jarrar Q, Iyire A, Assaf SM, Alyami H. Preclinical evaluation of novel synthesised nanoparticles based on tyrosine poly(ester amide) for improved targeted pulmonary delivery. Sci Rep. 2024 Apr 29;14(1):9845. doi: 10.1038/s41598-024-59588-1. PMID: 38684750; PMCID: PMC11058873. 6: Li S, Feng K, Lee J, Gong Y, Wu F, Newman B, Yoon M, Fang L, Zhao L, Gobburu JVS. Pharmacokinetic Models for Inhaled Fluticasone Propionate and Salmeterol Xinafoate to Quantify Batch-to-Batch Variability. AAPS J. 2024 Apr 26;26(3):56. doi: 10.1208/s12248-024-00913-x. PMID: 38671158. 7: Zhang J, Khanal D, Chan HK, Banaszak Holl MM. Nanoscale colocalized thermal and chemical mapping of pharmaceutical powder aerosols. Int J Pharm. 2024 May 10;656:124116. doi: 10.1016/j.ijpharm.2024.124116. Epub 2024 Apr 12. PMID: 38615803. 8: Gerde P, Sjöberg CO, Bäckroos H, Englund J, Wangheim M, Litorp H. Regional lung targeting with a fluticasone/salmeterol aerosol using a bolus breath hold method of the PreciseInhale® system: A first evaluation in humans. Eur J Pharm Sci. 2024 May 1;196:106742. doi: 10.1016/j.ejps.2024.106742. Epub 2024 Mar 7. PMID: 38460609. 9: Merckx P, Conickx G, Blomme E, Maes T, Bracke KR, Brusselle G, De Smedt SC, Raemdonck K. Evaluating β2-agonists as siRNA delivery adjuvants for pulmonary surfactant-coated nanogel inhalation therapy. Eur J Pharm Biopharm. 2024 Apr;197:114223. doi: 10.1016/j.ejpb.2024.114223. Epub 2024 Feb 15. PMID: 38367760. 10: Ahmed MI, Ahmed RI, Osama H, Khalifa AK, Alshehri AA, El-Saber Batiha G, Negm WA, Kamal M. Bronchodilator reversibility testing in morbidly obese non- smokers: fluticasone/salmeterol efficacy versus salbutamol bronchodilator. BMC Pulm Med. 2023 Oct 9;23(1):381. doi: 10.1186/s12890-023-02682-3. PMID: 37814253; PMCID: PMC10563321. 11: Li H, Dong T, Luan J. Efficacy and safety of fluticasone propionate/salmeterol and fluticasone propionate monotherapy in step-up treatment of childhood asthma: A systematic review and meta-analysis. Heart Lung. 2024 Jan-Feb;63:23-34. doi: 10.1016/j.hrtlng.2023.09.004. Epub 2023 Sep 21. PMID: 37740997. 12: Valovič P, Behuliak M, Vaněčková I, Zicha J. Impaired vascular β-adrenergic relaxation in spontaneously hypertensive rats: The differences between conduit and resistance arteries. Eur J Pharmacol. 2023 Nov 5;958:176045. doi: 10.1016/j.ejphar.2023.176045. Epub 2023 Sep 13. PMID: 37708986. 13: Albanna AS, Alhajji M, Alsowayan W, Soliman MH. The impact of unsupervised and unconsented switch of inhalers in patients with controlled asthma - A targeted literature review. Ann Thorac Med. 2023 Jul-Sep;18(3):103-115. doi: 10.4103/atm.atm_438_22. Epub 2023 May 16. PMID: 37663876; PMCID: PMC10473061. 14: Pitrez PM, Nanthapisal S, Castro APBM, Teli C, P G A. Managing moderate-to- severe paediatric asthma: a scoping review of the efficacy and safety of fluticasone propionate/salmeterol. BMJ Open Respir Res. 2023 Aug;10(1):e001706. doi: 10.1136/bmjresp-2023-001706. PMID: 37620110; PMCID: PMC10450074. 15: Liu J, Yang J, Du S, Guo R, Guo Y, Gao C, Xi R, Chen C. Clinical efficacy and safety of fluticasone/salmeterol inhalation powder combined with huaiqihuang granules in the treatment of children with cough variant asthma. Pak J Pharm Sci. 2023 May;36(3(Special)):1001-1007. PMID: 37587710. 16: Feldman WB, Kesselheim AS, Avorn J, Russo M, Wang SV. Comparative Effectiveness and Safety of Generic Versus Brand-Name Fluticasone-Salmeterol to Treat Chronic Obstructive Pulmonary Disease. Ann Intern Med. 2023 Aug;176(8):1047-1056. doi: 10.7326/M23-0615. Epub 2023 Aug 8. PMID: 37549393. 17: Steward M, Sheth S. Regular formoterol plus inhaled corticosteroid vs. salmeterol plus inhaled corticosteroid for asthma. Clin Exp Allergy. 2023 May;53(5):491-494. doi: 10.1111/cea.14322. Epub 2023 Apr 16. PMID: 37062536. 18: Reddel HK, Brusselle G, Lamarca R, Gustafson P, Anderson GP, Jorup C. Safety and Effectiveness of As-Needed Formoterol in Asthma Patients Taking Inhaled Corticosteroid (ICS)-Formoterol or ICS-Salmeterol Maintenance Therapy. J Allergy Clin Immunol Pract. 2023 Jul;11(7):2104-2114.e3. doi: 10.1016/j.jaip.2023.03.046. Epub 2023 Apr 11. PMID: 37054881. 19: Valizadeh M, Ameri Braki Z, Smiley E, Arghand A, Dastafkan P. Simultaneous Quantitative Analysis of Salmeterol and Fluticasone in Inhalation Spray Using HPLC and a Fast Spectrophotometric Technique Combined with a Time Series Neural Network and Multivariate Calibration Methods. J AOAC Int. 2023 Jul 17;106(4):1109-1117. doi: 10.1093/jaoacint/qsad015. PMID: 36715079. 20: van Zyl-Smit RN, Chapman KR, Kerstjens HAM, Gessner C, Sagara H, Tanase AM, Hosoe M, Pethe A, Lawrence D, Tillmann HC, D'Andrea P. Mometasone/Indacaterol/Glycopyrronium (MF/IND/GLY) and MF/IND at Different MF Strengths versus Fluticasone Propionate/Salmeterol Xinafoate (FLU/SAL) and FLU/SAL+ Tiotropium in Patients with Asthma. J Asthma Allergy. 2023 Jan 20;16:123-134. doi: 10.2147/JAA.S392975. PMID: 36714049; PMCID: PMC9880009.