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

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

MedKoo CAT#: 326763

CAS#: 94749-08-3 (xinafoate)

Description: 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)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 326763
Name: Salmeterol xinafoate
CAS#: 94749-08-3 (xinafoate)
Chemical Formula: C36H45NO7
Exact Mass: 0.00
Molecular Weight: 603.760
Elemental Analysis: C, 71.62; H, 7.51; N, 2.32; O, 18.55

Price and Availability

Size	Price	Availability
10mg	USD 425	2 weeks
25mg	USD 715	2 weeks
50mg	USD 1100	2 weeks
100mg	USD 1650	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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:

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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/

Solubility Data

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

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:	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.

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1: Carpenter JR. Functional antagonism of isoprenaline, salmefamol, fenoterol and pindolol by carbachol, methacholine and histamine in guinea pig isolated trachealis. Proc West Pharmacol Soc. 1986;29:383-4. PubMed PMID: 2876438.

2: Marmo E, Rossi F, Giordano L, Lampa E, Rsalti F, Di Mezza G. Salmefamol and salbutamol. An experimental comparative study of their action on tracheal and bronchial smooth muscles. Respiration. 1979;38(5):257-65. PubMed PMID: 231807.

3: Canfield SP, Curwain BP, King JA, Price C. Salmefamol: inhibitor or stimulant of gastric acid secretion? [proceedings]. Br J Pharmacol. 1978 Mar;62(3):445P. PubMed PMID: 580408; PubMed Central PMCID: PMC1668132.

4: Gottrup F, Ornsholt J, Daly MJ. The effect of a new beta2-adrenoceptor agonist, salmefamol, on pentagastrin-induced gastric acid secretion in conscious dogs [proceedings]. Br J Pharmacol. 1978 Mar;62(3):444P. PubMed PMID: 580407; PubMed Central PMCID: PMC1668145.

5: Hills EA, Davies S, Geary M. Salmefamol and Salbutamol in exercise-induced asthma in children. Br J Dis Chest. 1976 Apr;70(2):78-82. PubMed PMID: 8070.

6: Sillett RW, Dash CH, McNicol MW. Salmefamol orally in asthmatics - two doses compared. Eur J Clin Pharmacol. 1976 Feb 6;9(4):281-4. PubMed PMID: 786694.

7: Sillett RW, Dash CH, McNicol MW. Comparison of salmefamol with salbutamol aerosols in asthamatics. Eur J Clin Pharmacol. 1976 Feb 6;9(4):277-80. PubMed PMID: 786693.

8: Campbell IA, Dash CH, McHardy GJ, Shotter MV. Comparison of salmefamol and salbutamol in patients with chronic airways obstruction. Br J Clin Pharmacol. 1976 Feb;3(1):151-5. PubMed PMID: 788738; PubMed Central PMCID: PMC1428820.

9: McHardy GJ, Campbell IA, Shotter MV, Dash CH. Proceedings: Comparison of two bronchodilators--salmefamol and salbutamol. Tubercle. 1975 Jun;56(2):171. PubMed PMID: 1103399.

10: Kennedy MC, Posner E, Dash CH. New bronchodilator aerosol, salmefamol, in asthma. Acta Allergol. 1975 Apr;30(1):19-33. PubMed PMID: 1173987.

11: Evans ME, Shenfield GM, Paterson JW. The clinical pharmacology of salmefamol. Br J Clin Pharmacol. 1974 Oct;1(5):391-7. PubMed PMID: 22454916; PubMed Central PMCID: PMC1402468.

12: Lal S, Dash CH, Gribben MD. An economical method of comparing inhaled bronchodilators in reversible diffuse airways obstruction. With special reference to a beta-2 stimulant--salmefamol. Thorax. 1974 May;29(3):317-22. PubMed PMID: 4850526; PubMed Central PMCID: PMC470152.

13: Kennedy MC, Dash CH. The bronchodilator effect of a new adrenergic aerosol--Salmefamol. Acta Allergol. 1972 Feb;27(1):22-6. PubMed PMID: 5067420.

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Salmeterol xinafoate featured