CAS Number94749-08-3
SynonymsSalmeterol Xinafoate; GR 33343G; Salmeterol 1-hydroxy-2-naphthoate; MFCD00897708; Salmeterol (xinafoate)
Molecular FormulaC36H45NO7
Molecular Weight603.745
Purity97%
Density1.112g/cm3
Boiling Point603ºC at 760 mmHg
Melting Point137-138ºC
Appearancewhite solid
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 94749-08-3 |
| Catalog No. | 2A-1166731 |
| Chinese Name | 昔美酸沙美特罗 |
| Synonyms | Salmeterol Xinafoate; GR 33343G; Salmeterol 1-hydroxy-2-naphthoate; MFCD00897708; Salmeterol (xinafoate) |
| Molecular Formula | C36H45NO7 |
| Molecular Weight | 603.745 |
| Purity | 97 |
| Density | 1.112g/cm3 |
| Boiling Point | 603ºC at 760 mmHg |
| Melting Point | 137-138ºC |
| Appearance | white solid |
| Water Solubility | H2O: slightly soluble |
| Storage Condition | -20°C Freezer |
| Application | Salmeterol xinafoate is a long-acting β2-adrenergic receptor (β2AR) agonist with a Ki value of 1.5 nM for WT β2AR. |
| PubChem ID | 7847753 |
| SMILES | O=C(O)c1ccc2ccccc2c1O.OCc1cc(C(O)CNCCCCCCOCCCCc2ccccc2)ccc1O |
| InChI | InChI=1S/C25H37NO4.C11H8O3/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;12-10-8-4-2-1-3-7(8)5-6-9(10)11(13)14/h3-5,10-11,13-14,18,25-29H,1-2,6-9,12,15-17,19-20H2;1-6,12H,(H,13,14) |
| InChI Key | XTZNCVSCVHTPAI-UHFFFAOYSA-N |
| Hazard Symbols | transportation |
| MSDS | msds/166738_2_94749_08_3.pdf |
| Bioactivity | Salmeterol xinafoate is a long-acting beta-2 adrenergic receptor (β2AR) agonist, with Ki of 1.5 nM for WT β2AR, and used for asthma treatment. Related Catalog Signaling Pathways >> GPCR/G Protein >> Adrenergic Receptor Research Areas >> Inflammation/Immunology Target Ki: 1.5 nM (WT β2AR)[2] In Vitro Salmeterol significantly inhibits production of pro-inflammatory mediators by RAW264.7 and THP-1 cells. Salmeterol downregulates PgLPS-mediated phosphorylation of the ERK1/2 and JNK but not p38 MAP kinases (MAP-K). Salmeterol also attenuates the activation of NF-κB via inhibition of nuclear translocation of p65-NFκB, the transcriptional activity of NF-κB and IκBα phosphorylation[1]. Salmeterol shows very high selectivity for the WT β2AR (β1 Ki /β2 Ki ratio of approximately 1500) with Ki of 1.5±0.4 nM[2]. Salmeterol prevents phosphorylation levels of IRS-1Ser307 induced by tumor necrosis factor-α. Salmeterol alone prevents cell death in retinal Müller cells (p<0.05 versus 25 mM glucose). Salmeterol in conbination with IRS-1 shRNA shows a significant increase in cell death compared to salmeterol alone. Moreover, salmeterol alone treatment significantly reduces cytochrome C levels, with the effect lessened when salmeterol is combined with IRS-1 shRNA[3]. Salmeterol (100 μM) causes apoptosis of DCs, and can not affect the differentiation and maturation of DCs at 10 μM. Salmeterol (10 μM) decreases the mRNA and protein levels of pro-inflammatory cytokines in LPS-activated DCs and inhibits MAPK and NF-κB activation[4]. In Vivo The OVA/LPS groups with salmeterol result in a significant decrease in the enhanced AHR in allergic mice in a dose-dependent manner. Salmeterol contends with asthma via regulating the inflammation of the airway of the mice[4]. Kinase Assay The cells are rinsed twice with ice-cold phosphate-buffered saline and mechanically detached in ice-cold buffer containing 10 mM Tris·HCl, pH 7.4, 5 mM EDTA, 10 μg/mL benzamidine, 10 μg/mL soybean trypsin inhibitor (type II-S), and 5 μg/mL leupeptin (lysis buffer). The lysate is centrifuged at 45,000 ×g for 10 min at 4°C. The pellet is rehomogenized in lysis buffer, with a Potter-type homogenizer, and stored at −80°C until use. The competition binding assays are performed in buffer containing 75 mM Tris·HCl, pH 7.4, 12.5 mM MgCl2, and 2 mM EDTA, using 1-5 μg of membrane protein, 50 pM 125I-CYP, and 0-100 μM unlabeled ligand in the presence of 100 μM GTP, for 60 min at 37°C. The binding reaction is terminated by dilution and rapid filtration through Whatman GF/C filters; the filters are washed three times with solution containing 25 mM Tris·HCl, pH 7.4, and 1 mM MgCl2. Nonspecific binding is determined in the presence of 5 μM (±)-propranolol. The radioactivity on the filters is counted with a γ-counter. Animal Admin All mice are sensitized on days 0 and 14 by intraperitoneal injection of either PBS or 0.08 mg OVA and 0.1 mL aluminum hydroxide in 0.1 mL of PBS (pH 7.4). After sensitization, animals are exposed to aerosolized PBS-only (negative control), 1% OVS/PBS (acute exposure), 1% OVA/0.01% LPS/PBS (extra LPS exposure) or 1% OVA/0.01% LPS/salmeterol/PBS (sal treatment) for 40 min, once per day for 3 consecutive days (days 24-26). On day 27, the mice are killed and lungs are divided into two groups for analysis: the left lung lobes are lavaged three times with 1 mL of PBS with 1% fetal calf serum and 5 U/mL heparin, and the right halves are fixed by 4% paraformaldehyde for histological analysis. References [1]. Sharma M, et al. Salmeterol; A Long Acting β2-Aderenergic Receptor Agonist Inhibits Macrophage Activation by Lipopolysaccharide From Porphyromonas Gingivalis. J Periodontol. 2017 Mar 3:1-17. [2]. Isogaya M, et al. Identification of a key amino acid of the beta2-adrenergic receptor for high affinity binding of salmeterol. Mol Pharmacol. 1998 Oct;54(4):616-22. [3]. Walker RJ, Anderson NM, Bahouth S, Silencing of insulin receptor substrate-1 increases cell death in retinal Müller cells. Mol Vis. 2012;18:271-9. Epub 2012 Feb 1. [4]. Hu Z, et al. Salmeterol attenuates the inflammatory response in asthma and decreases the pro-inflammatory cytokine secretion of dendritic cells. Cell Mol Immunol. 2012 May;9(3):267-75. Chemical & Physical Properties Density 1.112g/cm3 Boiling Point 603ºC at 760 mmHg Melting Point 137-138ºC Molecular Formula C36H45NO7 Molecular Weight 603.745 Flash Point 318.5ºC Exact Mass 603.319580 PSA 139.48000 LogP 6.74190 Index of Refraction 1.565 InChIKey XTZNCVSCVHTPAI-UHFFFAOYSA-N SMILES O=C(O)c1ccc2ccccc2c1O.OCc1cc(C(O)CNCCCCCCOCCCCc2ccccc2)ccc1O Storage condition -20°C Freezer Water Solubility H2O: slightly soluble |
| Use of | Salmeterol xinafoate is a long-acting beta-2 adrenergic receptor (β2AR) agonist, with Ki of 1.5 nM for WT β2AR, and used for asthma treatment. Properties Articles38 Name Salmeterol Xinafoate Synonym More Synonyms Salmeterol Xinafoate Biological Activity Description Salmeterol xinafoate is a long-acting beta-2 adrenergic receptor (β2AR) agonist, with Ki of 1.5 nM for WT β2AR, and used for asthma treatment. Related Catalog Signaling Pathways >> GPCR/G Protein >> Adrenergic Receptor Research Areas >> Inflammation/Immunology Ki: 1.5 nM (WT β2AR)[2] In Vivo The OVA/LPS groups with salmeterol result in a significant decrease in the enhanced AHR in allergic mice in a dose-dependent manner. Salmeterol contends with asthma via regulating the inflammation of the airway of the mice[4]. References [1]. Sharma M, et al. Salmeterol; A Long Acting β2-Aderenergic Receptor Agonist Inhibits Macrophage Activation by Lipopolysaccharide From Porphyromonas Gingivalis. J Periodontol. 2017 Mar 3:1-17. [2]. Isogaya M, et al. Identification of a key amino acid of the beta2-adrenergic receptor for high affinity binding of salmeterol. Mol Pharmacol. 1998 Oct;54(4):616-22. [3]. Walker RJ, Anderson NM, Bahouth S, Silencing of insulin receptor substrate-1 increases cell death in retinal Müller cells. Mol Vis. 2012;18:271-9. Epub 2012 Feb 1. [4]. Hu Z, et al. Salmeterol attenuates the inflammatory response in asthma and decreases the pro-inflammatory cytokine secretion of dendritic cells. Cell Mol Immunol. 2012 May;9(3):267-75. Chemical & Physical Properties Molecular Formula C36H45NO7 Exact Mass 603.319580 PSA 139.48000 LogP 6.74190 Index of Refraction 1.565 InChIKey XTZNCVSCVHTPAI-UHFFFAOYSA-N Water Solubility H2O: slightly soluble |
| Transport Info | Product name: Purity: 96.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available See reverse side of invoice or packing slip. |
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