Xamoterol hemifumarate

• CAS: 73210-73-8
• Catalog Number: ACM73210738
• Category: Main Products
• Molecular Weight: 794.85
• Molecular Formula: C36H54N6O14
• Synonyms: N-[2-[[2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino]ethyl]morpholine-4-carboxamide
• Appearance: Crystalline solid

Case Study

Xamoterol Hemifumarate as a Beta-1 Adrenoceptor Agonist for Dissecting Adipocyte Recruitment versus Transdifferentiation in White Adipose Tissue

Barbatelli, G., et al. (2010). Am. J. Physiol. Endocrinol. Metab., 298, E1244-E1253.

Xamoterol hemifumarate serves as a selective beta₁-adrenoceptor agonist to distinguish preadipocyte recruitment from white-to-brown adipocyte transdifferentiation in murine white adipose tissue upon cold stress, providing mechanistic insight into adipose plasticity.
Experimental Protocol: Female 129Sv mice received daily intraperitoneal injections of xamoterol hemifumarate (0.144 mg/kg) or the beta₃-adrenoceptor agonist CL316,243 (0.1 mg/kg) for 3 or 5 days at room temperature. Subcutaneous white adipose tissue was harvested and processed for light microscopy, immunohistochemistry with anti-UCP1 antibody, and electron microscopy. Morphometric analysis quantified unilocular, paucilocular, and multilocular adipocytes, with preadipocyte density expressed as number per 100 adipocytes.
Performance Evaluation: Xamoterol administration increased only the number of preadipocytes in white adipose tissue, whereas CL316,243 induced the appearance of UCP1-immunoreactive brown adipocytes displaying paucilocular morphology. Cold exposure at 6 degrees C for 10 days increased brown adipocytes by 20-fold in subcutaneous white adipose tissue of wild-type mice, an effect that was blunted in beta₃-adrenoceptor knockout animals. These findings demonstrate that beta₁-adrenoceptor stimulation selectively mediates preadipocyte recruitment while beta₃-adrenoceptor activation governs transdifferentiation of mature white adipocytes into brown adipocytes.

Xamoterol Hemifumarate as a Weak Partial Beta-1 Adrenoceptor Agonist for Validating Endogenous Promoter-Driven Split Luciferase G Protein Biosensors

Humphrys, L.J., et al. (2024). bioRxiv, doi: 10.1101/2024.06.03.597093.

Xamoterol hemifumarate functions as a pharmacological probe to characterize beta-adrenoceptor subtype selectivity in a split nanoluciferase complementation-based mini-G protein recruitment assay using CRISPR/Cas9-modified HEK293T cells expressing tagged receptors at endogenous levels.
Experimental Protocol: HEK293T cells were genetically engineered using plasmid-based CRISPR/Cas9 to tag endogenous beta₁- and beta₂-adrenoceptors with NlucC fragments while replacing Galpha_s with NlucN-tagged minimal G_s protein. Concentration-response curves for xamoterol and standard agonists were generated in both overexpressed and CRISPR-modified native expression systems. Ligand-induced complementation of split luciferase fragments upon receptor-G protein interaction restored catalytic activity, producing bioluminescence upon furimazine substrate oxidation.
Performance Evaluation: In overexpressed systems, xamoterol acted as an antagonist at beta₂-adrenoceptors but displayed weak partial agonist activity at beta₁-adrenoceptors with a maximal efficacy of 14 plus-minus 1 percent relative to adrenaline. In the CRISPR/Cas9-modified endogenous system, xamoterol plateaued at a significantly higher level than with overexpression, enabling more accurate discrimination of partial agonist behavior. These results demonstrate that native receptor expression levels critically influence the pharmacological characterization of partial agonists.

Custom Q&A

What is the molecular formula of Xamoterol hemifumarate?

The molecular formula of Xamoterol hemifumarate is C36H54N6O14.

What is the molecular weight of Xamoterol hemifumarate?

The molecular weight of Xamoterol hemifumarate is 794.8 g/mol.

What is the IUPAC name of Xamoterol hemifumarate?

The IUPAC name of Xamoterol hemifumarate is (E)-but-2-enedioic acid;N-[2-[[2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino]ethyl]morpholine-4-carboxamide.

What is the InChIKey of Xamoterol hemifumarate?

The InChIKey of Xamoterol hemifumarate is QEDVGROSOZBGOZ-WXXKFALUSA-N.

What is the canonical SMILES of Xamoterol hemifumarate?

The canonical SMILES of Xamoterol hemifumarate is C1COCCN1C(=O)NCCNCC(COC2=CC=C(C=C2)O)O.C1COCCN1C(=O)NCCNCC(COC2=CC=C(C=C2)O)O.C(=CC(=O)O)C(=O)O.

What is the CAS number of Xamoterol hemifumarate?

The CAS number of Xamoterol hemifumarate is 73210-73-8.

How many hydrogen bond donor counts does Xamoterol hemifumarate have?

Xamoterol hemifumarate has 10 hydrogen bond donor counts.

How many hydrogen bond acceptor counts does Xamoterol hemifumarate have?

Xamoterol hemifumarate has 16 hydrogen bond acceptor counts.

How many rotatable bond counts does Xamoterol hemifumarate have?

Xamoterol hemifumarate has 18 rotatable bond counts.

What is the topological polar surface area of Xamoterol hemifumarate?

The topological polar surface area of Xamoterol hemifumarate is 281Ų.