Xamoterol fumarate
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MedKoo CAT#: 413295

CAS#: 73210-73-8

Description: Xamoterol fumarate is a β1-adrenoceptor partial agonist that has shown to improve systolic and diastolic function in studies with heart failure patients. It modulates the sympathetic control of the heart but has no agonist action on β2-adrenoceptors.


Chemical Structure

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Xamoterol fumarate
CAS# 73210-73-8

Theoretical Analysis

MedKoo Cat#: 413295
Name: Xamoterol fumarate
CAS#: 73210-73-8
Chemical Formula: C36H54N6O14
Exact Mass: 794.37
Molecular Weight: 794.860
Elemental Analysis: C, 54.40; H, 6.85; N, 10.57; O, 28.18

Price and Availability

Size Price Availability Quantity
1mg USD 205 2 Weeks
5mg USD 371 2 Weeks
10mg USD 600 2 Weeks
25mg USD 994 2 Weeks
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Synonym: Xamoterol fumarate; ICI1185876; ICI-1185876; ICI 1185876

IUPAC/Chemical Name: Bis(N-(2-((2-hydroxy-3-(4-hydroxyphenoxy)propyl)amino)ethyl)morpholine-4-carboxamide) fumarate

InChi Key: QEDVGROSOZBGOZ-WXXKFALUSA-N

InChi Code: InChI=1S/2C16H25N3O5.C4H4O4/c2*20-13-1-3-15(4-2-13)24-12-14(21)11-17-5-6-18-16(22)19-7-9-23-10-8-19;5-3(6)1-2-4(7)8/h2*1-4,14,17,20-21H,5-12H2,(H,18,22);1-2H,(H,5,6)(H,7,8)/b;;2-1+

SMILES Code: O=C(N1CCOCC1)NCCNCC(O)COC2=CC=C(O)C=C2.O=C(N3CCOCC3)NCCNCC(O)COC4=CC=C(O)C=C4.O=C(O)/C=C/C(O)=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

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:

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Soluble in DMSO 0.0 100.00

Preparing Stock Solutions

The following data is based on the product molecular weight 794.86 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.

Recalculate based on batch purity %
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:
In vitro protocol:
In vivo protocol:

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1: Ardestani PM, Evans AK, Yi B, Nguyen T, Coutellier L, Shamloo M. Modulation of neuroinflammation and pathology in the 5XFAD mouse model of Alzheimer's disease using a biased and selective beta-1 adrenergic receptor partial agonist. Neuropharmacology. 2017 Apr;116:371-386. doi: 10.1016/j.neuropharm.2017.01.010. Epub 2017 Jan 13. PMID: 28089846; PMCID: PMC5385159.

2: Marlow HF. Xamoterol, a beta 1-adrenoceptor partial agonist: review of the clinical efficacy in heart failure. Br J Clin Pharmacol. 1989;28 Suppl 1(Suppl 1):23S-30S. doi: 10.1111/j.1365-2125.1989.tb03570.x. PMID: 2572251; PMCID: PMC1379873.

3: Schutsky K, Ouyang M, Thomas SA. Xamoterol impairs hippocampus-dependent emotional memory retrieval via Gi/o-coupled β2-adrenergic signaling. Learn Mem. 2011 Aug 30;18(9):598-604. doi: 10.1101/lm.2302811. PMID: 21878527; PMCID: PMC3166789.

4: Cruickshank JM. Beta-blockers and heart failure. Indian Heart J. 2010 Mar- Apr;62(2):101-10. PMID: 21180298.

5: Furlong R, Brogden RN. Xamoterol. A preliminary review of its pharmacodynamic and pharmacokinetic properties, and therapeutic use. Drugs. 1988 Oct;36(4):455-74. doi: 10.2165/00003495-198836040-00004. PMID: 2906865.

6: Xamoterol--more trouble than it's worth? Drug Ther Bull. 1990 Jul 9;28(14):53-4. doi: 10.1136/dtb.28.14.53. PMID: 1983395.

7: Cruickshank JM. The xamoterol experience in the treatment of heart failure. Am J Cardiol. 1993 Mar 25;71(9):61C-64C. doi: 10.1016/0002-9149(93)90088-t. PMID: 8465800.

8: Malta E, Mian MA, Raper C. The in vitro pharmacology of xamoterol (ICI 118,587). Br J Pharmacol. 1985 May;85(1):179-87. doi: 10.1111/j.1476-5381.1985.tb08845.x. PMID: 2862938; PMCID: PMC1916765.

9: Schäfers RF, Karl I, Mennicke K, Daul AE, Philipp T, Brodde OE. Ketotifen and cardiovascular effects of xamoterol following single and chronic dosing in healthy volunteers. Br J Clin Pharmacol. 1999 Jan;47(1):59-66. doi: 10.1046/j.1365-2125.1999.00854.x. PMID: 10073741; PMCID: PMC2014201.

10: James MA, Papouchado M, Channer KS, Jones JV, Marlow HF, Bastain W, Barker NP, Harry JD, Wardleworth AG. The effect of oral dosing of xamoterol on systolic time intervals in man and xamoterol plasma concentrations in heart failure patients. Br J Clin Pharmacol. 1990 Apr;29(4):447-53. doi: 10.1111/j.1365-2125.1990.tb03663.x. PMID: 2139340; PMCID: PMC1380115.