Details
| Stereochemistry | RACEMIC |
| Molecular Formula | 2C16H25N3O5.C4H4O4 |
| Molecular Weight | 794.8458 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 2 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)\C=C\C(O)=O.OC(CNCCNC(=O)N1CCOCC1)COC2=CC=C(O)C=C2.OC(CNCCNC(=O)N3CCOCC3)COC4=CC=C(O)C=C4
InChI
InChIKey=QEDVGROSOZBGOZ-WXXKFALUSA-N
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+
| Molecular Formula | C16H25N3O5 |
| Molecular Weight | 339.3868 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
| Molecular Formula | C4H4O4 |
| Molecular Weight | 116.0722 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Optical Activity | NONE |
DescriptionCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/1967561 | https://www.ncbi.nlm.nih.gov/pubmed/1971596 | https://www.ncbi.nlm.nih.gov/pubmed/8465800
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/1967561 | https://www.ncbi.nlm.nih.gov/pubmed/1971596 | https://www.ncbi.nlm.nih.gov/pubmed/8465800
Xamoterol (ICI 118,587) is a partial agonist of beta1-adrenoceptors. Xamoterol acts on the cardiac beta 1-adrenergic receptor, modifies the response of the heart to variations in sympathetic activity. At rest, it produces modest improvements in cardiac contractility, relaxation, and filling without increase in myocardial oxygen demand. The improvements are maintained during exercise although the attendant tachycardia is attenuated. The beneficial effects of xamoterol on both systolic and diastolic function suggested that it would be effective in patients with mild-to-moderate heart failure, and this was demonstrated in small placebo-controlled studies where effort tolerance and symptoms were improved. Xamoterol produced improvements in exercise capacity, clinical signs, symptoms and quality of life with a low incidence of adverse experiences. Xamoterol is effective as monotherapy in heart failure.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Comparative analysis of beta-1 adrenoceptor agonist and antagonist potency and selectivity of cicloprolol, xamoterol and pindolol. | 1987 Sep |
|
| Contrasting effects of single doses of pindolol and xamoterol on left ventricular diastolic function. | 1989 |
|
| Xamoterol improves the control of chronic atrial fibrillation in elderly patients. | 1995 Jul |
|
| Cardioselective beta-blocker use in patients with reversible airway disease. | 2001 |
|
| The underreporting of results and possible mechanisms of 'negative' drug trials in patients with chronic heart failure. | 2001 Aug |
|
| Constitutive activity of the human beta(1)-adrenergic receptor in beta(1)-receptor transgenic mice. | 2001 Oct |
|
| beta-Adrenergic receptors, transgenic mice, and pharmacological model systems. | 2001 Oct |
|
| Rapid component I(Kr) of the guinea-pig cardiac delayed rectifier K(+) current is inhibited by beta(1)-adrenoreceptor activation, via cAMP/protein kinase A-dependent pathways. | 2002 Feb 1 |
|
| Characterization of beta-adrenoceptor subtype in bladder smooth muscle in cynomolgus monkey. | 2002 Jan |
|
| Adenylate cyclase activity in postmortem brain of suicide subjects: reduced response to beta-adrenergic stimulation. | 2003 Dec 15 |
|
| Pharmacological characterization of putative beta1-beta2-adrenergic receptor heterodimers. | 2003 Feb |
|
| Partial agonist activity of bucindolol is dependent on the activation state of the human beta1-adrenergic receptor. | 2003 Jul 22 |
|
| Functional and molecular characterization of beta-adrenoceptors in the internal anal sphincter. | 2003 May |
|
| Heme oxygenase-1 gene expression in pericentral hepatocytes through beta1-adrenoceptor stimulation. | 2004 Apr |
|
| Adrenergic regulation of vascular smooth muscle tone in calf digital artery. | 2004 Aug |
|
| Agonist binding and activation of the rat beta(1)-adrenergic receptor: role of Trp(134(3.28)), Ser(190(4.57)) and Tyr(356(7.43)). | 2004 Aug 15 |
|
| Role of adenylate and guanylate cyclases in beta1-, beta2-, and beta3-adrenoceptor-mediated relaxation of internal anal sphincter smooth muscle. | 2004 Mar |
|
| Dobutamine inhibits phorbol-myristate-acetate-induced activation of nuclear factor-kappaB in human T lymphocytes in vitro. | 2004 Nov |
|
| Effect of overexpressed adenylyl cyclase VI on beta 1- and beta 2-adrenoceptor responses in adult rat ventricular myocytes. | 2004 Oct |
|
| Glucocorticoid effects on memory retrieval require concurrent noradrenergic activity in the hippocampus and basolateral amygdala. | 2004 Sep 15 |
|
| Functional beta-adrenergic receptor signalling on nuclear membranes in adult rat and mouse ventricular cardiomyocytes. | 2006 Jul 1 |
|
| NNK activates ERK1/2 and CREB/ATF-1 via beta-1-AR and EGFR signaling in human lung adenocarcinoma and small airway epithelial cells. | 2006 Oct 1 |
|
| Understanding cardiac output. | 2008 |
|
| Carvedilol in the treatment of elderly patients with chronic heart failure. | 2008 |
|
| The adrenergic receptor subtypes present in frog (Rana esculenta) skin. | 2008 Aug |
|
| Beta-adrenergic receptor stimulation modulates iNOS protein levels through p38 and ERK1/2 signaling in human retinal endothelial cells. | 2008 Jul |
|
| Four close bupranolol analogues are antagonists at the low-affinity state of beta1-adrenoceptors. | 2009 Mar |
|
| Restoration of norepinephrine-modulated contextual memory in a mouse model of Down syndrome. | 2009 Nov 18 |
|
| Maintenance of beta-adrenergic receptor signaling can reduce Fas signaling in human retinal endothelial cells. | 2009 Oct |
|
| Chronic treatment with agonists of beta(2)-adrenergic receptors in neuropathic pain. | 2010 Jan |
|
| The emergence of cold-induced brown adipocytes in mouse white fat depots is determined predominantly by white to brown adipocyte transdifferentiation. | 2010 Jun |
|
| Beta-blockers and heart failure. | 2010 Mar-Apr |
|
| A full pharmacological analysis of the three turkey β-adrenoceptors and comparison with the human β-adrenoceptors. | 2010 Nov 30 |
Patents
Sample Use Guides
Xamoterol at 200 mg and 400 mg orally once daily had no effect on the mean resting heart rate but there was a small (5.7 beats min-1) but significant reduction in resting heart rate on 600 mg at 2-2.5 h after dosing. All three doses of xamoterol significantly reduced the maximum exercise heart rate at 2-2.5 h after dosing. Xamoterol at all three doses significantly increased exercise duration at 2-2.5 h after dosing but not at 24 h.
Route of Administration:
Oral
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:51:54 GMT 2023
by
admin
on
Fri Dec 15 18:51:54 GMT 2023
|
| Record UNII |
N87007N668
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C78322
Created by
admin on Fri Dec 15 18:51:55 GMT 2023 , Edited by admin on Fri Dec 15 18:51:55 GMT 2023
|
||
|
NCI_THESAURUS |
C48149
Created by
admin on Fri Dec 15 18:51:55 GMT 2023 , Edited by admin on Fri Dec 15 18:51:55 GMT 2023
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
BB-31
Created by
admin on Fri Dec 15 18:51:55 GMT 2023 , Edited by admin on Fri Dec 15 18:51:55 GMT 2023
|
PRIMARY | |||
|
6440459
Created by
admin on Fri Dec 15 18:51:55 GMT 2023 , Edited by admin on Fri Dec 15 18:51:55 GMT 2023
|
PRIMARY | |||
|
90730-93-1
Created by
admin on Fri Dec 15 18:51:55 GMT 2023 , Edited by admin on Fri Dec 15 18:51:55 GMT 2023
|
SUPERSEDED | |||
|
C152925
Created by
admin on Fri Dec 15 18:51:55 GMT 2023 , Edited by admin on Fri Dec 15 18:51:55 GMT 2023
|
PRIMARY | |||
|
m11523
Created by
admin on Fri Dec 15 18:51:55 GMT 2023 , Edited by admin on Fri Dec 15 18:51:55 GMT 2023
|
PRIMARY | Merck Index | ||
|
73210-73-8
Created by
admin on Fri Dec 15 18:51:55 GMT 2023 , Edited by admin on Fri Dec 15 18:51:55 GMT 2023
|
PRIMARY | |||
|
SUB05144MIG
Created by
admin on Fri Dec 15 18:51:55 GMT 2023 , Edited by admin on Fri Dec 15 18:51:55 GMT 2023
|
PRIMARY | |||
|
DBSALT002913
Created by
admin on Fri Dec 15 18:51:55 GMT 2023 , Edited by admin on Fri Dec 15 18:51:55 GMT 2023
|
PRIMARY | |||
|
N87007N668
Created by
admin on Fri Dec 15 18:51:55 GMT 2023 , Edited by admin on Fri Dec 15 18:51:55 GMT 2023
|
PRIMARY | |||
|
82133
Created by
admin on Fri Dec 15 18:51:55 GMT 2023 , Edited by admin on Fri Dec 15 18:51:55 GMT 2023
|
PRIMARY | RxNorm | ||
|
CHEMBL75753
Created by
admin on Fri Dec 15 18:51:55 GMT 2023 , Edited by admin on Fri Dec 15 18:51:55 GMT 2023
|
PRIMARY | |||
|
100000087903
Created by
admin on Fri Dec 15 18:51:55 GMT 2023 , Edited by admin on Fri Dec 15 18:51:55 GMT 2023
|
PRIMARY | |||
|
277-319-9
Created by
admin on Fri Dec 15 18:51:55 GMT 2023 , Edited by admin on Fri Dec 15 18:51:55 GMT 2023
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
PARENT -> SALT/SOLVATE |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |