Details
Stereochemistry | RACEMIC |
Molecular Formula | C16H25N3O5 |
Molecular Weight | 339.3868 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(CNCCNC(=O)N1CCOCC1)COC2=CC=C(O)C=C2
InChI
InChIKey=DXPOSRCHIDYWHW-UHFFFAOYSA-N
InChI=1S/C16H25N3O5/c20-13-1-3-15(4-2-13)24-12-14(21)11-17-5-6-18-16(22)19-7-9-23-10-8-19/h1-4,14,17,20-21H,5-12H2,(H,18,22)
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 | ( + / - ) |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/2862938 | https://www.ncbi.nlm.nih.gov/pubmed/6128041Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2862938 | https://www.ncbi.nlm.nih.gov/pubmed/6128041
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.
Originator
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 |
|
Binding pockets of the beta(1)- and beta(2)-adrenergic receptors for subtype-selective agonists. | 1999 Nov |
|
Constitutive activity of the human beta(1)-adrenergic receptor in beta(1)-receptor transgenic mice. | 2001 Oct |
|
Characterization of beta-adrenoceptor subtype in bladder smooth muscle in cynomolgus monkey. | 2002 Jan |
|
Functional and molecular characterization of beta-adrenoceptors in the internal anal sphincter. | 2003 May |
|
Effect of overexpressed adenylyl cyclase VI on beta 1- and beta 2-adrenoceptor responses in adult rat ventricular myocytes. | 2004 Oct |
|
A clinical, physiology and pharmacology evaluation of orthostatic hypotension in the elderly. | 2005 |
|
In vitro evidence that carteolol is a nonconventional partial agonist of guinea pig cardiac beta1-adrenoceptors: a comparison with xamoterol. | 2005 Dec |
|
Site of action of beta-ligands at the human beta1-adrenoceptor. | 2005 Jun |
|
Beta1-adrenergic receptors maintain fetal heart rate and survival. | 2006 |
|
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 |
|
Are we misunderstanding beta-blockers. | 2007 Aug 9 |
|
Sympathetic neurotransmission modulates expression of inflammatory markers in the rat retina. | 2007 Jan |
|
Effect of inhibition of extracellular signal-regulated kinase on relaxations to beta-adrenoceptor agonists in porcine isolated blood vessels. | 2009 Dec |
|
Four close bupranolol analogues are antagonists at the low-affinity state of beta1-adrenoceptors. | 2009 Mar |
|
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 |
|
Beta-blockers and heart failure. | 2010 Mar-Apr |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19523948
human microvascular retinal endothelial cells (HMREC) cultured in high (25 mM) and low glucose (5 mM) conditions were serum starved for 18-24 h, followed by treatment with a beta-1-adrenergic receptor agonist, xamoterol (10 microM), for 15, 30, and 45 min.
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 23:35:35 UTC 2023
by
admin
on
Wed Jul 05 23:35:35 UTC 2023
|
Record UNII |
7HE0JQL703
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C48149
Created by
admin on Wed Jul 05 23:35:35 UTC 2023 , Edited by admin on Wed Jul 05 23:35:35 UTC 2023
|
||
|
WHO-VATC |
QC01CX07
Created by
admin on Wed Jul 05 23:35:35 UTC 2023 , Edited by admin on Wed Jul 05 23:35:35 UTC 2023
|
||
|
WHO-ATC |
C01CX07
Created by
admin on Wed Jul 05 23:35:35 UTC 2023 , Edited by admin on Wed Jul 05 23:35:35 UTC 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
XAMOTEROL
Created by
admin on Wed Jul 05 23:35:35 UTC 2023 , Edited by admin on Wed Jul 05 23:35:35 UTC 2023
|
PRIMARY | |||
|
155774
Created by
admin on Wed Jul 05 23:35:35 UTC 2023 , Edited by admin on Wed Jul 05 23:35:35 UTC 2023
|
PRIMARY | |||
|
U-92
Created by
admin on Wed Jul 05 23:35:35 UTC 2023 , Edited by admin on Wed Jul 05 23:35:35 UTC 2023
|
PRIMARY | |||
|
DTXSID8045222
Created by
admin on Wed Jul 05 23:35:35 UTC 2023 , Edited by admin on Wed Jul 05 23:35:35 UTC 2023
|
PRIMARY | |||
|
D017307
Created by
admin on Wed Jul 05 23:35:35 UTC 2023 , Edited by admin on Wed Jul 05 23:35:35 UTC 2023
|
PRIMARY | |||
|
2848
Created by
admin on Wed Jul 05 23:35:35 UTC 2023 , Edited by admin on Wed Jul 05 23:35:35 UTC 2023
|
PRIMARY | |||
|
7HE0JQL703
Created by
admin on Wed Jul 05 23:35:35 UTC 2023 , Edited by admin on Wed Jul 05 23:35:35 UTC 2023
|
PRIMARY | |||
|
81801-12-9
Created by
admin on Wed Jul 05 23:35:35 UTC 2023 , Edited by admin on Wed Jul 05 23:35:35 UTC 2023
|
PRIMARY | |||
|
CHEMBL75753
Created by
admin on Wed Jul 05 23:35:35 UTC 2023 , Edited by admin on Wed Jul 05 23:35:35 UTC 2023
|
PRIMARY | |||
|
100000079329
Created by
admin on Wed Jul 05 23:35:35 UTC 2023 , Edited by admin on Wed Jul 05 23:35:35 UTC 2023
|
PRIMARY | |||
|
M11523
Created by
admin on Wed Jul 05 23:35:35 UTC 2023 , Edited by admin on Wed Jul 05 23:35:35 UTC 2023
|
PRIMARY | Merck Index | ||
|
C81344
Created by
admin on Wed Jul 05 23:35:35 UTC 2023 , Edited by admin on Wed Jul 05 23:35:35 UTC 2023
|
PRIMARY | |||
|
5271
Created by
admin on Wed Jul 05 23:35:35 UTC 2023 , Edited by admin on Wed Jul 05 23:35:35 UTC 2023
|
PRIMARY | |||
|
SUB00092MIG
Created by
admin on Wed Jul 05 23:35:35 UTC 2023 , Edited by admin on Wed Jul 05 23:35:35 UTC 2023
|
PRIMARY | |||
|
DB13781
Created by
admin on Wed Jul 05 23:35:35 UTC 2023 , Edited by admin on Wed Jul 05 23:35:35 UTC 2023
|
PRIMARY | |||
|
39801
Created by
admin on Wed Jul 05 23:35:35 UTC 2023 , Edited by admin on Wed Jul 05 23:35:35 UTC 2023
|
PRIMARY | RxNorm |
Related Record | Type | Details | ||
---|---|---|---|---|
|
SALT/SOLVATE -> PARENT | |||
|
ENANTIOMER -> RACEMATE | |||
|
ENANTIOMER -> RACEMATE | |||
|
TARGET -> AGONIST |
SHORT-ACTING
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |