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Details

Stereochemistry RACEMIC
Molecular Formula C16H25N3O5
Molecular Weight 339.3874
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of XAMOTEROL

SMILES

c1cc(ccc1O)OCC(CNCCN=C(N2CCOCC2)O)O

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)

HIDE SMILES / InChI

Molecular Formula C16H25N3O5
Molecular Weight 339.3874
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
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.

CNS Activity

Originator

Sources: BARLOW, J.J., MAIN, B.G., NUTTALL, A., MOORS, J. & SNOW, H.M. (1979). The cardiovascular activity of ICI118,587, a novel beta-adrenoceptor partial agonist. Br. J. Pharmac., 67, 412P.
Curator's Comment:: http://onlinelibrary.wiley.com/doi/10.1111/j.1476-5381.1979.tb08695.x/epdf

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CORWIN

Approved Use

Xamoterol (Fumarate) is primarily indicated in conditions like Heart failure.
PubMed

PubMed

TitleDatePubMed
Ketotifen and cardiovascular effects of xamoterol following single and chronic dosing in healthy volunteers.
1999 Jan
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
Bucindolol displays intrinsic sympathomimetic activity in human myocardium.
2002 May 21
Adenylate cyclase activity in postmortem brain of suicide subjects: reduced response to beta-adrenergic stimulation.
2003 Dec 15
Functional and molecular characterization of beta-adrenoceptors in the internal anal sphincter.
2003 May
Adrenergic regulation of vascular smooth muscle tone in calf digital artery.
2004 Aug
Dobutamine inhibits phorbol-myristate-acetate-induced activation of nuclear factor-kappaB in human T lymphocytes in vitro.
2004 Nov
Glucocorticoid effects on memory retrieval require concurrent noradrenergic activity in the hippocampus and basolateral amygdala.
2004 Sep 15
Sulfation in dog.
2005 Jun
Site of action of beta-ligands at the human beta1-adrenoceptor.
2005 Jun
PI 3-kinase, protein kinase C, and protein kinase A are involved in the trigger phase of beta1-adrenergic preconditioning.
2005 Jun 1
Carvedilol in the treatment of chronic heart failure: lessons from the Carvedilol Or Metoprolol European Trial.
2007
Carvedilol in the treatment of elderly patients with chronic heart failure.
2008
Effect of inhibition of extracellular signal-regulated kinase on relaxations to beta-adrenoceptor agonists in porcine isolated blood vessels.
2009 Dec
The emergence of cold-induced brown adipocytes in mouse white fat depots is determined predominantly by white to brown adipocyte transdifferentiation.
2010 Jun
Patents

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
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 Sat Jun 26 13:50:59 UTC 2021
Edited
by admin
on Sat Jun 26 13:50:59 UTC 2021
Record UNII
7HE0JQL703
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
XAMOTEROL
INN   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
4-MORPHOLINECARBOXAMIDE, N-(2-((2-HYDROXY-3-(4-HYDROXYPHENOXY)PROPYL)AMINO)ETHYL)-, (+/-)-
Systematic Name English
XAMOTEROL [USAN]
Common Name English
ICI-118587
Code English
XAMOTEROL [WHO-DD]
Common Name English
XAMOTEROL [MI]
Common Name English
4-MORPHOLINECARBOXAMIDE, N-(2-((2-HYDROXY-3-(4-HYDROXYPHENOXY)PROPYL)AMINO)ETHYL)-, (+/-)
Common Name English
(+/-)-N-(2-((2-HYDROXY-3-(P-HYDROXYPHENOXY)PROPYL)AMINO)ETHYL)-4-MORPHOLINECARBOXAMIDE
Common Name English
XAMOTEROL [INN]
Common Name English
ICI-118,587
Code English
Classification Tree Code System Code
NCI_THESAURUS C48149
Created by admin on Sat Jun 26 13:51:00 UTC 2021 , Edited by admin on Sat Jun 26 13:51:00 UTC 2021
WHO-VATC QC01CX07
Created by admin on Sat Jun 26 13:51:00 UTC 2021 , Edited by admin on Sat Jun 26 13:51:00 UTC 2021
WHO-ATC C01CX07
Created by admin on Sat Jun 26 13:51:00 UTC 2021 , Edited by admin on Sat Jun 26 13:51:00 UTC 2021
Code System Code Type Description
WIKIPEDIA
XAMOTEROL
Created by admin on Sat Jun 26 13:51:00 UTC 2021 , Edited by admin on Sat Jun 26 13:51:00 UTC 2021
PRIMARY
PUBCHEM
155774
Created by admin on Sat Jun 26 13:51:00 UTC 2021 , Edited by admin on Sat Jun 26 13:51:00 UTC 2021
PRIMARY
EPA CompTox
81801-12-9
Created by admin on Sat Jun 26 13:51:00 UTC 2021 , Edited by admin on Sat Jun 26 13:51:00 UTC 2021
PRIMARY
MESH
D017307
Created by admin on Sat Jun 26 13:51:00 UTC 2021 , Edited by admin on Sat Jun 26 13:51:00 UTC 2021
PRIMARY
DRUG CENTRAL
2848
Created by admin on Sat Jun 26 13:51:00 UTC 2021 , Edited by admin on Sat Jun 26 13:51:00 UTC 2021
PRIMARY
FDA UNII
7HE0JQL703
Created by admin on Sat Jun 26 13:51:00 UTC 2021 , Edited by admin on Sat Jun 26 13:51:00 UTC 2021
PRIMARY
CAS
81801-12-9
Created by admin on Sat Jun 26 13:51:00 UTC 2021 , Edited by admin on Sat Jun 26 13:51:00 UTC 2021
PRIMARY
ChEMBL
CHEMBL75753
Created by admin on Sat Jun 26 13:51:00 UTC 2021 , Edited by admin on Sat Jun 26 13:51:00 UTC 2021
PRIMARY
MERCK INDEX
M11523
Created by admin on Sat Jun 26 13:51:00 UTC 2021 , Edited by admin on Sat Jun 26 13:51:00 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C81344
Created by admin on Sat Jun 26 13:51:00 UTC 2021 , Edited by admin on Sat Jun 26 13:51:00 UTC 2021
PRIMARY
INN
5271
Created by admin on Sat Jun 26 13:51:00 UTC 2021 , Edited by admin on Sat Jun 26 13:51:00 UTC 2021
PRIMARY
EVMPD
SUB00092MIG
Created by admin on Sat Jun 26 13:51:00 UTC 2021 , Edited by admin on Sat Jun 26 13:51:00 UTC 2021
PRIMARY
DRUG BANK
DB13781
Created by admin on Sat Jun 26 13:51:00 UTC 2021 , Edited by admin on Sat Jun 26 13:51:00 UTC 2021
PRIMARY
RXCUI
39801
Created by admin on Sat Jun 26 13:51:00 UTC 2021 , Edited by admin on Sat Jun 26 13:51:00 UTC 2021
PRIMARY RxNorm
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
SHORT-ACTING
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY