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Details

Stereochemistry RACEMIC
Molecular Formula 2C16H25N3O5.C4H4O4
Molecular Weight 794.8472
Optical Activity ( + / - )
Defined Stereocenters 0 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of XAMOTEROL FUMARATE

SMILES

c1cc(ccc1O)OCC(CNCCN=C(N2CCOCC2)O)O.c1cc(ccc1O)OCC(CNCCN=C(N2CCOCC2)O)O.C(\[H])(=C(/[H])\C(=O)O)/C(=O)O

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+

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 ( + / - )

Molecular Formula C4H4O4
Molecular Weight 116.0723
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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
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
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
Pharmacological characterization of putative beta1-beta2-adrenergic receptor heterodimers.
2003 Feb
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
Glucocorticoid effects on memory retrieval require concurrent noradrenergic activity in the hippocampus and basolateral amygdala.
2004 Sep 15
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
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
Sympathetic neurotransmission modulates expression of inflammatory markers in the rat retina.
2007 Jan
The adrenergic receptor subtypes present in frog (Rana esculenta) skin.
2008 Aug
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
Beta-blockers and heart failure.
2010 Mar-Apr
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 05:09:15 UTC 2021
Edited
by admin
on Sat Jun 26 05:09:15 UTC 2021
Record UNII
N87007N668
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
XAMOTEROL FUMARATE
MART.   USAN   WHO-DD  
USAN  
Official Name English
XAMOTEROL FUMARATE [USAN]
Common Name English
ICI-118,587 HEMIFUMARATE
Common Name English
ICI-118587 HEMIFUMARATE
Common Name English
4-MORPHINOLINECARBOXAMIDE, N-*(2-((2-HYDROXY-3-(4-HYDROXYPHENOXY)PROPYL)AMINO)ETHYL)-, (+/-)-, (E)-2-BUTENEDIOATE (2:1) (SALT)
Common Name English
XAMOTEROL HEMIFUMARATE [MI]
Common Name English
XAMOTEROL FUMARATE [WHO-DD]
Common Name English
XAMOTEROL FUMARATE [MART.]
Common Name English
(+/-)-N-(2-((2-HYDROXY-3-(P-HYDROXYPHENOXY)PROPYL)AMINO)ETHYL)-4-MORPHOLINECARBOXAMIDE FUMARATE (2:1) (SALT)
Common Name English
XAMOTEROL FUMARATE [JAN]
Common Name English
ICI 118,587
Code English
XAMOTEROL HEMIFUMARATE
MI  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C78322
Created by admin on Sat Jun 26 05:09:15 UTC 2021 , Edited by admin on Sat Jun 26 05:09:15 UTC 2021
NCI_THESAURUS C48149
Created by admin on Sat Jun 26 05:09:15 UTC 2021 , Edited by admin on Sat Jun 26 05:09:15 UTC 2021
Code System Code Type Description
PUBCHEM
6440459
Created by admin on Sat Jun 26 05:09:15 UTC 2021 , Edited by admin on Sat Jun 26 05:09:15 UTC 2021
PRIMARY
CAS
90730-93-1
Created by admin on Sat Jun 26 05:09:15 UTC 2021 , Edited by admin on Sat Jun 26 05:09:15 UTC 2021
SUPERSEDED
NCI_THESAURUS
C152925
Created by admin on Sat Jun 26 05:09:15 UTC 2021 , Edited by admin on Sat Jun 26 05:09:15 UTC 2021
PRIMARY
MERCK INDEX
M11523
Created by admin on Sat Jun 26 05:09:15 UTC 2021 , Edited by admin on Sat Jun 26 05:09:15 UTC 2021
PRIMARY Merck Index
CAS
73210-73-8
Created by admin on Sat Jun 26 05:09:15 UTC 2021 , Edited by admin on Sat Jun 26 05:09:15 UTC 2021
PRIMARY
EVMPD
SUB05144MIG
Created by admin on Sat Jun 26 05:09:15 UTC 2021 , Edited by admin on Sat Jun 26 05:09:15 UTC 2021
PRIMARY
DRUG BANK
DBSALT002913
Created by admin on Sat Jun 26 05:09:15 UTC 2021 , Edited by admin on Sat Jun 26 05:09:15 UTC 2021
PRIMARY
FDA UNII
N87007N668
Created by admin on Sat Jun 26 05:09:15 UTC 2021 , Edited by admin on Sat Jun 26 05:09:15 UTC 2021
PRIMARY
RXCUI
82133
Created by admin on Sat Jun 26 05:09:15 UTC 2021 , Edited by admin on Sat Jun 26 05:09:15 UTC 2021
PRIMARY RxNorm
ChEMBL
CHEMBL75753
Created by admin on Sat Jun 26 05:09:15 UTC 2021 , Edited by admin on Sat Jun 26 05:09:15 UTC 2021
PRIMARY
ECHA (EC/EINECS)
277-319-9
Created by admin on Sat Jun 26 05:09:15 UTC 2021 , Edited by admin on Sat Jun 26 05:09:15 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY