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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
Structure of XAMOTEROL

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)

HIDE SMILES / InChI

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 ( + / - )

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
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
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
Pharmacological characterization of putative beta1-beta2-adrenergic receptor heterodimers.
2003 Feb
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
Site of action of beta-ligands at the human beta1-adrenoceptor.
2005 Jun
Beta1-adrenergic receptors maintain fetal heart rate and survival.
2006
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
beta(2) and beta(3)-adrenoceptor inhibition of alpha(1)-adrenoceptor-stimulated Ca(2+) elevation in human cultured prostatic stromal cells.
2007 Sep 10
Carvedilol in the treatment of elderly patients with chronic heart failure.
2008
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
A full pharmacological analysis of the three turkey β-adrenoceptors and comparison with the human β-adrenoceptors.
2010 Nov 30
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 Fri Dec 15 16:07:52 UTC 2023
Edited
by admin
on Fri Dec 15 16:07:52 UTC 2023
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 [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
Xamoterol [WHO-DD]
Common Name English
ICI-118,587
Code English
Classification Tree Code System Code
NCI_THESAURUS C48149
Created by admin on Fri Dec 15 16:07:52 UTC 2023 , Edited by admin on Fri Dec 15 16:07:52 UTC 2023
WHO-VATC QC01CX07
Created by admin on Fri Dec 15 16:07:52 UTC 2023 , Edited by admin on Fri Dec 15 16:07:52 UTC 2023
WHO-ATC C01CX07
Created by admin on Fri Dec 15 16:07:52 UTC 2023 , Edited by admin on Fri Dec 15 16:07:52 UTC 2023
Code System Code Type Description
WIKIPEDIA
XAMOTEROL
Created by admin on Fri Dec 15 16:07:52 UTC 2023 , Edited by admin on Fri Dec 15 16:07:52 UTC 2023
PRIMARY
PUBCHEM
155774
Created by admin on Fri Dec 15 16:07:52 UTC 2023 , Edited by admin on Fri Dec 15 16:07:52 UTC 2023
PRIMARY
USAN
U-92
Created by admin on Fri Dec 15 16:07:52 UTC 2023 , Edited by admin on Fri Dec 15 16:07:52 UTC 2023
PRIMARY
EPA CompTox
DTXSID8045222
Created by admin on Fri Dec 15 16:07:52 UTC 2023 , Edited by admin on Fri Dec 15 16:07:52 UTC 2023
PRIMARY
MESH
D017307
Created by admin on Fri Dec 15 16:07:52 UTC 2023 , Edited by admin on Fri Dec 15 16:07:52 UTC 2023
PRIMARY
DRUG CENTRAL
2848
Created by admin on Fri Dec 15 16:07:52 UTC 2023 , Edited by admin on Fri Dec 15 16:07:52 UTC 2023
PRIMARY
FDA UNII
7HE0JQL703
Created by admin on Fri Dec 15 16:07:52 UTC 2023 , Edited by admin on Fri Dec 15 16:07:52 UTC 2023
PRIMARY
CAS
81801-12-9
Created by admin on Fri Dec 15 16:07:52 UTC 2023 , Edited by admin on Fri Dec 15 16:07:52 UTC 2023
PRIMARY
ChEMBL
CHEMBL75753
Created by admin on Fri Dec 15 16:07:52 UTC 2023 , Edited by admin on Fri Dec 15 16:07:52 UTC 2023
PRIMARY
SMS_ID
100000079329
Created by admin on Fri Dec 15 16:07:52 UTC 2023 , Edited by admin on Fri Dec 15 16:07:52 UTC 2023
PRIMARY
MERCK INDEX
m11523
Created by admin on Fri Dec 15 16:07:52 UTC 2023 , Edited by admin on Fri Dec 15 16:07:52 UTC 2023
PRIMARY Merck Index
NCI_THESAURUS
C81344
Created by admin on Fri Dec 15 16:07:52 UTC 2023 , Edited by admin on Fri Dec 15 16:07:52 UTC 2023
PRIMARY
INN
5271
Created by admin on Fri Dec 15 16:07:52 UTC 2023 , Edited by admin on Fri Dec 15 16:07:52 UTC 2023
PRIMARY
EVMPD
SUB00092MIG
Created by admin on Fri Dec 15 16:07:52 UTC 2023 , Edited by admin on Fri Dec 15 16:07:52 UTC 2023
PRIMARY
DRUG BANK
DB13781
Created by admin on Fri Dec 15 16:07:52 UTC 2023 , Edited by admin on Fri Dec 15 16:07:52 UTC 2023
PRIMARY
RXCUI
39801
Created by admin on Fri Dec 15 16:07:52 UTC 2023 , Edited by admin on Fri Dec 15 16:07:52 UTC 2023
PRIMARY RxNorm
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
SHORT-ACTING
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY