This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Xamoterol
Accession Number
DB13781
Type
Small Molecule
Groups
Experimental
Description

Xamoterol is a β1-adrenoceptor partial agonist that has shown to improve systolic and diastolic function in studies with heart failure patients. It modulates the sympathetic control of the heart but has no agonist action on β2-adrenoceptors.

Structure
Thumb
Synonyms
Not Available
Categories
UNII
7HE0JQL703
CAS number
81801-12-9
Weight
Average: 339.392
Monoisotopic: 339.179420917
Chemical Formula
C16H25N3O5
InChI Key
DXPOSRCHIDYWHW-UHFFFAOYSA-N
InChI
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)
IUPAC Name
N-(2-{[2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino}ethyl)morpholine-4-carboximidic acid
SMILES
OC(CNCCN=C(O)N1CCOCC1)COC1=CC=C(O)C=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
ABeta-1 adrenergic receptor
partial agonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AcebutololThe therapeutic efficacy of Xamoterol can be decreased when used in combination with Acebutolol.
AcepromazineThe therapeutic efficacy of Xamoterol can be decreased when used in combination with Acepromazine.
AlfuzosinThe therapeutic efficacy of Xamoterol can be decreased when used in combination with Alfuzosin.
AlprenololThe therapeutic efficacy of Xamoterol can be decreased when used in combination with Alprenolol.
AmineptineThe risk or severity of hypertension can be increased when Amineptine is combined with Xamoterol.
AmitriptylineThe risk or severity of hypertension can be increased when Amitriptyline is combined with Xamoterol.
AmitriptylinoxideThe risk or severity of hypertension can be increased when Amitriptylinoxide is combined with Xamoterol.
AmoxapineThe risk or severity of hypertension can be increased when Amoxapine is combined with Xamoterol.
AnisodamineThe therapeutic efficacy of Xamoterol can be decreased when used in combination with Anisodamine.
AripiprazoleThe therapeutic efficacy of Xamoterol can be decreased when used in combination with Aripiprazole.
Food Interactions
Not Available

References

General References
  1. Snow HM: The pharmacology of xamoterol: a basis for modulation of the autonomic control of the heart. Br J Clin Pharmacol. 1989;28 Suppl 1:3S-13S. [PubMed:2572252]
  2. Marlow HF: Xamoterol, a beta 1-adrenoceptor partial agonist: review of the clinical efficacy in heart failure. Br J Clin Pharmacol. 1989;28 Suppl 1:23S-30S. [PubMed:2572251]
External Links
KEGG Compound
C11775
PubChem Compound
155774
PubChem Substance
347829315
ChemSpider
137213
ChEBI
10055
ChEMBL
CHEMBL75753
Wikipedia
Xamoterol
ATC Codes
C01CX07 — Xamoterol

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.01 mg/mLALOGPS
logP-0.22ALOGPS
logP-1.3ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)-3.4ChemAxon
pKa (Strongest Basic)15.05ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area106.78 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity89.05 m3·mol-1ChemAxon
Polarizability36.41 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as morpholine carboxylic acids and derivatives. These are heterocyclic compounds containing a morpholine ring substituted by one or more carboxylic acid groups (or derivative thereof).
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Oxazinanes
Sub Class
Morpholines
Direct Parent
Morpholine carboxylic acids and derivatives
Alternative Parents
4-alkoxyphenols / Phenoxy compounds / Phenol ethers / 1-hydroxy-2-unsubstituted benzenoids / Alkyl aryl ethers / Ureas / Secondary alcohols / 1,2-aminoalcohols / Oxacyclic compounds / Azacyclic compounds
show 6 more
Substituents
4-alkoxyphenol / Morpholine-4-carboxylic acid or derivatives / Phenoxy compound / Phenol ether / 1-hydroxy-2-unsubstituted benzenoid / Alkyl aryl ether / Phenol / Monocyclic benzene moiety / Benzenoid / 1,2-aminoalcohol
show 20 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
morpholines (CHEBI:10055)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Partial agonist
General Function
Receptor signaling protein activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...
Gene Name
ADRB1
Uniprot ID
P08588
Uniprot Name
Beta-1 adrenergic receptor
Molecular Weight
51322.1 Da
References
  1. Snow HM: The pharmacology of xamoterol: a basis for modulation of the autonomic control of the heart. Br J Clin Pharmacol. 1989;28 Suppl 1:3S-13S. [PubMed:2572252]

Drug created on June 23, 2017 14:48 / Updated on November 02, 2018 07:46