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

Identification

Generic Name
Xamoterol
DrugBank Accession Number
DB13781
Background

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.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 339.392
Monoisotopic: 339.179420917
Chemical Formula
C16H25N3O5
Synonyms
  • Xamoterol
  • Xamoterolum

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
ABeta-1 adrenergic receptor
partial agonist
Humans
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

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcebutololThe therapeutic efficacy of Xamoterol can be decreased when used in combination with Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Aceclofenac is combined with Xamoterol.
AcemetacinThe risk or severity of hypertension can be increased when Xamoterol is combined with Acemetacin.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Xamoterol.
AclidiniumThe risk or severity of Tachycardia can be increased when Aclidinium is combined with Xamoterol.
AdenosineThe risk or severity of Tachycardia can be increased when Adenosine is combined with Xamoterol.
AlclofenacThe risk or severity of hypertension can be increased when Alclofenac is combined with Xamoterol.
AlfentanilThe risk or severity of hypertension can be increased when Alfentanil is combined with Xamoterol.
AlfuzosinThe therapeutic efficacy of Xamoterol can be decreased when used in combination with Alfuzosin.
AliskirenXamoterol may decrease the antihypertensive activities of Aliskiren.
Interactions
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Xamoterol fumarateN87007N66890730-93-1QEDVGROSOZBGOZ-WXXKFALUSA-N
International/Other Brands
Corwin

Categories

ATC Codes
C01CX07 — Xamoterol
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1,2-aminoalcohol / 1-hydroxy-2-unsubstituted benzenoid / 4-alkoxyphenol / Alcohol / Alkyl aryl ether / Amine / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonic acid derivative
show 20 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
morpholines (CHEBI:10055)
Affected organisms
Not Available

Chemical Identifiers

UNII
7HE0JQL703
CAS number
81801-12-9
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-carboxamide
SMILES
OC(CNCCNC(=O)N1CCOCC1)COC1=CC=C(O)C=C1

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. [Article]
  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. [Article]
KEGG Drug
D06328
KEGG Compound
C11775
PubChem Compound
155774
PubChem Substance
347829315
ChemSpider
137213
RxNav
39801
ChEBI
10055
ChEMBL
CHEMBL75753
Wikipedia
Xamoterol

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility3.46 mg/mLALOGPS
logP-0.31ALOGPS
logP-0.82ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)9.95ChemAxon
pKa (Strongest Basic)8.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area103.29 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity88.13 m3·mol-1ChemAxon
Polarizability36.82 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

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
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. [Article]

Drug created at June 23, 2017 20:48 / Updated at February 21, 2021 18:54