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
Structure for Xamoterol (DB13781)
- Weight
- Average: 339.392
Monoisotopic: 339.179420917 - Chemical Formula
- C16H25N3O5
- Synonyms
- Xamoterol
- Xamoterolum
Pharmacology
- Indication
Not Available
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism ABeta-1 adrenergic receptor partial agonistHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcebutolol The therapeutic efficacy of Xamoterol can be decreased when used in combination with Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Aceclofenac is combined with Xamoterol. Acemetacin The risk or severity of hypertension can be increased when Xamoterol is combined with Acemetacin. Acetylsalicylic acid The risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Xamoterol. Aclidinium The risk or severity of Tachycardia can be increased when Aclidinium is combined with Xamoterol. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Xamoterol fumarate N87007N668 90730-93-1 QEDVGROSOZBGOZ-WXXKFALUSA-N - International/Other Brands
- Corwin
Categories
- ATC Codes
- C01CX07 — Xamoterol
- Drug Categories
- Adrenergic Agents
- Adrenergic Agonists
- Adrenergic beta-1 Receptor Agonists
- Adrenergic beta-Agonists
- Agents producing tachycardia
- Agents that produce hypertension
- Alcohols
- Amines
- Amino Alcohols
- Cardiac Stimulants Excl. Cardiac Glycosides
- Cardiac Therapy
- Morpholines
- Neurotransmitter Agents
- Oxazines
- Phenoxypropanolamines
- Propanolamines
- Propanols
- 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
- 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]
- 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]
- External Links
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
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
Property Value Source Water Solubility 3.46 mg/mL ALOGPS logP -0.31 ALOGPS logP -0.82 Chemaxon logS -2 ALOGPS pKa (Strongest Acidic) 9.95 Chemaxon pKa (Strongest Basic) 8.76 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 103.29 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 88.13 m3·mol-1 Chemaxon Polarizability 36.82 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-1279000000-f21bc6500ae6ccd8df92 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00dr-0569000000-a45550ab926d528f3664 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-2900000000-c3cdffb44a0f3e682d7d Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-000l-5962000000-6855977bf6f1c36b5d19 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4u-4910000000-f36189c88996e4aa66c7 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00kr-5910000000-5ba2c90335add21a9797 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 174.23897 predictedDeepCCS 1.0 (2019) [M+H]+ 176.59697 predictedDeepCCS 1.0 (2019) [M+Na]+ 182.69011 predictedDeepCCS 1.0 (2019)
Targets
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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
- 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