Identification
- Generic Name
- Arbutamine
- DrugBank Accession Number
- DB01102
- Background
Arbutamine, administered through a closed-loop, computer-controlled drug-delivery system, is indicated to elicit acute cardiovascular responses, similar to those produced by exercise, in order to aid in diagnosing the presence or absence of coronary artery disease in patients who cannot exercise adequately .
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Arbutamine (DB01102)
- Weight
- Average: 317.3795
Monoisotopic: 317.162708229 - Chemical Formula
- C18H23NO4
- Synonyms
- Arbutamina
- Arbutamine
- Arbutaminum
Pharmacology
- Indication
Used to elicit acute cardiovascular responses (cardiac stumulant), similar to those produced by exercise, in order to aid in diagnosing the presence or absence of coronary artery disease (CAD) in patients who cannot exercise adequately.
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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
Arbutamine is a synthetic catecholamine with positive chronotropic and inotropic properties. The chronotropic (increase in heart rate) and inotropic (increase in force of contraction) effects of arbutamine serve to mimic exercise by increasing cardiac work (producing stress) and provoke myocardial ischemia in patients with compromised coronary arteries. The increase in heart rate caused by arbutamine is thought to limit regional subendocardial perfusion, thereby limiting tissue oxygenation. In functional assays, arbutamine is more selective for beta-adrenergic receptors than for alpha-adrenergic receptors. The beta-agonist activity of arbutamine provides cardiac stress by increasing heart rate, cardiac contractility, and systolic blood pressure. The degree of hypotension that occurs for a given chronotropic activity is less with arbutamine than, for example, with isoproterenol because alpha receptor activity is retained.
Target Actions Organism ABeta-1 adrenergic receptor agonistHumans UBeta-2 adrenergic receptor agonistHumans UBeta-3 adrenergic receptor agonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
58%
- Metabolism
Primarily metabolized to methoxyarbutamine. Another possible metabolite is ketoarbutamine. The metabolites of arbutamine appear to have less pharmacological activity and a longer half-life and than the parental drug.
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- Route of elimination
Not Available
- Half-life
Elimination half-life is approximately 8 minutes.
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
Pathway Category Arbutamine Action Pathway Drug action - 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 Arbutamine can be decreased when used in combination with Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Arbutamine is combined with Aceclofenac. Acemetacin The risk or severity of hypertension can be increased when Arbutamine is combined with Acemetacin. Acetylsalicylic acid The risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Arbutamine. Aclidinium The risk or severity of Tachycardia can be increased when Arbutamine is combined with Aclidinium. - 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 Arbutamine hydrochloride K0NF2CPJ7F 125251-66-3 ATBUNPBAFFCFKY-FERBBOLQSA-N - International/Other Brands
- GenESA
Categories
- ATC Codes
- C01CA22 — Arbutamine
- Drug Categories
- Adrenergic Agents
- Adrenergic Agonists
- Adrenergic and Dopaminergic Agents
- Adrenergic beta-1 Receptor Agonists
- Adrenergic beta-2 Receptor Agonists
- Adrenergic beta-3 Receptor Agonists
- Adrenergic beta-Agonists
- Agents producing tachycardia
- Agents that produce hypertension
- Amines
- Benzene Derivatives
- Cardiac Stimulants Excl. Cardiac Glycosides
- Cardiac Therapy
- Cardiotonic Agents
- Cardiovascular Agents
- Catechols
- Compounds used in a research, industrial, or household setting
- Neurotransmitter Agents
- Phenols
- Protective Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenylbutylamines. These are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Phenylbutylamines
- Direct Parent
- Phenylbutylamines
- Alternative Parents
- Catechols / Aralkylamines / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Organopnictogen compounds / Hydrocarbon derivatives / Aromatic alcohols
- Substituents
- 1,2-aminoalcohol / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Alcohol / Amine / Aralkylamine / Aromatic alcohol / Aromatic homomonocyclic compound / Catechol / Hydrocarbon derivative
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- catecholamine (CHEBI:50580)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- B07L15YAEV
- CAS number
- 128470-16-6
- InChI Key
- IIRWWTKISYTTBL-SFHVURJKSA-N
- InChI
- InChI=1S/C18H23NO4/c20-15-7-4-13(5-8-15)3-1-2-10-19-12-18(23)14-6-9-16(21)17(22)11-14/h4-9,11,18-23H,1-3,10,12H2/t18-/m0/s1
- IUPAC Name
- 4-[(1R)-1-hydroxy-2-{[4-(4-hydroxyphenyl)butyl]amino}ethyl]benzene-1,2-diol
- SMILES
- O[C@@H](CNCCCCC1=CC=C(O)C=C1)C1=CC(O)=C(O)C=C1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015234
- KEGG Drug
- D02976
- PubChem Compound
- 60789
- PubChem Substance
- 46509010
- ChemSpider
- 54785
- 61609
- ChEBI
- 50580
- ChEMBL
- CHEMBL1201251
- Therapeutic Targets Database
- DAP000936
- PharmGKB
- PA164747979
- Wikipedia
- Arbutamine
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
Patent Number Pediatric Extension Approved Expires (estimated) Region US5395970 No 1995-03-07 2012-03-07 US 
US5234404 No 1993-08-10 2010-08-10 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 2.9 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0842 mg/mL ALOGPS logP 2.08 ALOGPS logP 2 Chemaxon logS -3.6 ALOGPS pKa (Strongest Acidic) 8.97 Chemaxon pKa (Strongest Basic) 9.76 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 92.95 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 89.78 m3·mol-1 Chemaxon Polarizability 35.54 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9464 Blood Brain Barrier - 0.9026 Caco-2 permeable - 0.7305 P-glycoprotein substrate Substrate 0.7596 P-glycoprotein inhibitor I Non-inhibitor 0.8011 P-glycoprotein inhibitor II Non-inhibitor 0.5135 Renal organic cation transporter Non-inhibitor 0.6511 CYP450 2C9 substrate Non-substrate 0.8014 CYP450 2D6 substrate Non-substrate 0.7951 CYP450 3A4 substrate Non-substrate 0.5827 CYP450 1A2 substrate Non-inhibitor 0.6669 CYP450 2C9 inhibitor Non-inhibitor 0.9295 CYP450 2D6 inhibitor Non-inhibitor 0.8282 CYP450 2C19 inhibitor Non-inhibitor 0.9358 CYP450 3A4 inhibitor Non-inhibitor 0.7648 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9401 Ames test Non AMES toxic 0.7687 Carcinogenicity Non-carcinogens 0.943 Biodegradation Not ready biodegradable 0.5579 Rat acute toxicity 1.9867 LD50, mol/kg Not applicable hERG inhibition (predictor I) Strong inhibitor 0.6306 hERG inhibition (predictor II) Inhibitor 0.7594
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0a4r-0900000000-beab4528e7ae0c5e38b5 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-014i-0519000000-614176faaef42f2795ca Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0309000000-9001c8ad880576ca992a Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00rb-1692000000-732fcba535682d711e76 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-015m-1953000000-86764bd5df3aa21af13b Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-00dr-0950000000-ea08975625add9a9784b Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-1910000000-63104761b66c2fe2b1a7 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]- 186.1895403 predictedDarkChem Lite v0.1.0 [M-H]- 184.8909403 predictedDarkChem Lite v0.1.0 [M-H]- 178.33269 predictedDeepCCS 1.0 (2019) [M+H]+ 187.4851403 predictedDarkChem Lite v0.1.0 [M+H]+ 184.6560403 predictedDarkChem Lite v0.1.0 [M+H]+ 180.88301 predictedDeepCCS 1.0 (2019) [M+Na]+ 186.9766403 predictedDarkChem Lite v0.1.0 [M+Na]+ 183.8399403 predictedDarkChem Lite v0.1.0 [M+Na]+ 188.80257 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Abou-Mohamed G, Nagarajan R, Ibrahim TM, Caldwell RW: Characterization of the adrenergic activity of arbutamine, a novel agent for pharmacological stress testing. Cardiovasc Drugs Ther. 1996 Mar;10(1):39-47. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Protein homodimerization activity
- Specific Function
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...
- Gene Name
- ADRB2
- Uniprot ID
- P07550
- Uniprot Name
- Beta-2 adrenergic receptor
- Molecular Weight
- 46458.32 Da
References
- Abou-Mohamed G, Nagarajan R, Ibrahim TM, Caldwell RW: Characterization of the adrenergic activity of arbutamine, a novel agent for pharmacological stress testing. Cardiovasc Drugs Ther. 1996 Mar;10(1):39-47. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Protein homodimerization activity
- Specific Function
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. Beta-3 is involved in the regulation of lipolysis and thermogenesis.
- Gene Name
- ADRB3
- Uniprot ID
- P13945
- Uniprot Name
- Beta-3 adrenergic receptor
- Molecular Weight
- 43518.615 Da
References
- Abou-Mohamed G, Nagarajan R, Ibrahim TM, Caldwell RW: Characterization of the adrenergic activity of arbutamine, a novel agent for pharmacological stress testing. Cardiovasc Drugs Ther. 1996 Mar;10(1):39-47. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:54