Dobutamine
Identification
- Summary
Dobutamine is a beta-1 agonist used to treat cardiac decompensation in patients with organic heart disease or from cardiac surgery.
- Generic Name
- Dobutamine
- DrugBank Accession Number
- DB00841
- Background
A beta-1 agonist catecholamine that has cardiac stimulant action without evoking vasoconstriction or tachycardia. It is proposed as a cardiotonic after myocardial infarction or open heart surgery.
- Type
- Small Molecule
- Groups
- Approved
- Structure
- Weight
- Average: 301.3801
Monoisotopic: 301.167793607 - Chemical Formula
- C18H23NO3
- Synonyms
- (±)-4-(2-((3-(p-hydroxyphenyl)-1-methylpropyl)amino)ethyl)pyrocatechol
- 3,4-dihydroxy-N-[3-(4-hydroxyphenyl)-1-methylpropyl]-β-phenylethylamine
- 4-{2-[3-(4-Hydroxy-phenyl)-1-methyl-propylamino]-ethyl}-benzene-1,2-diol
- DL-dobutamine
- Dobutamin
- Dobutamina
- Dobutamine
- Dobutaminum
- rac-dobutamine
- racemic-dobutamine
Pharmacology
- Indication
Indicated when parenteral therapy is necessary for inotropic support in the short-term treatment of patients with cardiac decompensation due to depressed contractility resulting either from organic heart disease or from cardiac surgical procedures.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Cardiac decompensation •••••••••••• Diagnostic agent Coronary artery disease ••• ••••• - Associated Therapies
- Contraindications & Blackbox Warnings
- 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
Dobutamine is a direct-acting inotropic agent whose primary activity results from stimulation of the beta-adrenoceptors of the heart while producing comparatively mild chronotropic, hypertensive, arrhythmogenic, and vasodilative effects. Dobutamine acts primarily on beta-1 adrenergic receptors, with negligible effects on beta-2 or alpha receptors. It does not cause the release of endogenous norepinephrine, as does dopamine.
- Mechanism of action
Dobutamine directly stimulates beta-1 receptors of the heart to increase myocardial contractility and stroke volume, resulting in increased cardiac output.
Target Actions Organism AAlpha-1 adrenergic receptors agonistHumans ABeta-1 adrenergic receptor agonistHumans UBeta-2 adrenergic receptor agonistHumans UEstrogen receptor alpha Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
In human urine, the major excretion products are the conjugates of dobutamine and 3-O-methyl dobutamine.
- Half-life
2 minutes
- 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
Pathway Category Dobutamine 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 softwareAbacavir Dobutamine may decrease the excretion rate of Abacavir which could result in a higher serum level. Acebutolol The therapeutic efficacy of Dobutamine can be decreased when used in combination with Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Dobutamine is combined with Aceclofenac. Acemetacin The risk or severity of hypertension can be increased when Dobutamine is combined with Acemetacin. Acetaminophen Acetaminophen may decrease the excretion rate of Dobutamine which could result in a higher serum level. - Food Interactions
- No interactions found.
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 Dobutamine hydrochloride 0WR771DJXV 49745-95-1 BQKADKWNRWCIJL-UHFFFAOYSA-N Dobutamine tartrate 5D1IB9AI6J 101626-66-8 WZIUXGZIVZDXIG-WUUYCOTASA-N - International/Other Brands
- Dobuject (Bayer) / Dobusafe (Claris) / Dobutamin (Sandoz) / Dobutan (Demo) / Dobutel (Novell) / Dobutil (Meizler) / Dopmin (Mylan Seiyaku) / Inotrex (Lilly)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Dobutamine Injection, solution 200 mg/100mL Intravenous HF Acquisition Co LLC, DBA HealthFirst 2019-04-07 Not applicable US Dobutamine 12.5mg/ml Solution 12.5 mg / mL Intravenous Ivax Pharmaceuticals Incorporated 1996-11-25 2015-10-26 Canada Dobutamine Hydrochloride Injection 100 mg/100mL Intravenous HF Acquisition Co LLC, DBA HealthFirst 2021-07-10 Not applicable US Dobutamine Hydrochloride Injection, solution 400 mg/100mL Intravenous Physicians Total Care, Inc. 2007-06-13 Not applicable US Dobutamine Hydrochloride in Dextrose Injection 400 mg/100mL Intravenous A-S Medication Solutions 1993-09-23 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Dobutamine Injection, solution 12.5 mg/1mL Intravenous General Injectables and Vaccines, Inc. 2014-11-10 Not applicable US DOBUTamine Injection, solution, concentrate 12.5 mg/1mL Intravenous Hospira, Inc. 1996-09-27 2007-08-01 US Dobutamine Injection, solution 12.5 mg/1mL Intravenous Hikma Pharmaceuticals USA Inc. 2023-05-03 Not applicable US Dobutamine Injection, solution, concentrate 12.5 mg/1mL Intravenous Hainan Poly Pharm. Co., Ltd. 2021-06-01 Not applicable US Dobutamine Injection, solution, concentrate 12.5 mg/1mL Intravenous HF Acquisition Co LLC, DBA HealthFirst 2018-11-26 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Dobutamine Hydrochloride in Dextrose Dobutamine hydrochloride (250 mg/100mL) + D-glucose monohydrate (5 g/100mL) Injection, solution Intravenous Baxter Healthcare Corporation 2005-12-14 2005-12-14 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image STERILE DOBUTAMIN CON. 250 MG/20 ML Dobutamine (250 mg/20ml) Injection, solution FİLİZ İLAÇ MÜMESSİL ECZA DEPOSU TİC LTD ŞT 2015-02-03 Not applicable Turkey
Categories
- ATC Codes
- C01CA07 — Dobutamine
- Drug Categories
- Adrenergic Agents
- Adrenergic Agonists
- Adrenergic alpha-1 Receptor Agonists
- Adrenergic alpha-Agonists
- Adrenergic and Dopaminergic Agents
- Adrenergic beta-1 Receptor Agonists
- Adrenergic beta-2 Receptor Agonists
- Adrenergic beta-Agonists
- Agents producing tachycardia
- Agents that produce hypertension
- Amines
- Autonomic Agents
- Benzene Derivatives
- Cardiac Stimulants Excl. Cardiac Glycosides
- Cardiac Therapy
- Cardiotonic Agents
- Cardiovascular Agents
- Catecholamines
- Catechols
- Compounds used in a research, industrial, or household setting
- COMT Substrates
- Drugs that are Mainly Renally Excreted
- Ethylamines
- Neurotransmitter Agents
- Peripheral Nervous System Agents
- Phenethylamines
- Phenols
- Protective Agents
- Selective Beta 1-adrenergic Agonists
- Sympathomimetic (Adrenergic) Agents
- Sympathomimetics
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as catecholamines and derivatives. These are compounds containing 4-(2-Aminoethyl)pyrocatechol [4-(2-aminoethyl)benzene-1,2-diol] or a derivative thereof formed by substitution.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Phenols
- Sub Class
- Benzenediols
- Direct Parent
- Catecholamines and derivatives
- Alternative Parents
- Phenethylamines / Aralkylamines / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Dialkylamines / Organopnictogen compounds / Organooxygen compounds / Hydrocarbon derivatives
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Amine / Aralkylamine / Aromatic homomonocyclic compound / Catecholamine / Hydrocarbon derivative / Monocyclic benzene moiety / Organic nitrogen compound / Organic oxygen compound
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- secondary amine, catecholamine (CHEBI:4670)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 3S12J47372
- CAS number
- 34368-04-2
- InChI Key
- JRWZLRBJNMZMFE-UHFFFAOYSA-N
- InChI
- InChI=1S/C18H23NO3/c1-13(2-3-14-4-7-16(20)8-5-14)19-11-10-15-6-9-17(21)18(22)12-15/h4-9,12-13,19-22H,2-3,10-11H2,1H3
- IUPAC Name
- 4-(2-{[4-(4-hydroxyphenyl)butan-2-yl]amino}ethyl)benzene-1,2-diol
- SMILES
- CC(CCC1=CC=C(O)C=C1)NCCC1=CC(O)=C(O)C=C1
References
- Synthesis Reference
R. R. Tuttle, J. Mills, DE 2317710 (1973). J. Mills, R. R. Tuttle, U.S. Patent 3,987,200 (1976).
US5442120- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014979
- KEGG Drug
- D03879
- KEGG Compound
- C06967
- PubChem Compound
- 36811
- PubChem Substance
- 46505241
- ChemSpider
- 33786
- BindingDB
- 50325274
- 3616
- ChEBI
- 4670
- ChEMBL
- CHEMBL926
- Therapeutic Targets Database
- DAP000245
- PharmGKB
- PA449381
- Guide to Pharmacology
- GtP Drug Page
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Dobutamine
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 4 Completed Diagnostic Free Flaps / Head And Neck Cancer / Hypotension / Oral Cancer 1 4 Completed Other General Anesthesia 1 4 Completed Prevention Mitral Valve Stenosis With Incompetence or Regurgitation 1 4 Completed Prevention Nfuence of Vasoactive Medication on Spinal Oxygenation 1 4 Completed Treatment Acute Coronary Syndrome (ACS) / Low Cardiac Output Syndrome / Pulmonary Edemas / Shock, Cardiogenic 1
Pharmacoeconomics
- Manufacturers
- Astrazeneca lp
- Baxter healthcare corp anesthesia and critical care
- Bedford laboratories div ben venue laboratories inc
- Hospira inc
- Luitpold pharmaceuticals inc
- Marsam pharmaceuticals llc
- Teva parenteral medicines inc
- Watson laboratories inc
- Baxter healthcare corp
- Eli lilly and co
- Packagers
- Baxter International Inc.
- Bedford Labs
- Ben Venue Laboratories Inc.
- Cardinal Health
- Hospira Inc.
- Physicians Total Care Inc.
- Teva Pharmaceutical Industries Ltd.
- Dosage Forms
Form Route Strength Solution Parenteral 250 mg Solution Intravenous 280.200 mg Injection Intravenous 50 mg/ml Injection Intravenous 1000 mcg/ml Injection Intravenous 2000 mcg/ml Injection Intravenous 4000 mcg/ml Injection, solution, concentrate Parenteral Solution Parenteral 500 mg Solution Parenteral 5 mg/ml Solution Parenteral 280 mg Solution Intravenous 250 mg Solution Intravenous 12.5 mg Injection, solution, concentrate Intravenous; Parenteral 250 MG/20ML Injection, solution, concentrate Intravenous 12.5 MG/ML Injection, solution Injection, solution 5 MG/ML Injection Intravenous 12.5 mg/1mL Injection, solution Intravenous 12.5 mg/1mL Injection, solution, concentrate Intravenous 12.5 mg/1mL Injection Intravenous Injection, powder, lyophilized, for solution Intravenous 12.5 mg/1mL Injection, solution Intravenous 400 mg/100mL Injection Intravenous 100 mg/100mL Injection Intravenous 200 mg/100mL Injection Intravenous 400 mg/100mL Injection, solution Intravenous Injection, solution Intravenous 100 mg/100mL Injection, solution Intravenous 200 mg/100mL Injection Intravenous 12.5 mg/ml Solution Intravenous 12.5 mg / mL Liquid Intravenous 12.5 mg / mL Solution Intravenous 250 mg / 20 mL Injection, solution, concentrate Parenteral 250 mg/20ml Injection, solution 50 mg/1ml Injection, solution, concentrate Intravenous Injection, solution Intravenous Injection, solution Intravenous 250 mg/20ml Solution Intravenous Solution Parenteral 250.000 mg Injection, solution, concentrate Intravenous 250 mg/20ml Injection, solution Parenteral 250 MG/20ML Injection Intravenous 250 mg/20ml Injection, solution 250 mg/20ml Solution 12.5 mg/1ml Solution 50 mg/1ml - Prices
Unit description Cost Unit Dobutamine 12.5 mg/ml vial 0.18USD ml Dobutamine 250 mg-d5w 500 ml 0.09USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 184-186 J. Mills, R. R. Tuttle, U.S. Patent 3,987,200 (1976). logP 3.6 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0137 mg/mL ALOGPS logP 2.97 ALOGPS logP 2.62 Chemaxon logS -4.3 ALOGPS pKa (Strongest Acidic) 10.14 Chemaxon pKa (Strongest Basic) 9.27 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 72.72 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 88.39 m3·mol-1 Chemaxon Polarizability 34.44 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 + 0.9937 Blood Brain Barrier - 0.7448 Caco-2 permeable + 0.5305 P-glycoprotein substrate Substrate 0.7571 P-glycoprotein inhibitor I Non-inhibitor 0.8782 P-glycoprotein inhibitor II Non-inhibitor 0.8383 Renal organic cation transporter Non-inhibitor 0.6336 CYP450 2C9 substrate Non-substrate 0.7235 CYP450 2D6 substrate Substrate 0.6265 CYP450 3A4 substrate Non-substrate 0.5296 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8231 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8827 Ames test Non AMES toxic 0.7215 Carcinogenicity Non-carcinogens 0.9306 Biodegradation Not ready biodegradable 0.9256 Rat acute toxicity 2.2261 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.828 hERG inhibition (predictor II) Inhibitor 0.8367
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 179.0937872 predictedDarkChem Lite v0.1.0 [M-H]- 174.37445 predictedDeepCCS 1.0 (2019) [M+H]+ 179.1170872 predictedDarkChem Lite v0.1.0 [M+H]+ 176.73247 predictedDeepCCS 1.0 (2019) [M+Na]+ 179.2408872 predictedDarkChem Lite v0.1.0 [M+Na]+ 182.8256 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Protein heterodimerization activity
- Specific Function
- This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Components:
Name | UniProt ID |
---|---|
Alpha-1A adrenergic receptor | P35348 |
Alpha-1B adrenergic receptor | P35368 |
Alpha-1D adrenergic receptor | P25100 |
References
- Ruffolo RR Jr, Spradlin TA, Pollock GD, Waddell JE, Murphy PJ: Alpha and beta adrenergic effects of the stereoisomers of dobutamine. J Pharmacol Exp Ther. 1981 Nov;219(2):447-52. [Article]
- 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
- Junker V, Becker A, Huhne R, Zembatov M, Ravati A, Culmsee C, Krieglstein J: Stimulation of beta-adrenoceptors activates astrocytes and provides neuroprotection. Eur J Pharmacol. 2002 Jun 20;446(1-3):25-36. [Article]
- La Rosee K, Huntgeburth M, Rosenkranz S, Bohm M, Schnabel P: The Arg389Gly beta1-adrenoceptor gene polymorphism determines contractile response to catecholamines. Pharmacogenetics. 2004 Nov;14(11):711-6. [Article]
- Bruck H, Leineweber K, Temme T, Weber M, Heusch G, Philipp T, Brodde OE: The Arg389Gly beta1-adrenoceptor polymorphism and catecholamine effects on plasma-renin activity. J Am Coll Cardiol. 2005 Dec 6;46(11):2111-5. Epub 2005 Nov 4. [Article]
- Raddatz A, Kubulus D, Winning J, Bauer I, Pradarutti S, Wolf B, Kreuer S, Rensing H: Dobutamine improves liver function after hemorrhagic shock through induction of heme oxygenase-1. Am J Respir Crit Care Med. 2006 Jul 15;174(2):198-207. Epub 2006 Apr 20. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [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
- Tibayan FA, Chesnutt AN, Folkesson HG, Eandi J, Matthay MA: Dobutamine increases alveolar liquid clearance in ventilated rats by beta-2 receptor stimulation. Am J Respir Crit Care Med. 1997 Aug;156(2 Pt 1):438-44. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Curator comments
- Weak activator
- General Function
- Zinc ion binding
- Specific Function
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
- Gene Name
- ESR1
- Uniprot ID
- P03372
- Uniprot Name
- Estrogen receptor
- Molecular Weight
- 66215.45 Da
References
- McRobb FM, Kufareva I, Abagyan R: In silico identification and pharmacological evaluation of novel endocrine disrupting chemicals that act via the ligand-binding domain of the estrogen receptor alpha. Toxicol Sci. 2014 Sep;141(1):188-97. doi: 10.1093/toxsci/kfu114. Epub 2014 Jun 13. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- O-methyltransferase activity
- Specific Function
- Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOP...
- Gene Name
- COMT
- Uniprot ID
- P21964
- Uniprot Name
- Catechol O-methyltransferase
- Molecular Weight
- 30036.77 Da
References
- Raxworthy MJ, Youde IR, Gulliver PA: Catechol-O-methyltransferase: substrate-specificity and stereoselectivity for beta-adrenoceptor agents. Xenobiotica. 1986 Jan;16(1):47-52. [Article]
- Yan M, Webster LT Jr, Blumer JL: Kinetic interactions of dopamine and dobutamine with human catechol-O-methyltransferase and monoamine oxidase in vitro. J Pharmacol Exp Ther. 2002 Apr;301(1):315-21. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54