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Identification
NameDobutamine
Accession NumberDB00841  (APRD00122)
TypeSmall Molecule
GroupsApproved
Description

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.

Structure
Thumb
Synonyms
(+-)-4-(2-((3-(P-Hydroxyphenyl)-1-methylpropyl)amino)ethyl)pyrocatechol
3,4-Dihydroxy-N-[3-(4-hydroxyphenyl)-1-methylpropyl]-beta-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
External Identifiers
  • 46236
  • 81929
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dobutamine 12.5mg/mlsolution12.5 mgintravenousIvax Pharmaceuticals Incorporated1996-11-252015-10-26Canada
Dobutamine Hydrochlorideinjection, solution400 mg/100mLintravenousPhysicians Total Care, Inc.2007-06-13Not applicableUs
Dobutamine Hydrochloride In Dextroseinjection100 mg/100mLintravenousBaxter Healthcare Corporation1993-09-27Not applicableUs
Dobutamine Hydrochloride In Dextroseinjection, solution400 mg/100mLintravenousHospira, Inc.1993-10-19Not applicableUs
Dobutamine Hydrochloride In Dextroseinjection, solution200 mg/100mLintravenousHospira, Inc.1993-10-19Not applicableUs
Dobutamine Hydrochloride In Dextroseinjection, solution100 mg/100mLintravenousHospira, Inc.1993-10-19Not applicableUs
Dobutamine Hydrochloride In Dextroseinjection400 mg/100mLintravenousBaxter Healthcare Corporation1993-09-23Not applicableUs
Dobutamine Hydrochloride In Dextroseinjection200 mg/100mLintravenousBaxter Healthcare Corporation1993-09-27Not applicableUs
Dobutamine Hydrochloride Injection USPsolution12.5 mgintravenousHospira Healthcare Corporation1996-10-24Not applicableCanada
Dobutamine Hydrochloride Injection-12.5mg/mlliquid12.5 mgintravenousSanofi Canada, Inc.1997-05-211998-10-24Canada
Dobutamine Hydrochloride Injection-12.5mg/mlliquid12.5 mgintravenousNovopharm Limited1997-02-01Not applicableCanada
Dobutamine Injection Sdzsolution12.5 mgintravenousSandoz Canada Incorporated2013-12-04Not applicableCanada
Dobutamine Injection USPsolution12.5 mgintravenousSterimax IncNot applicableNot applicableCanada
Dobutamine Injection USPliquid12.5 mgintravenousSandoz Canada Incorporated2000-10-02Not applicableCanada
Dobutrexsolution12.5 mgintravenousPharmaceutical Partners Of Canada Inc1988-12-312008-02-13Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dobutamineinjection, solution12.5 mg/mLintravenousHospira, Inc.1995-02-16Not applicableUs
Dobutamineinjection, solution12.5 mg/mLintravenousPhysicians Total Care, Inc.2006-12-11Not applicableUs
Dobutamineinjection, solution12.5 mg/mLintravenousGENERAL INJECTABLES AND VACCINES, INC.2014-11-10Not applicableUs
Dobutamine Hydrochlorideinjection, powder, lyophilized, for solution12.5 mg/mLintravenousGeneral Injectables & Vaccines, Inc2010-03-01Not applicableUs
Dobutamine Hydrochlorideinjection, solution, concentrate12.5 mg/mLintravenousHospira, Inc.1993-11-29Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
DobujectBayer
DobusafeClaris
DobutaminSandoz
DobutanDemo
DobutelNovell
DobutilMeizler
DopminMylan Seiyaku
InotrexLilly
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Dobutamine hydrochloride
Thumb
  • InChI Key: BQKADKWNRWCIJL-UHFFFAOYNA-N
  • Monoisotopic Mass: 337.144471346
  • Average Mass: 337.841
DBSALT000711
Categories
UNII3S12J47372
CAS number34368-04-2
WeightAverage: 301.3801
Monoisotopic: 301.167793607
Chemical FormulaC18H23NO3
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenols and derivatives
Direct ParentCatecholamines and derivatives
Alternative Parents
Substituents
  • Catecholamine
  • Phenylpropylamine
  • Phenethylamine
  • Aralkylamine
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor 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
PharmacodynamicsDobutamine 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 little effect on beta-2 or alpha receptors. It does not cause the release of endogenous norepinephrine, as does dopamine. Dobutamine is 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.
Mechanism of actionDobutamine directly stimulates beta-1 receptors of the heart to increase myocardial contractility and stroke volume, resulting in increased cardiac output.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationIn human urine, the major excretion products are the conjugates of dobutamine and 3-O-methyl dobutamine.
Half life2 minutes
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Dobutamine Action PathwayDrug actionSMP00662
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9937
Blood Brain Barrier-0.7448
Caco-2 permeable+0.5305
P-glycoprotein substrateSubstrate0.7571
P-glycoprotein inhibitor INon-inhibitor0.8782
P-glycoprotein inhibitor IINon-inhibitor0.8383
Renal organic cation transporterNon-inhibitor0.6336
CYP450 2C9 substrateNon-substrate0.7235
CYP450 2D6 substrateSubstrate0.6265
CYP450 3A4 substrateNon-substrate0.5296
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8231
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8827
Ames testNon AMES toxic0.7215
CarcinogenicityNon-carcinogens0.9306
BiodegradationNot ready biodegradable0.9256
Rat acute toxicity2.2261 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.828
hERG inhibition (predictor II)Inhibitor0.8367
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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
Dosage forms
FormRouteStrength
Injection, solutionintravenous12.5 mg/mL
Injection, powder, lyophilized, for solutionintravenous12.5 mg/mL
Injection, solution, concentrateintravenous12.5 mg/mL
Injectionintravenous100 mg/100mL
Injectionintravenous200 mg/100mL
Injectionintravenous400 mg/100mL
Injection, solutionintravenous100 mg/100mL
Injection, solutionintravenous200 mg/100mL
Injection, solutionintravenous400 mg/100mL
Solutionintravenous12.5 mg
Liquidintravenous12.5 mg
Prices
Unit descriptionCostUnit
Dobutamine 12.5 mg/ml vial0.18USD ml
Dobutamine 250 mg-d5w 500 ml0.09USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point184-186J. Mills, R. R. Tuttle, U.S. Patent 3,987,200 (1976).
logP3.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0137 mg/mLALOGPS
logP2.97ALOGPS
logP2.62ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)10.14ChemAxon
pKa (Strongest Basic)9.27ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area72.72 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity88.39 m3·mol-1ChemAxon
Polarizability34.44 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
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 ReferencesNot Available
External Links
ATC CodesC01CA07
AHFS Codes
  • 12:12.08.08
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Dobutamine.
AcetaminophenThe risk or severity of adverse effects can be increased when Dobutamine is combined with Acetaminophen.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Dobutamine is combined with Acetylsalicylic acid.
AminophyllineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Aminophylline.
AmphetamineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Amphetamine.
ArformoterolThe risk or severity of adverse effects can be increased when Dobutamine is combined with Arformoterol.
ArmodafinilThe risk or severity of adverse effects can be increased when Dobutamine is combined with Armodafinil.
ArticaineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Articaine.
AtomoxetineAtomoxetine may increase the hypertensive activities of Dobutamine.
BenzphetamineThe risk or severity of adverse effects can be increased when Benzphetamine is combined with Dobutamine.
ButalbitalThe risk or severity of adverse effects can be increased when Dobutamine is combined with Butalbital.
CaffeineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Caffeine.
Calcium AcetateThe therapeutic efficacy of Dobutamine can be decreased when used in combination with Calcium Acetate.
Calcium carbonateThe therapeutic efficacy of Dobutamine can be decreased when used in combination with Calcium carbonate.
Calcium ChlorideThe therapeutic efficacy of Dobutamine can be decreased when used in combination with Calcium Chloride.
Calcium citrateThe therapeutic efficacy of Dobutamine can be decreased when used in combination with Calcium citrate.
Calcium gluconateThe therapeutic efficacy of Dobutamine can be decreased when used in combination with Calcium gluconate.
ChlorphentermineThe risk or severity of adverse effects can be increased when Chlorphentermine is combined with Dobutamine.
ClenbuterolThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Dobutamine.
CocaineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Cocaine.
DexmethylphenidateThe risk or severity of adverse effects can be increased when Dobutamine is combined with Dexmethylphenidate.
DextroamphetamineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Dextroamphetamine.
DiethylpropionThe risk or severity of adverse effects can be increased when Dobutamine is combined with Diethylpropion.
DihydrocodeineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Dihydrocodeine.
DipivefrinThe risk or severity of adverse effects can be increased when Dobutamine is combined with Dipivefrin.
DopamineThe risk or severity of adverse effects can be increased when Dopamine is combined with Dobutamine.
DoxapramThe risk or severity of adverse effects can be increased when Dobutamine is combined with Doxapram.
DoxofyllineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Doxofylline.
DronabinolDronabinol may increase the tachycardic activities of Dobutamine.
DyphyllineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Dyphylline.
EphedrineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Ephedrine.
EpinephrineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Epinephrine.
FenoterolThe risk or severity of adverse effects can be increased when Fenoterol is combined with Dobutamine.
Fluticasone PropionateThe risk or severity of adverse effects can be increased when Dobutamine is combined with Fluticasone Propionate.
FormoterolThe risk or severity of adverse effects can be increased when Formoterol is combined with Dobutamine.
IndacaterolThe risk or severity of adverse effects can be increased when Dobutamine is combined with Indacaterol.
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Dobutamine.
Ipratropium bromideThe risk or severity of adverse effects can be increased when Dobutamine is combined with Ipratropium bromide.
IsomethepteneThe risk or severity of adverse effects can be increased when Dobutamine is combined with Isometheptene.
IsoprenalineThe risk or severity of adverse effects can be increased when Isoprenaline is combined with Dobutamine.
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Dobutamine.
LevonordefrinThe risk or severity of adverse effects can be increased when Dobutamine is combined with Levonordefrin.
LinezolidLinezolid may increase the hypertensive activities of Dobutamine.
LisdexamfetamineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Lisdexamfetamine.
MephentermineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Dobutamine.
MepivacaineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Mepivacaine.
MetaraminolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Dobutamine.
MethamphetamineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Dobutamine.
MethoxamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Dobutamine.
MethylphenidateThe risk or severity of adverse effects can be increased when Dobutamine is combined with Methylphenidate.
MidodrineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Midodrine.
ModafinilThe risk or severity of adverse effects can be increased when Dobutamine is combined with Modafinil.
NabiloneNabilone may increase the tachycardic activities of Dobutamine.
NaphazolineThe risk or severity of adverse effects can be increased when Naphazoline is combined with Dobutamine.
NorepinephrineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Norepinephrine.
OlodaterolThe risk or severity of adverse effects can be increased when Dobutamine is combined with Olodaterol.
OrciprenalineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Dobutamine.
OxymetazolineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Dobutamine.
PhendimetrazineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Phendimetrazine.
PheniramineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Pheniramine.
PhenmetrazineThe risk or severity of adverse effects can be increased when Phenmetrazine is combined with Dobutamine.
PhentermineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Phentermine.
PhenylephrineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Phenylephrine.
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Dobutamine.
PirbuterolThe risk or severity of adverse effects can be increased when Dobutamine is combined with Pirbuterol.
PropylhexedrineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Propylhexedrine.
PseudoephedrineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Pseudoephedrine.
RacepinephrineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Racepinephrine.
RitodrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Dobutamine.
SalbutamolThe risk or severity of adverse effects can be increased when Dobutamine is combined with Salbutamol.
SalmeterolThe risk or severity of adverse effects can be increased when Salmeterol is combined with Dobutamine.
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Dobutamine.
TerbutalineThe risk or severity of adverse effects can be increased when Terbutaline is combined with Dobutamine.
TheophyllineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Theophylline.
TolcaponeThe metabolism of Dobutamine can be decreased when combined with Tolcapone.
TriprolidineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Triprolidine.
VilanterolThe risk or severity of adverse effects can be increased when Dobutamine is combined with Vilanterol.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
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 equal affinity. Mediates Ras activation through G(s)-alpha- and cAMP-mediated signaling.
Gene Name:
ADRB1
Uniprot ID:
P08588
Molecular Weight:
51322.1 Da
References
  1. 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. [PubMed:12098582 ]
  2. 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. [PubMed:15564877 ]
  3. 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. [PubMed:16325050 ]
  4. 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. [PubMed:16627864 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
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 30-fold greater affinity than it does norepinephrine.
Gene Name:
ADRB2
Uniprot ID:
P07550
Molecular Weight:
46458.32 Da
References
  1. 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. [PubMed:9279221 ]

Enzymes

Kind
Protein
Organism
Human
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-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular Weight:
30036.77 Da
References
  1. Raxworthy MJ, Youde IR, Gulliver PA: Catechol-O-methyltransferase: substrate-specificity and stereoselectivity for beta-adrenoceptor agents. Xenobiotica. 1986 Jan;16(1):47-52. [PubMed:2868577 ]
  2. 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. [PubMed:11907189 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on December 05, 2014 11:54