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Record Information
Version4.0
Creation Date2012-09-06 15:16:50 UTC
Update Date2017-09-27 08:27:46 UTC
HMDB IDHMDB0014979
Secondary Accession Numbers
  • HMDB14979
Metabolite Identification
Common NameDobutamine
DescriptionDobutamine is only found in individuals that have used or taken this drug. It is a beta-2 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. [PubChem]Dobutamine directly stimulates beta-1 receptors of the heart to increase myocardial contractility and stroke volume, resulting in increased cardiac output.
Structure
Thumb
Synonyms
ValueSource
(+-)-4-(2-((3-(P-Hydroxyphenyl)-1-methylpropyl)amino)ethyl)pyrocatecholChEBI
3,4-Dihydroxy-N-[3-(4-hydroxyphenyl)-1-methylpropyl]-beta-phenylethylamineChEBI
4-{2-[3-(4-hydroxy-phenyl)-1-methyl-propylamino]-ethyl}-benzene-1,2-diolChEBI
DL-DobutamineChEBI
DobutaminaChEBI
DobutaminumChEBI
rac-DobutamineChEBI
Racemic-dobutamineChEBI
3,4-Dihydroxy-N-[3-(4-hydroxyphenyl)-1-methylpropyl]-b-phenylethylamineGenerator
3,4-Dihydroxy-N-[3-(4-hydroxyphenyl)-1-methylpropyl]-β-phenylethylamineGenerator
DobucorMeSH
DobujectMeSH
Dobutamin hexalMeSH
Dobutamin ratiopharmMeSH
Dobutamin-ratiopharmMeSH
Fresenius brand OF dobutamine hydrochlorideMeSH
Hydrochloride, dobutamineMeSH
Inibsa brand OF dobutamine hydrochlorideMeSH
Rovi brand OF dobutamine hydrochlorideMeSH
Dobutamin freseniusMeSH
Dobutamine hydrochlorideMeSH
Dobutamine tartrateMeSH
Dobutamine tartrate (1:1), (R-(r*,r*))-isomerMeSH
Dobutamine tartrate (1:1), (S-(r*,r*))-isomerMeSH
Dobutamine, (-)-isomerMeSH
Juste brand OF dobutamine hydrochlorideMeSH
Lactobionate, dobutamineMeSH
Pisa brand OF dobutamine hydrochlorideMeSH
Dobutamin solvayMeSH
Dobutamine phosphate (1:1) salt, (-)-isomerMeSH
Dobutamine, phosphate (1:1) salt (+)-isomerMeSH
Eli lilly brand OF dobutamine hydrochlorideMeSH
Irisfarma brand OF dobutamine hydrochlorideMeSH
Kendrick brand OF dobutamine hydrochlorideMeSH
Lilly brand OF dobutamine hydrochlorideMeSH
Solvay brand OF dobutamine hydrochlorideMeSH
Boehringer ingelheim brand OF dobutamine hydrochlorideMeSH
Dobutamina inibsaMeSH
Dobutamina roviMeSH
Dobutamine (+)-isomerMeSH
Dobutamine hydrobromideMeSH
Dobutamine lactobionateMeSH
DobutrexMeSH
Hexal brand OF dobutamine hydrochlorideMeSH
Hydrobromide, dobutamineMeSH
Lilly 81929MeSH
OxikenMeSH
PosijectMeSH
Tartrate, dobutamineMeSH
Ratiopharm brand OF dobutamine hydrochlorideMeSH
Chemical FormulaC18H23NO3
Average Molecular Weight301.3801
Monoisotopic Molecular Weight301.167793607
IUPAC Name4-(2-{[4-(4-hydroxyphenyl)butan-2-yl]amino}ethyl)benzene-1,2-diol
Traditional Namedobutamine
CAS Registry Number34368-04-2
SMILES
CC(CCC1=CC=C(O)C=C1)NCCC1=CC(O)=C(O)C=C1
InChI Identifier
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
InChI KeyJRWZLRBJNMZMFE-UHFFFAOYSA-N
Chemical 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
ClassPhenols
Sub ClassBenzenediols
Direct ParentCatecholamines and derivatives
Alternative Parents
Substituents
  • Catecholamine
  • Phenethylamine
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Monocyclic benzene moiety
  • Secondary aliphatic amine
  • Secondary amine
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.014 g/LNot Available
LogP3.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity88.39 m³·mol⁻¹ChemAxon
Polarizability34.44 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-057r-3900000000-f2923e02084170324b85View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0uk9-2454290000-9465513295fd096051a4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0009000000-72fe7c46458e5a5d842bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0409000000-f41b2ba5a7a16faab22eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-052r-0900000000-5a6988f6f954cc4d5970View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4r-1900000000-3760790cd7d468deb65bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4l-4900000000-8656459c9b16b99f096cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-05n0-0900000000-b4956c2ea5a7aa86eb32View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0009000000-99dd6da8a1a7db9cdda3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0f79-0903000000-297b7061da4a9bff6e29View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4r-1900000000-a5825e1ad3ae4837917cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4l-3900000000-84358b5b309fe282e24eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4l-8900000000-fbdc06bd7571ae3e38a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0419000000-f94f8045c53cdac06b38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k9j-0911000000-c07cfe14c28ee716fddbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a70-5900000000-ba6987861a46cdc959a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0109000000-83f213f0b5786d86e0deView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0429000000-a764f2b18bf3f07d9ed3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uk9-1910000000-a0ed2c4b984d7efe415fView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Dobutamine Action PathwayPw000639Pw000639 greyscalePw000639 simpleNot Available
Displaying 1 entry
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00841 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00841 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00841
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID33786
KEGG Compound IDC06967
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDobutamine
METLIN IDNot Available
PubChem Compound36811
PDB IDNot Available
ChEBI ID4670
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in magnesium ion binding
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
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 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
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
Gene Name:
ADRB1
Uniprot ID:
P08588
Molecular weight:
51322.1
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 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
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:
46458.3
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 ]