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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:44 UTC
HMDB IDHMDB0014979
Secondary Accession Numbers
  • HMDB14979
Metabolite Identification
Common NameDobutamine
DescriptionDobutamine, also known as dobucor or dobuject, belongs to the class of organic compounds known as catecholamines and derivatives. Catecholamines and derivatives are compounds containing 4-(2-Aminoethyl)pyrocatechol [4-(2-aminoethyl)benzene-1,2-diol] or a derivative thereof formed by substitution. It does not cause the release of endogenous norepinephrine, as does dopamine. Dobutamine is a very strong basic compound (based on its pKa). Dobutamine acts primarily on beta-1 adrenergic receptors, with negligible effects on beta-2 or alpha receptors. In humans, dobutamine is involved in dobutamine action pathway. 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 is only found in individuals that have used or taken this drug.
Structure
Data?1582753244
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
DobucorHMDB
DobujectHMDB
Dobutamin hexalHMDB
Dobutamin ratiopharmHMDB
Dobutamin-ratiopharmHMDB
Fresenius brand OF dobutamine hydrochlorideHMDB
Hydrochloride, dobutamineHMDB
Inibsa brand OF dobutamine hydrochlorideHMDB
Rovi brand OF dobutamine hydrochlorideHMDB
Dobutamin freseniusHMDB
Dobutamine hydrochlorideHMDB
Dobutamine tartrateHMDB
Dobutamine tartrate (1:1), (R-(r*,r*))-isomerHMDB
Dobutamine tartrate (1:1), (S-(r*,r*))-isomerHMDB
Dobutamine, (-)-isomerHMDB
Juste brand OF dobutamine hydrochlorideHMDB
Lactobionate, dobutamineHMDB
Pisa brand OF dobutamine hydrochlorideHMDB
Dobutamin solvayHMDB
Dobutamine phosphate (1:1) salt, (-)-isomerHMDB
Dobutamine, phosphate (1:1) salt (+)-isomerHMDB
Eli lilly brand OF dobutamine hydrochlorideHMDB
Irisfarma brand OF dobutamine hydrochlorideHMDB
Kendrick brand OF dobutamine hydrochlorideHMDB
Lilly brand OF dobutamine hydrochlorideHMDB
Solvay brand OF dobutamine hydrochlorideHMDB
Boehringer ingelheim brand OF dobutamine hydrochlorideHMDB
Dobutamina inibsaHMDB
Dobutamina roviHMDB
Dobutamine (+)-isomerHMDB
Dobutamine hydrobromideHMDB
Dobutamine lactobionateHMDB
DobutrexHMDB
Hexal brand OF dobutamine hydrochlorideHMDB
Hydrobromide, dobutamineHMDB
Lilly 81929HMDB
OxikenHMDB
PosijectHMDB
Tartrate, dobutamineHMDB
Ratiopharm brand OF dobutamine hydrochlorideHMDB
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
Description belongs to the class of organic compounds known as catecholamines and derivatives. Catecholamines and derivatives 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:

Process

Naturally occurring process:

Role

Industrial application:

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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-057r-3900000000-f2923e02084170324b85Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0uk9-2454290000-9465513295fd096051a4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0009000000-72fe7c46458e5a5d842bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0409000000-f41b2ba5a7a16faab22eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-052r-0900000000-5a6988f6f954cc4d5970Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4r-1900000000-3760790cd7d468deb65bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4l-4900000000-8656459c9b16b99f096cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-05n0-0900000000-b4956c2ea5a7aa86eb32Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0009000000-99dd6da8a1a7db9cdda3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0f79-0903000000-297b7061da4a9bff6e29Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4r-1900000000-a5825e1ad3ae4837917cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4l-3900000000-84358b5b309fe282e24eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4l-8900000000-fbdc06bd7571ae3e38a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0419000000-f94f8045c53cdac06b38Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k9j-0911000000-c07cfe14c28ee716fddbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a70-5900000000-ba6987861a46cdc959a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0109000000-83f213f0b5786d86e0deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0429000000-a764f2b18bf3f07d9ed3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uk9-1910000000-a0ed2c4b984d7efe415fSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00841 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00841 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00841
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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 ]