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
Thumb
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.

Pharmacology
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Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Contraindications
Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
ABeta-1 adrenergic receptor
agonist
Humans
UBeta-2 adrenergic receptor
agonist
Humans
AAlpha-1 adrenergic receptors
agonist
Humans
UEstrogen receptor alphaNot AvailableHumans
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
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Toxicity

Not Available

Pathways
PathwayCategory
Dobutamine Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
AbacavirDobutamine may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbaloparatideThe risk or severity of adverse effects can be increased when Dobutamine is combined with Abaloparatide.
AcebutololThe therapeutic efficacy of Dobutamine can be decreased when used in combination with Acebutolol.
AceclofenacAceclofenac may decrease the excretion rate of Dobutamine which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Dobutamine which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Dobutamine which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Dobutamine which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Dobutamine which could result in a higher serum level.
AclidiniumDobutamine may decrease the excretion rate of Aclidinium which could result in a higher serum level.
AcrivastineDobutamine may decrease the excretion rate of Acrivastine which could result in a higher serum level.
Interactions
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Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Dobutamine hydrochloride0WR771DJXV49745-95-1BQKADKWNRWCIJL-UHFFFAOYSA-N
Dobutamine tartrate5D1IB9AI6J101626-66-8WZIUXGZIVZDXIG-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
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
DobutamineInjection, solution200 mg/100mLIntravenousHF Acquisition Co LLC, DBA HealthFirst2019-04-07Not applicableUS flag
Dobutamine 12.5mg/mlSolution12.5 mg / mLIntravenousIvax Pharmaceuticals Incorporated1996-11-252015-10-26Canada flag
Dobutamine HydrochlorideInjection, solution400 mg/100mLIntravenousPhysicians Total Care, Inc.2007-06-13Not applicableUS flag
Dobutamine Hydrochloride in DextroseInjection200 mg/100mLIntravenousBaxter Healthcare Corporation1993-09-27Not applicableUS flag
Dobutamine Hydrochloride in DextroseInjection400 mg/100mLIntravenousA-S Medication Solutions1993-09-23Not applicableUS flag
Dobutamine Hydrochloride in DextroseInjection100 mg/100mLIntravenousBaxter Healthcare Corporation1993-09-27Not applicableUS flag
Dobutamine Hydrochloride in DextroseInjection400 mg/100mLIntravenousBaxter Healthcare Corporation1993-09-23Not applicableUS flag
Dobutamine Hydrochloride Injection-12.5mg/mlLiquid12.5 mg / mLIntravenousNovopharm Limited1997-02-012018-05-02Canada flag
Dobutamine Hydrochloride Injection-12.5mg/mlLiquid12.5 mg / mLIntravenousSanofi1997-05-211998-10-24Canada flag
Dobutamine in DextroseInjection, solution200 mg/100mLIntravenousHospira, Inc.2006-01-20Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
DobutamineInjection, solution, concentrate12.5 mg/1mLIntravenousHospira, Inc.2005-04-30Not applicableUS flag
DobutamineInjection12.5 mg/1mLIntravenousBedford Pharmaceuticals1995-01-022012-07-31US flag
DobutamineInjection, solution12.5 mg/1mLIntravenousHospira, Inc.2005-11-17Not applicableUS flag
DobutamineInjection, solution12.5 mg/1mLIntravenousGeneral Injectables and Vaccines, Inc.2014-11-10Not applicableUS flag
DOBUTamineInjection, solution, concentrate12.5 mg/1mLIntravenousHospira, Inc.1996-09-272007-08-01US flag
DobutamineInjection, solution, concentrate12.5 mg/1mLIntravenousHF Acquisition Co LLC, DBA HealthFirst2018-11-26Not applicableUS flag
DobutamineInjection, solution12.5 mg/1mLIntravenousPhysicians Total Care, Inc.2006-12-11Not applicableUS flag
Dobutamine HydrochlorideInjection, powder, lyophilized, for solution12.5 mg/1mLIntravenousGeneral Injectables & Vaccines2010-03-012016-11-02US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Dobutamine Hydrochloride in DextroseDobutamine hydrochloride (250 mg/100mL) + D-glucose monohydrate (5 g/100mL)Injection, solutionIntravenousBaxter Healthcare Corporation2005-12-142005-12-14US flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
STERILE DOBUTAMIN CON. 250 MG/20 MLDobutamine (250 mg/20ml)Injection, solutionFİLİZ İLAÇ MÜMESSİL ECZA DEPOSU TİC LTD ŞT2020-08-14Not applicableTurkey flag

Categories

ATC Codes
C01CA07 — Dobutamine
Drug Categories
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
Human Metabolome Database
HMDB0014979
KEGG Drug
D03879
KEGG Compound
C06967
PubChem Compound
36811
PubChem Substance
46505241
ChemSpider
33786
BindingDB
50325274
RxNav
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
AHFS Codes
  • 12:12.08.08 — Selective Beta 1-adrenergic Agonists
  • 12:12.00 — Sympathomimetic (Adrenergic) Agents

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedDiagnosticFree Flap / Head and Neck Carcinoma / Hypotension / Oral Cancers1
4CompletedPreventionMitral Valve Stenosis With Incompetence or Regurgitation1
4CompletedTreatmentAcute Coronary Syndrome (ACS) / Low Cardiac Output Syndrome / Pulmonary Edemas / Shock, Cardiogenic1
4CompletedTreatmentMajor Abdominal Surgery1
4Not Yet RecruitingOtherGeneral Anesthesia1
4Not Yet RecruitingPreventionNfuence of Vasoactive Medication on Spinal Oxygenation1
4RecruitingOtherHealthy Volunteers / Heart Failure1
4SuspendedTreatmentHeart Failure1
4Unknown StatusSupportive CareCardiovascular Disease (CVD)1
4Unknown StatusTreatmentArterial Hypotension1

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
FormRouteStrength
InjectionIntravenous1000 mcg/ml
InjectionIntravenous2000 mcg/ml
InjectionIntravenous4000 mcg/ml
Injection, solution, concentrateParenteral
SolutionParenteral
SolutionParenteral280 mg
SolutionIntravenous250 mg
SolutionIntravenous12.5 mg
Injection, solution, concentrateIntravenous
Injection, solution, concentrateIntravenous; Parenteral
SolutionParenteral250 mg
Injection, solution
InjectionIntravenous12.5 mg/1mL
Injection, solutionIntravenous12.5 mg/1mL
Injection, solution, concentrateIntravenous12.5 mg/1mL
InjectionIntravenous
Injection, powder, lyophilized, for solutionIntravenous12.5 mg/1mL
Injection, solutionIntravenous400 mg/100mL
InjectionIntravenous100 mg/100mL
InjectionIntravenous200 mg/100mL
InjectionIntravenous400 mg/100mL
Injection, solutionIntravenous
Injection, solutionIntravenous100 mg/100mL
Injection, solutionIntravenous200 mg/100mL
SolutionIntravenous12.5 mg / mL
LiquidIntravenous12.5 mg / mL
SolutionIntravenous250 mg / 20 mL
Injection, solution50 mg/1ml
Injection, solutionIntravenous
SolutionIntravenous
Injection, solutionParenteral
Solution12.5 mg/1ml
Solution50 mg/1ml
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)184-186J. 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-0009000000-72fe7c46458e5a5d842b
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-0409000000-f41b2ba5a7a16faab22e
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-052r-0900000000-5a6988f6f954cc4d5970
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4r-1900000000-3760790cd7d468deb65b
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4l-4900000000-8656459c9b16b99f096c
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-05n0-0900000000-b4956c2ea5a7aa86eb32
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0009000000-99dd6da8a1a7db9cdda3
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0f79-0903000000-297b7061da4a9bff6e29
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4r-1900000000-a5825e1ad3ae4837917c
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4l-3900000000-84358b5b309fe282e24e
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4l-8900000000-fbdc06bd7571ae3e38a5

Targets

Drugtargets
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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
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  5. 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
  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. [Article]
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:
References
  1. 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
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
  1. 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
  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. [Article]
  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. [Article]

Drug created on June 13, 2005 13:24 / Updated on June 17, 2021 15:27