dobutamine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
dopaminergic agents dopamine derivatives used as cardiac stimulant/antihypertensives/diuretics 937 34368-04-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • dobutamine
  • dobutamine hydrochloride
  • dobutamine HCl
A catecholamine derivative with specificity for BETA-1 ADRENERGIC RECEPTORS. It is commonly used as a cardiotonic agent after CARDIAC SURGERY and during DOBUTAMINE STRESS ECHOCARDIOGRAPHY.
  • Molecular weight: 301.39
  • Formula: C18H23NO3
  • CLOGP: 2.43
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 4
  • TPSA: 72.72
  • ALOGS: -4.34
  • ROTB: 7

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.50 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.10 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.13 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
CL (Clearance) 115 mL/min/kg Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
July 18, 1978 FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Stress cardiomyopathy 235.01 27.26 67 4446 7717 46673832
Cardiogenic shock 174.76 27.26 64 4449 16320 46665229
Multiple organ dysfunction syndrome 133.67 27.26 75 4438 51635 46629914
Cardiac failure 81.51 27.26 65 4448 79883 46601666
Renal injury 75.48 27.26 30 4483 9511 46672038
Renal failure 74.79 27.26 72 4441 113522 46568027
Fear 69.31 27.26 33 4480 16139 46665410
Ventricular tachycardia 58.92 27.26 30 4483 16937 46664612
Anhedonia 56.56 27.26 25 4488 10310 46671239
Septic shock 50.43 27.26 43 4470 57850 46623699
Cardiac arrest 47.91 27.26 51 4462 90348 46591201
Injury 47.39 27.26 37 4476 43990 46637559
Emotional distress 47.15 27.26 32 4481 30675 46650874
Ventricular fibrillation 44.84 27.26 22 4491 11474 46670075
Respiratory failure 44.18 27.26 50 4463 94766 46586783
Haemodynamic instability 43.28 27.26 19 4494 7706 46673843
Renal impairment 41.24 27.26 43 4470 74329 46607220
Local anaesthetic systemic toxicity 40.61 27.26 9 4504 369 46681180
Unevaluable event 39.59 27.26 34 4479 46141 46635408
Cardiovascular insufficiency 37.99 27.26 11 4502 1330 46680219
Right ventricular failure 37.88 27.26 22 4491 16071 46665478
Ureaplasma infection 33.57 27.26 8 4505 453 46681096
Fatigue 33.22 27.26 9 4504 608688 46072861
Hypotension 32.24 27.26 70 4443 232519 46449030
Cardiomyopathy 30.16 27.26 19 4494 16054 46665495
Pulmonary hypertension 27.83 27.26 25 4488 35968 46645581

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Multiple organ dysfunction syndrome 209.85 22.15 132 4998 63355 29883993
Cardiogenic shock 159.70 22.15 71 5059 16790 29930558
Stress 112.01 22.15 59 5071 20176 29927172
Fear 97.37 22.15 44 5086 10781 29936567
Injury 97.10 22.15 55 5075 21676 29925672
Appendicolith 91.85 22.15 23 5107 896 29946452
Renal injury 87.85 22.15 42 5088 11687 29935661
Anhedonia 84.84 22.15 37 5093 8332 29939016
Emotional distress 78.88 22.15 43 5087 15722 29931626
Unevaluable event 75.58 22.15 54 5076 31731 29915617
Ventricular fibrillation 72.18 22.15 40 5090 15098 29932250
Appendicitis 58.50 22.15 26 5104 6118 29941230
Renal failure 49.33 22.15 83 5047 128883 29818465
Ventricular tachycardia 48.71 22.15 37 5093 23825 29923523
Cardiac failure 48.02 22.15 65 5065 83353 29863995
Right ventricular failure 46.03 22.15 24 5106 8012 29939336
Shock 41.34 22.15 33 5097 22826 29924522
Renal impairment 40.17 22.15 60 5070 84124 29863224
Eosinophilic myocarditis 38.81 22.15 10 5120 437 29946911
Fatigue 38.18 22.15 5 5125 320668 29626680
Myocardial rupture 36.20 22.15 8 5122 179 29947169
Anxiety 33.19 22.15 57 5073 89814 29857534
Ascites 32.08 22.15 35 5095 35886 29911462
Low cardiac output syndrome 31.54 22.15 8 5122 328 29947020
Toxic epidermal necrolysis 30.53 22.15 25 5105 17915 29929433
Stress cardiomyopathy 30.25 22.15 11 5119 1538 29945810
Drug ineffective 29.86 22.15 126 5004 340261 29607087
Hypotension 29.42 22.15 88 5042 200477 29746871
Sepsis 28.18 22.15 71 5059 146324 29801024
Cardiac arrest 28.06 22.15 54 5076 92796 29854552
Cardiomyopathy 25.55 22.15 21 5109 15122 29932226
Pulmonary haematoma 25.47 22.15 5 5125 61 29947287
General physical health deterioration 23.02 22.15 52 5078 99892 29847456

Pharmacologic Action:

SourceCodeDescription
ATC C01CA07 CARDIOVASCULAR SYSTEM
CARDIAC THERAPY
CARDIAC STIMULANTS EXCL. CARDIAC GLYCOSIDES
Adrenergic and dopaminergic agents
FDA MoA N0000000245 Adrenergic beta-Agonists
FDA EPC N0000175555 beta-Adrenergic Agonist
MeSH PA D018663 Adrenergic Agents
MeSH PA D000322 Adrenergic Agonists
MeSH PA D058665 Adrenergic beta-1 Receptor Agonists
MeSH PA D000318 Adrenergic beta-Agonists
MeSH PA D002316 Cardiotonic Agents
MeSH PA D002317 Cardiovascular Agents
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D020011 Protective Agents
MeSH PA D013566 Sympathomimetics
CHEBI has role CHEBI:35522 beta-adrenergic receptor agonist
CHEBI has role CHEBI:35524 sympathomimetic
CHEBI has role CHEBI:38147 cardiotonic drugs

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Cardiogenic shock indication 89138009
Decompensated cardiac failure indication 195111005
Organic Cardiac Disease indication
Cardiac Decompensation Post Cardiac Surgery indication
Cardiac Decompensation indication
Ventricular premature beats contraindication 17338001
Myocardial infarction contraindication 22298006 DOID:5844
Hypovolemia contraindication 28560003
Hypertensive disorder contraindication 38341003 DOID:10763
Hypokalemia contraindication 43339004
Atrial fibrillation contraindication 49436004 DOID:0060224
Aortic valve stenosis contraindication 60573004 DOID:1712
Idiopathic hypertrophic subaortic stenosis contraindication 360465008

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.98 acidic
pKa2 10.59 acidic
pKa3 13.49 acidic
pKa4 9.03 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Beta-2 adrenergic receptor GPCR AGONIST EC50 6.20 WOMBAT-PK CHEMBL
Beta-1 adrenergic receptor GPCR AGONIST EC50 5.50 WOMBAT-PK CHEMBL
Sodium-dependent noradrenaline transporter Transporter Ki 6.42 DRUG MATRIX
Alpha-2B adrenergic receptor GPCR Ki 5.87 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 5.77 DRUG MATRIX
Sodium-dependent dopamine transporter Transporter Ki 6.91 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR Ki 7.35 DRUG MATRIX
Epidermal growth factor receptor Kinase IC50 5.26 DRUG MATRIX
Tyrosine-protein kinase Lck Kinase IC50 5.26 DRUG MATRIX
Tyrosine-protein kinase Fyn Kinase IC50 5.40 DRUG MATRIX
Carbonic anhydrase 5A, mitochondrial Enzyme Ki 6.14 CHEMBL
Carbonic anhydrase 2 Enzyme Ki 6.32 CHEMBL
Carbonic anhydrase 14 Enzyme Ki 4.92 CHEMBL
Carbonic anhydrase 7 Enzyme Ki 5.37 CHEMBL
Carbonic anhydrase 12 Enzyme Ki 5.36 CHEMBL
Carbonic anhydrase 9 Enzyme Ki 5.01 CHEMBL
Carbonic anhydrase 4 Enzyme Ki 5.05 CHEMBL
Carbonic anhydrase 1 Enzyme Ki 5.72 CHEMBL
Carbonic anhydrase 5B, mitochondrial Enzyme Ki 6.05 CHEMBL
Carbonic anhydrase 3 Enzyme Ki 5.13 CHEMBL
Carbonic anhydrase 13 Enzyme Ki 5.02 CHEMBL
Carbonic anhydrase 6 Enzyme Ki 5.02 CHEMBL
Catechol O-methyltransferase Enzyme Km 4.30 WOMBAT-PK
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 5.98 DRUG MATRIX
Sodium-dependent serotonin transporter Transporter Ki 6.00 DRUG MATRIX
Arachidonate 15-lipoxygenase Enzyme IC50 6.22 DRUG MATRIX
Alpha-1B adrenergic receptor GPCR Ki 6.73 DRUG MATRIX
Membrane-associated progesterone receptor component 1 Membrane receptor Ki 5.80 DRUG MATRIX
Carbonic anhydrase 15 Enzyme Ki 6.41 CHEMBL
Alpha-1A adrenergic receptor GPCR IC50 6.96 CHEMBL

External reference:

IDSource
4019730 VUID
N0000147822 NUI
D00632 KEGG_DRUG
49745-95-1 SECONDARY_CAS_RN
4017541 VANDF
4019730 VANDF
C0012963 UMLSCUI
CHEBI:4670 CHEBI
Y00 PDB_CHEM_ID
CHEMBL926 ChEMBL_ID
CHEMBL1200418 ChEMBL_ID
DB00841 DRUGBANK_ID
D004280 MESH_DESCRIPTOR_UI
36811 PUBCHEM_CID
535 IUPHAR_LIGAND_ID
3340 INN_ID
3S12J47372 UNII
203121 RXNORM
2871 MMSL
4625 MMSL
d00215 MMSL
000614 NDDF
000615 NDDF
26523005 SNOMEDCT_US
387145002 SNOMEDCT_US
90118002 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Dobutamine Hydrochloride in Dextrose HUMAN PRESCRIPTION DRUG LABEL 1 0338-1073 INJECTION 100 mg INTRAVENOUS NDA 18 sections
Dobutamine Hydrochloride in Dextrose HUMAN PRESCRIPTION DRUG LABEL 1 0338-1075 INJECTION 200 mg INTRAVENOUS NDA 18 sections
Dobutamine Hydrochloride in Dextrose HUMAN PRESCRIPTION DRUG LABEL 1 0338-1077 INJECTION 400 mg INTRAVENOUS NDA 18 sections
DOBUTAMINE HUMAN PRESCRIPTION DRUG LABEL 1 0409-2344 INJECTION, SOLUTION, CONCENTRATE 12.50 mg INTRAVENOUS ANDA 21 sections
DOBUTAMINE HUMAN PRESCRIPTION DRUG LABEL 1 0409-2344 INJECTION, SOLUTION, CONCENTRATE 12.50 mg INTRAVENOUS ANDA 21 sections
Dobutamine in Dextrose HUMAN PRESCRIPTION DRUG LABEL 1 0409-2346 INJECTION, SOLUTION 100 mg INTRAVENOUS NDA 12 sections
Dobutamine in Dextrose HUMAN PRESCRIPTION DRUG LABEL 1 0409-2347 INJECTION, SOLUTION 200 mg INTRAVENOUS NDA 12 sections
Dobutamine in Dextrose HUMAN PRESCRIPTION DRUG LABEL 1 0409-3724 INJECTION, SOLUTION 400 mg INTRAVENOUS NDA 12 sections
Dobutamine Hydrochloride in Dextrose HUMAN PRESCRIPTION DRUG LABEL 1 50090-4562 INJECTION 400 mg INTRAVENOUS NDA 18 sections
DOBUTAMINE HUMAN PRESCRIPTION DRUG LABEL 1 51662-1330 INJECTION, SOLUTION 200 mg INTRAVENOUS NDA 12 sections
DOBUTAMINE HUMAN PRESCRIPTION DRUG LABEL 1 51662-1337 INJECTION, SOLUTION, CONCENTRATE 12.50 mg INTRAVENOUS ANDA 12 sections
Dobutamine HUMAN PRESCRIPTION DRUG LABEL 1 54868-5717 INJECTION, SOLUTION 12.50 mg INTRAVENOUS ANDA 11 sections
Dobutamine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 54868-5777 INJECTION, SOLUTION 400 mg INTRAVENOUS NDA 12 sections