Details of the Drug

General Information of Drug (ID: DMD1B8Z)

Drug Name

Dobutamine

Synonyms

Dobutamina; Dobutaminum; Dobutamine Hcl; Dobutamine [USAN]; Dobutamine hydrobromide; LY 81929; Lilly 81929; DL-dobutamine; Dobutamina [INN-Spanish]; Dobutamine Hcl in Dextrose 5%; Dobutamine(usp); Dobutaminum [INN-Latin]; Rac-dobutamine; Racemic-Dobutamine; Dobutamine (USP/INN); Dobutamine [USAN:BAN:INN]; Dobutamine Tartrate (1:1), (S-(R*,R*))-Isomer; (+-)-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-hydroxyphenyl)-1-methylpropyl]amino}ethyl)benzene-1,2-diol; 4-(2-{[4-(4-hydroxyphenyl)butan-2-yl]amino}ethyl)benzene-1,2-diol; 4-[2-[4-(4-hydroxyphenyl)butan-2-ylamino]ethyl]benzene-1,2-diol

Indication

Disease Entry	ICD 11	Status	REF
Heart failure	BD10-BD13	Approved	[1]
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Therapeutic Class

Cardiotonic Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

301.4

Logarithm of the Partition Coefficient (xlogp)

3.4

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [2]
Clearance: The drug present in the plasma can be removed from the body at the rate of 115 mL/min/kg [3]
Elimination: 0.1% of drug is excreted from urine in the unchanged form [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 2 minutes [3]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.13272 micromolar/kg/day [4]

Chemical Identifiers

Formula: C18H23NO3
IUPAC Name: 4-[2-[4-(4-hydroxyphenyl)butan-2-ylamino]ethyl]benzene-1,2-diol
Canonical SMILES: CC(CCC1=CC=C(C=C1)O)NCCC2=CC(=C(C=C2)O)O
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
InChIKey: JRWZLRBJNMZMFE-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 36811
ChEBI ID: CHEBI:4670
CAS Number: 34368-04-2
DrugBank ID: DB00841
TTD ID: D0J7RK
INTEDE ID: DR1758

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Adrenergic receptor beta-1 (ADRB1)	TTR6W5O	ADRB1_HUMAN	Agonist	[5]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Catechol O-methyltransferase (COMT)_{Main DME}	DEV3T4A	COMT_HUMAN	Substrate	[6]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Beta-1 adrenergic receptor (ADRB1)	OTQBWN4U	ADRB1_HUMAN	Drug Response	[7]
Beta-2 adrenergic receptor (ADRB2)	OTSDOX4Q	ADRB2_HUMAN	Drug Response	[8]
Bile acid receptor (NR1H4)	OTWZLPTB	NR1H4_HUMAN	Gene/Protein Processing	[9]
Bile salt export pump (ABCB11)	OTRU7THO	ABCBB_HUMAN	Gene/Protein Processing	[10]
Cardiac phospholamban (PLN)	OTT3RRJN	PPLA_HUMAN	Drug Response	[11]
Catechol O-methyltransferase (COMT)	OTPWKTQG	COMT_HUMAN	Biotransformations	[12]
Fibroblast growth factor 2 (FGF2)	OT7YUJ9F	FGF2_HUMAN	Drug Response	[13]
Interleukin-1 beta (IL1B)	OT0DWXXB	IL1B_HUMAN	Gene/Protein Processing	[14]
Interleukin-6 (IL6)	OTUOSCCU	IL6_HUMAN	Gene/Protein Processing	[15]
Interleukin-8 (CXCL8)	OTS7T5VH	IL8_HUMAN	Gene/Protein Processing	[14]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Dobutamine

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Disease	REF
Carvedilol	DMHTEAO	Moderate	Additive hypotensive effects by the combination of Dobutamine and Carvedilol.	Heart failure [BD10-BD1Z]	[16]
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Coadministration of a Drug Treating the Disease Different from Dobutamine (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Methylene blue	DMJAPE7	Moderate	Additive hypertensive effects by the combination of Dobutamine and Methylene blue.	Acquired methaemoglobinaemia [3A93]	[17]
Droxidopa	DM5YF4M	Moderate	Additive hypertensive effects by the combination of Dobutamine and Droxidopa.	Autonomic nervous system disorder [8D87]	[18]
Levomilnacipran	DMV26S8	Moderate	Increased risk of rapid heart rate by the combination of Dobutamine and Levomilnacipran.	Chronic pain [MG30]	[19]
Selegiline	DM6034S	Moderate	Additive hypertensive effects by the combination of Dobutamine and Selegiline.	Depression [6A70-6A7Z]	[17]
Isocarboxazid	DMAF1NB	Moderate	Additive hypertensive effects by the combination of Dobutamine and Isocarboxazid.	Depression [6A70-6A7Z]	[17]
Milnacipran	DMBFE74	Moderate	Increased risk of rapid heart rate by the combination of Dobutamine and Milnacipran.	Depression [6A70-6A7Z]	[19]
Desvenlafaxine	DMHD4PE	Moderate	Additive hypertensive effects by the combination of Dobutamine and Desvenlafaxine.	Depression [6A70-6A7Z]	[19]
Procarbazine	DMIK367	Moderate	Additive hypertensive effects by the combination of Dobutamine and Procarbazine.	Hodgkin lymphoma [2B30]	[17]
Ozanimod	DMT6AM2	Moderate	Additive hypertensive effects by the combination of Dobutamine and Ozanimod.	Multiple sclerosis [8A40]	[17]
Sibutramine	DMFJTDI	Moderate	Additive hypertensive effects by the combination of Dobutamine and Sibutramine.	Obesity [5B80-5B81]	[20]
Opicapone	DM1BKA6	Moderate	Decreased metabolism of Dobutamine caused by Opicapone mediated inhibition of non-CYP450 enzyme.	Parkinsonism [8A00]	[21]
Rasagiline	DM3WKQ4	Moderate	Additive hypertensive effects by the combination of Dobutamine and Rasagiline.	Parkinsonism [8A00]	[17]
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⏷ Show the Full List of 12 DDI Information of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 535).
2	BDDCS applied to over 900 drugs
3	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
5	Beta-adrenoceptor alterations coupled with secretory response and experimental periodontitis in rat submandibular glands. Arch Oral Biol. 2008 Jun;53(6):509-16.
6	Catechol-O-methyltransferase: substrate-specificity and stereoselectivity for beta-adrenoceptor agents. Xenobiotica. 1986 Jan;16(1):47-52.
7	The Arg389Gly 1-adrenoceptor gene polymorphism influences the acute effects of -adrenoceptor blockade on contractility in the human heart. Clin Res Cardiol. 2011 Aug;100(8):641-7. doi: 10.1007/s00392-011-0288-1. Epub 2011 Feb 11.
8	A bivariate functional mapping model for identifying haplotypes that control drug response for systolic and diastolic blood pressures. Pac Symp Biocomput. 2006:572-83.
9	Investigation of imatinib and other approved drugs as starting points for antidiabetic drug discovery with FXR modulating activity. Biochem Pharmacol. 2012 Jun 15;83(12):1674-81. doi: 10.1016/j.bcp.2012.02.027. Epub 2012 Mar 7.
10	Evaluating the Role of Multidrug Resistance Protein 3 (MDR3) Inhibition in Predicting Drug-Induced Liver Injury Using 125 Pharmaceuticals. Chem Res Toxicol. 2017 May 15;30(5):1219-1229. doi: 10.1021/acs.chemrestox.7b00048. Epub 2017 May 4.
11	Chronic phospholamban inhibition prevents progressive cardiac dysfunction and pathological remodeling after infarction in rats. J Clin Invest. 2004 Mar;113(5):727-36. doi: 10.1172/JCI18716.
12	Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase. Mol Pharmacol. 2001 Feb;59(2):393-402. doi: 10.1124/mol.59.2.393.
13	Gene therapy in cardiac surgery: intramyocardial injection of naked plasmid DNA for chronic myocardial ischemia. Eur J Cardiothorac Surg. 2003 Nov;24(5):785-93. doi: 10.1016/s1010-7940(03)00455-x.
14	An in vitro coculture system of human peripheral blood mononuclear cells with hepatocellular carcinoma-derived cells for predicting drug-induced liver injury. Arch Toxicol. 2021 Jan;95(1):149-168. doi: 10.1007/s00204-020-02882-4. Epub 2020 Aug 20.
15	Myocardial ischemia induces interleukin-6 and tissue factor production in patients with coronary artery disease: a dobutamine stress echocardiography study. Circulation. 2005 Nov 22;112(21):3272-9. doi: 10.1161/CIRCULATIONAHA.104.532259. Epub 2005 Nov 14.
16	Lindenfeld JA, Lowes BD, Bristow MR "Hypotension with dobutamine: B-adrenergic antagonist selectivity at low doses of carvedilol." Ann Pharmacother 33 (1999): 1266-9. [PMID: 10630826]
17	Ban TA "Drug interactions with psychoactive drugs." Dis Nerv Syst 36 (1975): 164-6. [PMID: 1116424]
18	Product Information. Northera (droxidopa). Chelsea Therapeutics Inc, Charlotte, NC.
19	Product Information. Cymbalta (duloxetine). Lilly, Eli and Company, Indianapolis, IN.
20	Product Information. Meridia (sibutramine). Knoll Pharmaceutical Company, Whippany, NJ.
21	Illi A, Sundberg S, Ojala-Karlsson P, Korhonen P, Scheinin M, Gordin A "The effect of entacapone on the disposition and hemodynamic effects of intravenous isoproterenol and epinephrine." Clin Pharmacol Ther 58 (1995): 221-7. [PMID: 7648772]