DOPEXAMINE

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H32N2O2
Molecular Weight	356.5017
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC=C(CCNCCCCCCNCCC2=CC=CC=C2)C=C1O

InChI

InChIKey=RYBJORHCUPVNMB-UHFFFAOYSA-N

InChI=1S/C22H32N2O2/c25-21-11-10-20(18-22(21)26)13-17-24-15-7-2-1-6-14-23-16-12-19-8-4-3-5-9-19/h3-5,8-11,18,23-26H,1-2,6-7,12-17H2

HIDE SMILES / InChI

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/1970288

Dopexamine hydrochloride is a synthetic catecholamine, structurally related to dopamine, with marked intrinsic agonist activity at beta 2-adrenoceptors, lesser agonist activity at dopamine DA1- and DA2-receptors and beta 1-adrenoceptors, and an inhibitory action on the neuronal catecholamine uptake mechanism. The drug is administered by intravenous infusion, and is characterized by a rapid onset and short duration of action. Dopexamine is being tested as a treatment for heart failure and sepsis.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
D(2) dopamine receptor 58 Target ID: P14416 Gene ID: 1813.0 Gene Symbol: DRD2 Target Organism: Homo sapiens (Human) Sources: http://www.ncbi.nlm.nih.gov/pubmed/1363232	Agonist 2752
Beta-2 adrenergic receptor 209 Target ID: CHEMBL210 Sources: http://www.ncbi.nlm.nih.gov/pubmed/1363232	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Heart failure 106 Sources: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC481901/pdf/brheartj00117-0087.pdf	Primary		Phase II 1147	Unknown Approved Use Unknown
Septic shock 21 Sources: https://clinicaltrials.gov/ct2/show/NCT00134212	Primary		Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
124 mg/L REVIEW https://pubmed.ncbi.nlm.nih.gov/1970288/	180 μg/kg single, intravenous dose: 180 μg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		DOPEXAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
236 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8148227/	2 μg/kg/min single, intravenous dose: 2 μg/kg/min route of administration: Intravenous experiment type: SINGLE co-administered:		DOPEXAMINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
7 min REVIEW https://pubmed.ncbi.nlm.nih.gov/1970288/	180 μg/kg single, intravenous dose: 180 μg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		DOPEXAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
4 ug/kg/min 1 times / day multiple, intravenous Highest studied dose Dose: 4 ug/kg/min, 1 times / day Route: intravenous Route: multiple Dose: 4 ug/kg/min, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8850384/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8850384/	Disc. AE: Sinus tachycardia, Respiratory distress... AEs leading to discontinuation/dose reduction: Sinus tachycardia (5%) Respiratory distress (5%) Fatigue (5%) Chest tightness (5%) Sources: https://pubmed.ncbi.nlm.nih.gov/8850384/
1.2 ug/kg/min single, intravenous Studied dose Dose: 1.2 ug/kg/min Route: intravenous Route: single Dose: 1.2 ug/kg/min Sources: https://pubmed.ncbi.nlm.nih.gov/7915979/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7915979/	Other AEs: Supraventricular tachycardia... Other AEs: Supraventricular tachycardia (40%) Sources: https://pubmed.ncbi.nlm.nih.gov/7915979/

AEs

AE	Significance	Dose	Population
Chest tightness	5% Disc. AE	4 ug/kg/min 1 times / day multiple, intravenous Highest studied dose Dose: 4 ug/kg/min, 1 times / day Route: intravenous Route: multiple Dose: 4 ug/kg/min, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8850384/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8850384/
Fatigue	5% Disc. AE	4 ug/kg/min 1 times / day multiple, intravenous Highest studied dose Dose: 4 ug/kg/min, 1 times / day Route: intravenous Route: multiple Dose: 4 ug/kg/min, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8850384/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8850384/
Respiratory distress	5% Disc. AE	4 ug/kg/min 1 times / day multiple, intravenous Highest studied dose Dose: 4 ug/kg/min, 1 times / day Route: intravenous Route: multiple Dose: 4 ug/kg/min, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8850384/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8850384/
Sinus tachycardia	5% Disc. AE	4 ug/kg/min 1 times / day multiple, intravenous Highest studied dose Dose: 4 ug/kg/min, 1 times / day Route: intravenous Route: multiple Dose: 4 ug/kg/min, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8850384/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8850384/
Supraventricular tachycardia	40%	1.2 ug/kg/min single, intravenous Studied dose Dose: 1.2 ug/kg/min Route: intravenous Route: single Dose: 1.2 ug/kg/min Sources: https://pubmed.ncbi.nlm.nih.gov/7915979/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7915979/

PubMed

Title	Date	PubMed
Is dopexamine superior to dopamine in the treatment of multiple trauma patients--a prospective, double-blind, randomised study.	2010-05	19595327
Dopexamine and survival: areas of consistency.	2009-11	19825065
Pharmacological interventions for ischaemia reperfusion injury in liver resection surgery performed under vascular control.	2009-10-07	19821445
Hemodynamic effects of dobutamine and dopexamine after cardiopulmonary bypass in pediatric cardiac surgery.	2009-09	19650844
Meta-analysis on the effect of dopexamine on in-hospital mortality.	2009-06	19453310
Meta-analyses of the effects of dopexamine in major surgery: do all roads lead to Rome?	2009-06	19453309
The effect of fenoldopam and dopexamine on hepatic blood flow and hepatic function following coronary artery bypass grafting with hypothermic cardiopulmonary bypass.	2009-06	19406658
Association of arterial blood pressure and vasopressor load with septic shock mortality: a post hoc analysis of a multicenter trial.	2009	19917106
Clinical review: Goal-directed therapy in high risk surgical patients.	2009	19863764
Perioperative indocyanine green clearance is predictive for prolonged intensive care unit stay after coronary artery bypass grafting--an observational study.	2009	19747406
Gastric tonometry versus cardiac index as resuscitation goals in septic shock: a multicenter, randomized, controlled trial.	2009	19335912
Inotropic therapy for cardiac low output syndrome: comparison of hemodynamic effects of dopamine/dobutamine versus dopamine/dopexamine.	2008-10-27	19008172
Heme oxygenase-1 induction in the brain during lipopolysaccharide-induced acute inflammation.	2008-06	18830440
Effect of dopexamine infusion on mortality following major surgery: individual patient data meta-regression analysis of published clinical trials.	2008-04	18379261
Catecholamines induce an inflammatory response in human hepatocytes.	2008-03	18431272
The adenosine deaminase inhibitor erythro-9-[2-hydroxyl-3-nonyl]-adenine decreases intestinal permeability and protects against experimental sepsis: a prospective, randomised laboratory investigation.	2008	18847498
Inotropic therapy for cardiac low output syndrome: comparison of hemodynamic effects of dopamine/dobutamine versus dopamine/dopexamine.	2007-11-05	18024265
Synthetic inotropes inhibit the expression of adhesion molecules and augment the expression of L-selectin in polymorphonuclear neutrophils.	2007-08	17382451
Splanchnic blood flow and oxygen consumption: effects of enteral nutrition and dopexamine in the elderly cardiac surgery patient.	2007-05	17430318
The incidence of myocardial injury following post-operative Goal Directed Therapy.	2007-03-19	17371601
Year in review 2006: Critical Care--Multiple organ failure, sepsis, and shock.	2007	17764584
Could dopamine be a silent killer?	2007	17291329
An iterative Bayesian approach to health technology assessment: application to a policy of preoperative optimization for patients undergoing major elective surgery.	2006-09-26	16997926
The effects of dopexamine in bupivacaine and ropivacaine induced cardiotoxicity in isolated rat heart.	2006-08	16883451
Comparison of systemic and renal effects of dopexamine and dopamine in norepinephrine-treated septic shock.	2006-04	16616656
Effects of dopexamine on regional blood flow and leukotriene production in multiple splanchnic sites in endotoxemic rats.	2006-03-02	16506373
Advances in protocolising management of high risk surgical patients.	2006-02	16542482
Hemodynamic monitoring over the past 10 years.	2006-02	16542473
Dopexamine and norepinephrine versus epinephrine on gastric perfusion in patients with septic shock: a randomized study [NCT00134212].	2006-02	16507156
Prevention of acute renal failure--first do no harm!	2006-02	16430553
Inhaled beta-2 agonist salbutamol and acute lung injury: an association with improvement in acute lung injury.	2006-02	16420663
Hemodynamic optimization of sepsis-induced tissue hypoperfusion.	2006	17164014
Diagnostic value and prognostic implications of serum procalcitonin after cardiac surgery: a systematic review of the literature.	2006	17038199
Dobutamine reverses the vasopressin-associated impairment in cardiac index and systemic oxygen supply in ovine endotoxemia.	2006	17032443
Intravenous nitroglycerin does not preserve gastric microcirculation during gastric tube reconstruction: a randomized controlled trial.	2006	16970804
Year in review 2005: critical care--cardiology.	2006	16919175
Effects of dopexamine on the intestinal microvascular blood flow and leukocyte activation in a sepsis model in rats.	2006	16893450
Catecholamines: physiological immunomodulators during health and illness.	2006	16842192
Prospective, randomized trial comparing fluids and dobutamine optimization of oxygen delivery in high-risk surgical patients [ISRCTN42445141].	2006	16696864
The choice of catecholamines in septic shock: more and more good arguments to strengthen the known position, but don't lose the faith!	2006	16563178
Effects of dopexamine in a rat model of supracoeliac aortic cross-clamping and declamping.	2006	16549930
Effects of dopexamine on lipid peroxidation during aortic surgery in pigs: comparison with dopamine.	2005-12	16102983
Renal blood flow in sepsis.	2005-08	16137349
Bench-to-bedside review: Inotropic drug therapy after adult cardiac surgery -- a systematic literature review.	2005-06	15987381
Optimal management of the high risk surgical patient: beta stimulation or beta blockade?	2005	16356257
Highs and lows in high-risk surgery: the controversy of goal-directed haemodynamic management.	2005	16356256
Functional hemodynamic monitoring.	2005	16356240
Meta-analysis of hemodynamic optimization: relationship to methodological quality.	2005	16356226
Changes in central venous saturation after major surgery, and association with outcome.	2005	16356220
Early goal-directed therapy after major surgery reduces complications and duration of hospital stay. A randomised, controlled trial [ISRCTN38797445].	2005	16356219

Sample Use Guides

In Vivo Use Guide

0.5 ug/kg/min (heart failure), from 0.5 ug/kg/min with 0.5 ug/kg/min increments every 3 min (septic shock).

Route of Administration: Intravenous

In Vitro Use Guide

[3H]-Dopexamine was specifically bound to sections of human right or left ventricle. The binding was time-, temperature- and concentration-dependent and was dissociable. The apparent equilibrium constant of dissociation was 3·5 nM. A decreased [3H]-dopexamine binding capacity from the base to the apex and ventricles was noticeable.

Name

Type

Language

DOPEXAMINE

Official Name

English

DOPEXAMINE [MI]

Preferred Name

English

4-[2-[[6-(Phenethylamino)hexyl]amino]ethyl]pyrocatechol

Systematic Name

English

DOPEXAMINE [USAN]

Common Name

English

FPL 60278

Code

English

1,2-BENZENEDIOL, 4-(2-((6-((2-PHENYLETHYL)AMINO)HEXYL)AMINO)ETHYL)-

Systematic Name

English

Dopexamine [WHO-DD]

Common Name

English

dopexamine [INN]

Common Name

English

FPL-60278

Code

English

Classification Tree Code System Code

WHO-ATC

C01CA14