DOPEXAMINE

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=C(O)C=C(CCNCCCCCCNCCC2=CC=CC=C2)C=C1

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 2678
Beta-2 adrenergic receptor 203 Target ID: CHEMBL210 Sources: http://www.ncbi.nlm.nih.gov/pubmed/1363232	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Heart failure 103 Sources: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC481901/pdf/brheartj00117-0087.pdf	Primary		Phase II 1132	Unknown Approved Use Unknown
Septic shock 21 Sources: https://clinicaltrials.gov/ct2/show/NCT00134212	Primary		Phase II 1132	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Effect of dopexamine on hepatic metabolic activity in patients with septic shock.	2001 Jun	11386613
Impairment of renal function after cardiopulmonary bypass is not influenced by dopexamine.	2001 Mar	11417953
Effects of dobutamine and dopexamine on hepatic micro- and macrocirculation during experimental endotoxemia: an intravital microscopic study in the rat.	2001 Mar	11373427
Effects of dopexamine on acute necrotising pancreatitis in rats.	2001 Oct	11775728
Attenuation of lung inflammation by adrenergic agonists in murine acute lung injury.	2001 Oct	11605937
Dopexamine but not dopamine increases gastric mucosal oxygenation during mechanical ventilation in dogs.	2002 Apr	11940763
Dopexamine attenuates microvascular perfusion injury of the small bowel in pigs induced by extracorporeal circulation.	2002 Jun	12173204
Haemodynamic effects of dopexamine on postprandial splanchnic hyperaemia.	2004 Apr	15086358
Effect of adding dopexamine to intraoperative volume expansion in patients undergoing major elective abdominal surgery.	2004 Apr	15013962
Effects of dopexamine on rat cardiorenal functions during lipopolysaccharide-induced experimental sepsis.	2004 Mar-Apr	15080013
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
Dopexamine and its role in the protection of hepatosplanchnic and renal perfusion in high-risk surgical and critically ill patients.	2005 Apr	15653704
Hemodynamic monitoring over the past 10 years.	2006 Feb	16542473
Inhaled beta-2 agonist salbutamol and acute lung injury: an association with improvement in acute lung injury.	2006 Feb	16420663
Year in review 2006: Critical Care--Multiple organ failure, sepsis, and shock.	2007	17764584
Heme oxygenase-1 induction in the brain during lipopolysaccharide-induced acute inflammation.	2008 Jun	18830440
Association of arterial blood pressure and vasopressor load with septic shock mortality: a post hoc analysis of a multicenter trial.	2009	19917106
Gastric tonometry versus cardiac index as resuscitation goals in septic shock: a multicenter, randomized, controlled trial.	2009	19335912
The effect of fenoldopam and dopexamine on hepatic blood flow and hepatic function following coronary artery bypass grafting with hypothermic cardiopulmonary bypass.	2009 Jun	19406658
Is dopexamine superior to dopamine in the treatment of multiple trauma patients--a prospective, double-blind, randomised study.	2010 May	19595327

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

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

Systematic Name

English

DOPEXAMINE [USAN]

Common Name

English

FPL 60278

Code

English

DOPEXAMINE [MI]

Common Name

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