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

Molecular Formula	C22H32N2O2
Molecular Weight	356.5017
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
The effectiveness and relative effectiveness of intravenous inotropic drugs acting through the adrenergic pathway in patients with heart failure-a meta-regression analysis.	2002 Aug	12167393
The specific function of dopexamine: improvement of impaired oxygen delivery.	2002 Aug	12163836
Dopexamine attenuates microvascular perfusion injury of the small bowel in pigs induced by extracorporeal circulation.	2002 Jun	12173204
Blood-brain barrier breakdown in septic encephalopathy and brain tumours.	2002 Jun	12162731
Does dopexamine influence regional vascular tone and oxygenation during intestinal hypotension?	2002 Nov	12421194
Bench-to-bedside review: endothelial cell dysfunction in severe sepsis: a role in organ dysfunction?	2003 Apr	12720559
Effects of dopexamine and positive end-expiratory pressure on intestinal blood flow and oxygenation: the perfusion pressure perspective.	2003 Aug	12907561
Dopexamine reverses colonic but not gastric mucosal perfusion defects in lethal endotoxin shock.	2003 Dec	14633761
A review of anti-inflammatory strategies in cardiac surgery.	2003 Mar	12708760
[The effect of dopexamine and iloprost on plasma disappearance rate of indocyanine green in patients in septic shock].	2003 Nov	14992087
Effect of adding dopexamine to intraoperative volume expansion in patients undergoing major elective abdominal surgery.	2003 Nov	14570781
Should perioperative management target oxygen delivery?	2003 Nov	14570780
Dopexamine and cellular immune functions during systemic inflammation.	2004	15124857
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 in comparison with fenoterol on carbohydrate, fat and protein metabolism in healthy volunteers.	2004 Apr	14985966
[How can one miss the correction local perfusion?].	2004 Aug	15452978
Mechanisms of beta-receptor stimulation-induced improvement of acute lung injury and pulmonary edema.	2004 Aug	15312205
Clinical review: how to optimize management of high-risk surgical patients.	2004 Dec	15566623
Effects of ephedrine, dobutamine and dopexamine on cerebral haemodynamics: transcranial Doppler studies in healthy volunteers.	2004 Jan	14665551
Clinical review: influence of vasoactive and other therapies on intestinal and hepatic circulations in patients with septic shock.	2004 Jun	15153235
Effects of dopexamine, dobutamine or dopamine on prolactin and thyreotropin serum concentrations in high-risk surgical patients.	2004 Jun	15138671
Local metabolic effects of dopexamine on the intestine during mesenteric hypoperfusion.	2004 Mar	14770037
Effects of dopexamine on rat cardiorenal functions during lipopolysaccharide-induced experimental sepsis.	2004 Mar-Apr	15080013
Effects of dopamine, dobutamine, and dopexamine on microcirculatory blood flow in the gastrointestinal tract during sepsis and anesthesia.	2004 May	15114217
Survey of the use of catecholamines by French physicians.	2004 May	14997293
Adrenergic agents modify cerebral edema and microvessel ultrastructure in porcine sepsis.	2004 Sep	15343022
Dopexamine reverses the vasopressin-associated impairment in tissue oxygen supply but decreases systemic blood pressure in ovine endotoxemia.	2004 Sep	15333425
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
Renal blood flow in sepsis.	2005 Aug	16137349
Effects of dopexamine on lipid peroxidation during aortic surgery in pigs: comparison with dopamine.	2005 Dec	16102983
Clinical review: Evidence-based perioperative medicine?	2005 Feb	15693988
Kidney dysfunction in the postoperative period.	2005 Jul	15531622
Year in review 2005: critical care--cardiology.	2006	16919175
Effects of dopexamine in a rat model of supracoeliac aortic cross-clamping and declamping.	2006	16549930
Year in review 2006: Critical Care--Multiple organ failure, sepsis, and shock.	2007	17764584
Could dopamine be a silent killer?	2007	17291329
The incidence of myocardial injury following post-operative Goal Directed Therapy.	2007 Mar 19	17371601
Splanchnic blood flow and oxygen consumption: effects of enteral nutrition and dopexamine in the elderly cardiac surgery patient.	2007 May	17430318
Heme oxygenase-1 induction in the brain during lipopolysaccharide-induced acute inflammation.	2008 Jun	18830440
Catecholamines induce an inflammatory response in human hepatocytes.	2008 Mar	18431272
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
Meta-analyses of the effects of dopexamine in major surgery: do all roads lead to Rome?	2009 Jun	19453309
Dopexamine and survival: areas of consistency.	2009 Nov	19825065

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:21:17 GMT 2025` Edited by `admin` on `Mon Mar 31 18:21:17 GMT 2025`
Record UNII	398E7Z7JB5
Record Status	`Validated (UNII)`
Record Version

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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