U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C17H25NO4
Molecular Weight 307.3847
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IBOPAMINE

SMILES

CNCCC1=CC(OC(=O)C(C)C)=C(OC(=O)C(C)C)C=C1

InChI

InChIKey=WDKXLLJDNUBYCY-UHFFFAOYSA-N
InChI=1S/C17H25NO4/c1-11(2)16(19)21-14-7-6-13(8-9-18-5)10-15(14)22-17(20)12(3)4/h6-7,10-12,18H,8-9H2,1-5H3

HIDE SMILES / InChI

Molecular Formula C17H25NO4
Molecular Weight 307.3847
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Ibopamine is the prodrug of epinine or N-methyl dopamine. Ibopamine stimulates the DA1 and DA2 dopaminergic receptors, the beta 1 and beta 2 adrenoceptors, and the alpha 1 and alpha 2 adrenoceptors. Ibopamine has varying degrees of affinity for these various families, being the highest for the dopamine receptors and the lowest for the alpha adrenergic receptors. Ibopamine reduces systemic vascular resistance, increases cardiac output, and increases renal flow. Ibopamine also modulates the neuroendocrine reflexes in heart failure; plasma renin activity and norepinephrine and aldosterone plasma concentrations are reduced, both immediately and during sustained administration. In patients with heart failure (HF), low doses appear to exert beneficial neurohormonal, hemodynamic, and renal effects, without increased inotropic effects. However, at higher doses (> 200 mg) ibopamine exerts effects that do not appear to be clinically useful in long-term treatment of chronic HF. Several small trials have suggested a benefit of ibopamine on exercise performance in patients with mild to moderate HF. On the basis of these studies, ibopamine is now being used in Europe to treat patients with mild to moderate congestive heart failure (CHF). At doses of 100 or 200 mg/t.i.d., there has been no evidence of significant safety problems. Ibopamine was used in Europe to treat heart failure. In 1995, a study showed that ibopamine increased death rates in patients who had moderate to severe heart failure. In September 1995, doctors and pharmacists in the Netherlands were officially notified that ibopamine should be used only in patients with mild heart failure. Moreover, the official recommendations for when to use ibopamine were changed according to whether patients had mild or severe heart failure. Ibopamine, a sympathomimetic drug, is used in ophthalmology. t has a not-cycloplegic mydriatic activity. Its peak of action is at 45 minutes after instillation in the conjunctival sac. Its action lasts after about 360 minutes. Its D1-dopaminergic stimulation increases the aqueous humor production and it is a provocative test for evaluating the function of aqueous humor outflow structures also in relatives of glaucomatous patients. It is also useful to treat ocular hypotension. Its main use is in every ophthalmological assessment, either diagnostic or preoperative, where the cycloplegia is not adviced. It is useful for the safe mydriasis of patients treated with α-1 adrenergic receptor antagonists.

Approval Year

PubMed

PubMed

TitleDatePubMed
Confounding by contraindication in a nationwide cohort study of risk for death in patients taking ibopamine.
2001 Apr 3
The underreporting of results and possible mechanisms of 'negative' drug trials in patients with chronic heart failure.
2001 Aug
Effects of 2% ibopamine on pupil, refraction, anterior segment anatomy and intraocular pressure.
2001 Jun
Treatment of severe ocular hypotony in AIDS patients with cytomegalovirus retinitis and cidofovir-associated uveitis.
2001 Sep
Treatment of severe ocular hypotony in AIDS patients with cytomegalovirus retinitis and cidofovir-associated uveitis.
2001 Sep
Ibopamine test and frequency doubling perimetry in early glaucoma diagnosis.
2002
Current evidence supporting the role of diuretics in heart failure: a meta analysis of randomised controlled trials.
2002 Feb
The therapeutic potential of dopamine modulators on the cardiovascular and renal systems.
2002 May
Comparative study of the effects of 2% ibopamine, 10% phenylephrine, and 1% tropicamide on the anterior segment.
2003 Jan
Role of nonglycosidic inotropic agents: indications, ethics, and limitations.
2003 Mar
Effects of ibopamine eye drops on intraocular pressure and aqueous humor flow in healthy volunteers and patients with open-angle glaucoma.
2003 May
Effect of ibopamine on aqueous humor production in normotensive humans.
2003 Nov
Ibopamine provocative test and glaucoma: consideration of factors that may influence the examination.
2004 Mar
The effects of 2% ibopamine eye drops on the intraocular pressure and pupil motility of patients with open-angle glaucoma.
2004 Nov-Dec
Six minute corridor walk test as an outcome measure for the assessment of treatment in randomized, blinded intervention trials of chronic heart failure: a systematic review.
2005 Apr
The comparison of topical ibopamine 2% with tonography to identify the outflow resistance in eyes with ocular hypertension.
2005 Jan-Feb
Non-linear heart rate variability and risk stratification in cardiovascular disease.
2005 Jul 1
A new approach for treatment of hypertension: modifying D1 dopamine receptor function.
2006 Oct
Primary locus intervention: a novel approach to treating age-associated hormone insufficiency.
2007
Challenges facing age-management/longevity medicine.
2007
[Positive ibopamine provocative test in normal-tension glaucoma suspects].
2007 Apr
Inhibition by brimonidine of forskolin-induced nitric oxide synthase expression in human ciliary bodies in vitro.
2007 Apr 2
User's guide to the orthopaedic literature: how to use an article about a randomized trial?
2008 Apr
Telemetric monitoring of 24 h intraocular pressure in conscious and freely moving C57BL/6J and CBA/CaJ mice.
2008 Apr 18
[2% ibopamine vs. water-drinking test as a provocative test for glaucoma].
2008 Jul-Aug
Prognostic value of heart rate variability and ventricular arrhythmias during 13-year follow-up in patients with mild to moderate heart failure.
2009 Apr
Digoxin in management of heart failure in children: Should it be continued or relegated to the history books?
2009 Jul
Frequency Doubling Technology vs Standard Automated Perimetry in Ocular Hypertensive Patients.
2009 Mar 24
[Effects of 2% ibopamine eye drops on the results of computerized visual field].
2009 May-Jun
Efficacy of 2% ibopamine on the dilation of patients with pseudoexfoliation syndrome.
2010 Jan-Feb
Pigmented deposits on a Boston keratoprosthesis from topical ibopamine.
2010 Sep
Patents

Sample Use Guides

Congestive heart failure: Ibopamine was administered at a single oral dose of 100 mg. Ophthalmology: 2% ibopamine is recommended as a provocative test for glaucoma. Because both concentrations have similar ability to rise IOP, 1% ibopamine may be used to treat ocular hypotony.
Route of Administration: Other
In Vitro Use Guide
In the isolated guinea pig atria, ibopamine (10(-6)-10(-4) M) increased the atrial rate and the developed tension in a concentration-related manner.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:32:12 GMT 2023
Edited
by admin
on Sat Dec 16 17:32:12 GMT 2023
Record UNII
8ZCA2I2L11
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
IBOPAMINE
INN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
Ibopamine [WHO-DD]
Common Name English
IBOPAMINE [MART.]
Common Name English
IBOPAMINE [USAN]
Common Name English
ibopamine [INN]
Common Name English
4-[2-(Methylamino)ethyl]-O-phenylene diisobutyrate
Common Name English
SB 7505
Code English
IBOPAMINE [MI]
Common Name English
PROPANOIC ACID, 2-METHYL-, 4-(2-(METHYLAMINO)ETHYL)-1,2-PHENYLENE ESTER
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66884
Created by admin on Sat Dec 16 17:32:13 GMT 2023 , Edited by admin on Sat Dec 16 17:32:13 GMT 2023
WHO-ATC S01FB03
Created by admin on Sat Dec 16 17:32:13 GMT 2023 , Edited by admin on Sat Dec 16 17:32:13 GMT 2023
WHO-VATC QS01FB03
Created by admin on Sat Dec 16 17:32:13 GMT 2023 , Edited by admin on Sat Dec 16 17:32:13 GMT 2023
WHO-VATC QC01CA16
Created by admin on Sat Dec 16 17:32:13 GMT 2023 , Edited by admin on Sat Dec 16 17:32:13 GMT 2023
WHO-ATC C01CA16
Created by admin on Sat Dec 16 17:32:13 GMT 2023 , Edited by admin on Sat Dec 16 17:32:13 GMT 2023
Code System Code Type Description
DRUG CENTRAL
1405
Created by admin on Sat Dec 16 17:32:13 GMT 2023 , Edited by admin on Sat Dec 16 17:32:13 GMT 2023
PRIMARY
MESH
C023487
Created by admin on Sat Dec 16 17:32:13 GMT 2023 , Edited by admin on Sat Dec 16 17:32:13 GMT 2023
PRIMARY
INN
4806
Created by admin on Sat Dec 16 17:32:13 GMT 2023 , Edited by admin on Sat Dec 16 17:32:13 GMT 2023
PRIMARY
CAS
66195-31-1
Created by admin on Sat Dec 16 17:32:13 GMT 2023 , Edited by admin on Sat Dec 16 17:32:13 GMT 2023
PRIMARY
EPA CompTox
DTXSID3023138
Created by admin on Sat Dec 16 17:32:13 GMT 2023 , Edited by admin on Sat Dec 16 17:32:13 GMT 2023
PRIMARY
ECHA (EC/EINECS)
266-229-5
Created by admin on Sat Dec 16 17:32:13 GMT 2023 , Edited by admin on Sat Dec 16 17:32:13 GMT 2023
PRIMARY
ChEMBL
CHEMBL307739
Created by admin on Sat Dec 16 17:32:13 GMT 2023 , Edited by admin on Sat Dec 16 17:32:13 GMT 2023
PRIMARY
FDA UNII
8ZCA2I2L11
Created by admin on Sat Dec 16 17:32:13 GMT 2023 , Edited by admin on Sat Dec 16 17:32:13 GMT 2023
PRIMARY
SMS_ID
100000083666
Created by admin on Sat Dec 16 17:32:13 GMT 2023 , Edited by admin on Sat Dec 16 17:32:13 GMT 2023
PRIMARY
RXCUI
51253
Created by admin on Sat Dec 16 17:32:13 GMT 2023 , Edited by admin on Sat Dec 16 17:32:13 GMT 2023
PRIMARY RxNorm
EVMPD
SUB08094MIG
Created by admin on Sat Dec 16 17:32:13 GMT 2023 , Edited by admin on Sat Dec 16 17:32:13 GMT 2023
PRIMARY
NCI_THESAURUS
C65875
Created by admin on Sat Dec 16 17:32:13 GMT 2023 , Edited by admin on Sat Dec 16 17:32:13 GMT 2023
PRIMARY
DRUG BANK
DB13316
Created by admin on Sat Dec 16 17:32:13 GMT 2023 , Edited by admin on Sat Dec 16 17:32:13 GMT 2023
PRIMARY
PUBCHEM
68555
Created by admin on Sat Dec 16 17:32:13 GMT 2023 , Edited by admin on Sat Dec 16 17:32:13 GMT 2023
PRIMARY
MERCK INDEX
m6185
Created by admin on Sat Dec 16 17:32:13 GMT 2023 , Edited by admin on Sat Dec 16 17:32:13 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
Ibopamine
Created by admin on Sat Dec 16 17:32:13 GMT 2023 , Edited by admin on Sat Dec 16 17:32:13 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY