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
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
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.
Originator
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
The underreporting of results and possible mechanisms of 'negative' drug trials in patients with chronic heart failure. | 2001 Aug |
|
Treatment of severe ocular hypotony in AIDS patients with cytomegalovirus retinitis and cidofovir-associated uveitis. | 2001 Sep |
|
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 |
|
The comparison of topical ibopamine 2% with tonography to identify the outflow resistance in eyes with ocular hypertension. | 2005 Jan-Feb |
|
Ocular hypertension and corneal thickness: a long-term prospective study. Results after two years. | 2005 Sep-Oct |
|
Correlation between the ibopamine provocative test and the diurnal tension curve in glaucoma patients. | 2006 Jul-Aug |
|
[Prostaglandin analogues reduce the ibopamine provocative test specificity in glaucoma]. | 2006 Mar-Apr |
|
[Treatment of uveitis-associated refractory ocular hypotony with topical ibopamine]. | 2006 May |
|
Primary locus intervention: a novel approach to treating age-associated hormone insufficiency. | 2007 |
|
Challenges facing age-management/longevity medicine. | 2007 |
|
Inhibition by brimonidine of forskolin-induced nitric oxide synthase expression in human ciliary bodies in vitro. | 2007 Apr 2 |
|
Telemetric monitoring of 24 h intraocular pressure in conscious and freely moving C57BL/6J and CBA/CaJ mice. | 2008 Apr 18 |
|
Prognostic value of heart rate variability and ventricular arrhythmias during 13-year follow-up in patients with mild to moderate heart failure. | 2009 Apr |
|
Low pulse pressure is an independent predictor of mortality and morbidity in non ischaemic, but not in ischaemic advanced heart failure patients. | 2009 Jan 24 |
|
Digoxin in management of heart failure in children: Should it be continued or relegated to the history books? | 2009 Jul |
|
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
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3410586
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3795623
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.
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)