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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
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
Treatment of severe ocular hypotony in AIDS patients with cytomegalovirus retinitis and cidofovir-associated uveitis.
2001 Sep
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
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
Non-linear heart rate variability and risk stratification in cardiovascular disease.
2005 Jul 1
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
A new approach for treatment of hypertension: modifying D1 dopamine receptor function.
2006 Oct
Inhibition by brimonidine of forskolin-induced nitric oxide synthase expression in human ciliary bodies in vitro.
2007 Apr 2
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

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.
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
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WHO-ATC S01FB03
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WHO-VATC QS01FB03
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WHO-VATC QC01CA16
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WHO-ATC C01CA16
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Code System Code Type Description
DRUG CENTRAL
1405
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PRIMARY
MESH
C023487
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INN
4806
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CAS
66195-31-1
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EPA CompTox
DTXSID3023138
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ECHA (EC/EINECS)
266-229-5
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ChEMBL
CHEMBL307739
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FDA UNII
8ZCA2I2L11
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SMS_ID
100000083666
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RXCUI
51253
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PRIMARY RxNorm
EVMPD
SUB08094MIG
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NCI_THESAURUS
C65875
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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
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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
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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
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