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Details

Stereochemistry ACHIRAL
Molecular Formula C17H25NO4.ClH
Molecular Weight 343.846
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IBOPAMINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=ALIXRWKJZYLBJI-UHFFFAOYSA-N
InChI=1S/C17H25NO4.ClH/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;1H

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

Molecular Formula ClH
Molecular Weight 36.461
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
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
Current evidence supporting the role of diuretics in heart failure: a meta analysis of randomised controlled trials.
2002 Feb
Effect of ibopamine on aqueous humor production in normotensive humans.
2003 Nov
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
Non-linear heart rate variability and risk stratification in cardiovascular disease.
2005 Jul 1
[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
A new approach for treatment of hypertension: modifying D1 dopamine receptor function.
2006 Oct
Comparison between the 1% and 2% ibopamine provocative test in primary open-angle glaucoma patients: sensitivity, specificity and tolerability.
2006 Sep-Oct
[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
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
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 Fri Dec 15 15:09:28 GMT 2023
Edited
by admin
on Fri Dec 15 15:09:28 GMT 2023
Record UNII
3VXW2HU8GS
Record Status Validated (UNII)
Record Version
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Name Type Language
IBOPAMINE HYDROCHLORIDE
MART.   MI   WHO-DD  
Common Name English
Ibopamine hydrochloride [WHO-DD]
Common Name English
SB-7505
Code English
IBOPAMINE HYDROCHLORIDE [MART.]
Common Name English
IBOPAMINE HYDROCHLORIDE [JAN]
Common Name English
INOPAMIL
Brand Name English
IBOPAMINE HYDROCHLORIDE [MI]
Common Name English
SCANDINE
Brand Name English
4-(2-METHYLAMINOETHYL)-O-PHENYLENE DI-ISOBUTYRATE HYDROCHLORIDE
Code English
TRAZY
Brand Name English
Code System Code Type Description
FDA UNII
3VXW2HU8GS
Created by admin on Fri Dec 15 15:09:28 GMT 2023 , Edited by admin on Fri Dec 15 15:09:28 GMT 2023
PRIMARY
PUBCHEM
156320
Created by admin on Fri Dec 15 15:09:28 GMT 2023 , Edited by admin on Fri Dec 15 15:09:28 GMT 2023
PRIMARY
ECHA (EC/EINECS)
278-056-2
Created by admin on Fri Dec 15 15:09:28 GMT 2023 , Edited by admin on Fri Dec 15 15:09:28 GMT 2023
PRIMARY
SMS_ID
100000086979
Created by admin on Fri Dec 15 15:09:28 GMT 2023 , Edited by admin on Fri Dec 15 15:09:28 GMT 2023
PRIMARY
EPA CompTox
DTXSID0020864
Created by admin on Fri Dec 15 15:09:28 GMT 2023 , Edited by admin on Fri Dec 15 15:09:28 GMT 2023
PRIMARY
EVMPD
SUB02625MIG
Created by admin on Fri Dec 15 15:09:28 GMT 2023 , Edited by admin on Fri Dec 15 15:09:28 GMT 2023
PRIMARY
RXCUI
284157
Created by admin on Fri Dec 15 15:09:28 GMT 2023 , Edited by admin on Fri Dec 15 15:09:28 GMT 2023
PRIMARY RxNorm
MERCK INDEX
m6185
Created by admin on Fri Dec 15 15:09:28 GMT 2023 , Edited by admin on Fri Dec 15 15:09:28 GMT 2023
PRIMARY Merck Index
CAS
75011-65-3
Created by admin on Fri Dec 15 15:09:28 GMT 2023 , Edited by admin on Fri Dec 15 15:09:28 GMT 2023
PRIMARY
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