Ibopamine

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Ibopamine
File:Ibopamine.svg
Systematic (IUPAC) name
5-[2-(methylamino)ethyl]-2-[(2-methylpropanoyl)oxy]phenyl 2-methylpropanoate
Clinical data
AHFS/Drugs.com International Drug Names
Identifiers
CAS Number 66195-31-1 YesY
ATC code C01CA16 (WHO) S01FB03
PubChem CID: 68555
ChemSpider 61829 N
UNII 8ZCA2I2L11 YesY
KEGG D04488 YesY
Chemical data
Formula C17H25NO4
Molecular mass 307.385 g/mol
 NYesY (what is this?)  (verify)

Ibopamine is a sympathomimetic drug, designed as a prodrug of epinine, used in ophthalmology.[1] It induces mydriasis.[2] It also has been investigated for use in the treatment of congestive heart failure.[3]

It acts on D1[4][5] and α receptors as an agonist.[6]

Ibopamine was first prepared by Casagrande and co-workers.[7]

Instilled at 2% concentration, ibopamine exhibits several functions at ocular level such as pre- and post-operative mydriatic activity, D1 dopaminergic activity, etc.[8]

Pharmacokinetics

Due to the esterases existed in the aqueous humour and ocular tissues,

ibopamine can be rapidly hydrolysed to epinine which is the active molecule responsible for the mydriatic effect.[9] The epinine, an analogue of dopamine, can stimulate dopamine receptors and to a lesser degree adrenergic receptors.[10] Thus it is believed that epinine is the pharmacologically active moiety. It has been shown that the half-life of ibopamine is short to about 2 minutes in the aqueous humour owing to the fast hydrolysis.[11] So ibopamine can not be found in the aqueous humor after instillation.

Pharmacodynamics

After being hydrolysed to epinine, ibopamine is able to stimulate the alpha-adrenergic and D1 dopaminergic receptors, thereby exhibiting mydriatic effects.[12] In some randomized clinical trials, the D1 dopaminergic activity of ibopamine led to an increased production of aqueous humour and intraocular pressure (IOP) in primary open-angle glaucoma (POAG) patients.[13]

Toxicology

At systemic and local levels, ibopamine has been proved to be of low toxicity. It is well-tolerated since no obvious changes to the haematological and behavioural parameters have been observed after administration.[14] Ibopamine eye drop at 2% concentration, containing 1 mg of the compound, did not show any significant systemic side-effects and tachyphylaxis phenomena whereas the oral dosage is higher than 400 mg per day.[15]

Clinical Use

A fast and short-lasting mydriasis can be induced by ibopamine without systemic side-effects.

See also

References

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  5. Lieverse AG, Girbes AR, Van Veldhuisen DJ, et al. (July 1995). "The effects of ibopamine on glomerular filtration rate and plasma norepinephrine remain preserved during prolonged treatment in patients with congestive heart failure". Eur. Heart J. 16 (7): 937–42. PMID 7498209.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  6. "IngentaConnect Ibopamine Stimulates -Adrenergic Receptors and D1 Dopaminergic Re..."<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  7. Casagrande, C.; Santangelo, F.; Saini, C.; Doggi, F.; Gerli, F.; Cerri, O. (1986). "Synthesis and chemical properties of ibopamine and of related esters of N-substituted dopamines-synthesis of ibopamine metabolites". Arzneimittelforschung. 36: 291–303.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
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