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
  • O=C(Oc1cc(ccc1OC(=O)C(C)C)CCNC)C(C)C
  • 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 N
  • Key:WDKXLLJDNUBYCY-UHFFFAOYSA-N N
 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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