Ibopamine

Ibopamine
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • 5-[2-(methylamino)ethyl]-2-[(2-methylpropanoyl)oxy]phenyl 2-methylpropanoate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.060.189 Edit this at Wikidata
Chemical and physical data
FormulaC17H25NO4
Molar mass307.390 g·mol−1
3D model (JSmol)
  • 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
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Ibopamine is a sympathomimetic drug, designed as a prodrug of epinine (deoxyepinephrine or N-methyldopamine), 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-adrenergic 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.[6]

  1. ^ Magacho L, Costa ML, Dessimoni A, de Avila MP (2006). "Comparison between the 1% and 2% ibopamine provocative test in primary open-angle glaucoma patients: sensitivity, specificity and tolerability". Arquivos Brasileiros de Oftalmologia. 69 (5): 695–699. doi:10.1590/S0004-27492006000500015. PMID 17187138.
  2. ^ Marchini G, Babighian S, Tosi R, Perfetti S, Bonomi L (June 2001). "Effects of 2% ibopamine on pupil, refraction, anterior segment anatomy and intraocular pressure". Journal of Ocular Pharmacology and Therapeutics. 17 (3): 215–223. doi:10.1089/108076801750295254. PMID 11436942.
  3. ^ van Veldhuisen DJ, Man in 't Veld AJ, Dunselman PH, Lok DJ, Dohmen HJ, Poortermans JC, et al. (November 1993). "Double-blind placebo-controlled study of ibopamine and digoxin in patients with mild to moderate heart failure: results of the Dutch Ibopamine Multicenter Trial (DIMT)". Journal of the American College of Cardiology. 22 (6): 1564–1573. doi:10.1016/0735-1097(93)90579-P. PMID 7901256.
  4. ^ Metra M, Missale C, Spano PF, Cas LD (May 1995). "Dopaminergic drugs in congestive heart failure: hemodynamic and neuroendocrine responses to ibopamine, dopamine, and dihydroergotoxine". Journal of Cardiovascular Pharmacology. 25 (5): 732–740. doi:10.1097/00005344-199505000-00008. PMID 7630152. S2CID 37607224.
  5. ^ Lieverse AG, Girbes AR, Van Veldhuisen DJ, Smit AJ, Zijlstra JG, Meijer S, 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". European Heart Journal. 16 (7): 937–942. doi:10.1093/oxfordjournals.eurheartj.a061028. PMID 7498209.
  6. ^ a b Giuffre I (2007). "Ibopamine stimulates α-adrenergic receptors and D1 dopaminergic receptors in the eye". Current Drug Therapy. 2 (2): 127–132. doi:10.2174/157488507780619112.
  7. ^ Casagrande C, Santangelo F, Saini C, Doggi F, Gerli F, Cerri O (February 1986). "Synthesis and chemical properties of ibopamine and of related esters of N-substituted dopamines--synthesis of ibopamine metabolites". Arzneimittel-Forschung. 36 (2A): 291–303. PMID 3707640.