Malouetine

Last updated
Malouetine
Malouetine iodide.svg
Names
IUPAC name
[(3S,5S,8R,9S,10S,13S,14S)-10,13-Dimethyl-17-[(1S)-1-(trimethylazaniumyl)ethyl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]-trimethylazanium diiodide
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C27H52N2.2HI/c1-19(28(4,5)6)23-12-13-24-22-11-10-20-18-21(29(7,8)9)14-16-26(20,2)25(22)15-17-27(23,24)3;;/h19-25H,10-18H2,1-9H3;2*1H/q+2;;/p-2/t19-,20-,21-,22-,23+,24-,25-,26-,27+;;/m0../s1
    Key: ZKPCQHGEQUQGJK-DMZQXVSVSA-L
  • C[C@@H]([C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CC[C@@H](C4)[N+](C)(C)C)C)C)[N+](C)(C)C.[I-].[I-]
Properties
C27H52I2N2
Molar mass 658.536 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Malouetine is an aminosteroid neuromuscular blocking agent and antinicotinic alkaloid isolated from Malouetia spp. [1]

The structure of malouetine inspired the development of modern aminosteroid muscle relaxants such as pancuronium bromide and vecuronium bromide by workers at Organon. [2] [3] [4]

Related Research Articles

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<span class="mw-page-title-main">Vecuronium bromide</span> Muscle relaxant

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<span class="mw-page-title-main">Neuromuscular-blocking drug</span> Type of paralyzing anesthetic including lepto- and pachycurares

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<span class="mw-page-title-main">Rapacuronium bromide</span> Pharmaceutical drug

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<span class="mw-page-title-main">Aminosteroid</span> Class of chemical compounds

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<span class="mw-page-title-main">Cisatracurium besilate</span> Chemical compound

Cisatracurium besilate is a bisbenzyltetrahydroisoquinolinium that has effect as a neuromuscular-blocking drug non-depolarizing neuromuscular-blocking drugs, used adjunctively in anesthesia to facilitate endotracheal intubation and to provide skeletal muscle relaxation during surgery or mechanical ventilation. It shows intermediate duration of action. Cisatracurium is one of the ten isomers of the parent molecule, atracurium. Moreover, cisatracurium represents approximately 15% of the atracurium mixture.

<span class="mw-page-title-main">Alcuronium chloride</span> Muscle relaxant

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<span class="mw-page-title-main">Pipecuronium bromide</span> Chemical compound

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<span class="mw-page-title-main">Gantacurium chloride</span> Chemical compound

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<span class="mw-page-title-main">Candocuronium iodide</span> Chemical compound

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<span class="mw-page-title-main">Postoperative residual curarization</span> Medical condition

Postoperative residual curarization (PORC) or residual neuromuscular blockade (RNMB) is a residual paresis after emergence from general anesthesia that may occur with the use of neuromuscular-blocking drugs. Today residual neuromuscular blockade is defined as a train of four ratio of less than 0.9 when measuring the response to ulnar nerve stimulation at the adductor pollicis muscle using mechanomyography or electromyography. A meta-analysis reported that the incidence of residual neuromuscular paralysis was 41% in patients receiving intermediate neuromuscular blocking agents during anaesthesia. It is possible that > 100,000 patients annually in the USA alone, are at risk of adverse events associated with undetected residual neuromuscular blockade. Neuromuscular function monitoring and the use of the appropriate dosage of sugammadex to reverse blockade produced by rocuronium can reduce the incidence of postoperative residual curarization. In this study, with usual care group receiving reversal with neostigmine resulted in a residual blockade rate of 43%.

<span class="mw-page-title-main">Neuromuscular drug</span>

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References

  1. Janot MM; Laine F; Goutarel R (1960). "Steroid alkaloids. V. Alkaloids of Malouetia bequaertiana e. Woodson (Apocynaceae): Funtuphyllamine B and malouetine. Preliminary communication". Annales Pharmaceutiques Françaises. 18: 673–677. PMID   13789457.
  2. Alauddin, M.; Caddy, B.; Lewis, J.J.; Martin-Smith, M.; Sugrue, M.F. (January 1965). "Non-depolarising neuromuscular blockade by 3α,17α-bis(quaternary ammonium) 5α-androstanes". Journal of Pharmacy and Pharmacology. 17 (1): 55–59. doi:10.1111/j.2042-7158.1965.tb07569.x. PMID   14285698. S2CID   71497007.
  3. Buckett, W.R.; Hewett, C.L.; Savage, D.S. (October 1973). "Pancuronium bromide and other steroidal neuromuscular blocking agents containing acetylcholine fragments". Journal of Medicinal Chemistry. 16 (10): 1116–24. doi:10.1021/jm00268a011. PMID   4356139.
  4. McKenzie, A.G. (June 2000). "Prelude to pancuronium and vecuronium". Anaesthesia. 55 (6): 551–556. doi:10.1046/j.1365-2044.2000.01423.x. PMID   10866718. S2CID   22476701.