Atracurium structure

Mistry, N., Roberts, A.D., Tranter, G.E., Francis, P., Barylski, I., Ismail, I.M., Nicholson, J.K., and Lindon, J.C., Directly coupled chiral HPLC-NMR and HPLC-CP spectroscopy as complementary methods for structural and enantiomeric isomer identification application to atracurium besylate, Anal. Chem., 71, 2838, 1999. 

The design of atracurium (Fig. 11.40) was based on the structures of tubocurarine and suxamethonium. It is superior to both since it lacks cardiac side-effects and is rapidly broken down in blood. This rapid breakdown allows the drug to be administered as an intravenous drip. 

Category 2. Antibodies with recognition profiles confined to the ammonium groups but which cross-react with, and are inhibited almost equally well by, each of the NMBDs with the same or similar groups linked to the nitrogens. Examples include succinylcholine and decamethonium rf-mbocurarine and atracurium and pancuronium and vecuronium. However, since differences occur in the structures attached to the nitrogens in some NMBDs, antibodies to one NMBD, for example, succinylcholine, may not readily cross-react with, and be inhibited by, some other NMBDs, for example, rocuronium. 

Aiyai VN, Benn MH, Hanna T, Jacyno J, Roth SH, Wilkens JL (1979) The principal toxin of Delphinium brownii and its mode of action. Experientia 35 1367-1368 Chappie DJ, Clark JS (1983) Pharmacological action of breakdown products of atracurium and related substances. Br J Anaesth 55 Suppl 1 IIS Cohen HG, Seifen EE, Straub KD, Tiefenback C, Stermitz FR (1978) Structural specificity of the NaK-ATPase inhibition by sanguinarine. Biochem Pharmacol 27 2555 Dolejs L, Hanus V (1967) Mass spectrometry of rhoeadine type alkaloids. Tetrahedron23 2997 Horn AS, Rodgers JR (1976) Structural and conformational relationships between the opiates. Nature (London) 260 795-797... 

The development of these two new muscle relaxants highlights the improved understanding of structure-activity relationships in bis-benzyl tetrahydro isoquinolinium derivatives. This has allowed their chemistry and metabolism to be manipulated so as to yield drugs with a short (mivacurium), intermediate (atracurium), or long (doxacurium) duration of action (553). 

Figure 16.22 The chemical structure of the most ubiquitous component of atracurium.

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