Bupivacaine, structure

Some other anesthetics with similar structures are prilocaine, tetracaine, ropivacaine, bupivacaine, chloroprocaine, and mepivacaine ... 

Fig. 11. Representative GC-traces of spiked human plasma subjected to (top) MI-SPE and (bottom) SPE with a non-imprinted control polymer. Plasma was spiked with 160 nmol/1 bupivacaine. MIP was composed of MAA and EGDMA and imprinted with pentycaine as a structural analogue to bupivacaine. Reprinted with permission from Andersson LI (2000) Analyst 125 1515. Copyright 2000 The Royal Society of Chemistry...

An example of the use of GC with nitrogen selective detection is in the quantification of bupivacaine in plasma. Bupivacaine contains two nitrogen atoms in its structure which makes it a good candidate for this type of analysis. The limits of detection which can be achieved with a nitrogen selective detector for this compound are much better than methods based on flame ionisation detection, which are much less selective. 

Figure 12.6 shows the effect of the pH of the mobile phase on the four local anaesthetics shown in Figure 12.5. The largest effects of pH are on bupivacaine and pentycaine which are very close in structure the pH adjustment made in the example is within 1 pH unit of their pATa values. The least effect is on procaine, which has a...

Figure 5.4 Structural formulae showing tertiary (lidocaine (lignocaine), bupivacaine) and secondary (prilocaine) amines. Asymmetrical carbon atom.

Broadly speaking, it has been observed critically amongst all the known local anaesthetics , which are invariably employed in clinical practice, that there exists no clear-cut and obvious structure activity relationship in them. Besides, a plethora of these clinically prevalent and useful local anaesthetics are importantly tertiary amines , such as Butacaine, Bupivacaine, Dibucaine, Lidocaine, Mepivacaine, Prilocaine, Pramoxine, Proxymetacaine, Tetracaine etc. 

Stereochemistry of the local anesthetics, however, plays an important role in their observed toxicity and pharmacokinetic properties. For example, ropivacaine and levobupivacaine, the only optically active local anesthetics currently being marketed, have considerably lower cardiac toxicities than their close structural analogue, bupivacaine (45). Furthermore, the degree of separation between motor and sensory blockade is more apparent with ropivacaine and levobupivacaine relative to bupivacaine at a lower end of the dosage scale (46). Thus, the observed cardiac toxicity of bupivacaine has been attributed to the F -( + )-bupivacaine enantiomer (41,42,43). The exact mechanisms for this enantiomeric... 

Figure 1 Structure of bupivacaine conjugated to the Hyaluronan (HA) backbone by a...

These local anesthetics, including lidocaine (Xylocaine), mepivacaine (Carbo-caine), Prilocaine (Citanest), and bupivacaine (Marcaine) are weak sensitizers, but allergic reactions are sporadically reported, e. g., lidocaine (Turner 1977). Recently Fregert et al. (1979) described two patients developing lidocaine allergy after 8 and 1 month use of Xyloproct ointment (lidocaine 5%, hydrocortisone acetate) they also had positive patch tests to related amide anesthetics, both to mepivacaine, one to bupivacaine and prilocaine. A positive reaction to the chemically unrelated cincaine was interpreted as concomitant sensitivity rather than cross-sensitivity. Safe substitutes for benzocaine-sensitive patients include lidocaine, mepivacaine, prilocaine, bupivacaine, and pyrocaine (Fisher 1973 p. 312), all based on an amide structure. Lidocaine-sensitive patients may use tetracaine (pontocaine), a derivative of aminobenzoic acid. 

Examples Terbutylazine and simazine were used as structural analogue of the target atrazine [2], pentycaine for bupivacaine [3], compound E for the lead drug F [4] Check Table 1 for the structures. 

FIGURE 28.2 Structure of medicines amiodarone (antiarrythmic), amitriptyline (antidepressant), and bupivacaine (local anesthetic). 

A 22-G needle can be used for most therapeutic injections as it can reach most superficial musculoskeletal structures in children but a larger bore needle is usually required for aspiration. For therapeutic injections, usually a mixture of depomedrone and bupivacaine 0.5% is administered, with the dose varying according to the age of the child and the region being injected. 

High-resolution XRPD data have been used to determine the structures of three crystalline modifications of telmisartan, " the elusive form-II of enalapril maleate, and bupivacaine free base. ... 

Cheung, E. Y., Harris, K. D. M., Johnston, R. L., Kitchin, S. J., Hadden, K. L. and Zakrzewski, M. Rationalizing the structural properties of bupivacaine base—a local anesthetic—directly from powder X-ray diffraction data. J. Pharm. Sci. 93 667-674, 2004. 

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