Fleck, Christian published the artcileLocal anaesthetic effectivity and toxicity of fomocaine, five N-free fomocaine metabolites and two chiral fomocaine derivatives in rats compared with procaine, Name: 4-(Phenoxymethyl)benzoic acid, the publication is Arzneimittel-Forschung (2001), 51(6), 451-458, database is CAplus.
Until now, no optimal local anesthetic drug with long lasting effect and low toxicity has been developed. Fomocaine (CAS 17692-39-6), introduced in the German extrapharmacopoeia (DAC) in 1979, is a local anesthetic, which is largely in accordance with these aspects. Now the basic ether fomocaine, its metabolites O/Se 9 (CAS 3006-96-0), O/Se 10 (CAS 31719-76-3), O/Se 11, O/Se 12 (CAS 64264-21-7) and M5 and its chiral derivatives O/G 3 and O/G 5 were compared with procaine (CAS 59-46-1) and characterized more in detail in rats. The metabolism of fomocaine was investigated earlier with 14C-fomocaine in rats and beagle dogs. Rac-O/G 3 and Rac-O/G 5 could be separated into the enantiomers via the diastereomeric salts. Based on standard methods for the testing of the local anesthetic effects (estimation of infiltration and conduction anesthesia in rat tail, measurement of corneal anesthesia) and using a couple of tests characterizing the side effects and toxicity of local anesthetic (paresis of the N. ischiadicus, tissue irritation, determination of the approximative i.p. LD50) it can be concluded that: (a) the very good surface anesthesia caused by fomocaine could be stated, but, as expected, concerning conduction anesthesia, procaine is better qualified for clin. use. (b) Fomocaine is much more effective in conduction and surface anesthesia than its chiral derivatives O/G 3 and O/G 5. (c) Differences between the two enantiomers of the O/G-substances have been found, but these little discrepancies are without practical relevance. In the case of O/G 5, agonistic effects of both enantiomers could be shown. (d) Fomocaine undergoes extensive biotransformation with subsequent formation of 14 metabolites. Five of them (O/Se 9-O/Se 12; M5) are N-free and do not show any pharmacol. activity. (e) Compared to other local anesthetics, fomocaine is relatively non-toxic (nearly no tissue irritation, high approximative LD50), however, surprisingly the toxicity of the reference substance procaine has been found to be lower after i.p. administration instead of i.v. administration in comparison with fomocaine.
Arzneimittel-Forschung published new progress about 31719-76-3. 31719-76-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 4-(Phenoxymethyl)benzoic acid, and the molecular formula is C14H12O3, Name: 4-(Phenoxymethyl)benzoic acid.
Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia