The spatial arrangement of single stereoisomers may influence pharmacodynamic, pharmacokinetic and toxicological properties of a drug. Trapencaine (I. N. N.), (+/-)-trans-2-(pyrrolidin-1-yl)cyclohexylester of 3-(n)-pentyloxycarbanilic acid, was developed as an antiulcer drug with gastroprotective, local anaesthetic and spasmolytic effects. Limited information is available about the potential pharmacodynamic differences of the enantiomers of trapencaine. Therefore, the enantiomers of (+/-)-trans- or cis-2-(pyrrolidin-1-yl)cyclohexylester of 3-(n)-pentyloxy carbanilic acid were synthesised and tested on models of acute gastric damage induced by indomethacin and/or ethanol. A difference was found between their antiulcer effect, with the (+)-trans-enantiomer being the most effective and the (-)-cis-enantiomer the least effective in the models used.

01 Jul 2001·Ceska a Slovenska farmacie : casopis Ceske farmaceuticke spolecnosti a Slovenske farmaceuticke spolecnosti

[Anti-radical activity of certain anti-ulcer agents and local anesthetics].

Article

Author: Dovolil, J ; Benes, L

The free radical scavenging effect of the hydrochloride of (+/-)-trans-2-(1-pyrrolidinyl-)cyclohexylester of 3-(n)-pentyloxy carbanilic acid, pentacaine (trapencaine I.N.N), and its derivatives and other substances, lidocaine, stobadine, mannitol, and ascorbic acid was tested in the presence of diphenyl-p-picrylhydrazyl (decrease in absorbance). In this method, more pronounced antiradical activity was observed with trapencaine, more effective than stobadine, ascorbate, and mannitol. Trapencaine derivatives and lidocaine were less effective in comparison with trapencaine. After introducing a methylene group into the hydrophilic moiety of the trapencaine molecule (stereoisomers P-18, P-20), there was a loss of antiradical activity, but the cis-isomer is more effective than the transisomer. The results demonstrate the existence of relationships between the chemical structure, antiradical and gastric-cytoprotective activity.

01 Jun 1995·Die Pharmazie

Effect of trapencaine and some of its derivatives on gastric wall mucus in stressed rats.

Article

Author: Juránek, I ; Nosálová, V ; Babulová, A

The effect of selected carbanilates on the rat gastric mucus was tested after oral administration. The compounds K 1905 and K 2002 were found to increase gastric mucus content in nonstressed rats while compound P 2 was ineffective. The activity of K 1905 was comparable with that of the parent drug trapencaine. Cold-restraint stress decreased the gastric mucus content and induced haemorrhagic erosions in the glandular stomach. With the exception of compound P 2 pretreatment with carbanilates dose-dependently diminished the extent of stress-induced gastric damage and prevented the depletion of mucus after stress. The results indicate that pentyloxy-substitution in the meta and in the para position on the benzene ring of the parent structure (K 1905 and K 2002, respectively) seems to be more suitable for mucus enhancing activity than alkyloxy-substitution on the para position (P 2). The observed increased mucus secretion might be partly responsible for the gastroprotective action of the drugs tested.

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Indication	Highest Phase	Country/Location	Organization	Date
Anesthesia	Phase 1	-	Slovak Academy of Sciences	-
Helicobacter pylori infection	Phase 1	-	Slovak Academy of Sciences	-

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