Bot Detector
Download FREE Sample Issue or Article
Subscribe Today
A subscription to IJPC includes a print copy delivered by postal mail and on-line access to electronic PDF copies of your subscribed issues.

Kinetics of Tetracaine Solvolysis in Propylene Glycol

Author(s):  McPherson Timothy B, Neumann William L, Goolsby Michael, Kolling William M

Issue:  Jul/Aug 2018 - Volume 22, Number 4
View All Articles in Issue

Abstract:  Tetracaine is a potent ester-type local anesthetic. Recent publications describe the use of TC free base in topical anesthetic formulations containing propylene glycol. While solvolysis of tetracaine in propylene glycol solutions has been reported, there are no detailed reports on the kinetics of tetracaine reaction with propylene glycol. The objectives of the study were to characterize the kinetics and temperature dependence of tetracaine solvolysis in PG solutions. In this study, products of tetracaine degradation in propylene glycol solution at 60ÅãC were collected and analyzed by high-performance liquid chromatographymass spectrometry and nuclear magnetic resonance. The kinetics of tetracaine reaction with propylene glycol was studied at 22ÅãC, 30ÅãC, 40ÅãC, and 60ÅãC. The reaction of tetracaine with n-propanol and isopropanol was also studied. Analysis was performed by high-performance liquid chromatography-mass spectrometry with ultraviolet detection using a gradient elution method. Tetracaine concentrations were quantitated using a four-point standard curve. Tetracaine degradation rates were consistent with apparent first order kinetics at all temperatures studied. The data indicated that tetracaine degrades via transesterification with propylene glycol. The rate constants ranged from 2.26 Å~ 10-3 d-1 at 22ÅãC to 7.06 Å~ 10-2 d-1 at 60ÅãC. Arrhenius analysis indicated an activation energy for the reaction of 74.1 kJ/mol, which is similar to published values for the hydrolysis of pharmaceutical esters.

Related Keywords: Timothy B. McPherson, PhD, William L. Neumann, PhD, Michael Goolsby, PharmD, William M. Kolling, PhD, tetracaine, ester-type local anesthetic, topical preparation, solvolysis, propylene glycol, degradation kinetics, temperature


Printer-Friendly Version

Download in electronic PDF format for $55

Related Articles from IJPC
Title (Click for Abstract / Details) Author Issue Page View/Buy
Kinetics of Tetracaine Solvolysis in Propylene Glycol McPherson Timothy B, Neumann William L, Goolsby Michael, Kolling William M Jul/Aug 2018 329-334 Buy
Stability of Non-aqueous Topical Tetracaine and Clotrimazole Solutions in Polypropylene Droptainer Bottles McPherson Timothy B, Neumann William L, Kolling William M Nov/Dec 2013 508-511 Buy
Current Topical Treatments in Wound Healing - Part 1 Helmke Christopher D Jul/Aug 2004 269-274 Buy
Rapid-Dissolve Technology: An Interview With Loyd V. Allen, Jr., PhD, RPh Allen Loyd V Jr Nov/Dec 2003 449-450 Buy
Safe Use of Topical Local Anesthetic Medications for Pain Management Epshteyn Mikhail G, Pepin Steven M May/Jun 2009 218-219 Buy
Novel Approaches to Topical Psoriasis Therapy Koyama Gregory, Liu Jenny, Scaffidi Alyse, Khazraee Maryam, Epstein Benjamin Sep/Oct 2015 357-365 Buy
Physico-chemical Stability of MabThera Drug-product Solution for Subcutaneous Injection under In-use Conditions with Different Administration Materials Mueller Claudia, Dietel Elde, Heynen Severin R, Nalenz Heiko, Goldbach Pierre, Mahler Hanns-Christian, Schmidt Johannes, Grauschopf Ulla, Schoenhammer Karin May/Jun 2015 261-267 Buy
Design and Performance of an Inexpensive Water Activity Meter Gilda Sagar S, Schober Joseph M, McPherson Timothy Jan/Feb 2021 48-51 Buy
Compounded Local Anesthetics to Minimize Pain from Medical Procedures McElhiney Linda F May/Jun 2008 192-197 Buy
Tetracaine Hydrochloride 2% Topical Solution Allen Loyd V Jr Sep/Oct 2016 414 Buy