Tetracaine
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| AHFS/Drugs.com | Monograph |
| MedlinePlus | a682640 |
| Routes of administration | Topical, Epidural, Spinal |
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| Pharmacokinetic data | |
| Protein binding | 75.6 |
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| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.002.106 |
| Chemical and physical data | |
| Formula | C15H24N2O2 |
| Molar mass | 264.363 g/mol g·mol−1 |
| 3D model (JSmol) | |
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Tetracaine (INN, also known as amethocaine; trade name Pontocaine. Ametop and Dicaine) is a potent local anesthetic of the ester group. It is mainly used topically in ophthalmology and as an antipruritic, and it has been used in spinal anesthesia.
In biomedical research, tetracaine is used to alter the function of calcium release channels (ryanodine receptors) that control the release of calcium from intracellular stores. Tetracaine is an allosteric blocker of channel function. At low concentrations, tetracaine causes an initial inhibition of spontaneous calcium release events, while at high concentrations, tetracaine blocks release completely.[1]
Tetracaine is the T in Tac, a mixture of 5 to 12 per cent tetracaine, 5‱ (per myriad), a half per mille (0.5‰), or .05 per cent (1 part in 2000) adrenaline, and 4 or 10 per cent cocaine hydrochloride used in ear, nose & throat surgery and in the emergemcy department where numbing of the surface is needed rapidly, especially when children have been injured in the eye, ear, or other sensitive locations.[2]
It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.[3] A systematic review and meta-analysis of randomised controlled trials investigated tetracaine for use in emergency departments, especially for IV cannulation in children, in view of its analgesic and cost-saving properties - however it did not find a statistically significant improvement in first attempt cannulations.[4]
Synthesis
Tetracaine is synthesized from 4-butylaminobenzoic acid. The ethyl ester is formed through an acid-catalyzed esterification reaction. Base-catalyzed transesterification is achieved by boiling the ethyl ester of 4-butylaminobenzoic acid with excess 2-dimethylaminoethanol in the presence of a small amount of sodium ethoxide.[5]
References
- ^ Györke, S; Lukyanenko, V; et al. (1997). "Dual effects of tetracaine on spontaneous sodium release in rat ventricular myocytes". 500 (2). J Physiol: 297–309.
{{cite journal}}: Cite journal requires|journal=(help); Explicit use of et al. in:|author2=(help) - ^ Appleton's Nursing Manual - "Cocaine"
- ^ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.
- ^ Pywell, A; Xyrichis, A (2014). "Does topical Amethocaine cream increase first-time successful cannulation in children compared with a eutectic mixture of local anaesthetics (EMLA) cream? A systematic review and meta-analysis of randomised controlled trials". 0 (0). Emerg Med J: 1–5. doi:10.1136/emermed-2014-204066.
{{cite journal}}: Cite journal requires|journal=(help) - ^ Winthrop Chemical Company, Inc. U.S. Patent 1,889,645, 1932.
Further reading
- O. Eisleb, U.S. patent 1,889,645 (1932).
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