Proxymetacaine

Proxymetacaine (INN) or proparacaine (USAN) is a topical anesthetic drug of the aminoester group.

Proxymetacaine

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Topical (eye drops)
ATC code	S01HA04 (WHO)
Legal status
Legal status	BR: Class C1 (Other controlled substances)[1]
Pharmacokinetic data
Metabolism	Plasma
Identifiers
IUPAC name 2-(diethylamino)ethyl 3-amino-4-propoxybenzoate
CAS Number	499-67-2 Y 5875-06-9 (HCl)
PubChem CID	4935
IUPHAR/BPS	7283
DrugBank	DB00807 Y
ChemSpider	4766 Y
UNII	B4OB0JHI1X
KEGG	D08448 Y
ChEMBL	ChEMBL1196 Y
CompTox Dashboard (EPA)	DTXSID30198146
ECHA InfoCard	100.007.169
Chemical and physical data
Formula	C16H26N2O3
Molar mass	294.395 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(OCCN(CC)CC)c1ccc(OCCC)c(c1)N
InChI InChI=1S/C16H26N2O3/c1-4-10-20-15-8-7-13(12-14(15)17)16(19)21-11-9-18(5-2)6-3/h7-8,12H,4-6,9-11,17H2,1-3H3 Y Key:KCLANYCVBBTKTO-UHFFFAOYSA-N Y
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Clinical pharmacology

Proxymetacaine is a local anesthetic which on topical application penetrates sensory nerve endings in the corneal tissue.^[2]

Mechanism of action

Proxymetacaine is believed to act as an antagonist on voltage-gated sodium channels to affect the permeability of neuronal membranes; how this inhibits pain sensations and the exact mechanism of action of proxymetacaine are, however, unknown.^[3]

Indications and usage

Proxymetacaine hydrochloride ophthalmic solution (eye drops) is indicated for procedures such as tonometry, gonioscopy, removal of foreign bodies, or other similar procedures requiring topical anesthesia of the cornea and conjunctiva.^[4]

Warnings

Proxymetacaine is for topical ophthalmic use only, and it is specifically not intended for injection. Prolonged use of this or any other topical ocular anesthetic may produce permanent corneal opacification with accompanying visual loss.

How supplied

Proxymetacaine is available as its hydrochloride salt in ophthalmic solutions at a concentration of 0.5%. Although it is no longer on patent, it is still marketed under the trade names Alcaine, Ak-Taine, and others. Proparacaine 0.5% is marketed as Poencaina by Poen Laboratories.^[5]

References

1. Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
2. Draeger J, Langenbucher H, Bannert C (1984). "Efficacy of topical anaesthetics". Ophthalmic Research. 16 (3): 135–8. doi:10.1159/000265308. PMID 6472792.
3. Goodman LS, Gilman AG, Goodman A (1980). The Pharmacological Basis of Therapeutics (6th ed.). New York: MacMillan Pub. ISBN 978-0023447204.
4. Murphy PJ, Ntola AM (April 2009). "Prolonged corneal anaesthesia by proxymetacaine hydrochloride detected by a thermal cooling stimulus". Contact Lens & Anterior Eye. 32 (2): 84–7, quiz 99–100. doi:10.1016/j.clae.2008.12.006. PMID 19181566.
5. "Poen-Caina generic. Price of poen-caina. Uses, Indications and Description". ndrugs. Retrieved 15 March 2018.