Proxymetacaine

Proxymetacaine
Clinical data
Routes of; administration	Topical (eye drops)
ATC code	S01HA04 (WHO) ;
Pharmacokinetic data
Metabolism	Plasma
Identifiers
	IUPAC name 2-(diethylamino)ethyl 3-amino-4-propoxybenzoate;
CAS Number	499-67-2 ; 5875-06-9 (HCl);
PubChem CID	4935;
DrugBank	APRD00522;
ChemSpider	4766 ;
UNII	B4OB0JHI1X;
KEGG	D08448 ;
ChEMBL	ChEMBL1196 ;
CompTox Dashboard (EPA)	DTXSID30198146 ;
ECHA InfoCard	100.007.169
Chemical and physical data
Formula	C16H26N2O3
Molar mass	294.389 g/mol 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 ; Key:KCLANYCVBBTKTO-UHFFFAOYSA-N ;
	(verify)

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

Clinical pharmacology

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.

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.

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.

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.

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