Proxymetacaine

Proxymetacaine

Systematic (IUPAC) name
2-(diethylamino)ethyl 3-amino-4-propoxybenzoate
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	Topical (eye drops)
Pharmacokinetic data
Metabolism	Plasma
Identifiers
CAS Number	499-67-2 5875-06-9 (HCl)
ATC code	S01HA04 (WHO)
PubChem	CID 4935
IUPHAR/BPS	7283
DrugBank	DB00807
ChemSpider	4766
UNII	B4OB0JHI1X
KEGG	D08448
ChEMBL	CHEMBL1196
Chemical data
Formula	C16H26N2O3
Molar mass	294.389 g/mol
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
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Proxymetacaine (INN) or proparacaine (USAN) is a topical anesthetic drug of the aminoester group.

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.