Oxybuprocaine Explained

Oxybuprocaine (INN), also known as benoxinate or BNX, is an ester-type local anesthetic, which is used especially in ophthalmology and otolaryngology. Oxybuprocaine is sold by Novartis under the brand names Novesine or Novesin.

Safety for use in pregnancy and lactation has not been established.

Uses

Pharmacokinetics

Anaesthesia starts with a latency of 30 to 50 seconds and lasts for about 10 to 30 minutes, depending on perfusion. The drug is metabolised by esterases in blood plasma and liver.

Adverse effects

When used excessively, oxybuprocaine like any other topical anesthetic used in the eye and on mucous membranes (like for example tetracaine, proxymetacaine and proparacaine) can cause irritation, hypersensitivity, anaphylaxis, irreversible corneal damage and even complete destruction of the cornea.[3] (Excessive use means several times a day during several days or even weeks.)

Interactions

Oxybuprocaine is incompatible with silver and mercury salts, as well as alkaline substances. It also reduces the antimicrobial action of sulfonamides.

Synthesis

The nitration of 3-hydroxybenzoic acid [99-06-9] (0) gives 3-hydroxy-4-nitrobenzoic acid [619-14-7] (1). Fischer esterification with ethanol gives ethyl 3-hydroxy-4-nitrobenzoate [717-01-1] (2). The phenoxide ion was then prepared from potash (3). Alkylation with 1-bromobutane supplied ethyl 3-butoxy-4-nitrobenzoate, CID:13346201 (4). The product is crystallized from hydrochloric acid, and then halogenation with thionyl chloride gives 3-butoxy-4-nitrobenzoyl chloride [23442-21-9] (5). Esterification with diethylaminoethanol [100-37-8] (6) gives 2-(diethylamino)ethyl 3-butoxy-4-nitrobenzoate, CID:13346204 (7) Lastly, catalytic hydrogenation over Raney-Nickel completes the synthesis of Oxybuprocaine (8).

See also

Notes and References

  1. Drugs.com: Minims Oxybuprocaine Hydrochloride 0.4%
  2. Book: Austria-Codex. Jasek W . Österreichischer Apothekerverlag. Vienna. 2007. 2007/2008. 978-3-85200-181-4. de.
  3. McGee HT, Fraunfelder FW . Toxicities of topical ophthalmic anesthetics . Expert Opinion on Drug Safety . 6 . 6 . 637–40 . November 2007 . 17967152 . 10.1517/14740338.6.6.637 . 44377478 .