Oxybuprocaine

Last updated
Oxybuprocaine
Oxybuprocaine.svg
Clinical data
Trade names Novesin(e)
AHFS/Drugs.com International Drug Names
Pregnancy
category
  • AU:D
Routes of
administration
Topical
ATC code
Legal status
Legal status
Pharmacokinetic data
Metabolism Esterases in blood plasma and liver
Identifiers
  • 2-diethylaminoethyl 4-amino-3-butoxy-benzoate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C17H28N2O3
Molar mass 308.422 g·mol−1
3D model (JSmol)
  • O=C(OCCN(CC)CC)c1cc(OCCCC)c(cc1)N
  • InChI=1S/C17H28N2O3/c1-4-7-11-21-16-13-14(8-9-15(16)18)17(20)22-12-10-19(5-2)6-3/h8-9,13H,4-7,10-12,18H2,1-3H3 Yes check.svgY
  • Key:CMHHMUWAYWTMGS-UHFFFAOYSA-N Yes check.svgY
   (verify)

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.

Contents

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. [3]

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. [2] [4] (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. [3]

Synthesis

Thieme Synthesis: Patent: Sino: Precursor patent: Oxybuprocaine synthesis.svg
Thieme Synthesis: Patent: Sino: Precursor patent:

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

Related Research Articles

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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. 1 2 Drugs.com: Minims Oxybuprocaine Hydrochloride 0.4%
  3. 1 2 3 4 Jasek W, ed. (2007). Austria-Codex (in German) (2007/2008 ed.). Vienna: Österreichischer Apothekerverlag. ISBN   978-3-85200-181-4.
  4. McGee HT, Fraunfelder FW (November 2007). "Toxicities of topical ophthalmic anesthetics". Expert Opinion on Drug Safety. 6 (6): 637–40. doi:10.1517/14740338.6.6.637. PMID   17967152. S2CID   44377478.
  5. Büchi, J.; Stünzi, Elisabeth; Flury, M.; Hirt, R.; Labhart, P.; Ragaz, L. (1951). "Über lokalanästhetisch wirksame basische Ester und Amide verschiedener Alkoxy-amino-benzoesäuren". Helvetica Chimica Acta. 34 (4): 1002–1013. doi:10.1002/hlca.19510340404.
  6. Anon., GB 654484 (1951 to Wander AG).
  7. Lai Fuping, CN 106810463 (2017 to Shenzhen Oasis Pharmaceutical Co Ltd).
  8. 叶芳, CN 105669462A (2016).