Oxetacaine

Last updated
Oxetacaine
Oxetacaine.svg
Clinical data
AHFS/Drugs.com International Drug Names
Routes of
administration 		Oral, topical
ATC code
Pharmacokinetic data
Elimination half-life 1 hour
Identifiers
  • 2,2'-(2-hydroxyethylimino)bis [N-(1,1-dimethyl-2- phenylethyl)-N-methylacetamide]
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.004.346 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C28H41N3O3
Molar mass 467.654 g·mol−1
3D model (JSmol)
  • O=C(N(C(C)(C)Cc1ccccc1)C)CN(CCO)CC(=O)N(C(Cc2ccccc2)(C)C)C
  • InChI=1S/C28H41N3O3/c1-27(2,19-23-13-9-7-10-14-23)29(5)25(33)21-31(17-18-32)22-26(34)30(6)28(3,4)20-24-15-11-8-12-16-24/h7-16,32H,17-22H2,1-6H3 Yes check.svgY
  • Key:FTLDJPRFCGDUFH-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Oxetacaine (INN, also known as oxethazaine) is a potent local anesthetic. It is administered orally (usually in combination with an antacid) for the relief of pain associated with peptic ulcer disease or esophagitis. It is also used topically in the management of hemorrhoid pain. Oral oxetacaine preparations are available in several countries, including India, South Africa, Japan, Taiwan and Brazil, but not the United States. Unlike most local anesthetics, oxetacaine does not break down under strongly acidic conditions. [1]

It is known to produce mephentermine and phentermine as metabolites. [2] [3]

References

  1. ↑ Seifter J, Glassman JM, Hudyma GM (1962). "Oxethazaine and related congeners: a series of highly potent local anesthetics". Proc Soc Exp Biol Med. 109 (3): 664–8. doi:10.3181/00379727-109-27300. PMID   13910333. S2CID   39641018.
  2. ↑ Hsu MC, Lin SF, Kuan CP, Chu WL, Chan KH, Chang-Chien GP (March 2009). "Oxethazaine as the source of mephentermine and phentermine in athlete's urine". Forensic Sci Int. 185 (1–3): e1–5. doi:10.1016/j.forsciint.2008.12.009. PMID   19157735.
  3. ↑ Huang WH, Liu CH, Liu RH, Tseng YL (March 2010). "Confirming urinary excretion of mephentermine and phentermine following the ingestion of oxethazaine by gas chromatography-mass spectrometry analysis". J Anal Toxicol. 34 (2): 73–77. doi:10.1093/jat/34.2.73. PMID   20223098.


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