Oxetacaine

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 462267014

| IUPAC_name = 2,2'-(2-hydroxyethylimino)bis [N-(1,1-dimethyl-2- phenylethyl)-N-methylacetamide]

| image = Oxetacaine.svg

| width = 280

| tradename =

| Drugs.com = {{drugs.com|international|oxetacaine}}

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status =

| routes_of_administration = Oral, topical

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life = 1 hour

| excretion =

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 126-27-2

| ATC_prefix = C05

| ATC_suffix = AD06

| PubChem = 4621

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4460

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = IP8QT76V17

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D01152

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 127592

| C=28 | H=41 | N=3 | O=3

| smiles = O=C(N(C(C)(C)Cc1ccccc1)C)CN(CCO)CC(=O)N(C(Cc2ccccc2)(C)C)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = FTLDJPRFCGDUFH-UHFFFAOYSA-N

}}

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.{{cite journal |vauthors=Seifter J, Glassman JM, Hudyma GM |title=Oxethazaine and related congeners: a series of highly potent local anesthetics |journal=Proc Soc Exp Biol Med |volume=109 |pages=664–8 |year=1962 |issue=3 |pmid=13910333 |doi=10.3181/00379727-109-27300|s2cid=39641018 }}

It is known to produce mephentermine and phentermine as metabolites.{{cite journal | vauthors = Hsu MC, Lin SF, Kuan CP, Chu WL, Chan KH, Chang-Chien GP | title = Oxethazaine as the source of mephentermine and phentermine in athlete's urine | journal = Forensic Sci Int | volume = 185 | issue = 1-3 | pages = e1–5 | date = March 2009 | pmid = 19157735 | doi = 10.1016/j.forsciint.2008.12.009 | url = }}{{cite journal | vauthors = Huang WH, Liu CH, Liu RH, Tseng YL | title = Confirming urinary excretion of mephentermine and phentermine following the ingestion of oxethazaine by gas chromatography-mass spectrometry analysis | journal = J Anal Toxicol | volume = 34 | issue = 2 | pages = 73–77 | date = March 2010 | pmid = 20223098 | doi = 10.1093/jat/34.2.73 | url = }}