Oxetacaine

Oxetacaine
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral, topical
ATC code	C05AD06 (WHO) ;
Pharmacokinetic data
Elimination half-life	1 hour
Identifiers
	IUPAC name 2,2'-(2-hydroxyethylimino)bis [N-(1,1-dimethyl-2- phenylethyl)-N-methylacetamide];
CAS Number	126-27-2 ;
PubChem CID	4621;
ChemSpider	4460 ;
UNII	IP8QT76V17;
KEGG	D01152 ;
ChEMBL	ChEMBL127592 ;
CompTox Dashboard (EPA)	DTXSID0025818 ;
ECHA InfoCard	100.004.346
Chemical and physical data
Formula	C28H41N3O3
Molar mass	467.654 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(N(C(C)(C)Cc1ccccc1)C)CN(CCO)CC(=O)N(C(Cc2ccccc2)(C)C)C;
	InChI 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 ; Key:FTLDJPRFCGDUFH-UHFFFAOYSA-N ;
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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. One example of such a product is Mucaine Gel, indicated for "rapid and effective relief in gastritis, esophagitis, hiatus hernia, heartburn of pregnancy and peptic ulcer".^[1] 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.^[2]

It is known to produce mephentermine and phentermine as metabolites.^[3]^[4]

References

^ "Mucaine Gel". Pfizer.com. Pfizer. Retrieved 6 October 2022.
^ 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.
^ 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.
^ 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.

External links

Strocain Prescribing information from Eisai Co.

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[1] "Mucaine Gel". Pfizer.com. Pfizer. Retrieved 6 October 2022.

[2] 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.

[HsuLinKuan2009-3] 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.

[HuangLiuLiu2010-4] 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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Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Oral, topical
ATC code	C05AD06 (WHO)
Pharmacokinetic data
Elimination half-life	1 hour
Identifiers
IUPAC name 2,2'-(2-hydroxyethylimino)bis [N-(1,1-dimethyl-2- phenylethyl)-N-methylacetamide]
CAS Number	126-27-2^N
PubChem CID	4621
ChemSpider	4460^Y
UNII	IP8QT76V17
KEGG	D01152^Y
ChEMBL	ChEMBL127592^Y
CompTox Dashboard (EPA)	DTXSID0025818
ECHA InfoCard	100.004.346
Chemical and physical data
Formula	C₂₈H₄₁N₃O₃
Molar mass	467.654 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(N(C(C)(C)Cc1ccccc1)C)CN(CCO)CC(=O)N(C(Cc2ccccc2)(C)C)C
InChI 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^Y Key:FTLDJPRFCGDUFH-UHFFFAOYSA-N^Y
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