OXETHAZAINE

First approved in 1960

Details

Stereochemistry	ACHIRAL
Molecular Formula	C28H41N3O3
Molecular Weight	467.6434
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN(C(=O)CN(CCO)CC(=O)N(C)C(C)(C)CC1=CC=CC=C1)C(C)(C)CC2=CC=CC=C2

InChI

InChIKey=FTLDJPRFCGDUFH-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Description
Sources: http://www.eisai.jp/medical/products/di/EPI/SR_T-G_EPI.pdf
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/13910333 and http://home.intekom.com/pharm/akromed/mucaines.html

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. Its effectiveness at the acidity of the gastric environment is due to the fact that oxethazaine, a weak base, is relatively non-ionized at pH 1. It is also used topically in the management of hemorrhoid pain. Oral oxetacaine preparations are available in several countries, including India, South Africa and Brazil, but not the United States. It is marketed under the name Strocain in Japan.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Chronic hepatitis B virus replication 2 Target ID: Chronic hepatitis B virus replication Sources: http://www.ncbi.nlm.nih.gov/pubmed/26838678	Inhibitor 8297
Sodium channel alpha subunits; brain (Types I, II, III) 28 Target ID: CHEMBL2096682 Sources: http://www.ncbi.nlm.nih.gov/pubmed/2579237	Inhibitor 8297		2.3 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Esophagitis 4 Sources: http://www.eisai.jp/medical/products/di/EPI/SR_T-G_EPI.pdf	Palliative	Approved 8429	STROCAIN Approved Use Pain, hyperacidity symptoms, eructation, nausea, vomiting, stomach discomfort and defecation urgency resulting from the following diseases Esophagitis, gastritis, gastric/duodenal ulcer and irritable colon Launch Date 1962
Gastritis 45 Sources: http://www.eisai.jp/medical/products/di/EPI/SR_T-G_EPI.pdf	Palliative	Approved 8429	STROCAIN Approved Use Pain, hyperacidity symptoms, eructation, nausea, vomiting, stomach discomfort and defecation urgency resulting from the following diseases Esophagitis, gastritis, gastric/duodenal ulcer and irritable colon Launch Date 1962
Gastric ulcer 67 Sources: http://www.eisai.jp/medical/products/di/EPI/SR_T-G_EPI.pdf	Palliative	Approved 8429	STROCAIN Approved Use Pain, hyperacidity symptoms, eructation, nausea, vomiting, stomach discomfort and defecation urgency resulting from the following diseases Esophagitis, gastritis, gastric/duodenal ulcer and irritable colon Launch Date 1962

C_max

Value	Dose	Co-administered	Analyte	Population
20 ng/mL REVIEW https://www.msjonline.org/index.php/ijrms/article/viewFile/4410/3655	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:		OXETHAZAINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
1 h REVIEW https://www.msjonline.org/index.php/ijrms/article/viewFile/4410/3655	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:		OXETHAZAINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2C19 1478

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1692	inhibitor 3277 Sources: https://www.jstage.jst.go.jp/article/bpb/40/10/40_b17-00118/_pdf/-char/en#page=6 Page: 6.0	unlikely
CYP2C19 1553	inhibitor 3277 Sources: https://www.jstage.jst.go.jp/article/bpb/40/10/40_b17-00118/_pdf/-char/en#page=6 Page: 6.0	unlikely
CYP2C9 1819	inhibitor 3277 Sources: https://www.jstage.jst.go.jp/article/bpb/40/10/40_b17-00118/_pdf/-char/en#page=6 Page: 6.0	unlikely
CYP3A4 1925	inhibitor 3277 Sources: https://www.jstage.jst.go.jp/article/bpb/40/10/40_b17-00118/_pdf/-char/en#page=5 Page: 5.0	yes [Ki 3.08 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://www.jstage.jst.go.jp/article/bpb/40/10/40_b17-00118/_pdf/-char/en#page=5 Page: 5.0	yes [Ki 6.3 uM]

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY514970	https://www.001chemical.com/chem/126-27-2
3B Scientific (Wuhan) Corp	3B2-1661	http://www.3bsc.com/index/pro_info.php?id=55380
AA Blocks	AA000QLB	https://www.aablocks.com/goods/Goods/detail?id=AA000QLB
AHH Chemical co.,ltd	MT-57593	http://www.ahhchemical.com/product/MT-57593.html
AK Scientific, Inc. (AKSCI)	2622AH	http://www.aksci.com/item_detail.php?cat=2622AH
AbMole Bioscience	M2906	http://www.abmole.com/products/oxethazaine.html
Alfa Chemistry	AP126272	https://reagents.alfa-chemistry.com/product/oxethazaine-cas-126-27-2-3376.html
Alfa Chemistry	126-27-2	https://www.alfa-chemistry.com/oxethazaine-cas-126-27-2-item-289903.htm
Angel Pharmatech	AG-19788	http://www.angelpharmatech.com/126-27-2.html
ApexBio Technology	A8494	http://www.apexbt.com/oxethazaine.html
Aurora Fine Chemicals LLC	A17.912.887	http://online.aurorafinechemicals.com/info?ID=A17.912.887
BLD Pharm	BD146490	http://www.bldpharm.com/products/126-27-2.html
BioChemPartner	BCP07626	http://www.biochempartner.com/126-27-2-BCP07626
BioCrick	BCC3832	http://www.biocrick.com/Oxethazaine-BCC3832.html
BioSynth	J-005353	https://www.biosynth.com/en/products/all-products/products/J-005353.html
CSNpharm	CSN11632	https://www.csnpharm.com/products/oxethazaine.html
Chem Scene	CS-4432	http://www.chemscene.com/126-27-2.html
ChemMol	49426613	http://www.chemmol.com/chemmol/49426613.html
Chemspace	CSSB00000052514	https://chem-space.com/CSSB00000052514
Clearsynth	CS-O-30708	https://www.clearsynth.com/en/CSO30708.html
DC Chemicals	DC36781	http://www.dcchemicals.com//product_show-Oxethazaine.html
Debye Scientific	DB-041818	http://www.debyesci.com/cas_126-27-2.html
Finetech	FT-0603332	http://www.finetechnology-ind.com/prod/detail/pub/126-27-2.html
Hairui	HR142267	http://www.hairuichem.com/en/product/126-27-2.html
LGC Standards	LGCFOR1981.00	https://www.lgcstandards.com/US/en/p/LGCFOR1981.00
LGC Standards	MM1981.00	https://www.lgcstandards.com/US/en/p/MM1981.00
Lab Network	LN01301069	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01301069
MedChem Express	HY-B0955	https://www.medchemexpress.com/Oxethazaine.html
Molcore	MC514970	https://www.molcore.com/product/126-27-2
MuseChem	I001058	https://www.musechem.com/product/I001058.html
OChem	8802	http://www.ocheminc.com/index.php?act=psearch&pid=126O272
Sigma-Aldrich	O5380_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/o5380?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S538378	http://www.smolecule.com/products/s538378
THE BioTek	bt-277973	https://www.thebiotek.com/product/inhibitors/bt-277973
eNovation Chemicals	D672298	https://www.enovationchem.com/ProductDetails.asp?ProductID=D672298
iChemical	EBD45293	http://www.ichemical.com/products/126-27-2.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-5155939580	https://mcule.com/MCULE-5155939580/

PubMed

Title	Date	PubMed
Drug use in children: cohort study in three European countries.	2008 Nov 24	19029175

Patents

Sample Use Guides

In Vivo Use Guide

The usual adult dosage for oral use is 3 to 8 tablets (15 to 40 mg of oxethazaine) daily divided into three to four doses.

Route of Administration: Oral

In Vitro Use Guide

100 uM Oxethazaine caused almost complete red blood cell hemolysis in the presence of 1.3 mM Ca2+ with only a minimal effect in its absence, while higher concentrations of Oxethazaine (400 uM<) produced hemolysis without Ca2+.

Name

Type

Language

OXETHAZAINE

Official Name

English

ACETAMIDE, 2,2'-((2-HYDROXYETHYL)IMINO)BIS(N-(1,1-DIMETHYL-2-PHENYLETHYL)-N-METHYL-

Systematic Name

English

Oxetacaine [WHO-DD]

Common Name

English

OXETHAZAINE [JAN]

Common Name

English

oxetacaine [INN]

Common Name

English

NSC-758444

Code

English

OXETHAZAINE [USAN]

Common Name

English

OXETHAZAINE [MI]

Common Name

English

STROCAIN

Brand Name

English

WY-806

Code

English

OXETACAINE [MART.]

Common Name

English

OXETACAINE

Official Name

English

2,2'-((2-HYDROXYETHYL)IMINO)BIS(N-(.ALPHA.,.ALPHA.-DIMETHYLPHENETHYL)-N-METHYLACETAMIDE)

Systematic Name

English

Classification Tree Code System Code

WHO-VATC

QC05AD06