OXYPHENISATIN ACETATE

First approved in 1959

Details

Stereochemistry	ACHIRAL
Molecular Formula	C24H19NO5
Molecular Weight	401.4114
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)OC1=CC=C(C=C1)C2(C(=O)NC3=CC=CC=C23)C4=CC=C(OC(C)=O)C=C4

InChI

InChIKey=PHPUXYRXPHEJDF-UHFFFAOYSA-N

InChI=1S/C24H19NO5/c1-15(26)29-19-11-7-17(8-12-19)24(18-9-13-20(14-10-18)30-16(2)27)21-5-3-4-6-22(21)25-23(24)28/h3-14H,1-2H3,(H,25,28)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6893676 | https://www.ncbi.nlm.nih.gov/pubmed/5024726 | https://www.fda.gov/ohrms/dockets/ac/98/briefingbook/1998-3454B1_03_WL36.pdf

Oxyphenisatin is a stimulant laxative that has been used by mouth and as an enema. Oxyphenisatin was introduced as Lavema by Winthrop in US in 1959. Oxyphenisatin was used as a cleansing enema apart from x-ray studies and prior to urinary, gastro-intestinal and cholecystography x-ray examination. Oxyphenisatin was also used for preoperative preparation of the large intestine and colon. May be mixed with barium for x-ray examination of the large intestine. Oxyphenisatin may cause jaundice. Oxyphenisatin-induced liver damage usually occurs when the drug has been taken for at least six months and usually two years. Oxyphenisatin was withdrawn in most countries in the early 1970s.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
peristalsis 4 Target ID: GO:0030432 Sources: https://www.ncbi.nlm.nih.gov/pubmed/5024726	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Constipation 112 Sources: https://www.fda.gov/ohrms/dockets/ac/98/briefingbook/1998-3454B1_03_WL36.pdf https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1938258/pdf/canmedaj00845-0050a.pdf	Primary		Withdrawn	LAVEMA Approved Use Indications.-May be used as a cleansing enema apart from x-ray studies and prior to urinary, gastro-intestinal and cholecystography x-ray examination. Also preoperative preparation of the large intestine and colon. May be mixed with barium for x-ray examination of the large intestine.
Gastrointestinal disorders 95 Sources: https://www.fda.gov/ohrms/dockets/ac/98/briefingbook/1998-3454B1_03_WL36.pdf https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1938258/pdf/canmedaj00845-0050a.pdf	Diagnostic		Withdrawn	LAVEMA Approved Use Indications.-May be used as a cleansing enema apart from x-ray studies and prior to urinary, gastro-intestinal and cholecystography x-ray examination. Also preoperative preparation of the large intestine and colon. May be mixed with barium for x-ray examination of the large intestine.

Doses

Dose	Population	Adverse events
5 mg 2 times / day multiple, oral Dose: 5 mg, 2 times / day Route: oral Route: multiple Dose: 5 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4605276/	unhealthy, 19-84 years n = 32 Health Status: unhealthy Condition: chronic non-alcoholic liver disease Age Group: 19-84 years Sex: M+F Population Size: 32 Sources: https://pubmed.ncbi.nlm.nih.gov/4605276/	Other AEs: Liver damage... Other AEs: Liver damage Sources: https://pubmed.ncbi.nlm.nih.gov/4605276/
7.5 mg 1 times / day multiple, oral Dose: 7.5 mg, 1 times / day Route: oral Route: multiple Dose: 7.5 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/5113720	unhealthy, 65 years n = 1 Health Status: unhealthy Age Group: 65 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/5113720	Disc. AE: Hepatitis... AEs leading to discontinuation/dose reduction: Hepatitis Sources: https://pubmed.ncbi.nlm.nih.gov/5113720

AEs

AE	Significance	Dose	Population
Liver damage		5 mg 2 times / day multiple, oral Dose: 5 mg, 2 times / day Route: oral Route: multiple Dose: 5 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4605276/	unhealthy, 19-84 years n = 32 Health Status: unhealthy Condition: chronic non-alcoholic liver disease Age Group: 19-84 years Sex: M+F Population Size: 32 Sources: https://pubmed.ncbi.nlm.nih.gov/4605276/
Hepatitis	Disc. AE	7.5 mg 1 times / day multiple, oral Dose: 7.5 mg, 1 times / day Route: oral Route: multiple Dose: 7.5 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/5113720	unhealthy, 65 years n = 1 Health Status: unhealthy Age Group: 65 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/5113720

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY514214	https://www.001chemical.com/chem/125-13-3
3B Scientific (Wuhan) Corp	3B3-061746	http://www.3bsc.com/index/pro_info.php?id=100835
AA Blocks	AA000MVV	https://www.aablocks.com/goods/Goods/detail?id=AA000MVV
AEchem Scientific Corp., USA	AE041197	http://www.aechemsc.com/info_products/AE041197.php
Aaron Chemicals	AR000NNN	http://www.aaronchem.com/125-13-3
Alfa Chemistry	125-13-3	https://www.alfa-chemistry.com/cas_125-13-3.htm
BLD Pharm	BD81277	http://www.bldpharm.com/products/125-13-3.html
CSNpharm	CSN22096	https://www.csnpharm.com/products/oxyphenisatine.html
Chem Scene	CS-6312	http://www.chemscene.com/125-13-3.html
ChemShuttle	ZB1280	https://www.chemshuttle.com/catalogsearch/result/?q=125-13-3&cat=
Chemspace	CSSB00020616883	https://chem-space.com/CSSB00020616883
DC Chemicals	DC32631	http://www.dcchemicals.com//product_show-Oxyphenisatine.html
Debye Scientific	DB-080971	http://www.debyesci.com/cas_125-13-3.html
Finetech	FT-0614032	http://www.finetechnology-ind.com/prod/detail/pub/125-13-3.html
Frinton	FR-1193	https://www.frinton.com/search/?filtername=3,3-Bis(p-hydroxyphenyl)oxindole
Lab Network	LN01291747	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01291747
Matrix Scientific	172365	https://www.matrixscientific.com/172365.html
MedChem Express	HY-B2102	https://www.medchemexpress.com/Oxyphenisatine.html
Molcore	MC514214	https://www.molcore.com/product/125-13-3
MuseChem	R063341	https://www.musechem.com/product/R063341.html
Oakwood	342089	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=151063&ExtHyperLink=1
R&D Chemicals	FR-1193	http://www.rdchemicals.com/chemicals.php?mode=details&mol_id=2853
Sigma-Aldrich	S675407_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/s675407
Sinfoo Biotech	S020875	http://www.sinfoobiotech.com/product/1024273
Smolecule	S538432	http://www.smolecule.com/products/s538432
Smolecule	S749205	https://www.smolecule.com/products/s749205
THE BioTek	bt-278085	https://www.thebiotek.com/product/inhibitors/bt-278085
abcr GmbH	AB357772	http://www.abcr.com/shop/en/AB357772
eNovation Chemicals	D123527	https://www.enovationchem.com/ProductDetails.asp?ProductID=D123527
eNovation Chemicals	D678704	https://www.enovationchem.com/ProductDetails.asp?ProductID=D678704
eNovation Chemicals	Y1040583	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y1040583
iChemical	EBD33103	http://www.ichemical.com/chemicals/cas-125-13-3
mcule	MCULE-1522212653	https://mcule.com/MCULE-1522212653

PubMed

Title	Date	PubMed
Syntheses and antiproliferative evaluation of oxyphenisatin derivatives.	2007 May 15	17368900
Synthesis and antitumor effect in vitro and in vivo of substituted 1,3-dihydroindole-2-ones.	2010 Oct 14	20845961
Early detection of response to experimental chemotherapeutic Top216 with [18F]FLT and [18F]FDG PET in human ovary cancer xenografts in mice.	2010 Sep 24	20885974

Patents

Sample Use Guides

In Vivo Use Guide

Cleansing enema: Lavema (Oxyphenisatin) in a dosage of from 1.5 to 3 g. should be thoroughly mixed in 1 to 2 quarts of water. Radiopaque (barium) enema adjuvant: Lavema in a dosage of from 1.5 to 3 g. should be added to the usu-al 1 to 2 quarts of barium enema suspension and well mixed, preferably in an electric mixer, to obtain uniform dispersion (1/2 packet for elderly and debilitated patients).

Route of Administration: Other

In Vitro Use Guide

Oxyphenisatin (10(-5) M, mucosal side) and deoxycholate (3 X 10(-4) M, mucosal side) completely blocked net water and sodium absorption in an everted sac preparation of stripped rat colon.

Name

Type

Language

OXYPHENISATIN ACETATE

Official Name

English

ISOCRIN

Brand Name

English

OXYPHENISATIN ACETATE [MI]

Common Name

English

NSC-59687

Code

English

3,3-BIS(P-HYDROXYPHENYL)-2-INDOLINONE DIACETATE (ESTER)

Common Name

English

OXYPHENISATIN DIACETATE

Common Name

English

NSC-117186

Code

English

OXYPHENISATIN ACETATE [USAN]

Common Name

English

2H-INDOL-2-ONE, 3,3-BIS(4-(ACETYLOXY)PHENYL)-1,3-DIHYDRO-

Systematic Name

English

OXYPHENISATINE ACETATE

Common Name

English

OXYPHENISATINE ACETATE [MART.]

Common Name

English

Oxyphenisatine acetate [WHO-DD]

Common Name

English

Code System Code Type Description

MERCK INDEX

m8343