Oxyphenisatine | CAS#125-13-3 | laxative

MedKoo Cat#: 461197 | Name: Oxyphenisatine

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Oxyphenisatine is a laxative. Long-term use is associated with liver damage.

Chemical Structure

Oxyphenisatine

CAS#125-13-3

Theoretical Analysis

MedKoo Cat#: 461197

Name: Oxyphenisatine

CAS#: 125-13-3

Chemical Formula: C20H15NO3

Exact Mass: 317.1052

Molecular Weight: 317.34

Elemental Analysis: C, 75.70; H, 4.76; N, 4.41; O, 15.12

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 285.00	2 weeks

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Synonym

Oxyphenisatine; Critex; Diphenolisatin; Hoscolax; Isolax; Normalax; Veripaque; Propellax;

IUPAC/Chemical Name

3,3-bis(4-hydroxyphenyl)indolin-2-one

InChi Key

SJDACOMXKWHBOW-UHFFFAOYSA-N

InChi Code

InChI=1S/C20H15NO3/c22-15-9-5-13(6-10-15)20(14-7-11-16(23)12-8-14)17-3-1-2-4-18(17)21-19(20)24/h1-12,22-23H,(H,21,24)

SMILES Code

O=C1Nc2ccccc2C1(c3ccc(O)cc3)c4ccc(O)cc4

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Oxyphenisatine (Oxyphenisatin) is a laxative.

In vitro activity:

Results confirm that OXY (oxyphenisatin) inhibits the growth of the breast cancer cell lines MCF7, T47D, HS578T, and MDA-MB-468. Further examination confirmed that OXY treatment was associated with autophagy, mitochondrial dysfunction, and ROS generation. Additionally, treatment was associated with activation of both intrinsic and extrinsic apoptotic pathways. In the estrogen receptor (ER) positive MCF7 and T47D cells, OXY induced TNFα expression and TNFR1 degradation, indicating autocrine receptor-mediated apoptosis in these lines. Reference: Cancer Med. 2013 Oct;2(5):687-700. https://pubmed.ncbi.nlm.nih.gov/24403234/

In vivo activity:

Next, in order to reaffirm the potential of OXY (oxyphenisatin)-like molecules as clinical candidates, the agent was assessed for in vivo antitumor activity in an MCF7 xenograft animal model. Toxicity studies demonstrated that mice tolerated IP administration of OXY at 300 mg/kg once daily or 200 mg/kg twice daily. Administration of OXY at 300 mg/kg IP once daily for 10 days resulted in significantly smaller tumors from day 33 to day 52 (P < 0.05) (Fig. 4A). Consistent with in vitro data, tumors did not grow during the treatment period. Reference: Cancer Med. 2013 Oct;2(5):687-700. https://pubmed.ncbi.nlm.nih.gov/24403234/

Preparing Stock Solutions

The following data is based on the product molecular weight 317.34 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

Morrison BL, Mullendore ME, Stockwin LH, Borgel S, Hollingshead MG, Newton DL. Oxyphenisatin acetate (NSC 59687) triggers a cell starvation response leading to autophagy, mitochondrial dysfunction, and autocrine TNFα-mediated apoptosis. Cancer Med. 2013 Oct;2(5):687-700. doi: 10.1002/cam4.107. Epub 2013 Jul 23. PMID: 24403234; PMCID: PMC3892800.

In vitro protocol:

In vivo protocol:

1: Trojel-Hansen C, Erichsen KD, Christensen MK, Jensen PB, Sehested M, Nielsen SJ. Novel small molecule drugs inhibit tumor cell metabolism and show potent anti-tumorigenic potential. Cancer Chemother Pharmacol. 2011 Jul;68(1):127-38. doi: 10.1007/s00280-010-1453-3. Epub 2010 Sep 18. PubMed PMID: 20852860. 2: Sund RB, Hillestad B. Diphenolic laxatives and intestinal cAMP: experiments with oxyphenisatine in the rat in vivo. Acta Pharmacol Toxicol (Copenh). 1978 Apr;42(4):321-2. PubMed PMID: 207080. 3: Morrison BL, Mullendore ME, Stockwin LH, Borgel S, Hollingshead MG, Newton DL. Oxyphenisatin acetate (NSC 59687) triggers a cell starvation response leading to autophagy, mitochondrial dysfunction, and autocrine TNFα-mediated apoptosis. Cancer Med. 2013 Oct;2(5):687-700. doi: 10.1002/cam4.107. Epub 2013 Jul 23. PubMed PMID: 24403234; PubMed Central PMCID: PMC3892800. 4: Uddin MK, Reignier SG, Coulter T, Montalbetti C, Grånäs C, Butcher S, Krog-Jensen C, Felding J. Syntheses and antiproliferative evaluation of oxyphenisatin derivatives. Bioorg Med Chem Lett. 2007 May 15;17(10):2854-7. Epub 2007 Feb 25. PubMed PMID: 17368900. 5: Paktoris EA, Rogol' IuM, Sinaĭko GA, Papilova EI. [Isaphenine hepatitis]. Klin Med (Mosk). 1980 Oct;58(10):60-4. Russian. PubMed PMID: 6893727. 6: Teh LB, Chong R, Ho JM, Ong YY. Oxyphenisatin induced chronic active hepatitis--a potential health hazard in Singapore. Singapore Med J. 1988 Oct;29(5):508-12. PubMed PMID: 3241981. 7: Labayle D, Lenoir C, Buffet C, Chaput JC, Etienne P. [Drug-induced active hepatitis (author's transl)]. Nouv Presse Med. 1979 Jun 2;8(24):2013-5. Review. French. PubMed PMID: 386256. 8: Obisesan AA, Osinaike I. Study of the comparative effectiveness of Dulcolax, Laxadine, Dorbanex, Normacen and Senokot laxatives in the bowel preparation of patients for radiological examinations. Niger Med J. 1978 Nov;8(6):563-70. PubMed PMID: 753059. 9: Minker E, Matejka Z. Purinergic reflex activated by cathartics in the rat. Acta Physiol Acad Sci Hung. 1981;57(1):99-107. PubMed PMID: 6895147. 10: Soto JR, Burgos E, Armas R. [Jaundice due to an oxyphenisatin laxative]. Rev Med Chil. 1974 May;102(5):376-8. Spanish. PubMed PMID: 4471403. 11: Kotha P, Rake MO, Willatt D. Liver damage induced by oxyphenisatin. Br Med J. 1980 Dec 6;281(6254):1530. PubMed PMID: 6893676; PubMed Central PMCID: PMC1714947. 12: Sund RB, Hol L, Storbråten A. Studies in the rat on the absorption, biliary excretion, laxative action and interference with intestinal transport of some oxyphenisatin derivatives. Acta Pharmacol Toxicol (Copenh). 1979 Apr;44(4):251-9. PubMed PMID: 433618. 13: Scheuer PJ. Long-term effects on the liver. J Clin Pathol Suppl (R Coll Pathol). 1975;9:71-4. Review. PubMed PMID: 182727; PubMed Central PMCID: PMC1347185. 14: Maddrey WC, Boitnott JK. Drug-induced chronic hepatitis and cirrhosis. Prog Liver Dis. 1979;6:595-603. Review. PubMed PMID: 396573. 15: Safety of stool softeners. Med Lett Drugs Ther. 1977 Jun 3;19(11):45-6. PubMed PMID: 865409. 16: WAGGENER HU. Evaluation of oxyphenisatin in a disposable enema unit. Rocky Mt Med J. 1962 Nov;59:39-41. PubMed PMID: 13998195. 17: DONOVAN R. The use of dihydroxyphenylisatin in cholecystography. Xray Tech. 1958 Sep;30(2):84-6. PubMed PMID: 13581761. 18: Linder H. [Letter: Phenolisatine-induced liver diseases]. Dtsch Med Wochenschr. 1976 Mar 19;101(12):468-9. German. PubMed PMID: 1253716. 19: Bergan T, Fotland MH, Sund RB. Interaction between diphenolic laxatives and intestinal bacteria in vitro. Acta Pharmacol Toxicol (Copenh). 1982 Aug;51(2):165-72. PubMed PMID: 6896788. 20: Irwin JP, Peterson GH. Colon preparation for the barium enema: a guide for the radiologist. Gastrointest Radiol. 1982;7(1):75-8. PubMed PMID: 6174383.