oxyphenisatin

オキシフェニサチン

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/08/26 15:18:11」(JST)

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Oxyphenisatine

Names
Preferred IUPAC name 3,3-Bis(4-hydroxyphenyl)-1,3-dihydro-2H-indol-2-one
Other names Dihydroxydiphenylisatin; Diphenolisatin; Oxyphenisatin
Identifiers
CAS Number	125-13-3 N
3D model (JSmol)	Interactive image Interactive image
ChemSpider	29053 Y
DrugBank	DB04823 Y
ECHA InfoCard	100.004.299
EC Number	204-728-1
KEGG	D08326 Y
PubChem CID	31315
UNII	3BT0VQG2GQ Y
InChI 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) Y Key: SJDACOMXKWHBOW-UHFFFAOYSA-N Y InChI=1/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) Key: SJDACOMXKWHBOW-UHFFFAOYAU
SMILES Oc1ccc(cc1)C1(C(=O)Nc2ccccc12)c1ccc(O)cc1 OC1=CC=C(C=C1)C1(C(=O)NC2=C1C=CC=C2)C1=CC=C(O)C=C1
Properties
Chemical formula	C20H15NO3
Molar mass	317.34 g·mol−1
log P	1.398
Acidity (pKa)	9.423
Basicity (pKb)	4.574
Pharmacology
ATC code	A06AB01 (WHO)
Routes of administration	Oral, rectal
Legal status	Withdrawn
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Oxyphenisatine (or oxyphenisatin) is a laxative. It is closely related to bisacodyl, sodium picosulfate, and phenolphthalein. Long-term use is associated with liver damage, and as a result, it was withdrawn in most countries in the early 1970s. The acetate derivative oxyphenisatine acetate was also once used as a laxative.

Natural chemical compounds similar to oxyphenisatine may be present in prunes, but a recent review of the relevant scientific literature suggests that the laxative effect of prunes is due to other constituents including phenolic compounds (mainly neochlorogenic acids and chlorogenic acids) and sorbitol.

Synthesis

The ketone group of isatin (1) is nonenolizable and has interesting properties. In strong acid it becomes protonated, and the oxygen can be replaced by electron rich moieties.

Oxyphenisatin synthesis:

In 1885, it was reported that condensation of isatin with phenol 2 leads to 3, which is Acetylated to (4). Oxyphenisatin has cathartic properties.

• Triacetyldiphenolisatin (Laxagetten, Unilax, Trisatin), Nicoxyphenisatin & Cinnoxyphenisatin are chemical derivatives.

UpToDate Contents

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• 1. 自己免疫性肝炎：病因 autoimmune hepatitis pathogenesis

English Journal

• Oxyphenisatin acetate (NSC 59687) triggers a cell starvation response leading to autophagy, mitochondrial dysfunction, and autocrine TNFα-mediated apoptosis.

• Morrison BL1, Mullendore ME, Stockwin LH, Borgel S, Hollingshead MG, Newton DL.
• Cancer medicine.Cancer Med.2013 Oct;2(5):687-700. doi: 10.1002/cam4.107. Epub 2013 Jul 23.
• Oxyphenisatin (3,3-bis(4-hydroxyphenyl)-1H-indol-2-one) and several structurally related molecules have been shown to have in vitro and in vivo antiproliferative activity. This study aims to confirm and extend mechanistic studies by focusing on oxyphenisatin acetate (OXY, NSC 59687), the pro-drug of
• PMID 24403234

• Ornidazole-induced autoimmune hepatitis.

• Ersöz G1, Vardar R, Akarca US, Tekın F, Yilmaz F, Günşar F, Karasu Z.
• The Turkish journal of gastroenterology : the official journal of Turkish Society of Gastroenterology.Turk J Gastroenterol.2011 Oct;22(5):494-9.
• BACKGROUND/AIMS: Certain drugs including oxyphenisatin, methyldopa, nitrofurantoin, diclofenac, interferon, infliximab, pemoline, minocycline, atorvastatin, and rosuvastatin can induce hepatocellular injury that mimics autoimmune hepatitis. Whether drugs and herbs unmask or induce autoimmune hepatit
• PMID 22234756

• Novel small molecule drugs inhibit tumor cell metabolism and show potent anti-tumorigenic potential.

• Trojel-Hansen C1, Erichsen KD, Christensen MK, Jensen PB, Sehested M, Nielsen SJ.
• Cancer chemotherapy and pharmacology.Cancer Chemother Pharmacol.2011 Jul;68(1):127-38. doi: 10.1007/s00280-010-1453-3. Epub 2010 Sep 18.
• BACKGROUND: Rapidly dividing tumor cells have an increased demand for nutrients to support their characteristic unabated growth; this demand is met by an increased availability of nutrients such as amino acids through vasculogenesis and by the enhanced cellular entry of nutrients through the upregul
• PMID 20852860

Japanese Journal

• Drug-induced Hepatic Injury:A Review of the Japanese Articles for the Past 50 Years

• 鮫島 美子,水野 孝子,笹川 美年子,塩崎 安子,龍見 幸二
• 日本消化器病学会雑誌 73(10), 1214-1221, 1976
• … test, skin test, macrophage migration inhibitory test and lymphocyte transformation test of suspected drug was also performed as diagnostic aid.The most common drugs reported to have high mortality due to severe hepatic impairment were thorium dioxide, combination chemotherapeutics for tuberculosis pyrazinamide, oxyphenisatin, halothane in descending order.Eight-hundred and seventy-seven cases of drugs or poison ingestion for suicidal purposes, accidental inhalation of industrial or agricultural chemicals and food poisoning were also …
• NAID 130001062153

• 自己免疫性疾患における白血球遊走阻止試験に関する研究 : 第2編 慢性肝疾患, 特に自己免疫性肝炎における肝粥に対する白血球遊走阻止試験

• 沖本 芳春
• アレルギー 23(8), 540-547, 579-580, 1974-08-30
• … 自己免疫性肝炎患者6例, 自己免疫性肝炎の疑いの患者3例および oxyphenisatin 起因性ルポイド肝炎様症候群患者2例を検索対象とし, 慢性肝炎患者8例, 肝硬変症患者7例および正常人11人を対照として, ヒト肝粥, 熱変性子ウシ胸腺DNAならびにヒト白血球粥を抗原とした場合の白血球遊走阻止試験 (leukocyte migration test, LMT), およびリンパ球の幼若化現象の観察を併せ行い, 次のごとき成績を得た.1) 正常人ではヒト肝粥, DNAおよびヒ …
• NAID 110002409494

• LDH結合性免疫グロブリンの性状に関する研究-抗LDH単クローン性自己抗体の発見-

• 井本 勉,内田 壱夫,太田 美栄,吉田 真理子,井上 健三,高月 清,山沢 育宏
• 日本消化器病学会雑誌 71(12), 1249-1255, 1974
• … Total lactate dehydrogenase (LDH) activity in serum from a 64 year-old patient with Oxyphenisatin-induced lupoid hepatitis was 653 W. …
• NAID 130001525839

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• Chronic Active and Lupoid Hepatitis Caused by a Laxative ...

Original Article Chronic Active and Lupoid Hepatitis Caused by a Laxative, Oxyphenisatin Telfer B. Reynolds, M.D., Robert L. Peters, M.D., and Suyenori Yamada, M.D. ... Abstract In six patients with chronic constipation, chronic ...

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リンク元	「ビサチン」
拡張検索	「oxyphenisatine」「oxyphenisatin acetate」

「ビサチン」

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英

bisatin

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bisatinum

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イサシェン isacen、オキシフェニサチン oxyphenisatin

「oxyphenisatine」

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オキシフェニサチン

関

oxyphenisatin acetate

「oxyphenisatin acetate」

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酢酸オキシフェニサチン

関

oxyphenisatine