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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/09/18 10:00:23」(JST)

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Tamibarotene (brand name: Amnolake), also called retinobenzoic acid, is orally active, synthetic retinoid, developed to overcome all-trans retinoic acid (ATRA) resistance, with potential antineoplastic activity against acute promyelocytic leukaemia (APL) .^[1] It is currently marketed only in Japan and early trials have demonstrated that it tends to be better tolerated than ATRA.^[2] It has also been investigated as a possible treatment for Alzheimer's disease, multiple myeloma and Crohn's disease.^[2]^[3]

Synthesis

The tetralin-based compound tamibarotene (7) has been tested as an agent for treating leukaemias.

Reaction of the diol (1) with hydrogen chloride affords the corresponding dichloro derivative (2). Aluminum chloride mediated Friedel–Crafts alkylation of acetanilide with the dichloride affords the tetralin (3). Basic hydrolysis leads to the primary amine (4). Acylation of the primary amino group with the half acid chloride half ester from terephthalic acid (5) leads to the amide (6). Basic hydrolysis of the ester grouping then affords (7).^[4]

References

^ "Tamibarotene: AM 80, retinobenzoic acid, Tamibaro". Drugs in R&D 5 (6): 359–62. 2004. doi:10.2165/00126839-200405060-00010. PMID 15563242.
^ ^a ^b Miwako, I; Kagechika, H (August 2007). "Tamibarotene". Drugs Today (Barc) 43 (8): 563–568. doi:10.1358/dot.2007.43.8.1072615. PMID 17925887.
^ Fukasawa, H; Nakagomi, M; Yamagata, N; Katsuki, H; Kawahara, K; Kitaoka, K; Miki, T; Shudo, K (2012). "Tamibarotene: a candidate retinoid drug for Alzheimer's disease" (PDF). Biological & Pharmaceutical Bulletin 35 (8): 1206–1212. doi:10.1248/bpb.b12-00314. PMID 22863914.
^ Y. Hamada, I. Yamada, M. Uenaka, T. Sakata, U.S. Patent 5,214,202 (1993).

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UpToDate Contents

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1. 再発性および難治性の急性前骨髄球性白血病の治療 treatment of relapsed or refractory acute promyelocytic leukemia in adults

English Journal

Tamibarotene in patients with acute promyelocytic leukaemia relapsing after treatment with all-trans retinoic acid and arsenic trioxide.

Sanford D1, Lo-Coco F2, Sanz MA3,4, Di Bona E5, Coutre S6, Altman JK7, Wetzler M8, Allen SL9, Ravandi F1, Kantarjian H1, Cortes JE1.
British journal of haematology.Br J Haematol.2015 Nov;171(4):471-7. doi: 10.1111/bjh.13607. Epub 2015 Jul 24.
Treatment of acute promyelocytic leukaemia (APL) with arsenic trioxide (ATO) and all-trans retinoic acid (ATRA) is highly effective first-line therapy, although approximately 5-10% of patients relapse. Tamibarotene is a synthetic retinoid with activity in APL patients who relapse after chemotherapy
PMID 26205361

Activation of AMP-activated protein kinase by retinoic acid sensitizes hepatocellular carcinoma cells to apoptosis induced by sorafenib.

Ishijima N1, Kanki K1, Shimizu H1, Shiota G1.
Cancer science.Cancer Sci.2015 May;106(5):567-75. doi: 10.1111/cas.12633. Epub 2015 Mar 9.
To improve the outcome of cancer chemotherapy, strategies to enhance the efficacy of anticancer drugs are required. Sorafenib is the only drug to prolong overall survival of the patients with hepatocellular carcinoma (HCC), however, the outcome is still not satisfactory. Retinoids, vitamin A derivat
PMID 25683251

Activity analysis and preliminary inducer screening of the chicken DAZL gene promoter.

Zhang L1, Zhu R2, Zuo Q3, Li D4, Lian C5, Tang B6, Xiao T7, Zhang Y8, Li B9.
International journal of molecular sciences.Int J Mol Sci.2015 Mar 23;16(3):6595-605. doi: 10.3390/ijms16036595.
This study was aimed at identifying the active control area of chicken DAZL gene core promoter, to screen optimum inducers of the DAZL gene, thus to enhance the differentiation of embryonic stem cells into spermatogonial stem cells. Fragments of chicken DAZL gene promoter were cloned into fluorescen
PMID 25807265

Japanese Journal

急性骨髄性白血病の分子標的薬 : 現状と今後の展望 (特集血液疾患の分子標的薬 : 進化する血液疾患治療研究の最新動向) -- (治療研究)

高後裕,稲村純季,進藤基博
日本臨床 72(6), 1063-1067, 2014-06
NAID 40020100518

成人急性前骨髄球性白血病の治療

藤田浩之
臨床血液 55(10), 1817-1826, 2014
NAID 130004696074

Synthesis of Am80 (Tamibarotene) Prodrug Candidates, Congeners and Metabolites

Muratake Hideaki,Amano Yohei,Toda Takahiro [他],Sugiyama Kiyoshi,Shudo Koichi
Chemical and Pharmaceutical Bulletin 61(8), 846-852, 2013
… Compound 1 (IT-M-07000) was previously reported as a candidate prodrug of Am80 (Tamibarotene; …
NAID 130003360816

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リンク元

「タミバロテン」

Tamibarotene
	IUPAC name 4-[(1,1,4,4-tetramethyltetralin-6-yl)carbamoyl]benzoic acid
Identifiers
CAS number	94497-51-5
PubChem	108143
ChemSpider	97231
DrugBank	DB04942
ChEMBL	CHEMBL25202
Beilstein Reference	3564473
Jmol-3D images	Image 1
	SMILES O=C(O)c1ccc(cc1)C(=O)Nc2ccc3c(c2)C(CCC3(C)C)(C)C ;
	InChI InChI=InChI=1S/C22H25NO3/c1-21(2)11-12-22(3,4)18-13-16(9-10-17(18)21)23-19(24)14-5-7-15(8-6-14)20(25)26/h5-10,13H,11-12H2,1-4H3,(H,23,24)(H,25,26) ;
Properties
Molecular formula	C22H25NO3
Molar mass	351.44 g mol−1
	Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
	Infobox references

　　[★]

英: tamibarotene
商: アムノレイク

合成レチノイド、急性前骨髄球性白血病治療

[1] "Tamibarotene: AM 80, retinobenzoic acid, Tamibaro". Drugs in R&D 5 (6): 359–62. 2004. doi:10.2165/00126839-200405060-00010. PMID 15563242.

[drugs07-2] Miwako, I; Kagechika, H (August 2007). "Tamibarotene". Drugs Today (Barc) 43 (8): 563–568. doi:10.1358/dot.2007.43.8.1072615. PMID 17925887.

[3] Fukasawa, H; Nakagomi, M; Yamagata, N; Katsuki, H; Kawahara, K; Kitaoka, K; Miki, T; Shudo, K (2012). "Tamibarotene: a candidate retinoid drug for Alzheimer's disease" (PDF). Biological & Pharmaceutical Bulletin 35 (8): 1206–1212. doi:10.1248/bpb.b12-00314. PMID 22863914.

[4] Y. Hamada, I. Yamada, M. Uenaka, T. Sakata, U.S. Patent 5,214,202 (1993).

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tamibarotene