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安全信息

T3205

Sigma-Aldrich

Tamibarotene

≥98% (HPLC)

别名:

-((5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbamoyl)benzoic acid, 4-(((5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)amino)carbonyl)-benzoic acid, AM 80, AM80, AMNOLAKE, Amnoid, N-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl)-2-naphthyl)terephthalamic acid, N-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)terephthalamic acid, NSC 608000, UNII-08V52GZ3H9

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About This Item

经验公式（希尔记法）:
C22H25NO3
CAS号:
94497-51-5
分子量:
351.44
MDL编号:
MFCD00866188
UNSPSC代码:
12352200
PubChem化学物质编号:
329826742
NACRES:
NA.77

质量水平

100

检测方案

≥98% (HPLC)

形式

powder

颜色

white to off-white

溶解性

DMSO: ≥10 mg/mL

储存温度

room temp

SMILES字符串

CC1(C)CCC(C)(C)c2cc(NC(=O)c3ccc(cc3)C(O)=O)ccc12

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)

InChI key

MUTNCGKQJGXKEM-UHFFFAOYSA-N

应用

Tamibarotene has been used to study its mode of action and therapeutic potential.

生化/生理作用

Tamibarotene (Am80) is a RAR α agonist. Tamibarotene was developed to overcome resistance to ATRA and is currently approved in Japan for treatment of recurrent acute promyelocytic leukemia (APL). The compound induces HL-60 cells differentiation and apoptosis. Similarly to TTNPB, the compound neither binds to nor transactivates the RXRs. In contrast to TTNPB (pan RAR agonist), Tamibarotene is rather specific toward RAR α. The compound is approximate 10 times more potent than ATRA.
Tamibarotene is a synthetic retinoid drug, highly stable and potent inducer of differentiation than ATRA (all-trans retinoic acid). It showed mild growth inhibition in myeloma cells and HUVECs (human umbilical vein endothelial cell).

特点和优势

This compound is featured on the Nuclear Receptors (Non-Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

制备说明

Tamibarotene is soluble in DMSO at a concentration that is greater than or equal to 10 mg/ml.

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

法规信息

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Chie Miyabe et al.
Arthritis and rheumatism, 65(2), 503-512 (2012-12-04)
Vasculitis is characterized by leukocyte infiltration in the vessel walls, with destructive damage to mural structures. Retinoids are compounds that bind to retinoic acid receptors and exert biologic activities similar to those of vitamin A, including modulatory effects on cell
Madoka Nakagomi et al.
Pharmacology, biochemistry, and behavior, 104, 1-9 (2013-01-22)
Am80 is a synthetic retinoid that has been used clinically for patients with acute promyelocytic leukemia and has been reported to affect the brain and its neurons. We investigated the influence of Am80 on anti-anxiety-like behavior, which is a characteristic
Akira Uruno et al.
Journal of leukocyte biology, 90(2), 235-247 (2011-03-12)
ATRA and a synthetic RAR agonist tamibarotene (Am80) induce granulocytic differentiation of human acute leukemia HL-60 cells and have been used in antineoplastic therapy. ATRA induces CD38 antigen during HL-60 cell differentiation, which interacts with CD31 antigen on the vascular
Successful treatment of relapsed and refractory extramedullary acute promyelocytic leukemia with tamibarotene.
Harris V Naina et al.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 29(18), e534-e536 (2011-04-13)
Kazuki Morohoshi et al.
Cellular immunology, 270(1), 1-4 (2011-05-24)
We examined whether a synthetic retinoid Am80 prevented the development of autoimmune thyroiditis in iodide-treated nonobese diabetic mice, an animal model of Hashimoto's thyroiditis (HT). Am80 (0, 0.1 or 1 mg/kg/day) was orally administered in feed during the 8-week iodide
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