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T3205

Sigma-Aldrich

Tamibarotene

≥98% (HPLC)

Sinonimo/i:

-((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

Formula empirica (notazione di Hill):
C22H25NO3
Numero CAS:
94497-51-5
Peso molecolare:
351.44
Numero MDL:
MFCD00866188
Codice UNSPSC:
12352200
ID PubChem:
329826742
NACRES:
NA.77

Saggio

≥98% (HPLC)

Forma fisica

powder

Colore

white to off-white

Solubilità

DMSO: ≥10 mg/mL

Temperatura di conservazione

room temp

Stringa SMILE

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)
MUTNCGKQJGXKEM-UHFFFAOYSA-N

Applicazioni

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

Azioni biochim/fisiol

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).

Caratteristiche e vantaggi

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.

Nota sulla preparazione

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

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Certificati d'analisi (COA)

Cerca il Certificati d'analisi (COA) digitando il numero di lotto/batch corrispondente. I numeri di lotto o di batch sono stampati sull'etichetta dei prodotti dopo la parola ‘Lotto’ o ‘Batch’.

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Tampone fosfato salino pH 7.2, liquid, sterile-filtered, suitable for cell culture

SAFC

806544

Tampone fosfato salino

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
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
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)
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
Xin Liu et al.
Journal of biomedical nanotechnology, 9(9), 1586-1593 (2013-08-29)
The present work evaluated the feasibility of nanostructured lipid carriers (NLC) for the intravenous delivery of tamibarotene (Am80), a poorly water-soluble drug for the treatment of acute promyelocytic leukemia (APL). The objective of this research was to develop a suitable
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