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T3205

Sigma-Aldrich

Tamibarotene

≥98% (HPLC)

Sinónimos:

-((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

Fórmula empírica (notación de Hill):
C22H25NO3
Número de CAS:
94497-51-5
Peso molecular:
351.44
Número MDL:
MFCD00866188
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
329826742
NACRES:
NA.77

Nivel de calidad

100

Ensayo

≥98% (HPLC)

Formulario

powder

color

white to off-white

solubilidad

DMSO: ≥10 mg/mL

temp. de almacenamiento

room temp

cadena SMILES

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)

Clave InChI

MUTNCGKQJGXKEM-UHFFFAOYSA-N

Aplicación

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

Acciones bioquímicas o fisiológicas

Tamibarotene (Am80) is a RAR α agonist.
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).

Características y beneficios

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 de preparación

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

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
016M4745V
024M4733V
052M4704V
090M4706
011M4715V

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Ishido Miwako et al.
Drugs of today (Barcelona, Spain : 1998), 43(8), 563-568 (2007-10-11)
Tamibarotene is a new synthetic retinoid drug recently approved for relapsed or refractory acute promyelocytic leukemia (APL) in Japan. It is a specific agonist for retinoic acid receptor alpha/beta. Compared to all-trans retinoic acid (ATRA), a natural retinoid indicated for
Hiroshi Fukasawa et al.
Biological & pharmaceutical bulletin, 35(8), 1206-1212 (2012-08-07)
Tamibarotene (Am80), a synthetic retinoid approved in Japan for treatment of acute promyelocytic leukemia (APL), is a retinoic acid receptor (RAR) agonist with high specificity for RARα and RARβ over RARγ. Temporarily and spatially specific expression of RARs suggests their
Hikaru Hattori et al.
PloS one, 13(10), e0204850-e0204850 (2018-10-06)
All-trans retinoic acid (ATRA) and arsenic trioxide (ATO) are essential for acute promyelocytic leukemia (APL) treatment. It has been reported that mutations in PML-RARA confer resistance to ATRA and ATO, and are associated with poor prognosis. Although most PML-RARA mutations
Hiroshi Keino et al.
Investigative ophthalmology & visual science, 52(3), 1548-1556 (2010-09-24)
To determine whether synthetic retinoic acid receptor (RAR)-α/β-specific agonist Am80 reduces inflammation in experimental autoimmune uveoretinitis (EAU). Naive CD4(+) T cells were activated with anti-CD3, anti-CD28, and transforming growth factor (TGF)-β, in the presence or absence of Am80. Intracellular expression
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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