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T3205

Sigma-Aldrich

Tamibarotene

≥98% (HPLC)

Synonym(e):

-((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

Empirische Formel (Hill-System):
C22H25NO3
CAS-Nummer:
94497-51-5
Molekulargewicht:
351.44
MDL-Nummer:
MFCD00866188
UNSPSC-Code:
12352200
PubChem Substanz-ID:
329826742
NACRES:
NA.77

Qualitätsniveau

100

Assay

≥98% (HPLC)

Form

powder

Farbe

white to off-white

Löslichkeit

DMSO: ≥10 mg/mL

Lagertemp.

room temp

SMILES String

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)

InChIKey

MUTNCGKQJGXKEM-UHFFFAOYSA-N

Anwendung

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

Biochem./physiol. Wirkung

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).

Leistungsmerkmale und Vorteile

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.

Angaben zur Herstellung

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

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

Suchen Sie nach Analysenzertifikate (COA), indem Sie die Lot-/Chargennummer des Produkts eingeben. Lot- und Chargennummern sind auf dem Produktetikett hinter den Wörtern ‘Lot’ oder ‘Batch’ (Lot oder Charge) zu finden.

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Acitretin ≥98.0% (HPLC)

Sigma-Aldrich

44707

Acitretin

9-cis-Retinoic acid ≥98% (HPLC)

Sigma-Aldrich

R4643

9-cis-Retinoic acid

Ursodesoxycholsäure ≥99%

Sigma-Aldrich

U5127

Ursodesoxycholsäure

Retinsäure ≥98% (HPLC), powder

Sigma-Aldrich

R2625

Retinsäure

Hämin BioXtra, from Porcine, ≥96.0% (HPLC)

Sigma-Aldrich

51280

Hämin

Etoposid synthetic, 95.0-105.0%, powder

Sigma-Aldrich

E1383

Etoposid

Phosphatgepufferte Kochsalzlösung pH 7.2, liquid, sterile-filtered, suitable for cell culture

SAFC

806544

Phosphatgepufferte Kochsalzlösung

Kazuyoshi Kitaoka et al.
Neuropharmacology, 72, 58-65 (2013-04-30)
The retinoic acid (RA, a vitamin A metabolite) receptor (RAR) is a transcription factor. Vitamin A/RA administration improves the Alzheimer's disease (AD)- and age-related attenuation of memory/learning in mouse models. Recently, a disintegrin and metalloproteinase domain-containing protein 10 (ADAM10) was
Antimyeloma effects of a novel synthetic retinoid Am80 (Tamibarotene) through inhibition of angiogenesis
Sanda T, et al.
Leukemia, 19(6), 901-901 (2005)
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
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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