Skip to Content
Merck
All Photos(1)

Documents

T3205

Sigma-Aldrich

Tamibarotene

≥98% (HPLC)

Synonym(s):

-((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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C22H25NO3
CAS Number:
94497-51-5
Molecular Weight:
351.44
MDL number:
MFCD00866188
UNSPSC Code:
12352200
PubChem Substance ID:
329826742
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: ≥10 mg/mL

storage temp.

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)

InChI key

MUTNCGKQJGXKEM-UHFFFAOYSA-N

Application

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

Biochem/physiol Actions

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).

Features and Benefits

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.

Preparation Note

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
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
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
View All Related Papers

Articles

Nuclear Receptors (Non-Steroids)

We offer many products related to non-steroid nuclear receptors for your research needs.

Nuclear Receptors (Non-Steroids)

We offer many products related to non-steroid nuclear receptors for your research needs.

Nuclear Receptors (Non-Steroids)

We offer many products related to non-steroid nuclear receptors for your research needs.

Nuclear Receptors (Non-Steroids)

We offer many products related to non-steroid nuclear receptors for your research needs.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service