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T3205 Sigma-Aldrich

Tamibarotene

≥98% (HPLC)

Synonym: -((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

  • CAS Number 94497-51-5

  • Empirical Formula (Hill Notation) C22H25NO3

  • Molecular Weight 351.44

  •  MDL number MFCD00866188

  •  PubChem Substance ID 329826742

  •  NACRES NA.77

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience, Gene Regulation and Expression,
Quality Level   100
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

Description

Application

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

Packaging

5, 25 mg in glass bottle

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.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Nuclear Receptors (Non-Steroids)

The receptors for several classes of non-steroidal compounds, including retinoids, thyroid hormones and vitamin D, also act as ligand-dependent transcription factors. In addition, a large number of r...
Keywords: Absorption, Apoptosis, Atomic absorption spectroscopy, Cancer, Cardiovascular, Cell proliferation, Clinical, Detoxification, Diabetes, Diseases, Gene expression, Hormones, Ligands, Lipid Metabolism, Metabolism, Metabolites, Obesity, Transcription, Transduction, Vitamins

Peer-Reviewed Papers
15

References

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