T3205

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
• 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

Properties

• 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.[1]

Biochem/physiol Actions

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).[2] It showed mild growth inhibition in myeloma cells and HUVECs (human umbilical vein endothelial cell).[3]

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 Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable