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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

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About This Item

Empirical Formula (Hill Notation):
C22H25NO3
CAS Number:
94497-51-5
Molecular Weight:
351.44
NACRES:
NA.77
PubChem Substance ID:
329826742
UNSPSC Code:
12352200
MDL number:
MFCD00866188
Assay:
≥98% (HPLC)
Form:
powder
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Quality Segment

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

Application

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

Biochem/physiol Actions

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).
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.

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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