| Identification | Back Directory | [Name]
Tamibarotene | [CAS]
94497-51-5 | [Synonyms]
AM80
C12864
Amnoid
Amnolake
NSC 608000
Tamibarotene
UNII-08V52GZ
Retinoid AM 80
Tamibarotene, >=99%
Am 80 (pharmaceutical)
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
4-[(5,5,8,8-Tetramethyl-6,7-dihydronaphthalen-2-yl)carbamoyl]benzoic acid
4-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbamoyl]benzoicacid
-((5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbamoyl)benzoic acid
4-[(5,5,8,8-tetraMethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbaMoyl]benzoic acid
4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-ylaminocarbonyl)benzoic acid
4-[[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphthalen)-2-yl]aminocarbonyl]benzoic acid
4-[[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl)amino]carbonyl]benzoic acid
4-[[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)amino]carbonyl]benzoic Acid
4-[(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-naphthyl)carbaMoyl] benzoic acid | [EINECS(EC#)]
1806241-263-5 | [Molecular Formula]
C22H25NO3 | [MDL Number]
MFCD00866188 | [MOL File]
94497-51-5.mol | [Molecular Weight]
351.44 |
| Chemical Properties | Back Directory | [Appearance]
Crystalline Solid | [Melting point ]
231-232°C | [Boiling point ]
449.6±45.0 °C(Predicted) | [density ]
1.154±0.06 g/cm3(Predicted) | [RTECS ]
DH6940000 | [storage temp. ]
Store at RT | [solubility ]
Soluble to 50 mM in DMSO | [form ]
powder | [pka]
3.83±0.10(Predicted) | [color ]
white to off-white |
| Hazard Information | Back Directory | [Chemical Properties]
Crystalline Solid | [Uses]
A RARα agonist that induces differentiation and apoptosis | [Uses]
Synthetic retinoic acid receptor-a/?selective retinoid. Antineoplastic | [Uses]
Synthetic retinoic acid receptor-α/β-selective retinoid. Antineoplastic. | [Biological Activity]
Retinoic acid receptor α (RAR α ) agonist that induces differentiation (ED 50 = 0.79 nM) and apoptosis of HL-60 cells in vitro . Exhibits antiproliferative effects against a variety of human tumor cells lines (mean values of 35, 40 and 60% growth inhibition at 0.1, 1 and 10 μ M respectively) and displays anticancer activity against acute promyelocytic leukemia in vivo . | [Originator]
Toko Yakuhin Kogyo (Japan) | [Definition]
ChEBI: A dicarboxylic acid monoamide resulting from the condensation of one of the carboxy groups of terephthalic acid with the amino group of 5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine. | [Brand name]
Amnolake | [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. | [Synthesis]
Several synthesis of tamibarotene have been disclosed
in the literature including the process scale synthesis
as shown in the scheme. The synthesis started
with preparation of dichloride 134 in 82% yield from diol
133 by treating with concentrated HCL in DCM. Friedal
Crafts reaction of dichloride 134 with acetanilide in the presence
of aluminum chloride at -15??C for 2h provided
acetanilide derivative 136 in 78% yield. In a single pot, the
acetanilide was reacted with PCl5 and dimethylaniline at -25??C for 1.5h followed by quenching the reaction with
methanol for 2h after addition at -25??C. Addition of dimethylaniline
and terepthalic chloride mono-methylester at -30 - -
20??C for 1 hr provided the tamibarotene methyl easter 137 in
81% yield. Hydrolysis of the ester by heating with sodium
hydroxide in MeOH:water mixture for 1h followed isolation
and crystallization gave tamibarotene (XIX) in 92% yield.
| [storage]
Store at RT |
| Questions And Answer | Back Directory | [Description]
Tamibarotene (brand name: Amnolake) is a kind of orally
administrated synthetic retinoid. It is used to overcome the all-
trans retinoid acid (ATRA) resistance, having potential
antineoplastic activity against the acute promyelocytic leukaemia
(APL). It can also be used for the treatment of Alzheimer's disease,
multiple myeloma and Crohn's disease. Tamibarotene takes effect
through directly acting as the specific agonist for retinoid acid
receptor alpha/beta, and potentially binding to the retinoid X
receptors (RXR). Compared to the ATRA, Tamibarotene is chemically
more stable and much more potent as an inducer of differentiation
and apoptosis in promyelocytic leukemia cells. | [References]
https://en.wikipedia.org/wiki/Tamibarotene
https://www.drugbank.ca/drugs/DB04942
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