Compound: Tamibarotene
SMILES: O=C(O)c1ccc(C(=O)Nc2cc3c(C(CCC3(C)C)(C)C)cc2)cc1
InChIKey: MUTNCGKQJGXKEM-UHFFFAOYSA-N
Synonyms: Tamibarotene, 94497-51-5, Am 80, retinobenzoic acid, Am80, AM-80, 4-((5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbamoyl)benzoic acid, Amnoid, 4-[(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)carbamoyl]benzoic acid, TOS-80T, INNO-507, TM-411, 4-[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbamoyl]benzoic acid, Tamibaroteno, NSC-608000, DTXSID5046853, SY-1425, 08V52GZ3H9, OP-01, 4-((5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbamoyl)benzoic acid, NSC608000, RR-110, Benzoic acid, 4-(((5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)amino)carbonyl)-, DTXCID3026853, CHEBI:32181, Z-208, N-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)terephthalamic acid, tamibarotenum, 4-((5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)carbamoyl)benzoic acid, RefChem:891059, 4-((5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbamoyl), Amnolake, Tamibaro, C22H25NO3, MFCD00866188, Tamibarotene(Am-80), CHEMBL25202, NCGC00181111-01, 4-[(1,1,4,4-tetramethyltetralin-6-yl)carbamoyl]benzoic acid, 4-[[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)amino]carbonyl]benzoic acid, SMR002530320, CAS-94497-51-5, Tamibarotene [INN], NSC 608000, Amnoleuk, UNII-08V52GZ3H9, 2cbr, MUTNCGKQJGXKEM-UHFFFAOYSA-N, 4-(((5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)AMINO)CARBONYL)BENZOIC ACID, A80, Amnoid (TN), and OP-01, TAMIBAROTENE [MI], TAMIBAROTENE [JAN], Tamibarotene [USAN:INN], TAMIBAROTENE [USAN], SCHEMBL36207, TAMIBAROTENE [MART.], MLS003899239, MLS004774034, MLS006011150, TAMIBAROTENE [WHO-DD], GTPL2648, orb1300549, Tamibarotene (JAN/USAN/INN), TOS-80, SCHEMBL29373818, Tamibarotene, >=98% (HPLC), HMS3652H04, HMS3743C03, HMS5082N20, OMS-0728, WHO 7349, Tox21_112725, BDBM50061625, s4260, AKOS015902693, Tox21_112725_1, AC-7049, CCG-268044, CS-0654, DB04942, FT27993, NCGC00181111-02, 121GE003, AS-14083, HY-14652, NCI60_004716, SY110665, NS00068306, SW219913-1, D01418, SBI-0654073.0001, Q7681221, BRD-K36627727-001-05-4, 4-(((5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)amino)carbonyl)benzoic acid, 4-[[(5,6,7,8-Tetrahydro-5,5,8,8-tet ramethyl-2-naphthalenyl)amino]carbonyl]benzoic acid, Terephthalic acid mono-5,5,8,8-tetramethyl- 5,6,7, 8-tetrahydro-2-naphthylamide, Terephthalic acid mono-5,8,8-tetramethyl- 5,6,7,8-tetrahydro-2-naphthylamide
Theoretical properties:
molecular_formula: C22H25NO3
molecular_weight: 351.4 g/mol
exact_mass: 351.18344366 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 3
heavy_atom_count: 26
topological_polar_surface_area: 66.4 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
solubility: 5.75e-04 g/L
Descriptions:
pubchem: Tamibarotene is 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. It has a role as an antineoplastic agent and a retinoic acid receptor alpha/beta agonist. It is a retinoid, a dicarboxylic acid monoamide and a member of tetralins. It is functionally related to a terephthalic acid and a 4-carbamoylbenzoic acid.
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.
chembl: TAMIBAROTENE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Tamibarotene (brand name: Amnolake), also called retinobenzoic acid, is orally active, synthetic retinoid, developed to overcome all-trans retinoic acid (ATRA) resistance, with potential antineoplastic activity against acute promyelocytic leukaemia (APL) . It is currently marketed only in Japan and early trials have demonstrated that it tends to be better tolerated than ATRA. Tamibarotene has been tested in many other cancer types, including Acute Myeloid Leukemia where it shows no benefit, and lung cancer, where it accelerated the cancer growth and increased mortality.
It has also been investigated as a possible treatment for Alzheimer's disease, multiple myeloma and Crohn's disease. Tamibarotene shows a similar side effect profile to Tretinoin, but exhibits lower clearance, resulting in improved dosing regiments. Hyperlipidemia is a common finding from Tamibarotene dosing.