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    Tamibarotene

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

    DIGITAL CONTENT

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    2D Structure
    Also known as: 94497-51-5, Am 80, 4-((5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbamoyl)benzoic acid, Am-80, Retinobenzoic acid, Am80
    Molecular Formula
    C22H25NO3
    Molecular Weight
    351.4  g/mol
    InChI Key
    MUTNCGKQJGXKEM-UHFFFAOYSA-N
    FDA UNII
    08V52GZ3H9
    Tamibarotene is an orally active, synthetic retinoid, developed to overcome all-trans retinoic acid (ATRA) resistance, with potential antineoplastic activity. As a specific retinoic acid receptor (RAR) alpha/beta agonist, tamibarotene is approximately ten times more potent than ATRA in inducing cell differentiation and apoptosis in HL-60 (human promyelocytic leukemia) cell lines in vitro. Due to a lower affinity for cellular retinoic acid binding protein (CRABP), tamibarotene may show sustained plasma levels compared to ATRA. In addition, this agent may exhibit a lower toxicity profile than ATRA, in part, due to the lack of affinity for the RAR-gamma receptor, the major retinoic acid receptor in the dermal epithelium.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-[(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)carbamoyl]benzoic acid
    2.1.2 InChI
    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)
    2.1.3 InChI Key
    MUTNCGKQJGXKEM-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1(CCC(C2=C1C=CC(=C2)NC(=O)C3=CC=C(C=C3)C(=O)O)(C)C)C
    2.2 Other Identifiers
    2.2.1 UNII
    08V52GZ3H9
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 4-((5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbamoyl)benzoic Acid

    2. Am 80

    3. Am-80

    4. Am80

    2.3.2 Depositor-Supplied Synonyms

    1. 94497-51-5

    2. Am 80

    3. 4-((5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbamoyl)benzoic Acid

    4. Am-80

    5. Retinobenzoic Acid

    6. Am80

    7. Amnoid

    8. Amnolake

    9. Tamibaro

    10. 4-[(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)carbamoyl]benzoic Acid

    11. Tos-80t

    12. Inno-507

    13. 4-[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbamoyl]benzoic Acid

    14. Tm-411

    15. Nsc 608000

    16. Nsc-608000

    17. Sy-1425

    18. 4-((5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbamoyl)benzoic Acid

    19. Chembl25202

    20. Chebi:32181

    21. 08v52gz3h9

    22. Op-01

    23. Nsc608000

    24. Rr-110

    25. Benzoic Acid, 4-(((5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)amino)carbonyl)-

    26. Ncgc00181111-01

    27. Dsstox_cid_26853

    28. Dsstox_rid_81962

    29. Dsstox_gsid_46853

    30. 4-[[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)amino]carbonyl]benzoic Acid

    31. Smr002530320

    32. Cas-94497-51-5

    33. Tamibarotene [inn]

    34. Amnoleuk

    35. Unii-08v52gz3h9

    36. 2cbr

    37. 4-(((5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)amino)carbonyl)benzoic Acid

    38. A80

    39. Amnoid (tn)

    40. Mfcd00866188

    41. Tamibarotene(am-80)

    42. Tetrahydrofurfurylacrylate

    43. And Op-01

    44. Tamibarotene (jan/inn)

    45. Tamibarotene [mi]

    46. Tamibarotene [jan]

    47. Tamibarotene [usan:inn]

    48. Tamibarotene [usan]

    49. Schembl36207

    50. Tamibarotene [mart.]

    51. Mls003899239

    52. Mls004774034

    53. Mls006011150

    54. Tamibarotene [who-dd]

    55. Gtpl2648

    56. Tos-80

    57. Dtxsid5046853

    58. Tamibarotene, >=98% (hplc)

    59. 4-[(1,1,4,4-tetramethyltetralin-6-yl)carbamoyl]benzoic Acid

    60. Hms3652h04

    61. Hms3743c03

    62. Zinc538415

    63. Bcp07492

    64. Oms-0728

    65. Who 7349

    66. Tox21_112725

    67. Bdbm50061625

    68. S4260

    69. Akos015902693

    70. N-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)terephthalamic Acid

    71. Tox21_112725_1

    72. Ac-7049

    73. Ccg-268044

    74. Cs-0654

    75. Db04942

    76. Ncgc00181111-02

    77. 121ge003

    78. As-14083

    79. Hy-14652

    80. Nci60_004716

    81. Am20060757

    82. Ft-0601534

    83. Sw219913-1

    84. Z-208

    85. D01418

    86. 497t515

    87. A844987

    88. Q7681221

    89. 4-(((5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)amino)carbonyl)benzoic Acid

    90. 4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ylcarbamoyl)benzoic Acid

    91. 4-[[(5,6,7,8-tetrahydro-5,5,8,8-tet Ramethyl-2-naphthalenyl)amino]carbonyl]benzoic Acid

    92. Terephthalic Acid Mono-5,5,8,8-tetramethyl- 5,6,7, 8-tetrahydro-2-naphthylamide

    93. Terephthalic Acid Mono-5,8,8-tetramethyl- 5,6,7,8-tetrahydro-2-naphthylamide

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 351.4 g/mol
    Molecular Formula C22H25NO3
    XLogP35.4
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count3
    Exact Mass351.18344366 g/mol
    Monoisotopic Mass351.18344366 g/mol
    Topological Polar Surface Area66.4 Ų
    Heavy Atom Count26
    Formal Charge0
    Complexity546
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Investigated for use/treatment in leukemia (unspecified).

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Tamibarotene is a new synthetic retinoid drug recently approved for relapsed or refractory acute promyelocytic leukemia (APL) in Japan. It is a specific agonist for retinoic acid receptor alpha/beta. Compared to all-trans retinoic acid (ATRA), a natural retinoid indicated for a first-line treatment of APL, tamibarotene is chemically more stable and several times more potent as an inducer of differentiation in promyelocytic leukemia cells. In contrast to ATRA, whose plasma concentration declines considerably during daily administration, tamibarotene sustains plasma level probably due to a lower affinity for cellular retinoic acid binding protein. Furthermore, adverse side effects were milder than those of ATRA in clinical trials.

    5.2 Mechanism of Action

    Tamibarotene is a specific agonist for retinoic acid receptor alpha/beta with possible binding to retinoid X receptors (RXR).