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Tamibarotene

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Chemistry

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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

Tamibarotene

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 Formula	C₂₂H₂₅NO₃
Molecular Weight	351.4 g/mol
XLogP3	5.4
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Exact Mass	351.18344366 g/mol
Monoisotopic Mass	351.18344366 g/mol
Topological Polar Surface Area	66.4 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	546
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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).

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