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Afimoxifene

Afimoxifene

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Also known as: (z)-4-hydroxytamoxifen, Afimoxifene, 68047-06-3, Hydroxytamoxifen, Trans-4-hydroxytamoxifen, 4-monohydroxytamoxifen

Molecular Formula

C₂₆H₂₉NO₂

Molecular Weight

387.5 g/mol

InChI Key

TXUZVZSFRXZGTL-QPLCGJKRSA-N

FDA UNII

95K54647BZ

Afimoxifene is a tamoxifen metabolite with both estrogenic and anti-estrogenic effects. Afimoxifene has a higher affinity for the estrogen receptor than tamoxifen, and functions as an antagonist in breast cancer cells.

1 2D Structure

Afimoxifene

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[(Z)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol

2.1.2 InChI

InChI=1S/C26H29NO2/c1-4-25(20-8-6-5-7-9-20)26(21-10-14-23(28)15-11-21)22-12-16-24(17-13-22)29-19-18-27(2)3/h5-17,28H,4,18-19H2,1-3H3/b26-25-

2.1.3 InChI Key

TXUZVZSFRXZGTL-QPLCGJKRSA-N

2.1.4 Canonical SMILES

CCC(=C(C1=CC=C(C=C1)O)C2=CC=C(C=C2)OCCN(C)C)C3=CC=CC=C3

2.1.5 Isomeric SMILES

CC/C(=C(\C1=CC=C(C=C1)O)/C2=CC=C(C=C2)OCCN(C)C)/C3=CC=CC=C3

2.2 Other Identifiers

2.2.1 UNII

95K54647BZ

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4'-hydroxytamoxifen

2. 4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenylbut-1-enyl)phenol

3. 4-hydroxy-tamoxifen

4. 4-hydroxytamoxifen, (e)-isomer

5. 4-hydroxytamoxifen, (z)-isomer

6. 4-monohydroxytamoxifen

7. 4-oht Hydrotamoxifen

8. 4oh-tamoxifen

9. Afimoxifene

10. Hydroxytamoxifen

11. Ici 79280

12. Monohydroxytamoxifen

13. Para-hydroxytamoxifen

14. Phenol, 4-((1z)-1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenyl-1-buten-1-yl)-

15. Phenol, 4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenyl-1-butenyl)-

16. Phenol, 4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenyl-1-butenyl)-,

17. Tamoxifen Metabolite B

2.3.2 Depositor-Supplied Synonyms

1. (z)-4-hydroxytamoxifen

2. Afimoxifene

3. 68047-06-3

4. Hydroxytamoxifen

5. Trans-4-hydroxytamoxifen

6. 4-monohydroxytamoxifen

7. Tamogel

8. (z)-4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenylbut-1-en-1-yl)phenol

9. 68392-35-8

10. Ici 79280

11. 65213-48-1

12. (z)-4-hydroxy Tamoxifen

13. (e/z)-4-hydroxy Tamoxifen

14. Z-4-hydroxytamoxifen

15. C26h29no2

16. Chembl489

17. R-lipoic Acid Potassium Compund

18. Tamoxifen, 4-hydroxy-, (z)-

19. Mls000069742

20. 1077-29-8

21. Chebi:44616

22. (e/z)-4-hydroxytamoxifen

23. 95k54647bz

24. 4-hydroxy Tamoxifen

25. Smr000058939

26. 4-[(1z)-1-{4-[2-(dimethylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl]phenol

27. 4-[(z)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol

28. 4-hydroxy Tamoxifen-d5

29. 4-oh-tam

30. [3h]4-oht

31. 4-[(1z)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]phenol

32. Cis-4-hydroxytamoxifen

33. Sr-01000759243

34. Afimoxifene [usan:inn]

35. Ici 79,280

36. Brn 4910749

37. Unii-17197f0kym

38. Ccris 8580

39. Unii-95k54647bz

40. (z)-4-oht

41. 4-[(1z)-1-{4-[2-(dimethylamino)ethoxy]phenyl}-2-phenyl-1-buten-1-yl]phenol

42. 4-oh Tamoxifen

43. Tamogel (tn)

44. 2bj4

45. Opera_id_600

46. Afimoxifene (usan/inn)

47. Dsstox_cid_2384

48. 4-((1z)-1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenyl-1-butenyl)phenol

49. Phenol, 4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenyl-1-butenyl)-,

50. Trans-4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenyl-1-butenyl)phenol

51. Schembl9189

52. Dsstox_rid_76567

53. Bidd:pxr0104

54. Dsstox_gsid_22384

55. Afimoxifene, Z-isomer

56. Mls001077346

57. Bidd:er0193

58. Cid_449459

59. Dtxsid7022384

60. Bdbm20608

61. 17197f0kym

62. Hms2231f20

63. Zinc902197

64. Ex-a4661

65. Tox21_200943

66. 4-[1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenyl-1-butenyl]phenol

67. Hsci1_000353

68. Hy-16950a

69. Ici-79280

70. Mfcd00278780

71. Mfcd00468090

72. S8956

73. (z)-4-hydroxytamoxifen (z-4-oht)

74. 4-{1-[4-(2-dimethylamino-ethoxy)-phenyl]-2-phenyl-but-1-enyl}-phenol

75. Akos016010361

76. Db04468

77. Phenol, 4-((1z)-1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenyl-1-butenyl)-

78. Phenol, 4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenyl-1-butenyl)-, (z)-

79. Ncgc00164399-01

80. Ncgc00164399-02

81. Ncgc00258497-01

82. (z)-4-hydroxytamoxifen, >=98% Z Isomer

83. Cas-68047-06-3

84. Cs-0003592

85. C05011

86. D06551

87. 392h358

88. A904472

89. Q4689254

90. Sr-01000759243-3

91. Sr-01000759243-5

92. Brd-k04210847-001-01-1

93. 4-(1-[4-(dimethylaminoethoxy)phenyl]-2-phenyl-1-butenyl)phenol

94. (z)-4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenylbut-1-enyl)phenol

95. 4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenylbut-1-en-1-yl)phenol

96. 4-hydroxytamoxifen ??(1/2)70% Z Isomer (remainder Primarily E-isomer)

97. 4-[(1z)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]-phenol

98. 4-{(1z)-1-[4-(2-dimethylamino-ethoxy)-phenyl]-2-phenyl-but-1-enyl}-phenol

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₂₉NO₂
Molecular Weight	387.5 g/mol
XLogP3	6.8
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	8
Exact Mass	387.219829168 g/mol
Monoisotopic Mass	387.219829168 g/mol
Topological Polar Surface Area	32.7 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	493
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For the potential treatment of menstrual-cycle related mastalgia, fibrocystic breast disease, breast disease, gynecomastia and Keloid scarring.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

Selective Estrogen Receptor Modulators

A structurally diverse group of compounds distinguished from ESTROGENS by their ability to bind and activate ESTROGEN RECEPTORS but act as either an agonist or antagonist depending on the tissue type and hormonal milieu. They are classified as either first generation because they demonstrate estrogen agonist properties in the ENDOMETRIUM or second generation based on their patterns of tissue specificity. (Horm Res 1997;48:155-63) (See all compounds classified as Selective Estrogen Receptor Modulators.)

Estrogen Antagonists

Compounds which inhibit or antagonize the action or biosynthesis of estrogenic compounds. (See all compounds classified as Estrogen Antagonists.)

5.2 Absorption, Distribution and Excretion

Absorption

Absorbed following topical application.

5.3 Metabolism/Metabolites

4-Hydroxytamoxifen has known human metabolites that include 3,4-Dihydroxy-Tamoxifen, Endoxifen, Tamoxifen 4-O-glucuronide, and Tamoxifen 4-O-sulfate.

4-Hydroxytamoxifen is a known human metabolite of tamoxifen.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

5.4 Mechanism of Action

Afimoxifene binds to estrogen receptors (ER), inducing a conformational change in the receptor. This results in a blockage or change in the expression of estrogen dependent genes.