Please Wait
Applying Filters...
menu
    • menu
    Evonik

    Virtual Booth

    Contact Supplier

    Sharp is a global leader in pharmaceutical packaging and clinical trial supply services.

    Virtual Booth

    Contact Supplier

    xyz-pharma-m-2025-04-21

    Virtual Booth

    Contact Supplier

    Metrochem has been delivering customized volume & quality products to customers across the world, taking utmost care of their needs.

    Virtual Booth

    Contact Supplier

    USP reference standards; highly characterized specimens of drug substances, impurities, excipients, degradation products & more.

    Virtual Booth

    Contact Supplier

    xyz-pharma-m-2025-04-14

    Virtual Booth

    Contact Supplier

    Menu

    Afimoxifene

    PharmaCompass
    Xls

    Filters

    clear-filterReset all filters
    2D Structure
    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

    2D Structure

    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 Weight 387.5 g/mol
    Molecular Formula C26H29NO2
    XLogP36.8
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count8
    Exact Mass387.219829168 g/mol
    Monoisotopic Mass387.219829168 g/mol
    Topological Polar Surface Area32.7 Ų
    Heavy Atom Count29
    Formal Charge0
    Complexity493
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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.