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    Chemistry

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    Also known as: 54965-24-1, Zitazonium, Istubal, Kessar, Zemide, Tamoxifen (citrate)
    Molecular Formula
    C32H37NO8
    Molecular Weight
    563.6  g/mol
    InChI Key
    FQZYTYWMLGAPFJ-OQKDUQJOSA-N
    FDA UNII
    7FRV7310N6
    Tamoxifen Citrate
    One of the SELECTIVE ESTROGEN RECEPTOR MODULATORS with tissue-specific activities. Tamoxifen acts as an anti-estrogen (inhibiting agent) in the mammary tissue, but as an estrogen (stimulating agent) in cholesterol metabolism, bone density, and cell proliferation in the ENDOMETRIUM.
    1 2D Structure

    Tamoxifen Citrate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-[4-[(Z)-1,2-diphenylbut-1-enyl]phenoxy]-N,N-dimethylethanamine;2-hydroxypropane-1,2,3-tricarboxylic acid
    2.1.2 InChI
    InChI=1S/C26H29NO.C6H8O7/c1-4-25(21-11-7-5-8-12-21)26(22-13-9-6-10-14-22)23-15-17-24(18-16-23)28-20-19-27(2)3;7-3(8)1-6(13,5(11)12)2-4(9)10/h5-18H,4,19-20H2,1-3H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/b26-25-;
    2.1.3 InChI Key
    FQZYTYWMLGAPFJ-OQKDUQJOSA-N
    2.1.4 Canonical SMILES
    CCC(=C(C1=CC=CC=C1)C2=CC=C(C=C2)OCCN(C)C)C3=CC=CC=C3.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
    2.1.5 Isomeric SMILES
    CC/C(=C(\C1=CC=CC=C1)/C2=CC=C(C=C2)OCCN(C)C)/C3=CC=CC=C3.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    7FRV7310N6
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Citrate, Tamoxifen

    2. Ici 46,474

    3. Ici 46474

    4. Ici 47699

    5. Ici-46,474

    6. Ici-46474

    7. Ici-47699

    8. Ici46,474

    9. Ici46474

    10. Ici47699

    11. Nolvadex

    12. Novaldex

    13. Soltamox

    14. Tamoxifen

    15. Tomaxithen

    16. Zitazonium

    2.3.2 Depositor-Supplied Synonyms

    1. 54965-24-1

    2. Zitazonium

    3. Istubal

    4. Kessar

    5. Zemide

    6. Tamoxifen (citrate)

    7. Tamoxifen Citrate Salt

    8. Nourytam

    9. Tamofene

    10. Tomaxasta

    11. Ici 46474

    12. Ici 46,474

    13. Ici 46474 Citrate

    14. Ici-46474

    15. Nsc-180973

    16. Nsc-757345

    17. Tamoxifen Citrate (nolvadex)

    18. 54965-24-1 (citrate)

    19. 7frv7310n6

    20. I.c.i.46474 Citrate

    21. Nsc180973

    22. Ncgc00024928-06

    23. Cas-54965-24-1

    24. Dsstox_cid_1301

    25. (z)-2-(p-(1,2-diphenyl-1-butenyl)phenoxy)-n,n-dimethylethylamine Citrate (1:1)

    26. Dsstox_rid_76068

    27. Dsstox_gsid_21301

    28. Ethanamine, 2-[4-(1,2-diphenyl-1-butenyl)phenoxy]-n,n-dimethyl-, (z)-,2-hydroxy-1,2,3-propanetricarboxylate (1:1)

    29. Caditam

    30. Farmifeno

    31. Ginarsan

    32. Jenoxifen

    33. Ledertam

    34. Nourytan

    35. Noxitem

    36. Oncotam

    37. Tafoxen

    38. Tamofen

    39. Tamoxasta

    40. Terimon

    41. Zynoplex

    42. Emblon

    43. Genox

    44. Nolgen

    45. Noltam

    46. Tamax

    47. Tamoxifencitrate

    48. Tamox-puren

    49. (z)-2-(4-(1,2-diphenylbut-1-en-1-yl)phenoxy)-n,n-dimethylethanamine 2-hydroxypropane-1,2,3-tricarboxylate

    50. 2-[4-[(z)-1,2-diphenylbut-1-enyl]phenoxy]-n,n-dimethylethanamine;2-hydroxypropane-1,2,3-tricarboxylic Acid

    51. Ethanamine, 2-(4-(1,2-diphenyl-1-butenyl)phenoxy)-n,n-dimethyl, (z)-, 2-hydroxy-1,2,3-propanetricarboxylate (1:1)

    52. Smr000677949

    53. Z-tamoxifen Citrate

    54. Sr-01000075523

    55. Unii-7frv7310n6

    56. Ccris 6718

    57. Tamoxifeni Citras

    58. Nolvadex (tn)

    59. Soltamox (tn)

    60. 2-{4-[(1z)-1,2-diphenylbut-1-en-1-yl]phenoxy}-n,n-dimethylethanamine 2-hydroxypropane-1,2,3-tricarboxylate (salt)

    61. Prestwick_458

    62. Einecs 259-415-2

    63. Tamoxifen Citrate [usan:usp:jan]

    64. Mfcd00058321

    65. Tamoxifen (nolvadex)

    66. Tamoxifen Citrate,(s)

    67. Tamoxifen, Citrate Salt

    68. Lopac-t-9262

    69. Tamoxifen Z-isomer Citrate

    70. Chembl786

    71. Schembl6365

    72. Mls001055370

    73. Mls002154210

    74. Spectrum1500557

    75. Nolvadex (tn) (astrazeneca)

    76. Tamoxifen Citrate [mi]

    77. Tamoxifen Citrate [jan]

    78. Dtxsid8021301

    79. Tamoxifen Citrate (jp17/usp)

    80. Tamoxifen Citrate [usan]

    81. Hms500m20

    82. Tamoxifen Citrate Salt, >=99%

    83. Tamoxifen Citrate [vandf]

    84. Tamoxifen Citrate [mart.]

    85. Hms1568m14

    86. Hms1921c13

    87. Hms2092k17

    88. Hms2095m14

    89. Hms2232e08

    90. Hms3263b08

    91. Hms3675p04

    92. Hms3712m14

    93. Pharmakon1600-01500557

    94. Tamoxifen Citrate [usp-rs]

    95. Tamoxifen Citrate [who-dd]

    96. Tamoxifen Citrate [who-ip]

    97. Ex-a5777

    98. Hydroxypropane-1,2,3-tricarboxylate

    99. Tox21_110938

    100. Tox21_202070

    101. Tox21_300274

    102. Tox21_501203

    103. Ccg-39629

    104. Nsc757345

    105. S1238

    106. S1972

    107. Akos005111126

    108. Tox21_110938_1

    109. Cs-1852

    110. Ks-5046

    111. Lp01203

    112. Tamoxifen Citrate [orange Book]

    113. Tamoxifen Citrate [ep Monograph]

    114. Ncgc00016206-01

    115. Ncgc00016206-02

    116. Ncgc00016206-03

    117. Ncgc00016206-04

    118. Ncgc00016206-05

    119. Ncgc00016206-06

    120. Ncgc00024928-02

    121. Ncgc00024928-23

    122. Ncgc00094450-01

    123. Ncgc00094450-02

    124. Ncgc00094450-03

    125. Ncgc00094450-04

    126. Ncgc00254000-01

    127. Ncgc00259619-01

    128. Ncgc00261888-01

    129. Tamoxifen Citrate [usp Monograph]

    130. Tamoxifeni Citras [who-ip Latin]

    131. Hy-13757

    132. Bcp0726000223

    133. Tamoxifen Citrate - Cas 54965-24-1

    134. Eu-0101203

    135. Sw219368-1

    136. T2510

    137. (z)-2-(4-(1,2-diphenylbut-1-enyl)phenoxy)

    138. A19582

    139. D00966

    140. T 9262

    141. 965t241

    142. Q-201776

    143. Sr-01000075523-1

    144. Sr-01000075523-3

    145. Sr-01000075523-5

    146. Sr-01000075523-6

    147. Q27108378

    148. Sr-01000075523-10

    149. (z)-1-(4-dimethylaminoethoxyphenyl)-1,2-diphenyl-1-butene Citrate

    150. Tamoxifen Citrate, European Pharmacopoeia (ep) Reference Standard

    151. (z)-2-(4-(1,2-diphenyl-1-butenyl)phenoxy)-n,n-dimethylethanamine,citrate

    152. (z)-2-[4-(1,2-diphenyl-1-butenyl)phenoxy]-n,n-dimethylethanamine Citrate

    153. Tamoxifen Citrate, United States Pharmacopeia (usp) Reference Standard

    154. (z)-2-[ P-(1,2-diphenyl-1-butenyl)phenoxy]- N, N-dimethylethylamine Citrate (1:1)

    155. (z)-2-[4-(1,2-diphenyl-1-butenyl)phenoxy]-n,n-dimethyl-ethanamine Cirtrate (1:1)

    156. Tamoxifen Citrate For Performance Test, European Pharmacopoeia (ep) Reference Standard

    157. (2-{4-[1,2-diphenylbut-1-en-1-yl]phenoxy}ethyl)dimethylamine; 2-hydroxypropane-1,2,3-tricarboxylic Acid

    158. (z)-(2-(4-(1,2-diphenylbut-1-enyl)phenoxy)ethyl)dimethylammonium Dihydrogen 2-hydroxypropane-1,2,3-tricarboxylate

    159. (z)-2-(4-(1,2-diphenylbut-1-enyl)phenoxy)-n,n-dimethylethanamine 2-hydroxypropane-1,2,3-tricarboxylate

    160. {2-[4-(1,2-diphenyl-1-buten-1-yl)phenoxy]ethyl}dimethylamine 2-hydroxy-1,2,3-propanetricarboxylate Salt

    161. Ethanamine, 2-(4-((1z)-1,2-diphenyl-1-butenyl)phenoxy)-n,n-dimethyl-, 2-hydroxy-1,2,3-propanetricarboxylate (1:1)

    162. Ethanamine,2-diphenyl-1-butenyl)phenoxy]-n,n-dimethyl-, (z)-, 2-hydroxy-1,2,3-propanetricarboxylate (1:1)

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 563.6 g/mol
    Molecular Formula C32H37NO8
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count13
    Exact Mass563.25191714 g/mol
    Monoisotopic Mass563.25191714 g/mol
    Topological Polar Surface Area145 Ų
    Heavy Atom Count41
    Formal Charge0
    Complexity690
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameTamoxifen citrate
    Drug LabelNOLVADEX (tamoxifen citrate) Tablets, a nonsteroidal antiestrogen, are for oral administration. NOLVADEX Tablets are available as:...
    Active IngredientTamoxifen citrate
    Dosage FormTablet
    RouteOral
    Strengtheq 20mg base; eq 10mg base
    Market StatusPrescription
    CompanyTeva; Actavis Labs Fl; Apotex; Teva Pharms; Mylan

    2 of 2  
    Drug NameTamoxifen citrate
    Drug LabelNOLVADEX (tamoxifen citrate) Tablets, a nonsteroidal antiestrogen, are for oral administration. NOLVADEX Tablets are available as:...
    Active IngredientTamoxifen citrate
    Dosage FormTablet
    RouteOral
    Strengtheq 20mg base; eq 10mg base
    Market StatusPrescription
    CompanyTeva; Actavis Labs Fl; Apotex; Teva Pharms; Mylan

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Antineoplastic Agents, Hormonal

    Antineoplastic agents that are used to treat hormone-sensitive tumors. Hormone-sensitive tumors may be hormone-dependent, hormone-responsive, or both. A hormone-dependent tumor regresses on removal of the hormonal stimulus, by surgery or pharmacological block. Hormone-responsive tumors may regress when pharmacologic amounts of hormones are administered regardless of whether previous signs of hormone sensitivity were observed. The major hormone-responsive cancers include carcinomas of the breast, prostate, and endometrium; lymphomas; and certain leukemias. (From AMA Drug Evaluations Annual 1994, p2079) (See all compounds classified as Antineoplastic Agents, Hormonal.)

    Bone Density Conservation Agents

    Agents that inhibit BONE RESORPTION and/or favor BONE MINERALIZATION and BONE REGENERATION. They are used to heal BONE FRACTURES and to treat METABOLIC BONE DISEASES such as OSTEOPOROSIS. (See all compounds classified as Bone Density Conservation Agents.)

    Estrogen Antagonists

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

    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.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Selective Estrogen Receptor Modulators [MoA]; Estrogen Agonist/Antagonist [EPC]

    API Reference Price

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    04-Jan-2021
    15-Jul-2024
    KGS
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    DOSAGE - TABLET;ORAL - EQ 10MG BASE **Federal...DOSAGE - TABLET;ORAL - EQ 10MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 17970

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    DOSAGE - TABLET;ORAL - EQ 20MG BASE **Federal...DOSAGE - TABLET;ORAL - EQ 20MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 17970

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    DOSAGE - SOLUTION;ORAL - EQ 20MG BASE/10ML

    USFDA APPLICATION NUMBER - 21807

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