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Tox21_300274

Tox21_300274

Synopsis, Chemistry

APIs // Active Pharmaceutical Ingredients

30 API Suppliers, 11 USDMF, 6 CEP/COS, 2 JDMF, 4 KDMF, 14 NDC API, 19 Listed Suppliers

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11 Drug(s) in Development

11 Drug(s) in Development

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8 Suppliers

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112 Dossiers, 26 FDA Orange Book, 46 Europe, 6 Canada, 7 Australia, 9 South Africa, 18 Listed Dossiers

DRUG PRODUCT COMPOSITION

TABLET;ORAL - EQ 10MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, TABLET;ORAL - EQ 20MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, SOLUTION;ORAL - EQ 20MG BASE/10ML

TABLET;ORAL - EQ 10MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
TABLET;ORAL - EQ 20MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
SOLUTION;ORAL - EQ 20MG BASE/10ML

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GLOBAL SALES INFORMATION

16 US Medicaid Prescriptions, 45 Finished Drug Prices

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6 APIs, 9 DOSSIERS // FDF

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3 EDQM Standards, 1 USP Standards, 1 Other Ref. Standards

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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

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

Tox21_300274

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 Formula	C₃₂H₃₇NO₈
Molecular Weight	563.6 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	13
Exact Mass	563.25191714 g/mol
Monoisotopic Mass	563.25191714 g/mol
Topological Polar Surface Area	145 Å²
Heavy Atom Count	41
Formal Charge	0
Complexity	690
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	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Tamoxifen citrate
Drug Label	NOLVADEX (tamoxifen citrate) Tablets, a nonsteroidal antiestrogen, are for oral administration. NOLVADEX Tablets are available as:...
Active Ingredient	Tamoxifen citrate
Dosage Form	Tablet
Route	Oral
Strength	eq 20mg base; eq 10mg base
Market Status	Prescription
Company	Teva; Actavis Labs Fl; Apotex; Teva Pharms; Mylan

2 of 2
Drug Name	Tamoxifen citrate
Drug Label	NOLVADEX (tamoxifen citrate) Tablets, a nonsteroidal antiestrogen, are for oral administration. NOLVADEX Tablets are available as:...
Active Ingredient	Tamoxifen citrate
Dosage Form	Tablet
Route	Oral
Strength	eq 20mg base; eq 10mg base
Market Status	Prescription
Company	Teva; 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]