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1 Roquette
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Symbiotec Estradiol Benzoate

Synopsis

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Chemistry

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Also known as: 50-50-0, Benzhormovarine, Benzoestrofol, Benovocylin, Estradiol 3-benzoate, Oestradiol benzoate

Molecular Formula

C₂₅H₂₈O₃

Molecular Weight

376.5 g/mol

InChI Key

UYIFTLBWAOGQBI-BZDYCCQFSA-N

FDA UNII

1S4CJB5ZGN

Estradiol Benzoate is the synthetic benzoate ester of estradiol, a steroid sex hormone vital to the maintenance of fertility and secondary sexual characteristics in females. As the primary, most potent estrogen hormone produced by the ovaries, estradiol binds to and activates specific nuclear receptors. This agent exhibits mild anabolic and metabolic properties, and increases blood coagulability. (NCI04)

1 2D Structure

Estradiol Benzoate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] benzoate

2.1.2 InChI

InChI=1S/C25H28O3/c1-25-14-13-20-19-10-8-18(28-24(27)16-5-3-2-4-6-16)15-17(19)7-9-21(20)22(25)11-12-23(25)26/h2-6,8,10,15,20-23,26H,7,9,11-14H2,1H3/t20-,21-,22+,23+,25+/m1/s1

2.1.3 InChI Key

UYIFTLBWAOGQBI-BZDYCCQFSA-N

2.1.4 Canonical SMILES

CC12CCC3C(C1CCC2O)CCC4=C3C=CC(=C4)OC(=O)C5=CC=CC=C5

2.1.5 Isomeric SMILES

C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)OC(=O)C5=CC=CC=C5

2.2 Other Identifiers

2.2.1 UNII

1S4CJB5ZGN

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 17beta-estradiol-3-benzoate

2. Eston-b

3. Estradiol 3-benzoate

4. Oestradiol 3-benzoate

2.3.2 Depositor-Supplied Synonyms

1. 50-50-0

2. Benzhormovarine

3. Benzoestrofol

4. Benovocylin

5. Estradiol 3-benzoate

6. Oestradiol Benzoate

7. Estradiol Monobenzoate

8. Benzofoline

9. Follidrin

10. Ovasterol-b

11. Benzo-gynoestryl

12. Primogyn B

13. Progynon B

14. Progynon Benzoate

15. Eston-b

16. Diffollisterol

17. Difolliculine

18. Femestrone

19. Follicormon

20. Gynecormone

21. Gynformone

22. Hidroestron

23. Hormogynon

24. Unistradiol

25. Benztrone

26. Graafina

27. Solestro

28. Dimenformon Benzoate

29. De Graafina

30. Ovocyclin M

31. Primogyn I

32. Ovocyclin-mb

33. Diogyn B

34. Oestradiol 3-benzoate

35. Oestradiol Monobenzoate

36. Ovahormon Benzoate

37. Ovocyclin Benzoate

38. Agofollin Depot

39. 17-beta-estradiol 3-benzoate

40. Beta-estradiol 3-benzoate

41. Recthormone Oestradiol

42. Benzoic Acid Estradiol

43. Estradioli Benzoas

44. Benzoate D'estradiol

45. Benzoate D'oestradiol

46. Benzoato De Estradiol

47. 17beta-estradiol 3-benzoate

48. 17beta-estradiol Monobenzoate

49. Estradiol, 3-benzoate

50. Benzestrofol

51. Benzogynestryl

52. Dimenformone

53. Estrogin

54. Mesalin

55. Folone

56. Nsc-9566

57. Oestroform [bdh]

58. Dihydroestrin Benzoate

59. Hydroxyestrin Benzoate

60. [(8r,9s,13s,14s,17s)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] Benzoate

61. Benzoestrofol Difolliculin

62. Dihydrofolliculin Benzoate

63. .beta.-estradiol Benzoate

64. 1s4cjb5zgn

65. Estradiol (benzoate)

66. .beta.-estradiol 3-benzoate

67. 17.beta.-estradiol Benzoate

68. Estradiol-17.beta. Benzoate

69. Mls000028477

70. Ebz

71. 17.beta.-estradiol 3-benzoate

72. Estradiol-17.beta. 3-benzoate

73. 17.beta.-estradiol Monobenzoate

74. Chebi:77006

75. Ostrin

76. Ncgc00021274-03

77. (17beta)-17-hydroxyestra-1(10),2,4-trien-3-yl Benzoate

78. Metroval

79. Reglovar

80. Smr000058343

81. Benzo-ginestryl

82. Estradiolo Amsa

83. Benzo-gineostril

84. Oestradioli Benzoas

85. Gynecormone Gouttes

86. Primogyn B Oleosum

87. (8r,9s,13s,14s,17s)-17-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6h-cyclopenta[a]phenanthren-3-yl Benzoate

88. Oestraform (bdh)

89. Oestradiolum Benzoicum

90. Oestradiolum Benzoylatum

91. (17beta)-estra-1,3,5(10)-triene-3,17-diol 3-benzoate

92. Dihydrofolliculine Benzoate

93. Estradiol Benzoate (van)

94. Estradiol Benzoate [inn]

95. 17-beta-estradiol Benzoate

96. Estradiolo Benzoato

97. Estradiolo Benzoato [dcit]

98. Estradiol-17beta 3-benzoate

99. Ccris 281

100. Estradiol-17-beta-3-benzoate

101. Benzoate D'oestradiol [french]

102. 17-beta-oestradiol 3-benzoate

103. Estradioli Benzoas [inn-latin]

104. Benzoate D'estradiol [inn-french]

105. Nsc 9566

106. Einecs 200-043-7

107. Unii-1s4cjb5zgn

108. Benzoato De Estradiol [inn-spanish]

109. Brn 3107526

110. Benzogynoestryl

111. Difolliculin

112. Oestraform

113. Ai3-52465

114. Pelanin Benzoate

115. Progynon-b

116. Primogyn Boleosum

117. Estradiol-benzoate

118. Diffolisterol,(s)

119. Estra-1,3,5(10)-triene-3,17beta-diol, 3-benzoate

120. Estra-1,3,5(10)-triene-3,17-beta-diol, 3-benzoate

121. Estradiol Benzoate [usp:inn:ban:jan]

122. Estra-1,3,5(10)-triene-3,17-diol (17-beta)-3-benzoate

123. St075190

124. Ss-estradiol 3-benzoate

125. 17-estradiol 3-benzoate

126. Dsstox_cid_2998

127. .beta.-oestradiol Benzoate

128. 3-benzoyloxy-17ss-estrol

129. Dsstox_rid_76823

130. Dsstox_gsid_22998

131. I(2)-estradiol 3-benzoate

132. 4-09-00-00406 (beilstein Handbook Reference)

133. Mls002207215

134. .beta.-oestradiol 3-benzoate

135. Bidd:er0126

136. Schembl174896

137. Chembl282575

138. Cid_222757

139. Dtxsid9022998

140. Estradiol Benzoate [jan]

141. Bdbm56905

142. Estradiol Benzoate (jp17/usp)

143. Nsc9566

144. 17-.beta.-oestradiol 3-benzoate

145. Hms2232p14

146. Estradiol 3-benzoate [mi]

147. Estradiol Benzoate [mart.]

148. Amy22166

149. Bcp09252

150. Estra-1,3,5(10)-triene-3,17-diol, (17beta)-, 3-benzoate

151. Estradiol Benzoate [usp-rs]

152. Estradiol Benzoate [who-dd]

153. Hy-b1192

154. Zinc3881345

155. Tox21_110868

156. Beta-estradiol 3-benzoate, >=97%

157. S4110

158. Akos015955542

159. Ccg-268370

160. Cs-4780

161. Db13953

162. Estradiol Benzoate [green Book]

163. Cas-50-50-0

164. Estradiol Benzoate [ep Monograph]

165. Estradiol Benzoate [usp Impurity]

166. Estradiol Benzoate For System Suitability

167. Ncgc00021274-04

168. Ncgc00021274-05

169. As-13030

170. Estradiol Benzoate [usp Monograph]

171. Wln: L E5 B666ttt&j E1 Fq Oovr

172. E0329

173. D01953

174. D97619

175. 003e692

176. A828140

177. Sr-01000003080

178. 1,5(10)-estratriene-3,17.beta.-diol 3-benzoate

179. Q-201505

180. Sr-01000003080-3

181. 1,3,5(10)-estratriene-3,17.beta.-diol 3-benzoate

182. 3,17ss-dihydroxy-1,3,5(10)-estratriene 3-benzoate

183. Estra-1,3,5(10)-triene-3,17beta-diol 3-benzoate

184. Estra-1,5(10)-triene-3,17.beta.-diol, 3-benzoate

185. Q11450699

186. (17beta)estra-1,3,5(10)triene-3,17-diol-3-benzoate

187. 1,3,5(10)-oestratriene-3,17-.beta.-diol 3-benzoate

188. 3-benzoyloxy-17.beta.-hydroxyestra-1,3,5(10)-triene

189. Estra-1,3,5(10)-triene-3,17.beta.-diol, 3-benzoate

190. (17?)-17-hydroxyestra-1(10),2,4-trien-3-yl Benzoate

191. Estra-1,3,5(10)-triene-3,17-diol (17b)-, 3-benzoate

192. (17.beta.)-estra-1,3,5(10)-triene-3,17-diol 3-benzoate

193. Beta-estradiol 3-benzoate, Vetranal(tm), Analytical Standard

194. Estra-1,5(10)-triene-3,17-diol (17.beta.)-, 3-benzoate

195. 17-hydroxyestra-1(10),2,4-trien-3-yl Benzoate, (17.beta.)-

196. Estradiol Benzoate, European Pharmacopoeia (ep) Reference Standard

197. Estradiol Benzoate, United States Pharmacopeia (usp) Reference Standard

198. Estradiol Benzoate For System Suitability, European Pharmacopoeia (ep) Reference Standard

199. (8r,9s,13s,14s,17s)-17-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6h-cyclopenta[a]phenanthren-3-yl Benzoate;17beta-estradiol Benzoate; 1,3,5(10)-estratriene-3,17b-diol 3-benzoate; 3,17b-dihydroxy-1,3,5(10)-estratriene 3-benzoate

200. [(13s,17s)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] Benzoate

201. [(8r,9s,13s,14s,17s)-13-methyl-17-oxidanyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] Benzoate

202. Benzoic Acid [(8r,9s,13s,14s,17s)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] Ester

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₂₅H₂₈O₃
Molecular Weight	376.5 g/mol
XLogP3	4.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Exact Mass	376.20384475 g/mol
Monoisotopic Mass	376.20384475 g/mol
Topological Polar Surface Area	46.5 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	582
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
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

Estradiol benzoate is not currently available in any FDA or Health Canada approved products.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Estradiol, the principal intracellular human estrogen, is substantially more active than its metabolites, estrone and estriol, at the cellular level.

5.2 MeSH Pharmacological Classification

Contraceptive Agents, Hormonal

Contraceptive agents that act on the ENDOCRINE SYSTEM. (See all compounds classified as Contraceptive Agents, Hormonal.)

5.3 Metabolism/Metabolites

Exogenous estrogens are metabolized using the same mechanism as endogenous estrogens. Estrogens are partially metabolized by cytochrome P450.

5.4 Mechanism of Action

Estradiol enters target cells freely (e.g., female organs, breasts, hypothalamus, pituitary) and interacts with a target cell receptor. When the estrogen receptor has bound its ligand it can enter the nucleus of the target cell, and regulate gene transcription which leads to formation of messenger RNA. The mRNA interacts with ribosomes to produce specific proteins that express the effect of estradiol upon the target cell. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary.

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