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    Estradiol Benzoate

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

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    GLOBAL SALES INFORMATION

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    2D Structure
    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

    2D Structure

    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 Weight 376.5 g/mol
    Molecular Formula C25H28O3
    XLogP34.5
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count3
    Exact Mass376.20384475 g/mol
    Monoisotopic Mass376.20384475 g/mol
    Topological Polar Surface Area46.5 Ų
    Heavy Atom Count28
    Formal Charge0
    Complexity582
    Isotope Atom Count0
    Defined Atom Stereocenter Count5
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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.