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    Chemistry

    Click the arrow to open the dropdown
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    Also known as: 50-27-1, Oestriol, Trihydroxyestrin, Aacifemine, Estratriol, Ovestin
    Molecular Formula
    C18H24O3
    Molecular Weight
    288.4  g/mol
    InChI Key
    PROQIPRRNZUXQM-ZXXIGWHRSA-N
    FDA UNII
    FB33469R8E
    Estriol
    A hydroxylated metabolite of ESTRADIOL or ESTRONE that has a hydroxyl group at C3, 16-alpha, and 17-beta position. Estriol is a major urinary estrogen. During PREGNANCY, a large amount of estriol is produced by the PLACENTA. Isomers with inversion of the hydroxyl group or groups are called epiestriol.
    1 2D Structure

    Estriol

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (8R,9S,13S,14S,16R,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,16,17-triol
    2.1.2 InChI
    InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17+,18+/m1/s1
    2.1.3 InChI Key
    PROQIPRRNZUXQM-ZXXIGWHRSA-N
    2.1.4 Canonical SMILES
    CC12CCC3C(C1CC(C2O)O)CCC4=C3C=CC(=C4)O
    2.1.5 Isomeric SMILES
    C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H]([C@@H]2O)O)CCC4=C3C=CC(=C4)O
    2.2 Other Identifiers
    2.2.1 UNII
    FB33469R8E
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (16alpha,17beta)-estra-1,3,5(10)-triene-3,16,17-triol

    2. (16beta,17beta)-estra-1,3,5(10)-triene-3,16,17-triol

    3. 16 Alpha Hydroxy Estradiol

    4. 16-alpha-hydroxy-estradiol

    5. 16alpha,17beta Estriol

    6. 16alpha,17beta-estriol

    7. 16beta Hydroxy Estradiol

    8. 16beta-hydroxy-estradiol

    9. Epiestriol

    10. Estra-1,3,5(10)-triene-3,16beta,17beta-triol

    11. Ovestin

    2.3.2 Depositor-Supplied Synonyms

    1. 50-27-1

    2. Oestriol

    3. Trihydroxyestrin

    4. Aacifemine

    5. Estratriol

    6. Ovestin

    7. Ovestrion

    8. Destriol

    9. Tridestrin

    10. Theelol

    11. Oestratriol

    12. Orestin

    13. Holin

    14. 16alpha-hydroxyestradiol

    15. Ortho-gynest

    16. Deuslon-a

    17. Hemostyptanon

    18. Hormomed

    19. Klimoral

    20. Oestriolum

    21. Orgastyptin

    22. Overstin

    23. Thulol

    24. Triovex

    25. 16alpha,17beta-estriol

    26. Gynaesan

    27. Hormonin

    28. Stiptanon

    29. Synapause

    30. Triodurin

    31. Estriel

    32. Trihydroxyoestrin

    33. Follicular Hormone Hydrate

    34. 16-alpha-hydroxyestradiol

    35. Estriolo [italian]

    36. 16alpha-hydroxyoestradiol

    37. 16alpha,17beta-oestriol

    38. 16-alpha,17-beta-estriol

    39. 16-alpha,17-beta-oestriol

    40. Colpogyn

    41. Estriolo

    42. Incurin

    43. 16alpha-hydroxy-17beta-estradiol

    44. Estriol, Unconjugated

    45. (16alpha,17beta)-estra-1,3,5(10)-triene-3,16,17-triol

    46. 16-alpha-hydroxyoestradiol

    47. Deuslon A

    48. Nsc-12169

    49. 3,16alpha,17beta-estriol

    50. 3,16-alpha,17-beta-estriol

    51. 3,16-alpha,17-beta-oestriol

    52. 16.alpha.-hydroxyestradiol

    53. 16.alpha.,17.beta.-estriol

    54. 3,16alpha,17beta-trihydroxy-1,3,5(10)-estratriene

    55. 16.alpha.-estriol

    56. Chlorapatite

    57. Gynasan

    58. Ovesterin

    59. 1,3,5-estratriene-3beta,16alpha,17beta-triol

    60. Ovo-vinces

    61. 1,3,5-oestratriene-3beta,16alpha,17beta-triol

    62. A 13610

    63. Klimax E

    64. Estra-1,3,5(10)-trien-3,16alpha,17beta-triol

    65. Oestra-1,3,5(10)-triene-3,16alpha,17beta-triol

    66. 16.alpha.-hydroxyoestradiol

    67. 3,16alpha,17beta-trihydroxy-delta-1,3,5-oestratriene

    68. 3,16-alpha,17-beta-trihydroxy-delta-1,3,5-estratriene

    69. 3,16-alpha,17-beta-trihydroxy-delta-1,3,5-oestratriene

    70. 3,16-alpha,17-beta-trihydroxyestra-1,3,5(10)-triene

    71. 3,16-alpha,17-beta-trihydroxyoestra-1,3,5(10)-triene

    72. (16alpha,17beta)-oestra-1,3,5(10)-triene-3,16,17-triol

    73. 1,3,5(10)-estratriene-3,16alpha,17beta-triol

    74. 16.alpha.,17.beta.-oestriol

    75. 1,3,5(10)-estratriene-3,16-alpha,17beta-triol

    76. Chebi:27974

    77. Estra-1,3,5(10)-triene-3,16alpha,17beta-triol

    78. Oestra-1,3,5(10)-triene-3,16-alpha,17-beta-triol

    79. 3,16alpha,17beta-trihydroxy-delta(1,3,5)-estratriene

    80. (8r,9s,13s,14s,16r,17r)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,16,17-triol

    81. Oe3

    82. 16.alpha.-hydroxy-17.beta.-estradiol

    83. 16-epiestriol

    84. Fb33469r8e

    85. Nsc12169

    86. Estra-1,3,5(10)-triene-3,16,17-triol, (16a,17b)-

    87. Estra-1,3,5(10)-triene-3,16,17-triol

    88. Dsstox_cid_2366

    89. Dsstox_rid_76559

    90. Dsstox_gsid_22366

    91. 1306-04-3

    92. 3,16.alpha.,17.beta.-estriol

    93. Mfcd00003691

    94. 16a-hydroxyestradiol

    95. Folicular Hormone

    96. (1s,10r,11s,13r,14r,15s)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol

    97. 3,17.beta.-estriol

    98. Ccris 284

    99. Estriel (tn)

    100. 16-hydroxyestradiol

    101. Oestriol [steroidal Oestrogens]

    102. Estra-1,3,5(10)-triene-3,16,17-triol, (16.alpha.,17.beta.)-

    103. Hsdb 3590

    104. Sr-01000721851

    105. Einecs 200-022-2

    106. Nsc 12169

    107. 1,3,5(10)-estratriene-3,16.alpha.,17.beta.-triol

    108. Estra-1,3,5(10)-trien-3,16.alpha.,17.beta.-triol

    109. Estra-1,3,5(10)-triene-3,16.alpha.,17.beta.-triol

    110. 1,3,5(10)-estratriene-3,16,17-triol

    111. 1,3,5-estratriene-3.beta.,16-.alpha.,17-.beta.-triol

    112. 1,3,5-oestratriene-3-.beta.,16.alpha.,17.beta.-triol

    113. 3,16.alpha.,17.beta.-trihydroxy-1,3,5(10)-estratriene

    114. 3,16.alpha.,17.beta.-trihydroxyestra-1,3,5(10)-triene

    115. Brn 2508172

    116. Oestra-1,3,5(10)-triene-3,16.alpha., 17.beta.-triol

    117. 3,16.alpha.,17.beta.-trihydroxy-.delta.-1,3,5-estratriene

    118. Ovestinon

    119. Trimesta

    120. 3,16.alpha.,17.beta.-trihydroxy-.delta.-1,3,5-oestratriene

    121. Oestriol.

    122. Unii-fb33469r8e

    123. (16.alpha.,17.beta.)-estra-1,3,5(10)-triene-3,16,17-triol

    124. (16.alpha.,17.beta.)-oestra-1,3,5(10)-triene-3,16,17-triol

    125. Estriol [usp:inn:ban:jan]

    126. 3,16-.alpha.,17-.beta.-oestriol

    127. Estra-1,3,5(10)-triene-3,16,17-triol, (16alpha,17beta)-

    128. Holin V

    129. Cas-50-27-1

    130. 16a-estriol

    131. Ncgc00166111-01

    132. (8r,9s,13s,14s,16r,17r)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6h-cyclopenta[a]phenanthrene-3,16,17-triol

    133. 16a,17b-estriol

    134. Estriol, 98%

    135. Estriol [hsdb]

    136. Estriol, >=97%

    137. Estriol [jan]

    138. Estriol [mi]

    139. 3,16a,17b-estriol

    140. Estriol [mart.]

    141. Prestwick0_001096

    142. Prestwick1_001096

    143. Prestwick2_001096

    144. Prestwick3_001096

    145. Estriol (jp17/usp)

    146. E0218

    147. Estriol [usp-rs]

    148. Estriol [who-dd]

    149. Epitope Id:140131

    150. 1,3,5(10)-estratrien-3,16.alpha.,17.beta.-triol

    151. Estra-1,3,5(10)-triene-3,16-.alpha., L7-.beta.-triol

    152. Schembl78033

    153. Bspbio_001172

    154. Estriol [green Book]

    155. 3,16-.alpha.,17-.beta.-trihydroxyoestra-1,3,5(10)-triene

    156. 4-06-00-07550 (beilstein Handbook Reference)

    157. Mls000069812

    158. Bidd:er0124

    159. Spbio_003056

    160. Estriol [ep Monograph]

    161. Bpbio1_001290

    162. Chembl193482

    163. Gtpl2821

    164. Estriol [usp Monograph]

    165. Dtxsid9022366

    166. Estriol 1.0 Mg/ml In Methanol

    167. Hms1571k14

    168. Hms2090e20

    169. Hms2098k14

    170. Hms2234a18

    171. Hms3715k14

    172. Hms3884p19

    173. Bcp23357

    174. Hy-b0412

    175. Zinc3815418

    176. Estriol 100 Microg/ml In Methanol

    177. Tox21_112320

    178. Tox21_301604

    179. Bdbm50410506

    180. Lmst02010003

    181. S2466

    182. Estriol [ema Epar Veterinary]

    183. Estriol 1000 Microg/ml In Methanol

    184. Akos015894926

    185. Tox21_112320_1

    186. Bcp9000661

    187. Ccg-221096

    188. Db04573

    189. Estriol 100 Microg/ml In Acetonitrile

    190. Estriol, Purum, >=97.0% (hplc)

    191. Fd12050

    192. Smp1_000122

    193. Ncgc00166111-02

    194. Ncgc00179277-01

    195. Ncgc00255193-01

    196. Ncgc00274080-01

    197. As-13735

    198. Estriol, Meets Usp Testing Specifications

    199. Smr000059210

    200. Bcp0726000219

    201. Ab00514045

    202. B1507

    203. Estriol, Vetranal(tm), Analytical Standard

    204. Wln: L E5 B666ttt&j E1 Fq Gq Oq

    205. C05141

    206. D00185

    207. Estra-1,3,5(10)-triene-3,16a,17b-triol

    208. 1,3,5-estratriene-3b,16a,17b-triol

    209. 3,16a,17b-trihydroxyestra-1,3,5(10)-triene

    210. 3,17.beta.-trihydroxy-1,3,5(10)-estratriene

    211. 3,17.beta.-trihydroxyestra-1,3,5(10)-triene

    212. Ab00514045-08

    213. Ab00514045-09

    214. Ab00514045_10

    215. (16.alpha.,3,5(10)-triene-3,16,17-triol

    216. 003e691

    217. Q409721

    218. 3,17.beta.-trihydroxy-.delta.-1,3,5-estratriene

    219. 3,17.beta.-trihydroxy-.delta.-1,3,5-oestratriene

    220. Q-201072

    221. Sr-01000721851-3

    222. Sr-01000721851-4

    223. 1,5(10)-estratriene-3,16.alpha., 17.beta.-triol

    224. 1,5(10)-estratriene-3,16.alpha.,17.beta.-triol

    225. 3,16alpha,17beta-trihydroxyestra-1,3,5(10)-triene

    226. Brd-k17016787-001-03-5

    227. Brd-k17016787-001-16-7

    228. Estra-1,5(10)-trien-3,16.alpha.,17.beta.-triol

    229. Estra-1,5(10)-triene-3,16.alpha.,17.beta.-triol

    230. 1,5-estratriene-3.beta.,16-.alpha.,17-.beta.-triol

    231. 1,5-oestratriene-3-.beta.,16.alpha.,17.beta.-triol

    232. 13b-methyl-1,3,5(10)-gonatriene-3,16a,17b-triol

    233. Estra-1,5(10)-trien-3,16.alpha., 17.beta.-triol

    234. Estra-1,5(10)-triene-3,16.alpha., 17.beta.-triol

    235. Estriol, European Pharmacopoeia (ep) Reference Standard

    236. Oestra-1,5(10)-triene-3,16.alpha., 17.beta.-triol

    237. Oestra-1,5(10)-triene-3,16.alpha.,17.beta.-triol

    238. 6ec6f23b-a991-4606-8bc7-146d915dab31

    239. Estriol, United States Pharmacopeia (usp) Reference Standard

    240. (16a,17b)-estra-1,3,5(10)-triene-3,16,17-triol

    241. (s)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic Acidt-butyl Ester

    242. Estra-1(10),2,4-triene-3,16,17-triol, (16alpha,17beta)-

    243. Estra-1,5(10)-triene-3,16,17-triol, (16.alpha.,17.beta.)-

    244. (9beta,13alpha,16beta,17beta)-estra-1(10),2,4-triene-3,16,17-triol

    245. 13.beta.-methyl-1,3,5(10)-gonatriene-3,16.alpha.,17.beta.-triol

    246. Estriol For System Suitability, European Pharmacopoeia (ep) Reference Standard

    247. Estriol Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

    248. (13s,16r,17r)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6h-cyclopenta[a]phenanthrene-3,16,17-triol

    249. (8r,13s,16r,17r)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6h-cyclopenta[a]phenanthrene-3,16,17-triol

    250. (8r,9s,13s,14s,16r,17r)-13-methyl-6,7,8,9,11,12,14,15,16, 17-decahydrocyclopenta[a]phenanthrene-3,16,17-triol

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 288.4 g/mol
    Molecular Formula C18H24O3
    XLogP32.5
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count0
    Exact Mass288.17254462 g/mol
    Monoisotopic Mass288.17254462 g/mol
    Topological Polar Surface Area60.7 Ų
    Heavy Atom Count21
    Formal Charge0
    Complexity411
    Isotope Atom Count0
    Defined Atom Stereocenter Count6
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Therapeutic Uses

    /Estriol is indicated as/ hormone replacement therapy for treatment of atrophic vaginitis and kraurosis in post-menopausal women.

    Datapharm Communications Ltd; Electronic Medicines Compendium (eMC), Summary of Product Characteristics (SPC) for Gynest 0.01% w/w Cream (Last updated June 2009). Available from, as of March 16, 2011: https://www.medicines.org.uk/EMC/medicine/24108/SPC/Gynest+0.01++w+w+Cream/

    /Estriol is indicated for the/ treatment of pruritus vulvae and dyspareunia associated with atrophic vaginal epithelium.

    Datapharm Communications Ltd; Electronic Medicines Compendium (eMC), Summary of Product Characteristics (SPC) for Gynest 0.01% w/w Cream (Last updated June 2009). Available from, as of March 16, 2011: https://www.medicines.org.uk/EMC/medicine/24108/SPC/Gynest+0.01++w+w+Cream/

    4.2 Drug Warning

    Gynest Cream is not indicated during pregnancy. If pregnancy occurs during use of Gynest Cream, treatment should be withdrawn immediately.

    Datapharm Communications Ltd; Electronic Medicines Compendium (eMC), Summary of Product Characteristics (SPC) for Gynest 0.01% w/w Cream (Last updated June 2009). Available from, as of March 16, 2011: https://www.medicines.org.uk/EMC/medicine/24108/SPC/Gynest+0.01++w+w+Cream/

    Gynest Cream contains arachis oil (peanut oil) and should not be applied by patients known to be allergic to peanuts. As there is a possible relationship between allergy to peanuts and allergy to soya, patients with soya allergy should also avoid Gynest Cream.

    Datapharm Communications Ltd; Electronic Medicines Compendium (eMC), Summary of Product Characteristics (SPC) for Gynest 0.01% w/w Cream (Last updated June 2009). Available from, as of March 16, 2011: https://www.medicines.org.uk/EMC/medicine/24108/SPC/Gynest+0.01++w+w+Cream/

    Before initiating or re-instituting HRT, a complete personal and family medical history should be taken. Physical (including pelvic and breast) examination should be guided by this and by the contra-indications and warnings for use. During treatment, periodic check-ups are recommended of a frequency and nature adapted to the individual woman. Women should be advised what changes in their breasts should be reported to their doctor or nurse. Investigations, including mammography, should be carried out in accordance with currently accepted screening practices, modified to the clinical needs of the individual.

    Datapharm Communications Ltd; Electronic Medicines Compendium (eMC), Summary of Product Characteristics (SPC) for Gynest 0.01% w/w Cream (Last updated June 2009). Available from, as of March 16, 2011: https://www.medicines.org.uk/EMC/medicine/24108/SPC/Gynest+0.01++w+w+Cream/

    The risk of endometrial hyperplasia and carcinoma is increased when systemic estrogens are administered alone for prolonged periods of time. The endometrial safety of long-term or repeated use of topical vaginal estrogens is uncertain. Therefore, if repeated, treatment should be reviewed at least annually, with a special consideration given to any symptoms of endometrial hyperplasia or carcinoma.

    Datapharm Communications Ltd; Electronic Medicines Compendium (eMC), Summary of Product Characteristics (SPC) for Gynest 0.01% w/w Cream (Last updated June 2009). Available from, as of March 16, 2011: https://www.medicines.org.uk/EMC/medicine/24108/SPC/Gynest+0.01++w+w+Cream/

    For more Drug Warnings (Complete) data for ESTRIOL (40 total), please visit the HSDB record page.

    4.3 Drug Indication

    Used as a test to determine the general health of an unborn fetus.

    The treatment of hormone-dependent urinary incontinence due to sphincter mechanism incompetence in ovariohysterectomised bitches.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Estriol (also oestriol) is one of the three main estrogens produced by the human body. It is only produced in significant amounts during pregnancy as it is made by the placenta. In pregnant women with multiple sclerosis (MS), estriol reduces the disease's symptoms noticeably, according to researchers at UCLA's Geffen Medical School.

    5.2 ATC Code

    QG03CA04

    G03CA04

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    G - Genito urinary system and sex hormones

    G03 - Sex hormones and modulators of the genital system

    G03C - Estrogens

    G03CA - Natural and semisynthetic estrogens, plain

    G03CA04 - Estriol

    G - Genito urinary system and sex hormones

    G03 - Sex hormones and modulators of the genital system

    G03C - Estrogens

    G03CC - Estrogens, combinations with other drugs

    G03CC06 - Estriol

    5.3 Absorption, Distribution and Excretion

    Estriol is readily absorbed following intravaginal application. Peak serum estriol concentrations are generally observed within 2 hours following intravaginal application and remain elevated for 6 hours.

    Datapharm Communications Ltd; Electronic Medicines Compendium (eMC), Summary of Product Characteristics (SPC) for Gynest 0.01% w/w Cream (Last updated June 2009). Available from, as of March 16, 2011: https://www.medicines.org.uk/EMC/medicine/24108/SPC/Gynest+0.01++w+w+Cream/

    Systemic bioavailability on vaginal administration is better than after oral administration. Intravaginal application of 1 mg estriol in women with senile atrophy of the vaginal epithelium results in serum levels similar to those seen after oral administration of 10 mg estriol.

    Datapharm Communications Ltd; Electronic Medicines Compendium (eMC), Summary of Product Characteristics (SPC) for Gynest 0.01% w/w Cream (Last updated June 2009). Available from, as of March 16, 2011: https://www.medicines.org.uk/EMC/medicine/24108/SPC/Gynest+0.01++w+w+Cream/

    Plasma estriol levels increased from <90pmol/L (26 pg/mL) about fifty fold over a few hours after intravaginal administration of Gynest Cream. Eight to ten hours after administration, 50% of women still had estriol levels above 90pmol/L (26 pg/mL).

    Datapharm Communications Ltd; Electronic Medicines Compendium (eMC), Summary of Product Characteristics (SPC) for Gynest 0.01% w/w Cream (Last updated June 2009). Available from, as of March 16, 2011: https://www.medicines.org.uk/EMC/medicine/24108/SPC/Gynest+0.01++w+w+Cream/

    Estriol circulates with the blood, about 14% free, 8% bound to SHBG and the rest bound to albumin.

    Datapharm Communications Ltd; Electronic Medicines Compendium (eMC), Summary of Product Characteristics (SPC) for Gynest 0.01% w/w Cream (Last updated June 2009). Available from, as of March 16, 2011: https://www.medicines.org.uk/EMC/medicine/24108/SPC/Gynest+0.01++w+w+Cream/

    More than 95% of estriol is excreted in the urine, predominantly in the form of glucuronides.

    Datapharm Communications Ltd; Electronic Medicines Compendium (eMC), Summary of Product Characteristics (SPC) for Gynest 0.01% w/w Cream (Last updated June 2009). Available from, as of March 16, 2011: https://www.medicines.org.uk/EMC/medicine/24108/SPC/Gynest+0.01++w+w+Cream/

    5.4 Metabolism/Metabolites

    Primary metabolites of estriol include the 16-alpha-glucuronide, 3-glucuronide, 3-sulfate and 3-sulfate 16-alpha-glucuronide.

    Datapharm Communications Ltd; Electronic Medicines Compendium (eMC), Summary of Product Characteristics (SPC) for Gynest 0.01% w/w Cream (Last updated June 2009). Available from, as of March 16, 2011: https://www.medicines.org.uk/EMC/medicine/24108/SPC/Gynest+0.01++w+w+Cream/

    The metabolic disposition of estrogens includes oxidative metabolism (largely hydroxylation) and conjugative metabolism by glucuronidation, sulfonation and/or O-methylation. Estradiol is converted to estrone by a 17beta-hydroxysteroid dehydrogenase; the estrone produced is further metabolized to 16alpha-hydroxyoestrone and then to estriol.

    IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V91 145 (2007)

    Estriol is a common metabolite of estrone and estradiol-17-beta in animals and in humans. Estriol is excreted in humans as conjugated and unconjugated 2-hydroxy estriol after 2-hydroxylation.

    IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V21 336 (1979)

    5.5 Mechanism of Action

    Estriol levels can be measured to give an indication of the general health of the fetus. DHEA-S is produced by the adrenal cortex of the fetus. This is converted to estriol by the placenta. If levels of "unconjugated estriol" are abnormally low in a pregnant woman, this may indicate a problem with the development of the child. The drug 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 estriol 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.

    ... Synthetic estriol, is chemically and biologically identical to endogenous human estriol. Estriol, a weak estrogen, is a natural metabolite of estradiol, the predominant estrogen. Estriol exerts estrogenicity by binding to estrogen receptors, present in the female genital tract. Estriol, oral or vaginal, similar to estradiol, corrects lowered proliferation and abnormal physiology in the atrophic vaginal epithelium seen in estrogen deficient states, such as after natural or surgical menopause. In contrast, the histology of the endometrium after using Gynest Cream rarely shows minor signs of proliferation in previously atrophic endometria.

    Datapharm Communications Ltd; Electronic Medicines Compendium (eMC), Summary of Product Characteristics (SPC) for Gynest 0.01% w/w Cream (Last updated June 2009). Available from, as of March 16, 2011: https://www.medicines.org.uk/EMC/medicine/24108/SPC/Gynest+0.01++w+w+Cream/

    Estrogens have an important role in the reproductive, skeletal, cardiovascular, and central nervous systems in women, and act principally by regulating gene expression. Biologic response is initiated when estrogen binds to a ligand-binding domain of the estrogen receptor resulting in a conformational change that leads to gene transcription through specific estrogen response elements (ERE) of target gene promoters; subsequent activation or repression of the target gene is mediated through 2 distinct transactivation domains (ie, AF-1 and AF-2) of the receptor. The estrogen receptor also mediates gene transcription using different response elements (ie, AP-1) and other signal pathways. Recent advances in the molecular pharmacology of estrogen and estrogen receptors have resulted in the development of selective estrogen receptor modulators (eg, clomiphene, raloxifene, tamoxifen, toremifene), agents that bind and activate the estrogen receptor but that exhibit tissue-specific effects distinct from estrogen. Tissue-specific estrogen-agonist or -antagonist activity of these drugs appears to be related to structural differences in their estrogen receptor complex (eg, specifically the surface topography of AF-2 for raloxifene) compared with the estrogen (estradiol)-estrogen receptor complex. A second estrogen receptor also has been identified, and existence of at least 2 estrogen receptors (ER-alpha, ER-beta) may contribute to the tissue-specific activity of selective modulators. While the role of the estrogen receptor in bone, cardiovascular tissue, and the CNS continues to be studied, emerging evidence indicates that the mechanism of action of estrogen receptors in these tissues differs from the manner in which estrogen receptors function in reproductive tissue. /Estrogen General Statement/

    American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 3130

    Intracellular cytosol-binding proteins for estrogens have been identified in estrogen-responsive tissues including the female genital organs, breasts, pituitary, and hypothalamus. The estrogen-binding protein complex (ie, cytosol-binding protein and estrogen) distributes into the cell nucleus where it stimulates DNA, RNA, and protein synthesis. The presence of these receptor proteins is responsible for the palliative response to estrogen therapy in women with metastatic carcinoma of the breast. /Estrogen General Statement/

    American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 3130

    Estrogens have generally favorable effects on blood cholesterol and phospholipid concentrations. Estrogens reduce LDL-cholesterol and increase HDL-cholesterol concentrations in a dose-related manner. The decrease in LDL-cholesterol concentrations associated with estrogen therapy appears to result from increased LDL catabolism, while the increase in triglyceride concentrations is caused by increased production of large, triglyceride-rich, very-low-density lipoproteins (VLDLs); changes in serum HDL-cholesterol concentrations appear to result principally from an increase in the cholesterol and apolipoprotein A-1 content of HDL2- and a slight increase in HDL3-cholesterol. /Estrogen General Statement/

    American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 3130

    For more Mechanism of Action (Complete) data for ESTRIOL (12 total), please visit the HSDB record page.

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    04-Feb-2021
    11-Jul-2022
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