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    Chemistry

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    Also known as: 979-32-8, Estradiol 17-valerate, Delestrogen, Estradiol valerianate, Oestradiol valerate, Estraval
    Molecular Formula
    C23H32O3
    Molecular Weight
    356.5  g/mol
    InChI Key
    RSEPBGGWRJCQGY-RBRWEJTLSA-N
    FDA UNII
    OKG364O896
    Estradiol Valerate
    The 17-beta-isomer of estradiol, an aromatized C18 steroid with hydroxyl group at 3-beta- and 17-beta-position. Estradiol-17-beta is the most potent form of mammalian estrogenic steroids.
    1 2D Structure

    Estradiol Valerate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(8R,9S,13S,14S,17S)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] pentanoate
    2.1.2 InChI
    InChI=1S/C23H32O3/c1-3-4-5-22(25)26-21-11-10-20-19-8-6-15-14-16(24)7-9-17(15)18(19)12-13-23(20,21)2/h7,9,14,18-21,24H,3-6,8,10-13H2,1-2H3/t18-,19-,20+,21+,23+/m1/s1
    2.1.3 InChI Key
    RSEPBGGWRJCQGY-RBRWEJTLSA-N
    2.1.4 Canonical SMILES
    CCCCC(=O)OC1CCC2C1(CCC3C2CCC4=C3C=CC(=C4)O)C
    2.1.5 Isomeric SMILES
    CCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=C3C=CC(=C4)O)C
    2.2 Other Identifiers
    2.2.1 UNII
    OKG364O896
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 17 Beta Estradiol

    2. 17 Beta Oestradiol

    3. 17 Beta-estradiol

    4. 17 Beta-oestradiol

    5. Aerodiol

    6. Delestrogen

    7. Estrace

    8. Estraderm Tts

    9. Estradiol

    10. Estradiol 17 Alpha

    11. Estradiol 17 Beta

    12. Estradiol 17beta

    13. Estradiol Anhydrous

    14. Estradiol Hemihydrate

    15. Estradiol Hemihydrate, (17 Alpha)-isomer

    16. Estradiol Monohydrate

    17. Estradiol Valeriante

    18. Estradiol, (+-)-isomer

    19. Estradiol, (-)-isomer

    20. Estradiol, (16 Alpha,17 Alpha)-isomer

    21. Estradiol, (16 Alpha,17 Beta)-isomer

    22. Estradiol, (17-alpha)-isomer

    23. Estradiol, (8 Alpha,17 Beta)-(+-)-isomer

    24. Estradiol, (8 Alpha,17 Beta)-isomer

    25. Estradiol, (9 Beta,17 Alpha)-isomer

    26. Estradiol, (9 Beta,17 Beta)-isomer

    27. Estradiol, Monosodium Salt

    28. Estradiol, Sodium Salt

    29. Estradiol-17 Alpha

    30. Estradiol-17 Beta

    31. Estradiol-17beta

    32. Oestradiol

    33. Ovocyclin

    34. Progynon Depot

    35. Progynon-depot

    36. Progynova

    37. Vivelle

    2.3.2 Depositor-Supplied Synonyms

    1. 979-32-8

    2. Estradiol 17-valerate

    3. Delestrogen

    4. Estradiol Valerianate

    5. Oestradiol Valerate

    6. Estraval

    7. Neofollin

    8. Progynova

    9. Femogex

    10. Progynon-depot

    11. Atladiol

    12. Climaval

    13. Deladiol

    14. Duratrad

    15. Estate

    16. Dura-estradiol

    17. Exten Strone

    18. Depo Estro Med

    19. Repo-estra

    20. Delestrogen 4x

    21. Estraval Pa

    22. Estraval 2x

    23. Estroval-10

    24. Delahormone Unimatic

    25. Pelanin

    26. Depo-estro-med

    27. Femogen-l.a.

    28. Gynogen L.a. 20

    29. Gynogen L.a. 40

    30. Deladumone

    31. Estradiol, 17-valerate

    32. Nsc-17590

    33. Component Of Ditate

    34. 17-beta-estradiol 17-valerate

    35. B-estradiol 17-valerate

    36. Component Of Deluteval 2x

    37. Estradiol 17.beta.-valerate

    38. Component Of Mal-o-fem L.a

    39. .beta.-estradiol 17-valerate

    40. Mls000028449

    41. Chebi:31561

    42. Okg364o896

    43. 3-hydroxy-17beta-valeroyloxyestra-1,3,5(10)-trien

    44. [(8r,9s,13s,14s,17s)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] Pentanoate

    45. Cyclocur

    46. Gynokadin

    47. Merimono

    48. Nuvelle

    49. Postoval

    50. Primogyna

    51. Ronfase

    52. Smr000058346

    53. Estradiol Depot

    54. Primogyn-depot

    55. Beta-estradiol 17-valerate

    56. 17-pentanoyl-estra-1,3,5(10)-triene-3,17beta-diol

    57. Gynogen L.a. 10

    58. (17beta)-3-hydroxyestra-1,3,5(10)-trien-17-yl Valerate

    59. Valergen

    60. Estradiol 17beta-valerate

    61. Estradiol Valerate (van)

    62. Mfcd00056541

    63. Estradioli Valeras

    64. Valerate D'estradiol

    65. Ccris 5571

    66. Valerato De Estradiol

    67. Estradioli Valeras [inn-latin]

    68. Oestradiol-17b-valerate

    69. Valerate D'estradiol [inn-french]

    70. Einecs 213-559-2

    71. Nsc 17590

    72. Valerato De Estradiol [inn-spanish]

    73. Altadiol

    74. Pelanin Depot

    75. Unii-okg364o896

    76. Estradiol-valerate

    77. Gynogen La

    78. Deladumone (tn)

    79. Ncgc00094673-01

    80. (8r,9s,13s,14s,17s)-3-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6h-cyclopenta[a]phenanthren-17-yl Pentanoate

    81. 3-hydroxy-17beta-valeroyloxyestra-1,3,5(10)-triene

    82. Gynogen L.a.10

    83. Estradiol Valerate [usp:inn:ban:jan]

    84. St075188

    85. Estradiol Valerate Icrs

    86. Opera_id_444

    87. Estradiol 17?-valerate

    88. Dsstox_cid_3004

    89. Chembl1511

    90. Dsstox_rid_76827

    91. Dsstox_gsid_23004

    92. Schembl40563

    93. Mls001146931

    94. Gtpl7655

    95. Dtxsid8023004

    96. Estradiol Valerate [inn]

    97. Estradiol Valerate [jan]

    98. Estradiol Valerate [vandf]

    99. Hms2232l17

    100. Hms3259c12

    101. Hms3715b21

    102. Estradiol Valerate [mart.]

    103. Bcp11918

    104. Estra-1,3,5(10)-triene-3,17-diol (17-beta)-, 17-pentanoate

    105. Estra-1,3,5(10)-triene-3,17-diol(17beta)-, 17-pentanoate

    106. Estradiol Valerate (jan/usp/inn)

    107. Estradiol Valerate [usp-rs]

    108. Estradiol Valerate [who-dd]

    109. Hy-b0672

    110. Nsc17590

    111. Zinc3881556

    112. Estradiol 17-valerate [mi]

    113. Tox21_111312

    114. Estra-1,3,5(10)-triene-3,17-diol (17.beta.)-, 17-pentanoate

    115. Lmst02010039

    116. S3149

    117. Akos005267158

    118. Estradiol-17-valerate; 1,3,5(10)-estratriene-3,17b-diol 17-pentanote

    119. Ccg-221130

    120. Db13956

    121. Estradiol Valerate [green Book]

    122. Fd12049

    123. Ks-5213

    124. Nc00560

    125. Estradiol Valerate [orange Book]

    126. Estradiol Valerate [ep Monograph]

    127. Estradiol Valerate For System Suitability

    128. Ncgc00018166-02

    129. Ncgc00018166-14

    130. (1s,11s,14s,15s,10r)-5-hydroxy-15-methyltetracyclo[8.7.0.0<2,7>.0<11,15>]hepta Deca-2,4,6-trien-14-yl Pentanoate

    131. Cas-979-32-8

    132. Cpd000058346

    133. Estradiol Valerate [usp Monograph]

    134. B1506

    135. Ditate-ds Component Estradiol Valerate

    136. E0876

    137. D01413

    138. Ab00382980_15

    139. Estradiol Valerate Component Of Ditate-ds

    140. 979e328

    141. A845765

    142. Sr-01000003061

    143. Q-201506

    144. Q5401768

    145. Sr-01000003061-3

    146. 1,3,5(10)-estratrien-3,17beta-diol 17-valerate

    147. Brd-k66766661-001-19-2

    148. (17.beta.)-estra-1,3,5(10)-triene-3,17-diol 17-valerate

    149. (17beta)-3-hydroxyestra-1(10),2,4-trien-17-yl Pentanoate

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

    151. Estra-1,3,5(10)-triene-3,17-diol(17.beta.)-, 17-pentanoate

    152. [(13s,17s)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] Pentanoate

    153. [(8r,9s,13s,14s,17s)-13-methyl-3-oxidanyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] Pentanoate

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

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 356.5 g/mol
    Molecular Formula C23H32O3
    XLogP36
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count5
    Exact Mass356.23514488 g/mol
    Monoisotopic Mass356.23514488 g/mol
    Topological Polar Surface Area46.5 Ų
    Heavy Atom Count26
    Formal Charge0
    Complexity518
    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 Information
    1 of 4  
    Drug NameDelestrogen
    PubMed HealthEstradiol (Injection)
    Drug ClassesEndocrine-Metabolic Agent, Musculoskeletal Agent
    Drug LabelDELESTROGEN (estradiol valerate injection, USP) contains estradiol valerate, a long-acting estrogen in sterile oil solutions for intramuscular use. These solutions are clear, colorless to pale yellow. Formulations (per mL): 10 mg estradiol valerate...
    Active IngredientEstradiol valerate
    Dosage FormInjectable
    RouteInjection
    Strength20mg/ml; 40mg/ml; 10mg/ml
    Market StatusPrescription
    CompanyPar Sterile Products

    2 of 4  
    Drug NameEstradiol valerate
    Drug LabelEstradiol valerate injection, USP contains estradiol valerate, a long-acting estrogen in sterile oil solutions for intramuscular use. These solutions are clear, colorless to pale yellow. Formulations (per mL): 10 mg estradiol valerate in a vehicle co...
    Active IngredientEstradiol valerate
    Dosage FormInjectable
    RouteInjection
    Strength20mg/ml; 40mg/ml; 10mg/ml
    Market StatusPrescription
    CompanyLuitpold; Sandoz

    3 of 4  
    Drug NameDelestrogen
    PubMed HealthEstradiol (Injection)
    Drug ClassesEndocrine-Metabolic Agent, Musculoskeletal Agent
    Drug LabelDELESTROGEN (estradiol valerate injection, USP) contains estradiol valerate, a long-acting estrogen in sterile oil solutions for intramuscular use. These solutions are clear, colorless to pale yellow. Formulations (per mL): 10 mg estradiol valerate...
    Active IngredientEstradiol valerate
    Dosage FormInjectable
    RouteInjection
    Strength20mg/ml; 40mg/ml; 10mg/ml
    Market StatusPrescription
    CompanyPar Sterile Products

    4 of 4  
    Drug NameEstradiol valerate
    Drug LabelEstradiol valerate injection, USP contains estradiol valerate, a long-acting estrogen in sterile oil solutions for intramuscular use. These solutions are clear, colorless to pale yellow. Formulations (per mL): 10 mg estradiol valerate in a vehicle co...
    Active IngredientEstradiol valerate
    Dosage FormInjectable
    RouteInjection
    Strength20mg/ml; 40mg/ml; 10mg/ml
    Market StatusPrescription
    CompanyLuitpold; Sandoz

    4.2 Drug Indication

    Estradiol valerate is commercially available as an intramuscular injection as the product Delestrogen and is indicated for the treatment of moderate to severe vasomotor symptoms and vulvovaginal atrophy due to menopause, for the treatment of hypoestrogenism due to hypogonadism, castration or primary ovarian failure, and for the treatment of advanced androgen-dependent carcinoma of the prostate (for palliation only). Estradiol valerate is also available in combination with [DB09123] as the commercially available product Natazia used for the prevention of pregnancy and for the treatment of heavy menstrual bleeding.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Estrogen mediates its effects across the body through potent agonism of the Estrogen Receptor (ER), which is located in various tissues including in the breasts, uterus, ovaries, skin, prostate, bone, fat, and brain. Estradiol binds to both subtypes of the Estrogen Receptor: Estrogen Receptor Alpha (ER) and Estrogen Receptor Beta (ER). Estradiol also acts as a potent agonist of G Protein-coupled Estrogen Receptor (GPER), which has recently been recognized as a major mediator of estradiol's rapid cellular effects.

    5.2 MeSH Pharmacological Classification

    Estrogens

    Compounds that interact with ESTROGEN RECEPTORS in target tissues to bring about the effects similar to those of ESTRADIOL. Estrogens stimulate the female reproductive organs, and the development of secondary female SEX CHARACTERISTICS. Estrogenic chemicals include natural, synthetic, steroidal, or non-steroidal compounds. (See all compounds classified as Estrogens.)

    5.3 FDA Pharmacological Classification
    5.3.1 Pharmacological Classes
    Estrogen Receptor Agonists [MoA]; Estrogen [EPC]; Estradiol Congeners [CS]
    5.4 Absorption, Distribution and Excretion

    Absorption

    IM Injection: When conjugated with aryl and alkyl groups for parenteral administration, the rate of absorption of oily preparations is slowed with a prolonged duration of action, such that a single intramuscular injection of estradiol valerate or estradiol cypionate is absorbed over several weeks. Natazia: After oral administration of estradiol valerate, cleavage to 17-estradiol and valeric acid takes place during absorption by the intestinal mucosa or in the course of the first liver passage. This gives rise to estradiol and its metabolites, estrone and other metabolites. Maximum serum estradiol concentrations of 73.3 pg/mL are reached at a median of approximately 6 hours (range: 1.512 hours) and the area under the estradiol concentration curve [AUC(024h)] was 1301 pgh/mL after single ingestion of a tablet containing 3 mg estradiol valerate under fasted condition on Day 1 of the 28-day sequential regimen.

    Route of Elimination

    Estradiol, estrone and estriol are excreted in the urine along with glucuronide and sulfate conjugates.

    5.5 Metabolism/Metabolites

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

    5.6 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. Increases in the down-stream effects of ER binding reverses some of the symptoms of menopause, which are primarily caused by a loss of estrogenic activity.

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    27-Jan-2021
    16-Aug-2024
    KGS
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    Average Price (USD/KGS)

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    (USD/KGS)    		 Number of Transactions

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