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Chemistry

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Also known as: 313-06-4, Depofemin, Depoestradiol, Depo-estradiol, Depoestra, Estradep
Molecular Formula
C26H36O3
Molecular Weight
396.6  g/mol
InChI Key
UOACKFBJUYNSLK-XRKIENNPSA-N
FDA UNII
7E1DV054LO

Estradiol Cypionate
Estradiol Cypionate is the cypionate salt form of estradiol, the most potent, naturally produced estrogen. Estradiol cypionate diffuses through the cell membrane and binds to and subsequently activates the nuclear estrogen receptor found in the reproductive tract, breast, pituitary, hypothalamus, liver, and bone. The activated complex binds to the estrogen response element on the DNA and activates the transcription of genes involved in the functioning of the female reproductive system and secondary sex characteristics.
1 2D Structure

Estradiol Cypionate

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] 3-cyclopentylpropanoate
2.1.2 InChI
InChI=1S/C26H36O3/c1-26-15-14-21-20-10-8-19(27)16-18(20)7-9-22(21)23(26)11-12-24(26)29-25(28)13-6-17-4-2-3-5-17/h8,10,16-17,21-24,27H,2-7,9,11-15H2,1H3/t21-,22-,23+,24+,26+/m1/s1
2.1.3 InChI Key
UOACKFBJUYNSLK-XRKIENNPSA-N
2.1.4 Canonical SMILES
CC12CCC3C(C1CCC2OC(=O)CCC4CCCC4)CCC5=C3C=CC(=C5)O
2.1.5 Isomeric SMILES
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC(=O)CCC4CCCC4)CCC5=C3C=CC(=C5)O
2.2 Other Identifiers
2.2.1 UNII
7E1DV054LO
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Depo-estradiol

2. Estradiol 17 Beta-cyclopentanepropionate

3. Estradiol 17 Beta-cyclopentylpropionate

4. Estradiol 17 Beta-cypionate

2.3.2 Depositor-Supplied Synonyms

1. 313-06-4

2. Depofemin

3. Depoestradiol

4. Depo-estradiol

5. Depoestra

6. Estradep

7. Estrapo

8. Estro-depo

9. Dep-estro

10. Femogen Cyp

11. Depgynogen

12. Depoestradiol Cypionate

13. Beta-estradiol 17-cypionate

14. Estradiol 17-cypionate

15. Estradiol Cyclopentylpropionate

16. Estradiol (cypionate)

17. E. Ionate P.a.

18. Estradiol 17-cyclopentylpropionate

19. Depo-estradiol Cyclopentylpropionate

20. Nsc 3354

21. Estradiol Cipionate

22. Estradiol, 17-cyclopentanepropionate

23. Cyclopentanepropionic Acid, 17-ester With Estradiol

24. Nsc-3354

25. Estradiol Cypionate [usp]

26. 17.beta.-estradiol Cypionate

27. Estradiol 17.beta.-cypionate

28. 7e1dv054lo

29. Chebi:34745

30. Nsc3354

31. Estra-1,3,5(10)-triene-3,17-diol(17b)-, 17-cyclopentanepropanoate

32. Estradiol 17beta-cyclopentylpropionate

33. 17.beta.-estradiol Cyclopentylpropionate

34. Estradiol 17.beta.-cyclopentylpropionate

35. 17.beta.-estradiol Cyclopentanepropionate

36. Estradiol 17.beta.-cyclopentanepropanoate

37. Estradiol 17.beta.-cyclopentanepropionate

38. Pertradiol

39. 17.beta.-estradiol 17-cyclopentylpropionate

40. Dsstox_cid_2999

41. Estradiol Cypionate (usp)

42. Neoginon Depositum

43. Dsstox_rid_76824

44. Dsstox_gsid_22999

45. Ecp (van)

46. Estradiol 17beta-cypionate

47. [(8r,9s,13s,14s,17s)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] 3-cyclopentylpropanoate

48. Cas-313-06-4

49. Smr000058700

50. Estradiol 17-cyclopentanepropionate

51. Einecs 206-237-8

52. Estradiol 17beta-cylopentylpropionate

53. Estradiol 17beta-cyclopentanepropionate

54. Brn 3171075

55. Unii-7e1dv054lo

56. Depestro

57. 17beta-estradiol 17-cyclopentylpropionate

58. Estra-1,3,5(10)-triene-3,17-diol (17.beta.)-, 17-cyclopentanepropanoate

59. Estradiol-cypionate

60. Ncgc00166134-01

61. Mfcd00056558

62. Depo-estradiol (tn)

63. Estradiol Cypionate Salt

64. Schembl41551

65. 4-09-00-00047 (beilstein Handbook Reference)

66. Mls000069763

67. Mls001074891

68. 17beta-estradiol 17-cypionate

69. Chembl1200973

70. Dtxsid4022999

71. Hms2234k11

72. Estradiol Cypionate [vandf]

73. (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 3-cyclopentylpropanoate

74. Bcp11930

75. Estradiol Cipionate [mart.]

76. Hy-b1100

77. Zinc3876078

78. Tox21_110003

79. Tox21_112331

80. Tox21_301818

81. Estra-1,3,5(10)-triene-3,17beta-diol 17-(cyclopentanepropionate)

82. Estradiol Cipionate [who-dd]

83. Estradiol Cypionate [usp-rs]

84. Estradioli Cypionas [who-ip]

85. S4046

86. (17beta)-3-hydroxyestra-1(10),2,4-trien-17-yl 3-cyclopentylpropanoate

87. Akos015895730

88. Cyclopentanepropionic Acid, 3-hydroxyestra-1,3,5(10)-trien-17beta-yl Ester

89. Estra-1,3,5(10)-triene-3,17-diol (17beta)-, 17-cyclopentanepropanoate

90. Estra-1,3,5(10)-triene-3,17-diol, (17beta)-, 17-cyclopentanepropanoate

91. Tox21_112331_1

92. .beta.-estradiol 17-cypionate

93. Beta-estradiol 17-cyclopentylpropionate

94. Ccg-268613

95. Cs-4691

96. Db13954

97. Ks-5296

98. Estradiol 17.beta.-cylopentylpropionate

99. Estradiol Cypionate [orange Book]

100. Ncgc00013034-01

101. Ncgc00166134-02

102. Ncgc00166134-03

103. Ncgc00255333-01

104. (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 3-cyclopentylpropanoate

105. Nci60_002938

106. Estradiol Cypionate [usp Monograph]

107. Estradiol-17-cyclopentanepropionate

108. Lunelle Component Estradiol Cypionate

109. E0875

110. D04063

111. Estradiol Cypionate Component Of Lunelle

112. 313d064

113. Depo-testadiol Component Estradiol Cypionate

114. Q5401760

115. W-106910

116. Estradiol 17.beta.-cyclopentanepropanoate [mi]

117. Estradiol Cypionate Component Of Depo-testadiol

118. (17?)-3-hydroxyestra-1,3,5(10)-trien-17-yl 3-cyclopentylpropanoate

119. 17.beta.-[(3-cyclopentylpropanoyl)oxy]estra-1,3,5(10)-trien-3-ol

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

121. Estra-1,5(10)-triene-3,17-diol, (17.beta.)-, 17-cyclopentanepropanoate

122. Estradiol Cypionate, United States Pharmacopeia (usp) Reference Standard

123. (17.beta.)-estra-1,3,5(10)-triene-3,17-diol 17.beta.-cyclopentanepropanoate

124. Cyclopentanepropionic Acid, 3-hydroxyestra-1,3,5(10)-trien-17.beta.-yl Ester

125. Estra-1,3,5(10)-triene-3,17-diol, (17.beta.)-, 17-cyclopentanepropanoate

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 396.6 g/mol
Molecular Formula C26H36O3
XLogP37.1
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count5
Exact Mass396.26644501 g/mol
Monoisotopic Mass396.26644501 g/mol
Topological Polar Surface Area46.5 Ų
Heavy Atom Count29
Formal Charge0
Complexity597
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

Depo-Estradiol intramuscular depot injection is indicated for the treatment of moderate to severe vasomotor symptoms and hypoestrogenism due to hypogonadism.


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

Contraceptive Agents, Hormonal

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


Contraceptive Agents, Female

Chemical substances or agents with contraceptive activity in females. Use for female contraceptive agents in general or for which there is no specific heading. (See all compounds classified as Contraceptive Agents, Female.)


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

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.


Route of Elimination

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


Volume of Distribution

The distribution of exogenous estrogens is similar to that of endogenous estrogens. Estrogens are widely distributed in the body and are generally found in higher concentrations in the sex hormone target organs.


5.5 Metabolism/Metabolites

Exogenous estrogens are metabolized in the same manner as endogenous estrogens. Circulating estrogens exist in a dynamic equilibrium of metabolic interconversions. These transformations take place mainly in the liver. Estradiol is converted reversibly to estrone, and both can be converted to estriol, which is the major urinary metabolite. Estrogens also undergo enterohepatic recirculation via sulfate and glucuronide conjugation in the liver, biliary secretion of conjugates into the intestine, and hydrolysis in the gut followed by reabsorption. In postmenopausal women, a significant proportion of the circulating estrogens exist as sulfate conjugates, especially estrone sulfate, which serves as a circulating reservoir for the formation of more active estrogens.


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 and of hypoestrogenism, which are primarily caused by a loss of estrogenic activity.


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03-May-2024
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