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Estradiol Acetate

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3 API Suppliers, 1 USDMF, 1 NDC API, 2 Listed Suppliers

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5 FDF Dossiers, 5 FDA Orange Book

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INSERT, EXTENDED RELEASE;VAGINAL - EQ 0.05MG BASE/24HR, INSERT, EXTENDED RELEASE;VAGINAL - EQ 0.1MG BASE/24HR

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INSERT, EXTENDED RELEASE;VAGINAL - EQ 0.05MG BASE/24HR
INSERT, EXTENDED RELEASE;VAGINAL - EQ 0.1MG BASE/24HR

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1 SPI Pharma, 1 DKSH, 1 Gangwal Healthcare, 1 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd, 1 Gangwal Chemicals, 1 Sigachi Industries

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1 DKSH
1 Gangwal Healthcare
1 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd
1 Gangwal Chemicals
1 Sigachi Industries

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2 Lubricants & Glidants
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1 API Stability Enhancers
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ANALYTICAL

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1 BioAnalytical Methods

Symbiotec Estradiol Acetate

Synopsis

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Chemistry

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Also known as: Femring, Femtrace, Estradiol 3-acetate, Estradiol-3-acetate, 4245-41-4, Estradiol acetate [usan]

Molecular Formula

C₂₀H₂₆O₃

Molecular Weight

314.4 g/mol

InChI Key

FHXBMXJMKMWVRG-SLHNCBLASA-N

FDA UNII

5R97F5H93P

Estradiol Acetate is the acetate salt form of estradiol, the most potent, naturally produced estrogen. Estradiol acetate 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 Acetate

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] acetate

2.1.2 InChI

InChI=1S/C20H26O3/c1-12(21)23-14-4-6-15-13(11-14)3-5-17-16(15)9-10-20(2)18(17)7-8-19(20)22/h4,6,11,16-19,22H,3,5,7-10H2,1-2H3/t16-,17-,18+,19+,20+/m1/s1

2.1.3 InChI Key

FHXBMXJMKMWVRG-SLHNCBLASA-N

2.1.4 Canonical SMILES

CC(=O)OC1=CC2=C(C=C1)C3CCC4(C(C3CC2)CCC4O)C

2.1.5 Isomeric SMILES

CC(=O)OC1=CC2=C(C=C1)[C@H]3CC[C@]4([C@H]([C@@H]3CC2)CC[C@@H]4O)C

2.2 Other Identifiers

2.2.1 UNII

5R97F5H93P

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Femring

2. Femtrace

3. Estradiol 3-acetate

4. Estradiol-3-acetate

5. 4245-41-4

6. Estradiol Acetate [usan]

7. E3a

8. 5r97f5h93p

9. Estradiol Acetate (usan)

10. Dsstox_cid_25867

11. Dsstox_rid_81186

12. Dsstox_gsid_45867

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

14. Menoring

15. Cas-4245-41-4

16. 3-o-acetylestradiol

17. Estradiol, 3-acetate

18. 17beta-estradiol 3-acetate

19. Unii-5r97f5h93p

20. E 3a

21. Estradiol-acetate

22. Femring (tn)

23. 3-acetoxyestra-1,3,5(10)-trien-17beta-ol

24. 17beta-hydroxy-3-acetoxyestra-1,3,5(10)-triene

25. Schembl148561

26. Estra-1,3,5(10)-triene-3,17beta-diyl 3-acetate

27. Chembl1200430

28. Dtxsid7045867

29. Estradiol Acetate [vandf]

30. Chebi:135981

31. Estradiol 3-acetate [mi]

32. Estradiol Acetate [mart.]

33. Estradiol Acetate [who-dd]

34. Tox21_111359

35. Tox21_113661

36. Db13952

37. Estradiol Acetate [orange Book]

38. Ncgc00249885-01

39. D04061

40. 3-acetoxy-oestra-1,3,5(10)-trien-17beta-ol

41. 17beta-hydroxyestra-1,3,5(10)-trien-3-yl Acetate

42. 3-(acetyloxy)estra-1,3,5(10)-trien-17.beta.-ol

43. Q27262772

44. 17.beta.-hydroxyestra-1,3,5(10)-trien-3-yl Acetate

45. Estra-1,3,5(10)-triene-3,17-diol, (17beta)-, 3-acetate

46. Estra-1,3,5(10)-triene-3,17-diol, (17 Beta)-, 3-acetate

47. Estra-1,3,5(10)-triene-3,17-diol, (17.beta.)-, 3-acetate

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₂₆O₃
Molecular Weight	314.4 g/mol
XLogP3	2.8
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	2
Exact Mass	314.18819469 g/mol
Monoisotopic Mass	314.18819469 g/mol
Topological Polar Surface Area	46.5 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	476
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

Femring is indicated for the treatment of vasomotor and urogenital symptoms associated with menopause. Use of Femring (estradiol acetate) has been shown to improve symptoms caused by atrophy of the vagina (such as dryness, burning, pruritus and dyspareunia) and/or the lower urinary tract (urinary urgency and dysuria).

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 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Estrogen Receptor Agonists [MoA]; Estrogen [EPC]; Estradiol Congeners [CS]

5.3 Absorption, Distribution and Excretion

Absorption

Drug delivery from Femring is rapid for the first hour and then declines to a relatively constant rate for the remainder of the 3-month dosing interval. Estradiol acetate is rapidly hydrolyzed to estradiol which is absorbed through the vaginal mucosa as evidenced by the mean time to maximum concentration (tmax) for estradiol of about 1 hour (range 0.25 to 1.5 hrs). Following the maximum concentration (Cmax=1129pg/mL), serum estradiol decreases rapidly such that by 24 to 48 hours postdose, serum estradiol concentrations are relatively constant through the end of the 3-month dosing interval.

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.

5.4 Metabolism/Metabolites

Exogenous estrogens are metabolized using the same mechanism as endogenous estrogens. 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.

Estradiol acetate has known human metabolites that include 6-[(3-acetyloxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

5.5 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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