Ethinyl Estradiol

• CAT Number: A000604
• CAS Number: 57-63-6
• Molecular Formula: C20H24O2
• Molecular Weight: 296.4
• Purity: ≥95%
• Target: Estrogen/progestogen Receptor
• Solubility: >8.7mg/mL in DMSO
• Storage: -20°C
• InChI: 1S/C20H24O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,5,7,12,16-18,21-22H,4,6,8-11H2,2H3/t16-,17-,18+,19+,20+/m1/s1
• InChIKey: BFPYWIDHMRZLRN-SLHNCBLASA-N
• SMILES: CC12CCC3C(C1CCC2(C#C)O)CCC4=C3C=CC(=C4)O

Ethinyl Estradiol is a semisynthetic estrogen. The mechanism of action of ethinyl estradiol is as an Estrogen Receptor Agonist. It has high estrogenic potency when administered orally, and is often used as the estrogenic component in oral contraceptives. Ethinyl estradiol binds to the estrogen receptor complex and enters the nucleus, activating DNA transcription of genes involved in estrogenic cellular responses. This agent also inhibits 5-alpha reductase in epididymal tissue, which lowers testosterone levels and may delay progression of prostatic cancer. In addition to its antineoplastic effects, ethinyl estradiol protects against osteoporosis. In animal models, short-term therapy with this agent has been shown to provide long-term protection against breast cancer, mimicking the antitumor effects of pregnancy.

Reference

1: Catanese MC, Vandenberg LN. Developmental estrogen exposures and disruptions
to maternal behavior and brain: Effects of ethinyl estradiol, a common positive
control. Horm Behav. 2017 Nov 7. pii: S0018-506X(17)30330-6. doi:
10.1016/j.yhbeh.2017.10.013. [Epub ahead of print] PubMed PMID: 29107581.

2: Simmons KB, Kumar N, Plagianos M, Roberts K, Hoskin E, Han L, Alami M, Creasy
G, Variano B, Merkatz R. Effects of concurrent vaginal miconazole treatment on
the absorption and exposure of Nestorone® (segesterone acetate) and ethinyl
estradiol delivered from a contraceptive vaginal ring: A randomized, crossover
drug-drug interaction study. Contraception. 2017 Oct 30. pii:
S0010-7824(17)30498-5. doi: 10.1016/j.contraception.2017.10.010. [Epub ahead of
print] PubMed PMID: 29097225.

3: Nappi RE, Lobo Abascal P, Hsieh J, Micheletti MC. Cycle control with an
extended-regimen oral contraceptive combining levonorgestrel and ethinyl
estradiol that includes continuous low-dose ethinyl estradiol instead of the
traditional hormone-free interval. Int J Womens Health. 2017 Oct 5;9:739-747.
doi: 10.2147/IJWH.S142078. eCollection 2017. PubMed PMID: 29042818; PubMed
Central PMCID: PMC5633331.

4: LaPlante CD, Vandenberg LN. Data describing lack of effects of 17α-ethinyl
estradiol on mammary gland morphology in female mice exposed during pregnancy and
lactation. Data Brief. 2017 Jul 27;14:337-343. doi: 10.1016/j.dib.2017.07.062.
eCollection 2017 Oct. PubMed PMID: 28795111; PubMed Central PMCID: PMC5547231.

5: Zhu B, Nestorov I, Zhao G, Meka V, Leahy M, Kam J, Sheikh SI. Evaluation of
Potential Drug-Drug Interaction Between Delayed-Release Dimethyl Fumarate and a
Commonly Used Oral Contraceptive (Norgestimate/Ethinyl Estradiol) in Healthy
Women. Clin Pharmacol Drug Dev. 2017 Nov;6(6):604-613. doi: 10.1002/cpdd.377.
Epub 2017 Aug 7. PubMed PMID: 28783872.

6: Catanese MC, Vandenberg LN. Low doses of 17α-ethinyl estradiol alter the
maternal brain and induce stereotypies in CD-1 mice exposed during pregnancy and
lactation. Reprod Toxicol. 2017 Oct;73:20-29. doi:
10.1016/j.reprotox.2017.07.007. Epub 2017 Jul 21. PubMed PMID: 28736173.

7: Manshack LK, Conard CM, Johnson SA, Alex JM, Bryan SJ, Deem SL, Holliday DK,
Ellersieck MR, Rosenfeld CS. Corrigendum to /Effects of developmental exposure to
bisphenol A and ethinyl estradiol on spatial navigational learning and memory in
painted turtles (Chrysemys picta)/ [Horm. Behav. 85 (2016) 48-55]. Horm Behav.
2017 Jul;93:203. doi: 10.1016/j.yhbeh.2017.05.010. Epub 2017 May 25. PubMed PMID:
28551168.

8: Bitzer J, Römer T, Lopes da Silva Filho A. The use of cyproterone
acetate/ethinyl estradiol in hyperandrogenic skin symptoms – a review. Eur J
Contracept Reprod Health Care. 2017 Jun;22(3):172-182. doi:
10.1080/13625187.2017.1317339. Epub 2017 Apr 27. PubMed PMID: 28447864.

9: Gear RB, Belcher SM. Impacts of Bisphenol A and Ethinyl Estradiol on Male and
Female CD-1 Mouse Spleen. Sci Rep. 2017 Apr 12;7(1):856. doi:
10.1038/s41598-017-00961-8. PubMed PMID: 28404993; PubMed Central PMCID:
PMC5429804.

10: Saeedi Saravi SS, Arefidoust A, Saeedi Saravi SS, Yaftian R, Bayati M, Salehi
M, Dehpour AR. Mammalian target of rapamycin (mTOR)/nitric oxide system possibly
modulate antidepressant-like effect of 17α-ethinyl estradiol in ovariectomized
mice. Biomed Pharmacother. 2017 May;89:591-604. doi:
10.1016/j.biopha.2017.02.078. Epub 2017 Mar 1. PubMed PMID: 28259097.