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MedKoo Cat#: 317795 | Name: Ethinyl Estradiol
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Ethinyl Estradiol
Ethinyl Estradiol
CAS#57-63-6 (ethinyl)

Theoretical Analysis

MedKoo Cat#: 317795

Name: Ethinyl Estradiol

CAS#: 57-63-6 (ethinyl)

Chemical Formula: C20H24O2

Exact Mass: 296.1776

Molecular Weight: 296.40

Elemental Analysis: C, 81.04; H, 8.16; O, 10.80

Price and Availability

Size Price Availability Quantity
1g USD 285.00 2 weeks
5g USD 650.00 2 weeks
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Related CAS #
50-28-2 50-50-0 (benzoate) 313-06-4 (cypionate) 113-38-2 (dipropionate) 172377-52-5 (sulfamate) 979-32-8 (valerate) 57-63-6 (ethinyl) 3571-53-7 (undecylate)
Synonym
Ethinyl Estradiol; Ethynylestradiol; Ethinyloestradiol; Ethynyl estradiol; ETHINYLESTRADIOL; Ginestrene; Microfollin Forte; Organon; Brand of Ethinyl Estradiol; Progynon C;
IUPAC/Chemical Name
(8R,9S,13S,14S,17R)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
InChi Key
BFPYWIDHMRZLRN-SLHNCBLASA-N
InChi Code
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
SMILES Code
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=C3C=CC(=C4)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Ethynyl Estradiol (17α-Ethynylestradiol;Ethynylestradiol) is an estrogen used in almost all modern formulations of combined oral contraceptive pills.
In vitro activity:
E and E-E2 (ethinyl-estradiol) inhibited the PAT1-mediated uptake of proline and taurine in Caco-2 cells with IC50 values of 10.0-50.0 μM without major effect on other solute carriers such as the taurine transporter (TauT), di/tri-peptide transporter (PEPT1), and serotonin transporter (SERT1). In PAT1-expressing oocytes E and E-E2 were non-translocated inhibitors. In Caco-2 cells, E and E-E2 lowered the maximal uptake capacity of PAT1 in a non-competitive manner. Likewise, the transepithelial permeability of proline and taurine was reduced in presence of E and E-E2. Reference: J Pharm Sci. 2021 Jan;110(1):354-364. https://pubmed.ncbi.nlm.nih.gov/32835702/
In vivo activity:
A rat trauma-hemorrhage model, consisting of a midline laparotomy and controlled bleeding (60% blood loss) without fluid resuscitation, was used. The EES IC50 value was 1.52 × 10-8 Mol/L, consistent with pharmacologic efficacy. Ethinyl estradiol sulfate raised mean arterial pressure and ±derivative of pressure over time (dP/dT) significantly (but did not fully restore) within a 30-minute window. Levels of apoptosis and activation of NF-κB were dramatically reduced, as was elaboration of nitric oxide (NO) by inducible nitric oxide synthase. Phospho-endothelial nitric oxide synthase (eNOS) was restored to physiological levels. The restoration of cellular signaling occurs before restoration of cardiac contractility. Reference: J Trauma Acute Care Surg. 2021 Feb 1;90(2):353-359. https://pubmed.ncbi.nlm.nih.gov/33048911/
Solvent mg/mL mM
Solubility
DMF 20.0 67.48
Ethanol 44.5 150.13
Ethanol:PBS (pH 7.2) (1:7) 0.1 0.42
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 296.40 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Nielsen CU, Pedersen M, Müller S, Kæstel T, Bjerg M, Ulaganathan N, Nielsen S, Carlsen KL, Nøhr MK, Holm R. Inhibitory Effects of 17-α-Ethinyl-Estradiol and 17-β-Estradiol on Transport Via the Intestinal Proton-Coupled Amino Acid Transporter (PAT1) Investigated In Vitro and In Vivo. J Pharm Sci. 2021 Jan;110(1):354-364. doi: 10.1016/j.xphs.2020.08.010. Epub 2020 Aug 21. PMID: 32835702. 2. Chang SY, Chen C, Yang Z, Rodrigues AD. Further assessment of 17alpha-ethinyl estradiol as an inhibitor of different human cytochrome P450 forms in vitro. Drug Metab Dispos. 2009 Aug;37(8):1667-75. doi: 10.1124/dmd.109.026997. Epub 2009 May 19. PMID: 19454483. 3. Hubbard WJ, Yang S, Chaudry IH. Ethinyl estradiol sulfate acts without fluid resuscitation through estrogen receptors to rapidly protect the cardiovascular system from severe hemorrhage. J Trauma Acute Care Surg. 2021 Feb 1;90(2):353-359. doi: 10.1097/TA.0000000000002978. PMID: 33048911. 4. Edwards MR, Dai R, Heid B, Cowan C, Werre SR, Cecere T, Ahmed SA. Low-dose 17α-ethinyl estradiol (EE) exposure exacerbates lupus renal disease and modulates immune responses to TLR7/9 agonists in genetically autoimmune-prone mice. Sci Rep. 2020 Mar 23;10(1):5210. doi: 10.1038/s41598-020-62124-6. PMID: 32251357; PMCID: PMC7090002.
In vitro protocol:
1. Nielsen CU, Pedersen M, Müller S, Kæstel T, Bjerg M, Ulaganathan N, Nielsen S, Carlsen KL, Nøhr MK, Holm R. Inhibitory Effects of 17-α-Ethinyl-Estradiol and 17-β-Estradiol on Transport Via the Intestinal Proton-Coupled Amino Acid Transporter (PAT1) Investigated In Vitro and In Vivo. J Pharm Sci. 2021 Jan;110(1):354-364. doi: 10.1016/j.xphs.2020.08.010. Epub 2020 Aug 21. PMID: 32835702. 2. Chang SY, Chen C, Yang Z, Rodrigues AD. Further assessment of 17alpha-ethinyl estradiol as an inhibitor of different human cytochrome P450 forms in vitro. Drug Metab Dispos. 2009 Aug;37(8):1667-75. doi: 10.1124/dmd.109.026997. Epub 2009 May 19. PMID: 19454483.
In vivo protocol:
1. Hubbard WJ, Yang S, Chaudry IH. Ethinyl estradiol sulfate acts without fluid resuscitation through estrogen receptors to rapidly protect the cardiovascular system from severe hemorrhage. J Trauma Acute Care Surg. 2021 Feb 1;90(2):353-359. doi: 10.1097/TA.0000000000002978. PMID: 33048911. 2. Edwards MR, Dai R, Heid B, Cowan C, Werre SR, Cecere T, Ahmed SA. Low-dose 17α-ethinyl estradiol (EE) exposure exacerbates lupus renal disease and modulates immune responses to TLR7/9 agonists in genetically autoimmune-prone mice. Sci Rep. 2020 Mar 23;10(1):5210. doi: 10.1038/s41598-020-62124-6. PMID: 32251357; PMCID: PMC7090002.
1: Shiga T, Nakamura TJ, Komine C, Goto Y, Mizoguchi Y, Yoshida M, Kondo Y, Kawaguchi M. A Single Neonatal Injection of Ethinyl Estradiol Impairs Passive Avoidance Learning and Reduces Expression of Estrogen Receptor α in the Hippocampus and Cortex of Adult Female Rats. PLoS One. 2016 Jan 7;11(1):e0146136. doi: 10.1371/journal.pone.0146136. eCollection 2016. PubMed PMID: 26741502; PubMed Central PMCID: PMC4712149. 2: Archer DF, Thomas MA, Conard J, Merkatz RB, Creasy GW, Roberts K, Plagianos M, Blithe D, Sitruk-Ware R. Impact on hepatic estrogen-sensitive proteins by a 1-year contraceptive vaginal ring delivering Nestorone® and ethinyl estradiol. Contraception. 2016 Jan;93(1):58-64. doi: 10.1016/j.contraception.2015.09.008. Epub 2015 Sep 25. PubMed PMID: 26408374. 3: Lobo Abascal P, Luzar-Stiffler V, Giljanovic S, Howard B, Weiss H, Trussell J. Differences in reporting Pearl Indices in the United States and Europe: Focus on a 91-day extended-regimen combined oral contraceptive with low-dose ethinyl estradiol supplementation. Eur J Contracept Reprod Health Care. 2016 Feb;21(1):88-91. doi: 10.3109/13625187.2015.1059416. Epub 2015 Jun 26. PubMed PMID: 26115381. 4: Waellnitz K, Duijkers I, Klipping C, Rautenberg T, Rohde B, Zurth C. A two-centre, open-label, randomised study of ovulation inhibition with three transdermal contraceptive patches, each containing different amounts of ethinyl estradiol and gestodene in healthy, young women. J Obstet Gynaecol. 2016 Jan;36(1):106-13. doi: 10.3109/01443615.2015.1041882. Epub 2015 Sep 30. PubMed PMID: 26421957. 5: Patel G, King A, Dutta S, Korb S, Wade JR, Foulds P, Sumeray M. Evaluation of the effects of the weak CYP3A inhibitors atorvastatin and ethinyl estradiol/norgestimate on lomitapide pharmacokinetics in healthy subjects. J Clin Pharmacol. 2016 Jan;56(1):47-55. doi: 10.1002/jcph.581. Epub 2015 Sep 10. PubMed PMID: 26120010. 6: Johnson SA, Painter MS, Javurek AB, Ellersieck MR, Wiedmeyer CE, Thyfault JP, Rosenfeld CS. Sex-dependent effects of developmental exposure to bisphenol A and ethinyl estradiol on metabolic parameters and voluntary physical activity. J Dev Orig Health Dis. 2015 Dec;6(6):539-52. doi: 10.1017/S2040174415001488. Epub 2015 Sep 18. PubMed PMID: 26378919. 7: Simone J, Bogue EA, Bhatti DL, Day LE, Farr NA, Grossman AM, Holmes PV. Ethinyl estradiol and levonorgestrel alter cognition and anxiety in rats concurrent with a decrease in tyrosine hydroxylase expression in the locus coeruleus and brain-derived neurotrophic factor expression in the hippocampus. Psychoneuroendocrinology. 2015 Dec;62:265-78. doi: 10.1016/j.psyneuen.2015.08.015. Epub 2015 Aug 28. PubMed PMID: 26352480. 8: Kendziorski JA, Belcher SM. Effects of whole life exposure to Bisphenol A or 17α-ethinyl estradiol in uterus of nulligravida CD1 mice. Data Brief. 2015 Nov 3;5:948-53. doi: 10.1016/j.dib.2015.10.034. eCollection 2015 Dec. PubMed PMID: 26702426; PubMed Central PMCID: PMC4669472. 9: Winkler J, Goldammer M, Ludwig M, Rohde B, Zurth C. Pharmacokinetic drug-drug interaction between ethinyl estradiol and gestodene, administered as a transdermal fertility control patch, and two CYP3A4 inhibitors and a CYP3A4 substrate. Eur J Drug Metab Pharmacokinet. 2015 Dec;40(4):389-99. doi: 10.1007/s13318-014-0215-8. Epub 2014 Jul 6. PubMed PMID: 24997757. 10: Jourabchi N, Rhee SM, Lazarus GS. Pre-menstrual flares of pyoderma gangrenosum controlled with use of a combined oral contraceptive and antiandrogen (Ethinyl Estradiol/Drospirenone). Br J Dermatol. 2015 Nov 30. doi: 10.1111/bjd.14332. [Epub ahead of print] PubMed PMID: 26616160. 11: Moini A, Ahmadi F, Jahangiri N, Ahmadi J, Akhoond MR. A randomized controlled trial evaluating the effect of ethinyl estradiol during clomiphene citrate cycles among women with polycystic ovary syndrome. Int J Gynaecol Obstet. 2015 Nov;131(2):129-32. doi: 10.1016/j.ijgo.2015.06.032. Epub 2015 Sep 8. PubMed PMID: 26391671. 12: Mhao NS, Al-Hilli AS, Hadi NR, Jamil DA, Al-Aubaidy HA. A comparative study to illustrate the benefits of using ethinyl estradiol-cyproterone acetate over metformin in patients with polycystic ovarian syndrome. Diabetes Metab Syndr. 2015 Nov 12. pii: S1871-4021(15)30051-5. doi: 10.1016/j.dsx.2015.10.001. [Epub ahead of print] PubMed PMID: 26703220. 13: Bhattacharya SM, Jha A, DasMukhopadhyay L. Comparison of two contraceptive pills containing drospirenone and 20μg or 30μg ethinyl estradiol for polycystic ovary syndrome. Int J Gynaecol Obstet. 2015 Nov 6. pii: S0020-7292(15)00651-7. doi: 10.1016/j.ijgo.2015.06.065. [Epub ahead of print] PubMed PMID: 26613823. 14: Volkova K, Reyhanian Caspillo N, Porseryd T, Hallgren S, Dinnetz P, Olsén H, Porsch Hällström I. Transgenerational effects of 17α-ethinyl estradiol on anxiety behavior in the guppy, Poecilia reticulata. Gen Comp Endocrinol. 2015 Nov 1;223:66-72. doi: 10.1016/j.ygcen.2015.09.027. Epub 2015 Sep 30. PubMed PMID: 26431611. 15: Kriszt R, Winkler Z, Polyák Á, Kuti D, Molnár C, Hrabovszky E, Kalló I, Szőke Z, Ferenczi S, Kovács KJ. Xenoestrogens Ethinyl Estradiol and Zearalenone Cause Precocious Puberty in Female Rats via Central Kisspeptin Signaling. Endocrinology. 2015 Nov;156(11):3996-4007. doi: 10.1210/en.2015-1330. Epub 2015 Aug 6. PubMed PMID: 26248220. 16: Kroll R, Ackerman R, Feldman R, Howard B, Weiss H, Hsieh J, Ricciotti N. Efficacy and safety of a 21/7-active combined oral contraceptive with continuous low-dose ethinyl estradiol. Contraception. 2015 Oct 20. pii: S0010-7824(15)00623-X. doi: 10.1016/j.contraception.2015.10.007. [Epub ahead of print] PubMed PMID: 26499407. 17: Grandi G, Napolitano A, Xholli A, Tirelli A, Di Carlo C, Cagnacci A. Effect of oral contraceptives containing estradiol and nomegestrol acetate or ethinyl-estradiol and chlormadinone acetate on primary dysmenorrhea. Gynecol Endocrinol. 2015 Oct;31(10):774-8. doi: 10.3109/09513590.2015.1063118. Epub 2015 Aug 17. PubMed PMID: 26291811. 18: Al-Jefout M, Nawaiseh N. Continuous Norethisterone Acetate versus Cyclical Drospirenone 3 mg/Ethinyl Estradiol 20 μg for the Management of Primary Dysmenorrhea in Young Adult Women. J Pediatr Adolesc Gynecol. 2015 Sep 3. pii: S1083-3188(15)00310-1. doi: 10.1016/j.jpag.2015.08.009. [Epub ahead of print] PubMed PMID: 26342733. 19: Ma X, Zhang C, Deng J, Song Y, Li Q, Guo Y, Li C. Simultaneous Degradation of Estrone, 17β-Estradiol and 17α-Ethinyl Estradiol in an Aqueous UV/H₂O₂ System. Int J Environ Res Public Health. 2015 Sep 25;12(10):12016-29. doi: 10.3390/ijerph121012016. PubMed PMID: 26404330; PubMed Central PMCID: PMC4626952. 20: Beltz AM, Hampson E, Berenbaum SA. Oral contraceptives and cognition: A role for ethinyl estradiol. Horm Behav. 2015 Aug;74:209-17. doi: 10.1016/j.yhbeh.2015.06.012. Epub 2015 Jun 27. PubMed PMID: 26122296.