| Size | Price | Stock | Qty |
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| 1g |
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| 2g |
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| 5g |
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| Other Sizes |
Purity: ≥98%
| Targets |
Ethynodiol diacetate targets the progesterone receptor. As a prodrug, it binds to cytoplasmic progesterone receptors in the reproductive system after being converted to its active form, norethindrone. This binding subsequently activates progesterone receptor-mediated gene expression. Through a negative feedback mechanism, it modulates the hypothalamic-pituitary-ovarian axis. In addition to its progestogenic activity, ethynodiol diacetate itself exhibits significant intrinsic estrogenic activity (relative potency of 3.4), while possessing minimal androgenic effects (0.6).
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| ln Vitro |
Nordihydroguaiaretic acid (NDGA) (< 1.5 μM) decreases the percentage of sister chronnatid exchanges (SCEs) in human lymphocyte culture treated with ethynodiol diacetate (150 μg/mL). Since the NDGA treatment, in the presence of S9 mix, reduce the genotoxic damage by ethynodiol diacetate, the reduction may be due to the inhibition of cytochrome P450s which prevents the metabolic activation of ethynodiol diacetate or NDGA may act as a free radical scavenger. Ethynodiol diacetate (150 μg/mL) increases sister chromatid exchanges (SCEs) and chromosomal aberrations (CAs) frequencies and inhibits lymphocyte proliferation in the presence of S9 mix in human lymphocyte.
In vitro, Ethynodiol diacetate has been shown to increase sister chromatid exchange frequencies and inhibit lymphocyte proliferation in human lymphocyte cultures at a concentration of 150 µg/mL in the presence of an S9 metabolic mix. Its estrogenic potency is approximately 14-fold higher than that of norethindrone, making it useful for ER-mediated gene expression assays in progesterone receptor-positive cell lines. The compound's unique progestogenic and estrogenic profile distinguishes it from other progestins. |
| ln Vivo |
Ethynodiol diacetate (6 mg/kg b.w. daily) significantly increases the amounts of excreted 3alpha-hydroxy-5alpha-pregnan-20-one and A-homo-3-oxa-5alpha-pregnane-4,20-dione in urine in female rats. Significant increase in the weights of pituitary, liver and kidneys are noted in rats treated with ethynodiol diacetate (6 mg/kg b.w. daily). Norgestrel (75 μg/day) and ethynodiol diacetate (150 μg/day), co-administered with ethinyl estradiol (7.5 μg/day), lowers the plasma concentrations of HDL cholesterol in cynomolgus monkeys. |
| Enzyme Assay |
Non-cellular enzyme/receptor binding assays for Ethynodiol diacetate typically involve studying its interaction with the progesterone receptor. These assays often use purified receptor preparations or cell lysates to measure binding affinity. As a prodrug, its activity is sometimes assessed after metabolic activation. The compound's affinity for the progesterone receptor is a key parameter in these assays. Such experiments help to characterize its potency as a progestogen and distinguish it from other steroids.
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| Cell Assay |
In vitro cell-based assays for Ethynodiol diacetate are used to evaluate its hormonal activity. For example, studies have used human lymphocyte cultures to assess its effects on cell proliferation and genotoxicity. Additionally, it is used in assays with progesterone receptor-positive cell lines to study its progestogenic and estrogenic effects, such as gene expression and cell growth. These experiments are crucial for understanding its cellular mechanism of action and its unique dual hormonal profile.
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| Animal Protocol |
150 μg/day Monkeys |
| ADME/Pharmacokinetics |
Ethynodiol diacetate is a prodrug that is rapidly converted in the liver to its active form, norethindrone, with a half-life of 4-6.9 hours. This conversion is a key aspect of its pharmacokinetic profile. As a steroid hormone, it is expected to be well-absorbed after oral administration. The compound is a solid powder with a molecular weight of 384.5 g/mol. It has a solubility of 3.97e-03 g/L in water. For research use, it is recommended to be stored in a dry, dark place at 0-4°C for short-term storage or at -20°C for long-term storage.
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| Toxicity/Toxicokinetics |
Protein Binding
50-85% The toxicological profile of Ethynodiol diacetate is consistent with that of other synthetic progestogens. In vitro, it has been shown to increase sister chromatid exchange frequencies and inhibit lymphocyte proliferation. However, comprehensive toxicological data are not extensively detailed in standard summaries, as it is primarily a research compound. As with all steroidal hormones, its use is associated with potential hormonal side effects. Ethynodiol diacetate is not intended for human use and is strictly a research chemical. |
| References |
J Environ Biol.2007 Apr;28(2):279-82;Endocr Regul.1998 Sep;32(3):125-131.
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| Additional Infomation |
Ethynyl glycol diacetate is a steroidal ester and a terminal alkyne compound. It is used as an estrogen receptor modulator, a contraceptive, and a synthetic oral contraceptive. Its function is related to ethynyl glycol, a synthetic progestin that can be used alone or in combination with estrogen as an oral contraceptive. Although ethynyl glycol is sometimes used synonymously with ethynyl glycol diacetate, it usually refers to ethynyl glycol diacetate, not ethynyl glycol (which is a standalone drug that has never been marketed; see [DB13866]). Ethynyl glycol diacetate is the diacetate form of ethynyl glycol, a semi-synthetic progestin agonist. Ethynyl glycol diacetate binds to cytoplasmic progestin receptors in the reproductive system, subsequently activating progesterone receptor-mediated gene expression. Due to a negative feedback mechanism, the release of luteinizing hormone (LH) is inhibited, thereby suppressing ovulation and altering cervical mucus and the endometrium. Furthermore, ethynyl glycol diacetate exhibits weak estrogenic and androgenic activity.
A synthetic progestin, which can be used alone or in combination with estrogen as an oral contraceptive (oral contraceptive). Indications For the prevention of pregnancy in women who choose to use this product as a method of contraception.Mechanism of Action Binding to progestin and estrogen receptors. Target cells include the female reproductive tract, mammary glands, hypothalamus, and pituitary gland. Once a progestin (such as ethinyl estradiol diacetate) binds to its receptor, it slows the frequency of gonadotropin-releasing hormone (GnRH) release from the hypothalamus and inhibits the pre-ovulatory surge of luteinizing hormone (LH).Pharmacodynamics Ethinyl estradiol diacetate is used as a female contraceptive.Ethinyl estradiol diacetate is a progestin, a synthetic form of the natural female sex hormone progesterone. In a woman's normal menstrual cycle, an egg matures and is released from the ovary (ovulation). Subsequently, the ovary produces progesterone, which prevents the release of more eggs and prepares the uterine lining for a possible pregnancy. If pregnancy occurs, progesterone levels remain high to maintain the uterine lining. If pregnancy does not occur, progesterone levels drop, leading to menstruation. Ethynyl diacetate tricks the body into thinking ovulation has occurred by maintaining high levels of synthetic progesterone. This prevents the release of an egg from the ovary. Ethynodiol diacetate is a first-generation synthetic progestogen belonging to the 19-nortestosterone class. It is a prodrug that is metabolized to the active progestin norethindrone. Unlike many progestins, it exhibits significant intrinsic estrogenic activity. This dual progestogenic and estrogenic profile, along with minimal androgenic effects, made it a useful component in hormonal contraceptives. It is not currently approved for clinical use as a single agent and is available as a research compound. |
| Molecular Formula |
C₂₄H₃₂O₄
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|---|---|
| Molecular Weight |
384.51
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| Exact Mass |
384.23
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| CAS # |
297-76-7
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| Related CAS # |
1231-93-2;297-76-7 (diacetate);
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| PubChem CID |
9270
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| Appearance |
White to off-white solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
461.1±45.0 °C at 760 mmHg
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| Melting Point |
128 - 131ºC
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| Flash Point |
221.8±27.1 °C
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| Vapour Pressure |
0.0±1.1 mmHg at 25°C
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| Index of Refraction |
1.546
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| LogP |
5.44
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
28
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| Complexity |
758
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| Defined Atom Stereocenter Count |
7
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| SMILES |
CC(=O)O[C@H]1CC[C@@H]2[C@H]3CC[C@]4([C@H]([C@@H]3CCC2=C1)CC[C@]4(C#C)OC(=O)C)C
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| InChi Key |
ONKUMRGIYFNPJW-KIEAKMPYSA-N
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| InChi Code |
InChI=1S/C24H32O4/c1-5-24(28-16(3)26)13-11-22-21-8-6-17-14-18(27-15(2)25)7-9-19(17)20(21)10-12-23(22,24)4/h1,14,18-22H,6-13H2,2-4H3/t18-,19-,20+,21+,22-,23-,24-/m0/s1
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| Chemical Name |
(3S,8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diyl diacetate
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| Synonyms |
Luteonorm, Luto-Metrodiol, Metrodiol,Continuin, Femulen, norethindrol diacetate, ethynodiol diacetate
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 3.75 mg/mL (9.75 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 37.5 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 3.75 mg/mL (9.75 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 37.5 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 3.75 mg/mL (9.75 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.6007 mL | 13.0036 mL | 26.0071 mL | |
| 5 mM | 0.5201 mL | 2.6007 mL | 5.2014 mL | |
| 10 mM | 0.2601 mL | 1.3004 mL | 2.6007 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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