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1g |
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2g |
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5g |
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Other Sizes |
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Purity: ≥98%
Ethynodiol diacetate (Luteonorm, Luto-Metrodiol, Metrodiol, Continuin, Femulen, norethindrol diacetate), the diacetate ester form of ethynodiol, is one of the first synthetic steroidal progestogens used as a contraceptive drug.
ln Vitro |
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ln Vivo |
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Animal Protocol |
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Toxicity/Toxicokinetics |
Protein Binding
50-85% |
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References |
J Environ Biol.2007 Apr;28(2):279-82;Endocr Regul.1998 Sep;32(3):125-131.
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Additional Infomation |
Ethynodiol diacetate is a steroid ester and a terminal acetylenic compound. It has a role as an estrogen receptor modulator, a contraceptive drug and a synthetic oral contraceptive. It is functionally related to an ethynodiol.
A synthetic progestational hormone used alone or in combination with estrogens as an oral contraceptive. Although etynodiol or ethynodiol are sometimes used as a synonym for ethynodiol diacetate, what is usually being referred to is actually ethynodiol diacetate and not ethynodiol (which is a separate drug that has never been marketed, see [DB13866]). Ethynodiol Diacetate is the diacetate salt form of ethynodiol, a semi-synthetic progestational hormone agonist. Ethynodiol diacetate binds to cytoplasmic progesterone receptors in the reproductive system and subsequently activates progesterone receptor mediated gene expression. As a result of the negative feedback mechanism, luteinizing hormone (LH) release is inhibited, which leads to an inhibition of ovulation and an alteration in the cervical mucus and endometrium. In addition, ethynodiol diacetate has weak oestrogenic and androgenic properties. A synthetic progestational hormone used alone or in combination with estrogens as an oral contraceptive (CONTRACEPTIVES, ORAL). Drug Indication For the prevention of pregnancy in women who elect to use this product as a method of contraception. Mechanism of Action Binds to the progesterone and estrogen receptors. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Once bound to the receptor, progestins like Ethynodiol Diacetate will slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH (luteinizing hormone) surge. Pharmacodynamics Ethynodiol Diacetate is used as a female contraceptive. Ethynodiol Diacetate is a progestin or a synthetic form of the naturally occurring female sex hormone, progesterone. In a woman's normal menstrual cycle, an egg matures and is released from the ovaries (ovulation). The ovary then produces progesterone, preventing the release of further eggs and priming the lining of the womb for a possible pregnancy. If pregnancy occurs, progesterone levels in the body remain high, maintaining the womb lining. If pregnancy does not occur, progesterone levels in the body fall, resulting in a menstrual period. Ethynodiol Diacetate tricks the body processes into thinking that ovulation has already occurred, by maintaining high levels of the synthetic progesterone. This prevents the release of eggs from the ovaries. |
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.