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Mestranol

Alias:
Cat No.:V1739 Purity: ≥98%
Mestranol (Ethinyl Estradiol 3 Methyl Ether; Devocin; Norquen; Ovastol), the 3-methyl ether of ethinyl estradiol, is a potent estrogen receptor agonist that has been used as an oral contraceptive.
Mestranol
Mestranol Chemical Structure CAS No.: 72-33-3
Product category: Estrogenprogestogen Receptor
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Mestranol (Ethinyl Estradiol 3 Methyl Ether; Devocin; Norquen; Ovastol), the 3-methyl ether of ethinyl estradiol, is a potent estrogen receptor agonist that has been used as an oral contraceptive. Mestranol is a prodrug of ethinylestradiol and is biologically inactive. It has to be activated through demethylation in the liver.

Biological Activity I Assay Protocols (From Reference)
ln Vitro
Mestranol, a synthetic estrogen with modest potency, has demonstrated much greater stability in hepatoma cell culture as compared to 17β-Estradiol [3]. Over a period of six days, mestranol (10 μM) can boost the proliferation of ERpositive MCF-7 WS8 cells up to 250% over control levels. Tamoxifen can partially reverse this growth stimulation. Mestranol (10 μM; 6 days) on Hep G2 hepatoma cells, however, reduces the development of Hep 3B cells by 40% in comparison to control cells. It is possible to stop cell proliferation using mestranol alone or in combination with tamoxifen. Additionally, tamoxifen and cotreatment have a cumulative effect on growth inhibition[2].
ln Vivo
Mestranol (0.2 mg/kg) results in an increased percentage of liver occupied by AHF expressing glutathione S-transferase (PGST) in rats. Mestranol administration increases the focal hepatocyte labeling index compared with the control with a trend at the lower dose and a significant difference at the higher dose. Mestranol (0.02 mg/kg and 0.2 mg/kg diet) results in a decrease in the non-focal labeling index compared with that observed for the corresponding concentration of Mestranol alone. Mestranol significantly increases the non-focal hepatic labeling index in uninitiated rats compared with that observed in rats administered the basal diet only. Mestranol (50 mg/100 g b.wt.) has a significant reduction in the apparent number of alpha-2-adrenoceptors in the frontal cortex and nucleus tractus solitarius (NTS) of rat, while apparent numbers of both alpha-1 and alpha-2-adrenoceptors are depressed in the locus coeruleus.
Animal Protocol
0.02 mg/kg and 0.2 mg/kg diet
Rats
ADME/Pharmacokinetics
Absorption, Distribution and Excretion
Mestranol binds poorly to the estrogen receptor and its estrogenic effect is due to its rapid demethylation in the liver to form ethinylestradiol; however, demethylation is not complete and more mestranol must be administered than ethinylestradiol to achieve similar effects.
The excretion of metabolites in urine ranged from 10-27%; that of ethinyloestradiol metabolites ranges from 36-54%. When position 2 or 4 of the mestranol molecule is tritiated or marked with (14)C, between 14-45% of the radioactivity is released into the body water.
Metabolism / Metabolites
Mestranol is rapidly absorbed and extensively metabolised to ethinylestradiol. Ethinylestradiol is rapidly and well absorbed from the gastro-intestinal tract but is subject to some first-pass metabolism in the gut-wall. Compared to many other estrogens it is only slowly metabolized in the liver. Excretion is via the kidneys with some appearing also in the feces.
In the body it undergoes rapid hepatic demethylation to ethinyl estradiol, which is its active form. /Estrogens/
Mestranol, the 3-methyl ether of ethinyloestradiol, is more lipophilic than ethinyloestradiol and has a greater affinity for adipose tissues, as shown by experiments in rats. Mestranol itself does not bind significantly to estrogen receptors at the sites of their antifertility action; its hormonal effectiveness relies on transformation to ethinyloestradiol. About 35% of a mestranol dose is transformed into ethinyloestradiol in rats, 61% in mice, 56% in rabbits and 54% in man. The demethylated portion then follows the pathways for ethinyloestradiol that are typical for the particular species, e.g., 2-hydroxylation in rats and D-homoannulation in rabbits and guinea-pigs. Mestranol is also demethylated to ethinylestradiol in non-human primates.
The metabolism of mestranol in humans is closely related to that of ethinyloestradiol. Mestranol is transformed to ethinyloestradiol by demethylation: after i.v. administration of (14)C-mestranol to human volunteers, about 50% of the dose is demethylated to ethinylestradiol. The main compound found in plasma is ethinyloestradiol-3-sulfate.
For more Metabolism/Metabolites (Complete) data for MESTRANOL (6 total), please visit the HSDB record page.
Mestranol has known human metabolites that include ethinylestradiol.
References

[1]. Affinity of ethynyl-estradiol and mestranol for the uterine estrogen receptor and for the microsomal mixed function oxidase of the liver. J Steroid Biochem. 1973 Mar;4(2):121-8.

[2]. Pharmacokinetics of ethinyl estradiol and mestranol. Am J Obstet Gynecol. 1990 Dec;163(6 Pt 2):2114-9.

[3]. Tamoxifen inhibits hepatoma cell growth through an estrogen receptor independent mechanism. J Hepatol. 1995 Dec;23(6):712-9.

Additional Infomation
Mestranol can cause cancer according to an independent committee of scientific and health experts.
Mestranol is a terminal acetylenic compound that is (17alpha)-17-ethynylestra-1(10),2,4-triene substituted by a methoxy group at position 3 and a hydroxy group at position 17. It has a role as a prodrug and a xenoestrogen. It is a 17beta-hydroxy steroid, a terminal acetylenic compound and an aromatic ether. It is functionally related to a 17beta-estradiol.
The 3-methyl ether of ethinyl estradiol. It must be demethylated to be biologically active. It is used as the estrogen component of many combination ORAL contraceptives.
Mestranol is an Estrogen. The mechanism of action of mestranol is as an Estrogen Receptor Agonist.
Mestranol has been reported in Cunninghamella elegans with data available.
Mestranol is a semisynthetic estrogen. Metabolized by the liver to ethynyl estradiol, mestranol serves as the estrogen component in several combination oral contraceptives. (NCI04)
The 3-methyl ether of ethinyl estradiol. It must be demethylated to be biologically active. It is used as the estrogen component of many combination ORAL contraceptives.
The 3-methyl ether of ETHINYL ESTRADIOL. It must be demethylated to be biologically active. It is used as the estrogen component of many combination ORAL CONTRACEPTIVES.
Drug Indication
Mestranol was used as one of the first oral contraceptives.
Mechanism of Action
Mestranol is the 3-methyl ether of ethinylestradiol. Ethinylestradiol, is a synthetic derivative of estradiol. Ethinylestradiol is orally bio-active and the estrogen used in almost all modern formulations of combined oral contraceptive pills. It binds to (and activates) the estrogen receptor. Mestranol is a biologically inactive prodrug of ethinylestradiol to which it is demethylated in the liver with a conversion efficiency of 70%. Estrogens diffuse into their target cells and interact with a protein receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. 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. The combination of an estrogen with a progestin suppresses the hypothalamic-pituitary system, decreasing the secretion of gonadotropin-releasing hormone (GnRH).
The mode of action of Norinyl-1 is similar to that of other progestogen/estrogen oral contraceptives and includes the inhibition of ovulation, the thickening of cervical mucus so as to constitute a barrier to sperm and the rendering of the endometrium unreceptive to implantation. Such activity is exerted through a combined effect on one or more of the following: hypothalamus, anterior pituitary, ovary, endometrium and cervical mucus.
Estrogens have an important role in the reproductive, skeletal, cardiovascular, and central nervous systems in women, and act principally by regulating gene expression. Biologic response is initiated when estrogen binds to a ligand-binding domain of the estrogen receptor resulting in a conformational change that leads to gene transcription through specific estrogen response elements (ERE) of target gene promoters; subsequent activation or repression of the target gene is mediated through 2 distinct transactivation domains (ie, AF-1 and AF-2) of the receptor. The estrogen receptor also mediates gene transcription using different response elements (ie, AP-1) and other signal pathways. Recent advances in the molecular pharmacology of estrogen and estrogen receptors have resulted in the development of selective estrogen receptor modulators (eg, clomiphene, raloxifene, tamoxifen, toremifene), agents that bind and activate the estrogen receptor but that exhibit tissue-specific effects distinct from estrogen. Tissue-specific estrogen-agonist or -antagonist activity of these drugs appears to be related to structural differences in their estrogen receptor complex (eg, specifically the surface topography of AF-2 for raloxifene) compared with the estrogen (estradiol)-estrogen receptor complex. A second estrogen receptor also has been identified, and existence of at least 2 estrogen receptors (ER-alpha, ER-beta) may contribute to the tissue-specific activity of selective modulators. While the role of the estrogen receptor in bone, cardiovascular tissue, and the CNS continues to be studied, emerging evidence indicates that the mechanism of action of estrogen receptors in these tissues differs from the manner in which estrogen receptors function in reproductive tissue. /Estrogen General Statement/
Intracellular cytosol-binding proteins for estrogens have been identified in estrogen-responsive tissues including the female genital organs, breasts, pituitary, and hypothalamus. The estrogen-binding protein complex (ie, cytosol-binding protein and estrogen) distributes into the cell nucleus where it stimulates DNA, RNA, and protein synthesis. The presence of these receptor proteins is responsible for the palliative response to estrogen therapy in women with metastatic carcinoma of the breast. /Estrogen General Statement/
Estrogens have generally favorable effects on blood cholesterol and phospholipid concentrations. Estrogens reduce LDL-cholesterol and increase HDL-cholesterol concentrations in a dose-related manner. The decrease in LDL-cholesterol concentrations associated with estrogen therapy appears to result from increased LDL catabolism, while the increase in triglyceride concentrations is caused by increased production of large, triglyceride-rich, very-low-density lipoproteins (VLDLs); changes in serum HDL-cholesterol concentrations appear to result principally from an increase in the cholesterol and apolipoprotein A-1 content of HDL2- and a slight increase in HDL3-cholesterol. /Estrogen General Statement/
For more Mechanism of Action (Complete) data for MESTRANOL (7 total), please visit the HSDB record page.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C21H26O2
Molecular Weight
310.43
Exact Mass
310.193
CAS #
72-33-3
Related CAS #
Mestranol-d2;Mestranol-d4
PubChem CID
6291
Appearance
White to off-white solid powder
Density
1.2±0.1 g/cm3
Boiling Point
442.3±45.0 °C at 760 mmHg
Melting Point
153-155 °C(lit.)
Flash Point
190.8±23.0 °C
Vapour Pressure
0.0±1.1 mmHg at 25°C
Index of Refraction
1.591
LogP
5.17
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
2
Heavy Atom Count
23
Complexity
519
Defined Atom Stereocenter Count
5
SMILES
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=C3C=CC(=C4)OC
InChi Key
IMSSROKUHAOUJS-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H26O2/c1-4-21(22)12-10-19-18-7-5-14-13-15(23-3)6-8-16(14)17(18)9-11-20(19,21)2/h1,6,8,13,17-19,22H,5,7,9-12H2,2-3H3
Chemical Name
17-ethynyl-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol
Synonyms

Ethinyl Estradiol 3 Methyl Ether;Devocin; Norquen; Ovastol; Ethynylestradiol 3-methyl ether; Ethinyl Estradiol 3-Methyl Ether

HS Tariff Code
2934.99.9001
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)
Solubility Data
Solubility (In Vitro)
DMSO:15 mg/mL (48.3 mM)
Water:<1 mg/mL
Ethanol:25 mg/mL (80.5 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (6.70 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 20.8 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.

Solubility in Formulation 2: ≥ 2.08 mg/mL (6.70 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.2213 mL 16.1067 mL 32.2134 mL
5 mM 0.6443 mL 3.2213 mL 6.4427 mL
10 mM 0.3221 mL 1.6107 mL 3.2213 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.

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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.

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