Mestranol
featured

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

MedKoo CAT#: 318194

CAS#: 72-33-3

Description: Mestranol is an Estrogen. The mechanism of action of mestranol is as an Estrogen Receptor Agonist. It is used as the estrogen component of many combination oral contraceptives.


Chemical Structure

img
Mestranol
CAS# 72-33-3

Theoretical Analysis

MedKoo Cat#: 318194
Name: Mestranol
CAS#: 72-33-3
Chemical Formula: C21H26O2
Exact Mass: 310.19
Molecular Weight: 310.437
Elemental Analysis: C, 81.25; H, 8.44; O, 10.31

Price and Availability

Size Price Availability Quantity
500mg USD 450 2 weeks
Bulk inquiry

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

IUPAC/Chemical Name: (17α)-3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17-ol

InChi Key: IMSSROKUHAOUJS-CRSSMBPESA-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/t17-,18-,19+,20+,21-/m1/s1

SMILES Code: C#C[C@@]1(O)CC[C@@]2([H])[C@]3([H])CCC4=C(C=CC(OC)=C4)[C@@]3([H])CC[C@]12C

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:
Biological target: Mestranol acts as an estrogen receptor agonist.
In vitro activity: In the human hepatoma cell line Hep 3B, tamoxifen inhibited cell growth in a concentration and time-dependent manner with effective concentrations ranging from 0.1 microM to 10 microM. Mestranol inhibited cell growth at a concentration of 10 microM and had an additive effect with tamoxifen on growth inhibition. Reference: J Hepatol. 1995 Dec;23(6):712-9. https://pubmed.ncbi.nlm.nih.gov/8750171/
In vivo activity: In this study brain alpha-1 and alpha-2-adrenoceptor binding was measured in female rats treated with estradiol and/or the synthetic estrogen mestranol. Rats treated biweekly for 12 weeks with mestranol (50 micrograms/100 g b.wt.) had a significant reduction in the apparent number of alpha-2-adrenoceptors in the frontal cortex and nucleus tractus solitarius (NTS), while apparent numbers of both alpha-1 and alpha-2-adrenoceptors were depressed in the locus coeruleus. Reference: Brain Res Bull. 1988 Aug;21(2):329-33. https://pubmed.ncbi.nlm.nih.gov/2847856/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 24.2 77.84
Ethanol 13.0 41.88
Water 0.7 2.16

Preparing Stock Solutions

The following data is based on the product molecular weight 310.44 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. Nagaraj V, Mikhail M, Baronio M, Gatto A, Nayak A, Theis T, Cavallaro U, Schachner M. Antagonistic L1 Adhesion Molecule Mimetic Compounds Inhibit Glioblastoma Cell Migration In Vitro. Biomolecules. 2022 Mar 12;12(3):439. doi: 10.3390/biom12030439. PMID: 35327631; PMCID: PMC8946856. 2. Jiang SY, Shyu RY, Yeh MY, Jordan VC. Tamoxifen inhibits hepatoma cell growth through an estrogen receptor independent mechanism. J Hepatol. 1995 Dec;23(6):712-9. doi: 10.1016/0168-8278(95)80038-7. PMID: 8750171. 3. Dragan YP, Singh J, Pitot HC. Effect of the separate and combined administration of mestranol and phenobarbital on the development of altered hepatic foci expressing placental form of glutathione S-transferase in the rat. Carcinogenesis. 1996 Sep;17(9):2043-52. doi: 10.1093/carcin/17.9.2043. PMID: 8824533. 4. Shackelford DP Jr, McConnaughey MM, Iams SG. The effects of estradiol and mestranol on alpha-adrenoceptors in select regions of the rat brain. Brain Res Bull. 1988 Aug;21(2):329-33. doi: 10.1016/0361-9230(88)90249-3. PMID: 2847856.
In vitro protocol: 1. Nagaraj V, Mikhail M, Baronio M, Gatto A, Nayak A, Theis T, Cavallaro U, Schachner M. Antagonistic L1 Adhesion Molecule Mimetic Compounds Inhibit Glioblastoma Cell Migration In Vitro. Biomolecules. 2022 Mar 12;12(3):439. doi: 10.3390/biom12030439. PMID: 35327631; PMCID: PMC8946856. 2. Jiang SY, Shyu RY, Yeh MY, Jordan VC. Tamoxifen inhibits hepatoma cell growth through an estrogen receptor independent mechanism. J Hepatol. 1995 Dec;23(6):712-9. doi: 10.1016/0168-8278(95)80038-7. PMID: 8750171.
In vivo protocol: 1. Dragan YP, Singh J, Pitot HC. Effect of the separate and combined administration of mestranol and phenobarbital on the development of altered hepatic foci expressing placental form of glutathione S-transferase in the rat. Carcinogenesis. 1996 Sep;17(9):2043-52. doi: 10.1093/carcin/17.9.2043. PMID: 8824533. 2. Shackelford DP Jr, McConnaughey MM, Iams SG. The effects of estradiol and mestranol on alpha-adrenoceptors in select regions of the rat brain. Brain Res Bull. 1988 Aug;21(2):329-33. doi: 10.1016/0361-9230(88)90249-3. PMID: 2847856.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Hu JH, Wang L, Li WS, Dai DP, Cai JP, Hu GX. Effect of CYP2C9 Genetic
Polymorphism in a Chinese Population on the Metabolism of Mestranol in vitro.
Pharmacology. 2015;95(5-6):218-23. doi: 10.1159/000381189. Epub 2015 Apr 25.
PubMed PMID: 25924705.


2: Schmider J, Greenblatt DJ, von Moltke LL, Karsov D, Vena R, Friedman HL,
Shader RI. Biotransformation of mestranol to ethinyl estradiol in vitro: the role
of cytochrome P-450 2C9 and metabolic inhibitors. J Clin Pharmacol. 1997
Mar;37(3):193-200. PubMed PMID: 9089421.


3: Gawrońska-Szklarz B, Droździk M, Kwiatkowski A, Wójcicki J. [Effect of
mestranol on pharmacokinetics of phenazone in the rabbit]. Ginekol Pol. 1996
Jan;67(1):1-6. Polish. PubMed PMID: 8655012.


4: Abas N, Koivunen DG, Johnson JA. Pressor responsiveness in rats with
hypertension induced by mestranol. Contraception. 1994 Oct;50(4):383-9. PubMed
PMID: 7813226.


5: Abas N, Koivunen DG, Johnson JA. Arterial sodium concentration in rats with
hypertension induced by mestranol. Contraception. 1993 Jul;48(1):71-9. PubMed
PMID: 8403907.


6: Nguyen HT, Shiu GK, Worsley WN, Skelly JP. Dissolution testing of
norethindrone:ethinyl estradiol, norethindrone:mestranol, and norethindrone
acetate:ethinyl estradiol combination tablets. J Pharm Sci. 1990 Feb;79(2):163-7.
PubMed PMID: 2324966.


7: Okada S, Hiroshige R, Tanaka M, Murai M, Kimura T. [Mestranol Reference
Standard (Control 881) of National Institute of Hygienic Sciences]. Eisei
Shikenjo Hokoku. 1990;(108):138-41. Japanese. PubMed PMID: 1364344.


8: Al-Azzawi F, Smith D, Parkin D, Hart DM, Lindsay R. Blood coagulation profile
in long-term hormone replacement therapy with mestranol. Maturitas. 1989
Jun;11(2):95-101. PubMed PMID: 2787887.


9: Tavassoli FA, Casey HW, Norris HJ. The morphologic effects of synthetic
reproductive steroids on the mammary gland of rhesus monkeys. Mestranol,
ethynerone, mestranol-ethynerone, chloroethynyl norgestrel-mestranol, and
anagestone acetate-mestranol combinations. Am J Pathol. 1988 May;131(2):213-34.
PubMed PMID: 3358452; PubMed Central PMCID: PMC1880606.


10: Coezy E, Auzan C, Lonigro A, Philippe M, Menard J, Corvol P. Effect of
mestranol on cell proliferation and angiotensinogen production in HepG2 cells:
relation with the cell cycle and action of tamoxifen. Endocrinology. 1987
Jan;120(1):133-41. PubMed PMID: 3023023.


11: Johnson JA, Dostal DE. Effects of captopril and bradykinin on arterial
pressure in rats with mestranol-induced hypertension. Contraception. 1986
Sep;34(3):303-10. PubMed PMID: 3539511.


12: Fowler WL Jr, Johnson JA, Kurz KD, Zeigler DW, Dostal DE, Payne CG. Body
fluid volumes in rats with mestranol-induced hypertension. Am J Physiol. 1986
Jul;251(1 Pt 2):H190-5. PubMed PMID: 3728696.


13: Rudolf K, Kunkel S, Rudolf H, Herzmann A, Herzmann H. [Effect of mestranol
and chlormadinone acetate on TSH, T4, TBC and FT4 index in Turner syndrome].
Zentralbl Gynakol. 1986;108(9):551-9. German. PubMed PMID: 2425513.


14: Mizokami K, Suzuki K, Inoue K, Sunouchi M, Hirakawa S, Goto S, Takanaka A,
Kanke Y. Effects of oral contraceptive steroids (norethisterone/mestranol) on the
activities of hepatic drug-metabolizing enzymes in iron-deficient anemic rats.
Experientia. 1985 Jun 15;41(6):734-6. PubMed PMID: 3924648.


15: Rudolf K, Kunkel S, Pelz L. [Effect of mestranol and chlormadinone acetate on
basal and TRH-stimulated PRL secretion in Turner's syndrome]. Zentralbl Gynakol.
1985;107(23):1446-53. German. PubMed PMID: 2420101.


16: Yager JD, Campbell HA, Longnecker DS, Roebuck BD, Benoit MC. Enhancement of
hepatocarcinogenesis in female rats by ethinyl estradiol and mestranol but not
estradiol. Cancer Res. 1984 Sep;44(9):3862-9. PubMed PMID: 6744303.


17: Abdalla HI, Beastall GH, Hart DM. The effect of oestrogen (mestranol) on the
thyrotrophin response to thyrotrophin releasing hormone in postmenopausal
oophorectomised women. Clin Endocrinol (Oxf). 1984 Jul;21(1):65-9. PubMed PMID:
6430605.


18: Coutinho EM, Silva AR, Carreira C, Barbosa I. Ovulation inhibition following
vaginal administration of pills containing norethindrone and mestranol.
Contraception. 1984 Feb;29(2):197-202. PubMed PMID: 6723313.


19: Warren BL, Bellward GD. Effects of chronic mestranol and (or)norethindrone
treatment on ethanol-associated decreases in hepatic benzo[a]pyrene hydroxylase
activity and increases in central vein fat accumulation in the female Wistar rat.
Can J Physiol Pharmacol. 1983 Aug;61(8):808-15. PubMed PMID: 6627123.


20: Spellacy WN, Buhi WC, Birk SA. The effects of two years of mestranol
treatment on carbohydrate metabolism. Metabolism. 1982 Oct;31(10):1006-8. PubMed
PMID: 6752633.