Mestranol | CAS#72-33-3

MedKoo Cat#: 318194 | Name: Mestranol

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Description:

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

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

Mestranol

CAS#72-33-3

Theoretical Analysis

MedKoo Cat#: 318194

Name: Mestranol

CAS#: 72-33-3

Chemical Formula: C21H26O2

Exact Mass: 310.1933

Molecular Weight: 310.44

Elemental Analysis: C, 81.25; H, 8.44; O, 10.31

Price and Availability

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500mg	USD 450.00	2 weeks

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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

Product Data

Instruction

View handling instruction

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/

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

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 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.

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:

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.

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.