Moxestrol

Last updated
Moxestrol
Moxestrol structure.svg
Moxestrol molecule ball.png
Clinical data
Trade names Surestryl
Other namesR-2858, RU-2858, NSC-118191; 11β-Methoxy-17α-ethynylestradiol; 11β-MeO-EE 11β-Methoxy-17α-ethynylestra-1,3,5(10)-triene-3,17β-diol
Pregnancy
category
  • X (Contraindicated)
Routes of
administration
By mouth
Drug class Estrogen; Estrogen ether
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability 33% [1]
Protein binding Minimal [1]
Metabolism Liver [2]
Elimination half-life 8.2 hours [1]
Identifiers
  • (8S,9S,11S,13S,14S,17R)-17-ethynyl-11-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C21H26O3
Molar mass 326.436 g·mol−1
3D model (JSmol)
  • CC12CC(C3C(C1CCC2(C#C)O)CCC4=C3C=CC(=C4)O)OC
  • InChI=1S/C21H26O3/c1-4-21(23)10-9-17-16-7-5-13-11-14(22)6-8-15(13)19(16)18(24-3)12-20(17,21)2/h1,6,8,11,16-19,22-23H,5,7,9-10,12H2,2-3H3/t16-,17-,18-,19+,20-,21-/m0/s1
  • Key:MTMZZIPTQITGCY-OLGWUGKESA-N

Moxestrol, sold under the brand name Surestryl, is an estrogen medication which has been used in Europe for the treatment of menopausal symptoms and menstrual disorders. [3] [4] [2] [5] [6] It is taken by mouth. [6] In addition to its use as a medication, moxestrol has been used in scientific research as a radioligand of the estrogen receptor. [7]

Contents

Medical uses

Moxestrol is or has been used in the treatment of menopausal symptoms and menstrual disorders. [2] [6] It has been used at dosages of 50 to 150 μg per week for long-term therapy to 25 to 250 μg per day for short-term therapy. [6]

Pharmacology

Pharmacodynamics

Moxestrol is an estrogen, or an agonist of the estrogen receptors. [2] [5] It is the 11β-methoxy derivative of ethinylestradiol and is one of the most potent estrogens known, being some 10 to 100 times more potent than estradiol and about 5-fold more potent than ethinylestradiol. [2] [5] The very high potency of moxestrol has been attributed to its high affinity for the estrogen receptor (ER), its negligible plasma binding to sex hormone binding globulin and low binding to serum albumin, [1] and its lower relative rate of metabolism. [2] [5] In contrast to estradiol, which has roughly the same affinity for both ERs (Ki = 0.12 nM and 0.15 nM, respectively), moxestrol possesses several-fold selectivity for the ERα (Ki = 0.50 nM) over ERβ (Ki = 2.6 nM). [8]

Relative affinities (%) of moxestrol and related steroids
Compound PR Tooltip Progesterone receptor AR Tooltip Androgen receptor ER Tooltip Estrogen receptor GR Tooltip Glucocorticoid receptor MR Tooltip Mineralocorticoid receptor SHBG Tooltip Sex hormone-binding globulin CBG Tooltip Corticosteroid binding globulin
Estradiol 2.67.91000.60.138.7<0.1
Ethinylestradiol 15–251–31121–3<1 ? ?
Moxestrol (11β-MeO-EE)0.8<0.1123.2<0.1<0.2<0.1
RU-16117 (11α-MeO-EE)1–3<113<1<1 ? ?
Notes: Values are percentages (%). Reference ligands (100%) were progesterone for the PR Tooltip progesterone receptor, testosterone for the AR Tooltip androgen receptor, E2 for the ER Tooltip estrogen receptor, DEXA Tooltip dexamethasone for the GR Tooltip glucocorticoid receptor, aldosterone for the MR Tooltip mineralocorticoid receptor, DHT Tooltip dihydrotestosterone for SHBG Tooltip sex hormone-binding globulin, and cortisol for CBG Tooltip Corticosteroid-binding globulin. Sources: [9] [10] [11] [12]

Pharmacokinetics

The bioavailability of moxestrol is 33%. [1] Its plasma protein binding is minimal. [1] The medication is metabolized in the liver. [2] Its biological half-life is 8.2 hours. [1]

Chemistry

Moxestrol, also known as 11β-methoxy-17α-ethynylestradiol (11β-MeO-EE) or as 11β-methoxy-17α-ethynylestra-1,3,5(10)-triene-3,17β-diol, is a synthetic estrane steroid and a derivative of estradiol. [3] It is specifically a derivative of ethinylestradiol (17α-ethynylestradiol) with a methoxy group at the C11β position and a derivative of 11β-methoxyestradiol with an ethynyl group at the C17α position. [3] The compound is the C11β isomer or C11 epimer of RU-16117 (11α-methoxy-17α-ethynylestradiol. [13]

Society and culture

Generic names

Moxestrol is the generic name of the drug and its INN Tooltip International Nonproprietary Name. [3] [4] It is also known by its developmental code name R-2858 or RU-2858. [3] [4]

Brand names

Moxestrol is or has been marketed under the brand name Surestryl. [3] [4]

Availability

Moxestrol is or has been marketed in Europe. [2]

Related Research Articles

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<span class="mw-page-title-main">Mestranol</span> Chemical compound

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<span class="mw-page-title-main">Dienogest</span> Chemical compound

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References

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  6. 1 2 3 4 William Martindale; Royal Pharmaceutical Society of Great Britain. Dept. of Pharmaceutical Sciences (1993). The Extra Pharmacopoeia. Pharmaceutical Press. p. 1188. ISBN   978-0-85369-300-0. Moxestrol is a synthetic oestrogen with actions and uses similar to thosre described for the oestrogens in general. Moxestrol is reponed to have a prolonged duration of action. It has been given by mouth in the treatment of menopausal, postmenopausal, and menstrual symptoms. Dose have ranged from 50 to 100 μg weekly for long-term therapy to 25 to 250 μg daily for short-term use.
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