Moxestrol

Source: Wikipedia, the free encyclopedia.
Moxestrol
Clinical data
Trade namesSurestryl
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)
Estrogen ether
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability33%[1]
Protein bindingMinimal[1]
MetabolismLiver[2]
Elimination half-life8.2 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
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

scientific research as a radioligand of the estrogen receptor.[7]

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

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 PRTooltip Progesterone receptor ARTooltip Androgen receptor ERTooltip Estrogen receptor GRTooltip Glucocorticoid receptor MRTooltip Mineralocorticoid receptor SHBGTooltip Sex hormone-binding globulin
CBG
Tooltip Corticosteroid binding globulin
Estradiol 2.6 7.9 100 0.6 0.13 8.7 <0.1
Ethinylestradiol 15–25 1–3 112 1–3 <1 ? ?
Moxestrol (11β-MeO-EE) 0.8 <0.1 12 3.2 <0.1 <0.2 <0.1
RU-16117 (11α-MeO-EE) 1–3 <1 13 <1 <1 ? ?
Notes: Values are percentages (%). Reference
CBGTooltip 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

See also: List of estrogens and List of estrogen esters § Ethers of steroidal estrogens

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

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

INNTooltip 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]

References

  1. ^
    PMID 6887930
    .
  2. ^
    ISBN 978-1-4613-9208-8
    .
  3. ^
    ISBN 978-1-4757-2085-3
    .
  4. ^
    ISBN 978-0-7514-0499-9
    .
  5. ^
    ISBN 978-0-8247-8624-3
    .
  6. ^
    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.
  7. PMID 679210
    .
  8. PMID 16452668
    .
  9. ISBN 9781483216102
    .
  10. PMID 359134
    .
  11. PMID 3695484
    .
  12. PMID 7421203
    .
  13. ISBN 978-1-4831-5308-7
    .
Retrieved from "https://en.wikipedia.org/w/index.php?title=Moxestrol&oldid=1188981293"