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Chemical compound
Moxestrol
Trade names Surestryl Other names R-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
Routes of administration
By mouth
Drug class
Estrogen ;
Estrogen ether
ATC code
Legal status
In general: ℞ (Prescription only)
Bioavailability 33%
[1]
Protein binding Minimal
[1]
Metabolism
Liver
[2]
Elimination half-life 8.2 hours
[1]
(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 )
Formula C 21 H 26 O 3
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]
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
2.6
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
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]
References
^
a
b
c
d
e
f
g Salmon J, Coussediere D, Cousty C, Raynaud JP (August 1983). "Pharmacokinetics and metabolism of moxestrol in animals--rat, dog and monkey". Journal of Steroid Biochemistry . 19 (2): 1223–1234.
doi :
10.1016/0022-4731(83)90421-1 .
PMID
6887930 .
^
a
b
c
d
e
f
g
h Li JJ, Nandi S, Li SA (6 December 2012).
Hormonal Carcinogenesis: Proceedings of the First International Symposium . Springer Science & Business Media. pp. 184–.
ISBN
978-1-4613-9208-8 .
^
a
b
c
d
e
f Elks J (14 November 2014).
The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies . Springer. pp. 841–.
ISBN
978-1-4757-2085-3 .
^
a
b
c
d Morton IK, Hall JM (31 October 1999).
Concise Dictionary of Pharmacological Agents: Properties and Synonyms . Springer Science & Business Media. pp. 186–.
ISBN
978-0-7514-0499-9 .
^
a
b
c
d Nunn AD (19 June 1992).
Radiopharmaceuticals: Chemistry and Pharmacology . CRC Press. pp. 342–.
ISBN
978-0-8247-8624-3 .
^
a
b
c
d 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.
^ Raynaud JP, Martin PM, Bouton MM, Ojasoo T (September 1978).
"11beta-Methoxy-17-ethynyl-1,3,5(10)-estratriene-3,17beta-diol (moxestrol), a tag for estrogen receptor binding sites in human tissues" . Cancer Research . 38 (9): 3044–3050.
PMID
679210 .
^ Lund TD, Hinds LR, Handa RJ (February 2006).
"The androgen 5alpha-dihydrotestosterone and its metabolite 5alpha-androstan-3beta, 17beta-diol inhibit the hypothalamo-pituitary-adrenal response to stress by acting through estrogen receptor beta-expressing neurons in the hypothalamus" . The Journal of Neuroscience . 26 (5): 1448–1456.
doi :
10.1523/JNEUROSCI.3777-05.2006 .
PMC
6675494 .
PMID
16452668 .
^ Raynaud JP, Ojasoo T, Bouton MM, Philibert D (1979).
"Receptor Binding as a Tool in the Development of New Bioactive Steroids" . Drug Design . Medicinal Chemistry: A Series of Monographs. Vol. 11. Academic Press. pp. 169–214.
doi :
10.1016/B978-0-12-060308-4.50010-X .
ISBN
9781483216102 .
^ Ojasoo T, Raynaud JP (November 1978).
"Unique steroid congeners for receptor studies" . Cancer Research . 38 (11 Pt 2): 4186–4198.
PMID
359134 .
^ Ojasoo T, Delettré J, Mornon JP, Turpin-VanDycke C, Raynaud JP (1987). "Towards the mapping of the progesterone and androgen receptors". Journal of Steroid Biochemistry . 27 (1–3): 255–269.
doi :
10.1016/0022-4731(87)90317-7 .
PMID
3695484 .
^ Raynaud JP, Bouton MM, Moguilewsky M, Ojasoo T, Philibert D, Beck G, et al. (January 1980). "Steroid hormone receptors and pharmacology". Journal of Steroid Biochemistry . 12 : 143–157.
doi :
10.1016/0022-4731(80)90264-2 .
PMID
7421203 .
^ Kaye AM, Kaye M (22 October 2013).
Development of Responsiveness to Steroid Hormones: Advances in the Biosciences . Elsevier Science. pp. 61–.
ISBN
978-1-4831-5308-7 .
Estrogens
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Certain
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Clomestrone
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Estradiol
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Estramustine phosphate
Estriol
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estriol succinate ,
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Estrogenic substances
Estrone
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Ethinylestradiol #
Hydroxyestrone diacetate
Mestranol
Methylestradiol
Moxestrol
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Prasterone (dehydroepiandrosterone; DHEA)
Promestriene
Quinestradol
Quinestrol
Progonadotropins
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domperidone ,
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Agonists
Steroidal:
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16α-LE2
16β-Hydroxyestrone
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17α-Estradiol (
alfatradiol )
17α-Dihydroequilenin
17α-Dihydroequilin
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17α-Ethynyl-3α-androstanediol
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ent -Estradiol
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Hexolame
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Norethisterone
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Orestrate
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Prodiame
Prolame
Promestriene
RU-16117
Quinestradol
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Tibolone
Xenoestrogens:
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anethole ,
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dianethole ,
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phlorizin (phloridzin) ,
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Metalloestrogens (e.g.,
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Resorcylic acid lactones (e.g.,
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zearalenone ,
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SERMs Tooltip Selective estrogen receptor modulators ) Antagonists
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GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown