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| Clinical data | |
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| 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 |
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| Routes of administration | By mouth |
| Drug class | Estrogen;Estrogen ether |
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| Pharmacokinetic data | |
| Bioavailability | 33%[1] |
| Protein binding | Minimal[1] |
| Metabolism | Liver[2] |
| Eliminationhalf-life | 8.2 hours[1] |
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| Chemical and physical data | |
| Formula | C21H26O3 |
| Molar mass | 326.436 g·mol−1 |
| 3D model (JSmol) | |
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Moxestrol, sold under the brand nameSurestryl, is anestrogen medication which has been used inEurope for the treatment ofmenopausal symptoms andmenstrual disorders.[3][4][2][5][6] It is takenby mouth.[6] In addition to its use as a medication, moxestrol has been used inscientific research as aradioligand of theestrogen receptor.[7]
Moxestrol is or has been used in the treatment ofmenopausal symptoms andmenstrual 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]
Moxestrol is anestrogen, or anagonist of theestrogen receptors.[2][5] It is the 11β-methoxy derivative ofethinylestradiol and is one of the mostpotent estrogens known, being some 10 to 100 times more potent thanestradiol and about 5-fold more potent than ethinylestradiol.[2][5] The very high potency of moxestrol has been attributed to its highaffinity for theestrogen receptor (ER), its negligibleplasma binding tosex hormone binding globulin and low binding toserum albumin,[1] and its lower relative rate ofmetabolism.[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-foldselectivity for theERα (Ki = 0.50 nM) overERβ (Ki = 2.6 nM).[8]
| Compound | PRTooltip Progesterone receptor | ARTooltip Androgen receptor | ERTooltip Estrogen receptor | GRTooltip Glucocorticoid receptor | MRTooltip Mineralocorticoid receptor | SHBGTooltip Sex hormone-binding globulin | CBGTooltip 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 (%). Referenceligands (100%) wereprogesterone for thePRTooltip progesterone receptor,testosterone for theARTooltip androgen receptor,E2 for theERTooltip estrogen receptor,DEXATooltip dexamethasone for theGRTooltip glucocorticoid receptor,aldosterone for theMRTooltip mineralocorticoid receptor,DHTTooltip dihydrotestosterone forSHBGTooltip sex hormone-binding globulin, andcortisol forCBGTooltip Corticosteroid-binding globulin.Sources:[9][10][11][12] | |||||||
Thebioavailability of moxestrol is 33%.[1] Itsplasma protein binding is minimal.[1] The medication ismetabolized in theliver.[2] Itsbiological half-life is 8.2 hours.[1]
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 asyntheticestranesteroid and aderivative ofestradiol.[3] It is specifically a derivative ofethinylestradiol (17α-ethynylestradiol) with amethoxy group at the C11β position and a derivative of11β-methoxyestradiol with anethynyl group at the C17α position.[3] The compound is the C11βisomer or C11epimer ofRU-16117 (11α-methoxy-17α-ethynylestradiol.[13]
Moxestrol is thegeneric name of the drug and itsINNTooltip International Nonproprietary Name.[3][4] It is also known by its developmental code nameR-2858 orRU-2858.[3][4]
Moxestrol is or has been marketed under the brand nameSurestryl.[3][4]
Moxestrol is or has been marketed inEurope.[2]
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.
