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34816-55-2-Moxestrol Moxestrol

Moxestrol

For research use only. Not for therapeutic Use.

  • CAT Number: I032705
  • CAS Number: 34816-55-2
  • Molecular Formula: C21H26O3
  • Molecular Weight: 326.43
  • Purity: 98%
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Related Small Molecules: Acetylvaline     CCCI-01     4-(4-Bromophenoxy)piperidine hydrochloride    

Moxestrol is a synthetic estrogen agonist. It is a medication which is or was used in Europe for the treatment of menopausal symptoms and menstrual disorders.


Catalog Number I032705
CAS Number 34816-55-2
Synonyms

Moxestrol; R 2858; R 2858; R 2858; RU 2858; RU 2858; RU 2858; Surestryl;

Molecular Formula C21H26O3
Purity 98%
Solubility Soluble in DMSO
Appearance Solid powder
Storage Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
IUPAC Name (8S,9S,11S,13S,14S,17R)-17-ethynyl-11-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
InChI 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
InChIKey MTMZZIPTQITGCY-OLGWUGKESA-N
SMILES OC(C=C1)=CC2=C1[C@@]3([H])[C@@H](OC)C[C@]4(C)[C@@](C#C)(O)CC[C@@]4([H])[C@]3([H])CC2
Reference

1: De Boer W, Snippe L, Ab G, Gruber M. Estrogen receptor in avian embryo and adult liver: estrogen receptor activation and dissociation kinetics of estradiol, ethynylestradiol, and moxestrol. Endocrinology. 1982 Apr;110(4):1217-24. PubMed PMID: 7060523.
2: Salmon J, Coussediere D, Cousty C, Raynaud JP. Pharmacokinetics and metabolism of moxestrol in humans. J Steroid Biochem. 1983 May;18(5):565-73. PubMed PMID: 6855232.
3: Salmon J, Coussediere D, Cousty C, Raynaud JP. Pharmacokinetics and metabolism of moxestrol in animals–rat, dog and monkey. J Steroid Biochem. 1983 Aug;19(2):1223-34. PubMed PMID: 6887930.
4: Blom MJ, Wassink MG, Kloosterboer HJ, Ederveen AG, Lambert JG, Goos HJ. Metabolism of estradiol, ethynylestradiol, and moxestrol in rat uterus, vagina, and aorta: influence of sex steroid treatment. Drug Metab Dispos. 2001 Jan;29(1):76-81. PubMed PMID: 11124233.
5: Feenstra A, Nolten GM, Vaalburg W, Reiffers S, Woldring MG. Radiotracers binding to estrogen receptors: I: Tissue distribution of 17 alpha-ethynylestradiol and moxestrol in normal and tumor-bearing rats. J Nucl Med. 1982 Jul;23(7):599-605. PubMed PMID: 6806452.
6: Veldhuis JD. Mechanisms subserving the bipotential actions of estrogen on ovarian cells: studies with a selective anti-estrogen, LY156758, and the sparingly metabolizable estrogen agonist, moxestrol. J Steroid Biochem. 1986 May;24(5):977-82. PubMed PMID: 3459942.
7: Euvrard C, Labrie F, Boissier JR. Effect of moxestrol on haloperidol-induced changes in striatal acetylcholine levels and dopamine turn-over. Commun Psychopharmacol. 1979;3(5):329-34. PubMed PMID: 548211.
8: Glick BB, Brenner RM, Jensen JN, Phoenix CH. Moxestrol (R2858), estradiol benzoate, and sexual behavior of cynomolgus macaques (Macaca fascicularis). Horm Behav. 1982 Mar;16(1):59-65. PubMed PMID: 7068127.
9: Becú-Villalobos D, Libertun C. Ontogenesis of [3H]serotonin binding sites in the hypothalamus of the female rat: relation to serotonin-induced LH release in moxestrol-pretreated rats. Brain Res. 1986 Feb;390(1):111-6. PubMed PMID: 3948023.
10: Morel G, Raynaud JP, Dubois PM. [Ultrastructural localization of estradiol and moxestrol in the gonadotropic cells of rat by immunocytology after cryo-ultramicrotomy: evidence for hormonal specificity (author’s transl)]. Experientia. 1981 Jan 15;37(1):98-100. French. PubMed PMID: 6781931.
11: Raynaud JP, Martin PM, Bouton MM, Ojasoo T. 11beta-Methoxy-17-ethynyl-1,3,5(10)-estratriene-3,17beta-diol (moxestrol), a tag for estrogen receptor binding sites in human tissues. Cancer Res. 1978 Sep;38(9):3044-50. PubMed PMID: 679210.
12: Salmon J, Coussediere D, Cousty C, Delaroff V, Raynaud JP. Reference compounds for the study of moxestrol metabolism. Steroids. 1979 Oct;34(4):381-400. PubMed PMID: 516111.
13: Euvrard C, Oberlander C, Boissier JR. Antidopaminergic effect of estrogens at the striatal level. J Pharmacol Exp Ther. 1980 Jul;214(1):179-85. PubMed PMID: 7391967.
14: Robyn C, Vekemans M, Rozencweig M, Chigot D, Raynaud JP. Double-blind crossover clinical pharmacology study comparing moxestrol (R 2858) and ethinyl estradiol in postmenopausal women. J Clin Pharmacol. 1978 Jan;18(1):29-34. PubMed PMID: 338643.
15: Cornilleau T, Simonsen M, Vang M, Taib-Maamar N, Dessolin J, Audrain H, Hermange P, Fouquet E. Last-Step Pd-Mediated [(11)C]CO Labeling of a Moxestrol-Conjugated o-Iodobenzyl Alcohol: From Model Experiments to in Vivo Positron Emission Tomography Studies. Bioconjug Chem. 2017 Nov 15;28(11):2887-2894. doi: 10.1021/acs.bioconjchem.7b00583. Epub 2017 Oct 27. PubMed PMID: 29077399.
16: Gerlach JL, McEwen BS, Toran-Allerand CD, Friedman WJ. Perinatal development of estrogen receptors in mouse brain assessed by radioautography, nuclear isolation and receptor assay. Brain Res. 1983 Dec;313(1):7-18. PubMed PMID: 6661666.
17: Lorenzen A, Casley WL, Moon TW. A reverse transcription-polymerase chain reaction bioassay for avian vitellogenin mRNA. Toxicol Appl Pharmacol. 2001 Nov 1;176(3):169-80. PubMed PMID: 11714249.
18: Friedman WJ, McEwen BS, Toran-Allerand CD, Gerlach JL. Perinatal development of hypothalamic and cortical estrogen receptors in mouse brain: methodological aspects. Brain Res. 1983 Dec;313(1):19-27. PubMed PMID: 6661664.
19: Bahadur U, Ganjam GK, Vasudevan N, Kondaiah P. Estrogen regulation of chicken riboflavin carrier protein gene is mediated by ERE half sites without direct binding of estrogen receptor. Mol Cell Endocrinol. 2005 Feb 28;231(1-2):1-11. Epub 2005 Jan 23. PubMed PMID: 15713531.
20: de Boer W, Ab G, Gruber M. Estrogen receptor in chicken oviduct: receptor dissociation kinetics and transformation. J Steroid Biochem. 1985 Jul;23(1):9-18. PubMed PMID: 4021495.

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