RU 58668 | CAS#151555-47-4 | antiestrogen

MedKoo Cat#: 461531 | Name: RU 58668

Description:

WARNING: This product is for research use only, not for human or veterinary use.

RU 58668 is a steroidal antiestrogen that induces a long-term regression of human mammary MCF-7 tumors implanted in nude mice.

Chemical Structure

RU 58668

CAS#151555-47-4

Theoretical Analysis

MedKoo Cat#: 461531

Name: RU 58668

CAS#: 151555-47-4

Chemical Formula: C34H43F5O5S

Exact Mass: 658.2751

Molecular Weight: 658.76

Elemental Analysis: C, 61.99; H, 6.58; F, 14.42; O, 12.14; S, 4.87

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

RU 58668; RU58668; RU-58668;

IUPAC/Chemical Name

(8S,9R,11S,13S,14S,17S)-13-methyl-11-(4-((5-((4,4,5,5,5-pentafluoropentyl)sulfonyl)pentyl)oxy)phenyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol

InChi Key

SDCUWFRXMLQNCS-LFAPAAFUSA-N

InChi Code

InChI=1S/C34H43F5O5S/c1-32-21-28(31-26-13-9-24(40)20-23(26)8-12-27(31)29(32)14-15-30(32)41)22-6-10-25(11-7-22)44-17-3-2-4-18-45(42,43)19-5-16-33(35,36)34(37,38)39/h6-7,9-11,13,20,27-31,40-41H,2-5,8,12,14-19,21H2,1H3/t27-,28+,29-,30-,31+,32-/m0/s1

SMILES Code

C[C@@]12[C@@H](O)CC[C@@]1([H])[C@]3([H])CCC4=C(C=CC(O)=C4)[C@@]3([H])[C@@H](C5=CC=C(OCCCCCS(=O)(CCCC(F)(F)C(F)(F)F)=O)C=C5)C2

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 658.76 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Ameller T, Marsaud V, Legrand P, Gref R, Renoir JM. Pure antiestrogen RU 58668-loaded nanospheres: morphology, cell activity and toxicity studies. Eur J Pharm Sci. 2004 Feb;21(2-3):361-70. PubMed PMID: 14757510. 2: Maillard S, Gauduchon J, Marsaud V, Gouilleux F, Connault E, Opolon P, Fattal E, Sola B, Renoir JM. Improved antitumoral properties of pure antiestrogen RU 58668-loaded liposomes in multiple myeloma. J Steroid Biochem Mol Biol. 2006 Jul;100(1-3):67-78. Epub 2006 Jun 5. PubMed PMID: 16753295. 3: Van de Velde P, Nique F, Planchon P, Prévost G, Brémaud J, Hameau MC, Magnien V, Philibert D, Teutsch G. RU 58668: further in vitro and in vivo pharmacological data related to its antitumoral activity. J Steroid Biochem Mol Biol. 1996 Dec;59(5-6):449-57. PubMed PMID: 9010350. 4: Devin-Leclerc J, Meng X, Delahaye F, Leclerc P, Baulieu EE, Catelli MG. Interaction and dissociation by ligands of estrogen receptor and Hsp90: the antiestrogen RU 58668 induces a protein synthesis-dependent clustering of the receptor in the cytoplasm. Mol Endocrinol. 1998 Jun;12(6):842-54. PubMed PMID: 9626660. 5: Vagell ME, McGinnis MY. Effects of the antiestrogen, RU 58668, on female sexual behavior in rats. Brain Res Bull. 1996;41(2):121-4. PubMed PMID: 8879676. 6: Vagell ME, McGinnis MY. Inhibition of brain oestrogen receptors by RU 58668. J Neuroendocrinol. 1997 Oct;9(10):797-800. PubMed PMID: 9355049. 7: Ameller T, Marsaud V, Legrand P, Gref R, Barratt G, Renoir JM. Polyester-poly(ethylene glycol) nanoparticles loaded with the pure antiestrogen RU 58668: physicochemical and opsonization properties. Pharm Res. 2003 Jul;20(7):1063-70. PubMed PMID: 12880293. 8: Van de Velde P, Nique F, Brémaud J, Hameau MC, Philibert D, Teutsch G. Exploration of the therapeutic potential of the antiestrogen RU 58668 in breast cancer treatment. Ann N Y Acad Sci. 1995 Jun 12;761:164-75. PubMed PMID: 7625719. 9: Ameller T, Marsaud V, Legrand P, Gref R, Renoir JM. In vitro and in vivo biologic evaluation of long-circulating biodegradable drug carriers loaded with the pure antiestrogen RU 58668. Int J Cancer. 2003 Sep 1;106(3):446-54. PubMed PMID: 12845687. 10: Vagell ME, McGinnis MY. The role of gonadal steroid receptor activation in the restoration of sociosexual behavior in adult male rats. Horm Behav. 1998 Jun;33(3):163-79. PubMed PMID: 9698500. 11: Estrada-Camarena E, López-Rubalcava C, Fernández-Guasti A. Facilitating antidepressant-like actions of estrogens are mediated by 5-HT1A and estrogen receptors in the rat forced swimming test. Psychoneuroendocrinology. 2006 Sep;31(8):905-14. Epub 2006 Jul 13. PubMed PMID: 16843610. 12: Van de Velde P, Nique F, Bouchoux F, Brémaud J, Hameau MC, Lucas D, Moratille C, Viet S, Philibert D, Teutsch G. RU 58,668, a new pure antiestrogen inducing a regression of human mammary carcinoma implanted in nude mice. J Steroid Biochem Mol Biol. 1994 Feb;48(2-3):187-96. PubMed PMID: 8142294. 13: Müller V, Jensen EV, Knabbe C. Partial antagonism between steroidal and nonsteroidal antiestrogens in human breast cancer cell lines. Cancer Res. 1998 Jan 15;58(2):263-7. PubMed PMID: 9443403. 14: Fog CK, Christensen IJ, Lykkesfeldt AE. Characterization of a human breast cancer cell line, MCF-7/RU58R-1, resistant to the pure antiestrogen RU 58,668. Breast Cancer Res Treat. 2005 May;91(2):133-44. PubMed PMID: 15868441. 15: Gauduchon J, Seguin A, Marsaud V, Clay D, Renoir JM, Sola B. Pure antiestrogen-induced G1-arrest in myeloma cells results from the reduced kinase activity of cyclin D3/CDK6 complexes whereas apoptosis is mediated by endoplasmic reticulum-dependent caspases. Int J Cancer. 2008 May 1;122(9):2130-41. doi: 10.1002/ijc.23310. PubMed PMID: 18183592. 16: Marsaud V, Gougelet A, Maillard S, Renoir JM. Various phosphorylation pathways, depending on agonist and antagonist binding to endogenous estrogen receptor alpha (ERalpha), differentially affect ERalpha extractability, proteasome-mediated stability, and transcriptional activity in human breast cancer cells. Mol Endocrinol. 2003 Oct;17(10):2013-27. Epub 2003 Jul 10. PubMed PMID: 12855746. 17: Newton CJ, Bilko D, Pappa S, Atkin SL. Dexamethasone blocks antioestrogen- and oxidant-induced death of pituitary tumour cells. J Endocrinol. 2001 May;169(2):249-61. PubMed PMID: 11312142. 18: Tena-Sempere M, Navarro VM, Mayen A, Bellido C, Sánchez-Criado JE. Regulation of estrogen receptor (ER) isoform messenger RNA expression by different ER ligands in female rat pituitary. Biol Reprod. 2004 Mar;70(3):671-8. Epub 2003 Nov 12. PubMed PMID: 14613904. 19: Laïos I, Journe F, Laurent G, Nonclercq D, Toillon RA, Seo HS, Leclercq G. Mechanisms governing the accumulation of estrogen receptor alpha in MCF-7 breast cancer cells treated with hydroxytamoxifen and related antiestrogens. J Steroid Biochem Mol Biol. 2003 Nov;87(2-3):207-21. PubMed PMID: 14672741. 20: Kandouz M, Siromachkova M, Jacob D, Chretien Marquet B, Therwath A, Gompel A. Antagonism between estradiol and progestin on Bcl-2 expression in breast-cancer cells. Int J Cancer. 1996 Sep 27;68(1):120-5. PubMed PMID: 8895551.