LY 117018 | CAS#63676-25-5 | estrogen receptor modulator

MedKoo Cat#: 525465 | Name: LY 117018

Description:

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

LY 117018 is a selective estrogen receptor modulator. LY 117018 is a raloxifene analog.

Chemical Structure

LY 117018

CAS#63676-25-5

Theoretical Analysis

MedKoo Cat#: 525465

Name: LY 117018

CAS#: 63676-25-5

Chemical Formula: C27H25NO4S

Exact Mass: 459.1504

Molecular Weight: 459.56

Elemental Analysis: C, 70.57; H, 5.48; N, 3.05; O, 13.93; S, 6.98

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Synonym

LY 117018; LY117018; LY-117018.

IUPAC/Chemical Name

Methanone, (6-hydroxy-2-(4-hydroxyphenyl)benzo(b)thien-3-yl)(4-(2-(1-pyrrolidinyl)ethoxy)phenyl)-

InChi Key

JLERVPBPJHKRBJ-UHFFFAOYSA-N

InChi Code

InChI=1S/C27H25NO4S/c29-20-7-3-19(4-8-20)27-25(23-12-9-21(30)17-24(23)33-27)26(31)18-5-10-22(11-6-18)32-16-15-28-13-1-2-14-28/h3-12,17,29-30H,1-2,13-16H2

SMILES Code

O=C(C1=C(C2=CC=C(O)C=C2)SC3=CC(O)=CC=C31)C4=CC=C(OCCN5CCCC5)C=C4

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

>2 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

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

LY117018, a Raloxifene analog, is a selective estrogen receptor modulator.

In vitro activity:

E2 and LY117018 treatments of T47D cells also caused differential effects on intracellular structures. Thus, LY117018 treatment induces changes in the level/activity of p53 and pRb and ultrastructure of T47D cells. Importantly, LY11708 inhibits estrogen-induced cell proliferation while mimicking E2 actions on p53 induction and pRb phosphorylation. Reference: Horm Mol Biol Clin Investig. 2010 Aug 1;2(1):211-7. https://pubmed.ncbi.nlm.nih.gov/25961194/

In vivo activity:

This study investigated whether the osteocyte-sparing effect of 17beta-estradiol can be mimicked by the SERM LY 117018 in a rat model of OVX. Treatment of OVX animals with either 17beta-estradiol at a dose rate of 0.125 mg/kg/day or LY 117018 at a dose rate of 3 mg/kg/day prevented these increases in osteocyte apoptosis similarly. Reference: Calcif Tissue Int. 2007 Aug;81(2):139-44. https://pubmed.ncbi.nlm.nih.gov/17638036/

Preparing Stock Solutions

The following data is based on the product molecular weight 459.56 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

Formulation protocol:

1. Dinda S, Sanchez A, Moudgil VK. Effects of LY117018 (a SERM analog of raloxifene) on tumor suppressor proteins and proliferation of breast cancer cells. Horm Mol Biol Clin Investig. 2010 Aug 1;2(1):211-7. doi: 10.1515/HMBCI.2010.021. PMID: 25961194. 2. Baumann KH, Klusmeier E, Eggemann I, Reinartz S, Almeroth A, Kalder M, Wagner U. Effects of celecoxib and ly117018 combination on human breast cancer cells in vitro. Breast Cancer (Auckl). 2009 Apr 7;3:23-34. doi: 10.4137/bcbcr.s2291. PMID: 21556247; PMCID: PMC3086307. 3. Huber C, Collishaw S, Mosley JR, Reeve J, Noble BS. Selective estrogen receptor modulator inhibits osteocyte apoptosis during abrupt estrogen withdrawal: implications for bone quality maintenance. Calcif Tissue Int. 2007 Aug;81(2):139-44. doi: 10.1007/s00223-007-9049-6. Epub 2007 Jul 20. PMID: 17638036. 4. Hodsman AB, Watson PH, Drost D, Holdsworth D, Thornton M, Hock J, Bryant H, Fraher LJ. Assessment of maintenance therapy with reduced doses of PTH(1-34) in combination with a raloxifene analogue (LY117018) following anabolic therapy in the ovariectomized rat. Bone. 1999 May;24(5):451-5. doi: 10.1016/s8756-3282(99)00015-0. PMID: 10321904.

In vitro protocol:

In vivo protocol:

1. Huber C, Collishaw S, Mosley JR, Reeve J, Noble BS. Selective estrogen receptor modulator inhibits osteocyte apoptosis during abrupt estrogen withdrawal: implications for bone quality maintenance. Calcif Tissue Int. 2007 Aug;81(2):139-44. doi: 10.1007/s00223-007-9049-6. Epub 2007 Jul 20. PMID: 17638036. 2. Hodsman AB, Watson PH, Drost D, Holdsworth D, Thornton M, Hock J, Bryant H, Fraher LJ. Assessment of maintenance therapy with reduced doses of PTH(1-34) in combination with a raloxifene analogue (LY117018) following anabolic therapy in the ovariectomized rat. Bone. 1999 May;24(5):451-5. doi: 10.1016/s8756-3282(99)00015-0. PMID: 10321904.

1: Wutzl A, Gruber R, Brozek W, Hofbauer G, Lernbass I, Brosch S, Pietschmann P. Mechanisms involved in the inhibition of osteoclast generation by the benzothiophene SERM LY117018. Wien Klin Wochenschr. 2010 Nov;122(21-22):626-32. doi: 10.1007/s00508-010-1469-z. Epub 2010 Oct 15. PubMed PMID: 20938747. 2: Dinda S, Sanchez A, Moudgil VK. Effects of LY117018 (a SERM analog of raloxifene) on tumor suppressor proteins and proliferation of breast cancer cells. Horm Mol Biol Clin Investig. 2010 Aug 1;2(1):211-7. doi: 10.1515/HMBCI.2010.021. PubMed PMID: 25961194. 3: Baumann KH, Klusmeier E, Eggemann I, Reinartz S, Almeroth A, Kalder M, Wagner U. Effects of celecoxib and ly117018 combination on human breast cancer cells in vitro. Breast Cancer (Auckl). 2009 Apr 7;3:23-34. PubMed PMID: 21556247; PubMed Central PMCID: PMC3086307. 4: Yu J, Eto M, Kozaki K, Akishita M, Okabe T, Ouchi Y. Raloxifene analogue LY117018 suppresses oxidative stress-induced endothelial cell apoptosis through activation of ERK1/2 signaling pathway. Eur J Pharmacol. 2008 Jul 28;589(1-3):32-6. doi: 10.1016/j.ejphar.2008.04.052. Epub 2008 May 5. PubMed PMID: 18541231. 5: Nobuzane T, Tashiro S, Kudo Y. Morphologic effects of epithelial ion channels on the mouse uterus: differences between raloxifene analog (LY117018) and estradiol treatments. Am J Obstet Gynecol. 2008 Oct;199(4):363.e1-6. doi: 10.1016/j.ajog.2008.03.047. Epub 2008 May 5. PubMed PMID: 18456231. 6: Levine L. Tamoxifen and the Rafoxifene analog LY117018: their effects on arachidonic acid release from cells in culture and on prostaglandin I2 production by rat liver cells. BMC Cancer. 2004 Aug 13;4:49. PubMed PMID: 15310397; PubMed Central PMCID: PMC514706. 7: Tulipano G, Bonfanti C, Poiesi C, Burattin A, Turazzi S, Barone G, Cozzi R, Bollati A, Valle D, Giustina A. Effects of the selective estrogen receptor modulator LY117018 on growth hormone secretion: In vitro studies. Metabolism. 2004 May;53(5):563-70. PubMed PMID: 15131758. 8: McMurray R, Islamov R, Murashov AK. Raloxifene analog LY117018 enhances the regeneration of sciatic nerve in ovariectomized female mice. Brain Res. 2003 Aug 1;980(1):140-5. PubMed PMID: 12865169. 9: Hernández G, Hernández-Jiménez JG, Guelmes P, Sánchez-Criado JE, Bellido C, Martínez-Morales JR, Prieto L, Marín F, Glidewell-Kenney C, López FJ, Alonso R. Effect of treatment with the selective oestrogen receptor modulator LY117018-HCl on pituitary sensitivity to GnRH and subsequent ovulation. Reproduction. 2003 Apr;125(4):597-606. PubMed PMID: 12683930. 10: Hisamoto K, Ohmichi M, Kanda Y, Adachi K, Nishio Y, Hayakawa J, Mabuchi S, Takahashi K, Tasaka K, Miyamoto Y, Taniguchi N, Murata Y. Induction of endothelial nitric-oxide synthase phosphorylation by the raloxifene analog LY117018 is differentially mediated by Akt and extracellular signal-regulated protein kinase in vascular endothelial cells. J Biol Chem. 2001 Dec 14;276(50):47642-9. Epub 2001 Oct 10. PubMed PMID: 11595733. 11: Schafer JM, Lee ES, Dardes RC, Bentrem D, O'Regan RM, De Los Reyes A, Jordan VC. Analysis of cross-resistance of the selective estrogen receptor modulators arzoxifene (LY353381) and LY117018 in tamoxifen-stimulated breast cancer xenografts. Clin Cancer Res. 2001 Aug;7(8):2505-12. PubMed PMID: 11489833. 12: Russell JC, McKendrick JD, Dubé PJ, Dolphin PJ, Radomski MW. Effects of LY117018 and the estrogen analogue, 17alpha-ethinylestradiol, on vascular reactivity, platelet aggregation, and lipid metabolism in the insulin-resistant JCR:LA-cp male rat: role of nitric oxide. J Cardiovasc Pharmacol. 2001 Jan;37(1):119-28. PubMed PMID: 11152369. 13: Essmann M, Larsen B. Protective effect of the selective estrogen receptor modulator LY117018 on rat vaginal Candida albicans colonization. Gynecol Obstet Invest. 2000;49(1):57-61. PubMed PMID: 10629375. 14: Hodsman AB, Watson PH, Drost D, Holdsworth D, Thornton M, Hock J, Bryant H, Fraher LJ. Assessment of maintenance therapy with reduced doses of PTH(1-34) in combination with a raloxifene analogue (LY117018) following anabolic therapy in the ovariectomized rat. Bone. 1999 May;24(5):451-5. PubMed PMID: 10321904. 15: Hodsman AB, Drost D, Fraher LJ, Holdsworth D, Thornton M, Hock J, Bryant H, Watson PH. The addition of a raloxifene analog (LY117018) allows for reduced PTH(1-34) dosing during reversal of osteopenia in ovariectomized rats. J Bone Miner Res. 1999 May;14(5):675-9. PubMed PMID: 10320515. 16: Li X, Takahashi M, Kushida K, Inoue T. The preventive and interventional effects of raloxifene analog (LY117018 HCL) on osteopenia in ovariectomized rats. J Bone Miner Res. 1998 Jun;13(6):1005-10. PubMed PMID: 9626632. 17: Rahimian R, Laher I, Dube G, van Breemen C. Estrogen and selective estrogen receptor modulator LY117018 enhance release of nitric oxide in rat aorta. J Pharmacol Exp Ther. 1997 Oct;283(1):116-22. PubMed PMID: 9336315. 18: Picariello L, Fiorelli G, Benvenuti S, Brandi ML, Galli G, Malentacchi C, Montali E, Bigozzi U, Ficari F, Tonelli F. In vitro bioeffects of the antiestrogen LY117018 on desmoid tumor and colon cancer cells. Anticancer Res. 1997 May-Jun;17(3C):2099-104. PubMed PMID: 9216671. 19: Bowman AR, Sass DA, Marshall I, Ma YF, Liang H, Jee WS, Epstein S. Raloxifene analog (LY117018 HCL) ameliorates cyclosporin A-induced osteopenia in oophorectomized rats. J Bone Miner Res. 1996 Aug;11(8):1191-8. PubMed PMID: 8854256. 20: Kym PR, Anstead GM, Pinney KG, Wilson SR, Katzenellenbogen JA. Molecular structures, conformational analysis, and preferential modes of binding of 3-aroyl-2-arylbenzo[b]thiophene estrogen receptor ligands: LY117018 and aryl azide photoaffinity labeling analogs. J Med Chem. 1993 Nov 26;36(24):3910-22. PubMed PMID: 8254621.