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

MedKoo CAT#: 319762

CAS#: 533884-09-2

Description: Erteberel, also known as LY500307, is a selective estrogen receptor beta (ERβ) agonist that was developed for the treatment of benign prostatic hyperplasia. LY500307 was well tolerated in BPH patients with LUTS at doses up to 25 mg once daily for 24 weeks. The study was terminated early because of inadequate efficacy.

Chemical Structure

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Erteberel
CAS# 533884-09-2
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 319762
Name: Erteberel
CAS#: 533884-09-2
Chemical Formula: C18H18O3
Exact Mass: 282.13
Molecular Weight: 282.339
Elemental Analysis: C, 76.57; H, 6.43; O, 17.00

Price and Availability

Size Price Availability Quantity
1mg USD 240 2 Weeks
5mg USD 540 2 Weeks
10mg USD 885 2 Weeks
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Synonym: LY500307; LY-500307; LY 500307; Erteberel

IUPAC/Chemical Name: (3aS,4R,9bR)-4-(4-hydroxyphenyl)-1,2,3,3a,4,9b-hexahydrocyclopenta[c]chromen-8-ol

InChi Key: XIESSJVMWNJCGZ-VKJFTORMSA-N

InChi Code: InChI=1S/C18H18O3/c19-12-6-4-11(5-7-12)18-15-3-1-2-14(15)16-10-13(20)8-9-17(16)21-18/h4-10,14-15,18-20H,1-3H2/t14-,15+,18+/m1/s1

SMILES Code: OC1=CC=C2C([C@@](CCC3)([H])[C@@]3([H])[C@H](C4=CC=C(O)C=C4)O2)=C1

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, not in water

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: Erteberel (LY500307) is an estrogen receptor beta (ERβ) agonist with Ki and EC50 of 1.54 nM and 3.61 nM, respectively.
In vitro activity: Treatment with LY500307 significantly reduced the viability of various GBM cell lines in a dose-dependent manner. In contrast, viability of normal astrocytes was not affected at the tested doses, suggesting that LY500307 has tumor cell–specific activity (Fig. 1a). Cell Titer-Glo luminescent cell viability assays revealed that LY500307 reduced the viability of various patient-derived GBM cells in a dose dependent manner (Fig. 1b). As shown in Fig. 1c, LY500307 significantly reduced the colony formation of U87 and U251 GBM cells. LY500307 significantly induced Annexin V-positive apoptotic cells in U87, U251 (Fig. 1d,e) and patient derived primary GBM (GBM10) cells (Supplementary Fig. 1b). Collectively, these results suggested that LY500307 has potential to selectively reduce cell viability, decrease survival and induce apoptosis of GBM cells. Reference: Sci Rep. 2016; 6: 24185. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4850367/
In vivo activity: In detail, the number of lung metastatic nodules in mice of the 4T1 model treated with LY500307 was significantly lower than that in mice of the 4T1 model treated with control (Fig. 1B; P < 0.05). Moreover, the overall survival in the LY500307 treatment group of the 4T1 murine model was significantly longer than that of the control group (Fig. 1C; P < 0.05). Reference: Proc Natl Acad Sci U S A. 2018 Apr 17; 115(16): E3673–E3681. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5910874/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 30.0 106.26
DMF 30.0 106.26
Ethanol 30.0 106.26

Preparing Stock Solutions

The following data is based on the product molecular weight 282.34 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.

Recalculate based on batch purity %
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. Sareddy GR, Li X, Liu J, Viswanadhapalli S, Garcia L, Gruslova A, Cavazos D, Garcia M, Strom AM, Gustafsson JA, Tekmal RR, Brenner A, Vadlamudi RK. Selective Estrogen Receptor β Agonist LY500307 as a Novel Therapeutic Agent for Glioblastoma. Sci Rep. 2016 Apr 29;6:24185. doi: 10.1038/srep24185. PMID: 27126081; PMCID: PMC4850367. 2. Zhao L, Huang S, Mei S, Yang Z, Xu L, Zhou N, Yang Q, Shen Q, Wang W, Le X, Lau WB, Lau B, Wang X, Yi T, Zhao X, Wei Y, Warner M, Gustafsson JÅ, Zhou S. Pharmacological activation of estrogen receptor beta augments innate immunity to suppress cancer metastasis. Proc Natl Acad Sci U S A. 2018 Apr 17;115(16):E3673-E3681. doi: 10.1073/pnas.1803291115. Epub 2018 Mar 28. PMID: 29592953; PMCID: PMC5910874. 3. Sareddy GR, Li X, Liu J, Viswanadhapalli S, Garcia L, Gruslova A, Cavazos D, Garcia M, Strom AM, Gustafsson JA, Tekmal RR, Brenner A, Vadlamudi RK. Selective Estrogen Receptor β Agonist LY500307 as a Novel Therapeutic Agent for Glioblastoma. Sci Rep. 2016 Apr 29;6:24185. doi: 10.1038/srep24185. PMID: 27126081; PMCID: PMC4850367.
In vitro protocol: 1. Sareddy GR, Li X, Liu J, Viswanadhapalli S, Garcia L, Gruslova A, Cavazos D, Garcia M, Strom AM, Gustafsson JA, Tekmal RR, Brenner A, Vadlamudi RK. Selective Estrogen Receptor β Agonist LY500307 as a Novel Therapeutic Agent for Glioblastoma. Sci Rep. 2016 Apr 29;6:24185. doi: 10.1038/srep24185. PMID: 27126081; PMCID: PMC4850367.
In vivo protocol: 1. Zhao L, Huang S, Mei S, Yang Z, Xu L, Zhou N, Yang Q, Shen Q, Wang W, Le X, Lau WB, Lau B, Wang X, Yi T, Zhao X, Wei Y, Warner M, Gustafsson JÅ, Zhou S. Pharmacological activation of estrogen receptor beta augments innate immunity to suppress cancer metastasis. Proc Natl Acad Sci U S A. 2018 Apr 17;115(16):E3673-E3681. doi: 10.1073/pnas.1803291115. Epub 2018 Mar 28. PMID: 29592953; PMCID: PMC5910874. 2. Sareddy GR, Li X, Liu J, Viswanadhapalli S, Garcia L, Gruslova A, Cavazos D, Garcia M, Strom AM, Gustafsson JA, Tekmal RR, Brenner A, Vadlamudi RK. Selective Estrogen Receptor β Agonist LY500307 as a Novel Therapeutic Agent for Glioblastoma. Sci Rep. 2016 Apr 29;6:24185. doi: 10.1038/srep24185. PMID: 27126081; PMCID: PMC4850367.

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1: Wu W, Warner M, Wang L, He WW, Zhao R, Guan X, Botero C, Huang B, Ion C, Coombes C, Gustafsson JA. Drivers and suppressors of triple-negative breast cancer. Proc Natl Acad Sci U S A. 2021 Aug 17;118(33):e2104162118. doi: 10.1073/pnas.2104162118. PMID: 34389675; PMCID: PMC8379974.


2: Karakas B, Aka Y, Giray A, Temel SG, Acikbas U, Basaga H, Gul O, Kutuk O. Mitochondrial estrogen receptors alter mitochondrial priming and response to endocrine therapy in breast cancer cells. Cell Death Discov. 2021 Jul 22;7(1):189. doi: 10.1038/s41420-021-00573-2. PMID: 34294688; PMCID: PMC8298581.


3: Sareddy GR, Pratap UP, Venkata PP, Zhou M, Alejo S, Viswanadhapalli S, Tekmal RR, Brenner AJ, Vadlamudi RK. Activation of estrogen receptor beta signaling reduces stemness of glioma stem cells. Stem Cells. 2021 May;39(5):536-550. doi: 10.1002/stem.3337. Epub 2021 Feb 1. PMID: 33470499.


4: Sareddy GR, Li X, Liu J, Viswanadhapalli S, Garcia L, Gruslova A, Cavazos D, Garcia M, Strom AM, Gustafsson JA, Tekmal RR, Brenner A, Vadlamudi RK. Selective Estrogen Receptor β Agonist LY500307 as a Novel Therapeutic Agent for Glioblastoma. Sci Rep. 2016 Apr 29;6:24185. doi: 10.1038/srep24185. PMID: 27126081; PMCID: PMC4850367.


5: Zhao L, Huang S, Mei S, Yang Z, Xu L, Zhou N, Yang Q, Shen Q, Wang W, Le X, Lau WB, Lau B, Wang X, Yi T, Zhao X, Wei Y, Warner M, Gustafsson JÅ, Zhou S. Pharmacological activation of estrogen receptor beta augments innate immunity to suppress cancer metastasis. Proc Natl Acad Sci U S A. 2018 Apr 17;115(16):E3673-E3681. doi: 10.1073/pnas.1803291115. Epub 2018 Mar 28. PMID: 29592953; PMCID: PMC5910874.


6: Hu L, Jin Y, Li YG, Borel A. Population pharmacokinetic/pharmacodynamic assessment of pharmacological effect of a selective estrogen receptor β agonist on total testosterone in healthy men. Clin Pharmacol Drug Dev. 2015 Jul;4(4):305-14. doi: 10.1002/cpdd.184. Epub 2015 Jun 8. PMID: 27136911.


7: Hilbish KG, Breslin WJ, Johnson JT, Sloter ED. Fertility and developmental toxicity assessment in rats and rabbits with LY500307, a selective estrogen receptor beta (ERβ) agonist. Birth Defects Res B Dev Reprod Toxicol. 2013 Oct;98(5):400-15. doi: 10.1002/bdrb.21083. Epub 2013 Dec 9. PMID: 24323950.


8: Roehrborn CG, Spann ME, Myers SL, Serviss CR, Hu L, Jin Y. Estrogen receptor beta agonist LY500307 fails to improve symptoms in men with enlarged prostate secondary to benign prostatic hypertrophy. Prostate Cancer Prostatic Dis. 2015 Mar;18(1):43-8. doi: 10.1038/pcan.2014.43. Epub 2014 Nov 4. PMID: 25348255.