ERTEBEREL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H18O3
Molecular Weight	282.3337
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12CCC[C@@]1([H])C3=CC(O)=CC=C3O[C@H]2C4=CC=C(O)C=C4

InChI

InChIKey=XIESSJVMWNJCGZ-VKJFTORMSA-N

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

HIDE SMILES / InChI

Molecular Formula	C18H18O3
Molecular Weight	282.3337
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17034120
Curator's Comment: description was created based on several sources, including: http://adisinsight.springer.com/drugs/800031986 | https://www.ncbi.nlm.nih.gov/pubmed/27126081

Synthetic compound Erteberel (LY500307) is a highly potent and selective ERβ agonist; it has a 12-fold higher affinity for ERβ than ERα and exhibits 32-fold more functional potency. LY500307 was well tolerated in benign prostatic hypertrophy (BPH) patients with no side effects and it is currently being tested in phase 2 clinical trials for improving negative symptoms and cognitive impairment associated with Schizophrenia. In BPH clinical trial incidence of adverse events was comparable between treatment groups, and no clinically meaningful changes in laboratory tests were observed.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Estrogen receptor beta 110 Target ID: CHEMBL242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17034120	Agonist 2678		0.19 nM [Ki]
Estrogen receptor alpha 127 Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17034120	Agonist 2678		2.68 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Benign prostatic hyperplasia 28 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25348255	Primary	Phase II 1132	Unknown Approved Use Unknown
Schizophrenia 298 Sources: https://clinicaltrials.gov/ct2/show/NCT01874756	Primary	Phase II 1132	Unknown Approved Use Unknown
Glioblastoma 65 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27126081	Primary	Preclinical	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00DI6T	https://www.1pchem.com/search?query=1P00DI6T
AK Scientific	X7545	https://aksci.com/item_detail.php?cat=X7545
AstaTech	40678	http://astatechinc.com/CPSResult.php?CRNO=40678
Chem Scene	CS-0007402	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0007402
Debye Scientific	DA-33424	https://www.debyesci.com/index.php?id=product&ext[cno]=DA-33424
MedChem Express	HY-18295	https://www.medchemexpress.com/search.html?q=HY-18295&ft=&fa=&fp=
MolPort	MolPort-016-633-249	https://www.molport.com/shop/molecule-link/MolPort-016-633-249
Molnova	M14897	https://www.molnova.com/en/serch-list.html?keywords=M14897
MuseChem	I006706	https://www.musechem.com/product/I006706.html
Toronto Research Chemicals	E649895	https://www.trc-canada.com/product-detail/?CatNum=E649895
Toronto Research Chemicals	P839035	https://www.trc-canada.com/product-detail/?CatNum=P839035
eMolecules	32278104	https://orderbb.emolecules.com/search/#?query=32278104
mcule	MCULE-8155191339	https://mcule.com/MCULE-8155191339/
mcule	MCULE-8334599085	https://mcule.com/MCULE-8334599085/

PubMed

Title	Date	PubMed
Fertility and developmental toxicity assessment in rats and rabbits with LY500307, a selective estrogen receptor beta (ERβ) agonist.	2013 Oct	24323950
Estrogen receptor beta agonist LY500307 fails to improve symptoms in men with enlarged prostate secondary to benign prostatic hypertrophy.	2015 Mar	25348255
Selective Estrogen Receptor β Agonist LY500307 as a Novel Therapeutic Agent for Glioblastoma.	2016 Apr 29	27126081

Patents

Sample Use Guides

In Vivo Use Guide

1, 3, 10 and 25 mg once daily for 24 weeks

Route of Administration: Oral

In Vitro Use Guide

LY500307 (5 uM during 24 h) treatment significantly increased the percentage of cells in G2/M phase in U87, U251, LN229 and GBM10 cells when compared to vehicle.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:45:59 GMT 2023` Edited by `admin` on `Fri Dec 15 18:45:59 GMT 2023`
Record UNII	2ZUL6758TZ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ERTEBEREL

Official Name

English

erteberel [INN]

Common Name

English

ERTEBEREL [USAN]

Common Name

English

(3AS,4R,9BR)-4-(4-HYDROXYPHENYL)-1,2,3,3A,4,9B-HEXAHYDROCYCLOPENTA(C)(1)BENZOPYRAN-8-OL

Common Name

English

LY500307

Code

English

CYCLOPENTA(C)(1)BENZOPYRAN-8-OL, 1,2,3,3A,4,9B-HEXAHYDRO-4-(4-HYDROXYPHENYL)-, (3AS,4R,9BR)-

Common Name

English

LY-500307

Code

English

SERBA-1

Common Name

English

Erteberel [WHO-DD]

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID70201547