PRINABEREL

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H10FNO3
Molecular Weight	271.2432
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC2=C(OC(=N2)C3=CC=C(O)C(F)=C3)C(C=C)=C1

InChI

InChIKey=MQIMZDXIAHJKQP-UHFFFAOYSA-N

InChI=1S/C15H10FNO3/c1-2-8-5-10(18)7-12-14(8)20-15(17-12)9-3-4-13(19)11(16)6-9/h2-7,18-19H,1H2

HIDE SMILES / InChI

Molecular Formula	C15H10FNO3
Molecular Weight	271.2432
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18097065 | https://www.ncbi.nlm.nih.gov/pubmed/20556817 | https://www.ncbi.nlm.nih.gov/pubmed/14500559

Prinaberel is a selective agonist of estrogen receptor beta. Although initially developed for the treatment of endometriosis, the drug was also shown to be effective in vitro in other inflammatory diseases. Phase II clinical studied revealed its effectiveness in case of Crohn's disease and endometriosis, but the drug failed to demonstrate antiinflammatory efficacy in RA patients.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Estrogen receptor beta 113 Target ID: CHEMBL242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14500559	Agonist 2752		5.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Endometriosis 32 Sources: https://www.clinicaltrials.gov/ct2/show/NCT00110487	Primary	Phase II 1147	Unknown Approved Use Unknown
Rheumatoid arthritis 320 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20556817	Palliative	Phase II 1147	Unknown Approved Use Unknown
Crohn's disease 64 Sources: https://clinicaltrials.gov/ct2/show/NCT00245947	Palliative	Phase I 438	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
75 mg 1 times / day multiple, oral Dose: 75 mg, 1 times / day Route: oral Route: multiple Dose: 75 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20556817	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/20556817	Sources: https://pubmed.ncbi.nlm.nih.gov/20556817

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645842#sid=440681730	inconclusive [IC50 26.837 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645840#sid=440681730	yes [IC50 21.3174 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645841#sid=440681730	yes [IC50 6.7412 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346987#sid=363677934	no

PubMed

Title	Date	PubMed
Selectivity of natural, synthetic and environmental estrogens for zebrafish estrogen receptors.	2014-10-01	25106122
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006-11	16497524
Evaluation of an estrogen receptor-beta agonist in animal models of human disease.	2003-10	14500559

Patents

Sample Use Guides

In Vivo Use Guide

In phase II patients received 5, 25, or 75 mg of prinaberel for 12 weeks.

Route of Administration: Oral

In Vitro Use Guide

Human U2OS osteosarcoma cell lines stably expressing a tetracycline regulated ERalpha or beta were treated with 1 ug/ml doxycycline to induce ER expression and then with increasing concentrations of prinaberel (10(-6)-10(-11) M) to test drug effect on proinflammatory genes.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:14:24 GMT 2025` Edited by `admin` on `Mon Mar 31 18:14:24 GMT 2025`
Record UNII	A9C8MNF7CA
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PRINABEREL

Official Name

English

ERB-041

Preferred Name

English

PF-00913086

Code

English

PRINABEREL [USAN]

Common Name

English

7-Ethenyl-2-(3-fluoro-4-hydroxyphenyl)benzoxazol-5-ol

Systematic Name

English

prinaberel [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1821