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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 of PRINABEREL

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

Description

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 TargetPharmacologyConditionPotency
5.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Palliative
Unknown
Palliative
Unknown

Doses

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as victim

PubMed

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.