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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=CC(C=C)=C2OC(=NC2=C1)C3=CC(F)=C(O)C=C3

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

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

Curator's Comment: # Wyeth Research

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1216.0 nM [IC50]
5.0 nM [IC50]
5.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse 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: Page: p.1590
unhealthy, ADULT
n = 74
Health Status: unhealthy
Condition: rheumatoid arthritis
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 74
Sources: Page: p.1590
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
PubMed

PubMed

TitleDatePubMed
Evaluation of an estrogen receptor-beta agonist in animal models of human disease.
2003 Oct
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Selectivity of natural, synthetic and environmental estrogens for zebrafish estrogen receptors.
2014 Oct 1
Patents

Sample Use Guides

In phase II patients received 5, 25, or 75 mg of prinaberel for 12 weeks.
Route of Administration: Oral
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 Fri Dec 15 15:57:14 UTC 2023
Edited
by admin
on Fri Dec 15 15:57:14 UTC 2023
Record UNII
A9C8MNF7CA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PRINABEREL
INN   USAN  
USAN   INN  
Official 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
ERB-041
Code English
Classification Tree Code System Code
NCI_THESAURUS C1821
Created by admin on Fri Dec 15 15:57:14 UTC 2023 , Edited by admin on Fri Dec 15 15:57:14 UTC 2023
Code System Code Type Description
INN
8771
Created by admin on Fri Dec 15 15:57:14 UTC 2023 , Edited by admin on Fri Dec 15 15:57:14 UTC 2023
PRIMARY
DRUG BANK
DB06832
Created by admin on Fri Dec 15 15:57:14 UTC 2023 , Edited by admin on Fri Dec 15 15:57:14 UTC 2023
PRIMARY
SMS_ID
300000034321
Created by admin on Fri Dec 15 15:57:14 UTC 2023 , Edited by admin on Fri Dec 15 15:57:14 UTC 2023
PRIMARY
CAS
524684-52-4
Created by admin on Fri Dec 15 15:57:14 UTC 2023 , Edited by admin on Fri Dec 15 15:57:14 UTC 2023
PRIMARY
EPA CompTox
DTXSID301030354
Created by admin on Fri Dec 15 15:57:14 UTC 2023 , Edited by admin on Fri Dec 15 15:57:14 UTC 2023
PRIMARY
WIKIPEDIA
Prinaberel
Created by admin on Fri Dec 15 15:57:14 UTC 2023 , Edited by admin on Fri Dec 15 15:57:14 UTC 2023
PRIMARY
PUBCHEM
656954
Created by admin on Fri Dec 15 15:57:14 UTC 2023 , Edited by admin on Fri Dec 15 15:57:14 UTC 2023
PRIMARY
USAN
QQ-08
Created by admin on Fri Dec 15 15:57:14 UTC 2023 , Edited by admin on Fri Dec 15 15:57:14 UTC 2023
PRIMARY
FDA UNII
A9C8MNF7CA
Created by admin on Fri Dec 15 15:57:14 UTC 2023 , Edited by admin on Fri Dec 15 15:57:14 UTC 2023
PRIMARY
NCI_THESAURUS
C76959
Created by admin on Fri Dec 15 15:57:14 UTC 2023 , Edited by admin on Fri Dec 15 15:57:14 UTC 2023
PRIMARY
ChEMBL
CHEMBL450940
Created by admin on Fri Dec 15 15:57:14 UTC 2023 , Edited by admin on Fri Dec 15 15:57:14 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST
200 FOLD SELECTIVITY OVER ALPHA RECEPTOR
AGONIST
IC50
BINDER->LIGAND
BINDING
IC50
Related Record Type Details
ACTIVE MOIETY