BHFF

Details

Stereochemistry	RACEMIC
Molecular Formula	C17H21F3O3
Molecular Weight	330.342
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)(C)C1=CC2=C(OC(=O)C2(O)C(F)(F)F)C(=C1)C(C)(C)C

InChI

InChIKey=RVNOANDLZIIFHB-UHFFFAOYSA-N

InChI=1S/C17H21F3O3/c1-14(2,3)9-7-10(15(4,5)6)12-11(8-9)16(22,13(21)23-12)17(18,19)20/h7-8,22H,1-6H3

HIDE SMILES / InChI

Molecular Formula	C17H21F3O3
Molecular Weight	330.342
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18536733
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/20089372 | https://www.ncbi.nlm.nih.gov/pubmed/27108932 | https://www.ncbi.nlm.nih.gov/pubmed/26471422

RAC BHFF is the potent and selective GABAB receptor positive allosteric modulator that increases the potency and efficacy of GABA. Exhibits anxiolytic and anticonvulsant activity in vivo and is orally active. RAC BHFF reduces alcohol’s reinforcing properties in alcohol-preferring rats and adds further support to the hypothesis that the positive allosteric modulators of the GABAB receptor may constitute a novel class of agents with therapeutic potential for alcohol dependence.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-B receptor 32 Target ID: CHEMBL2111463 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18536733	Positive Allosteric Modulator 179		234.0 nM [EC50]

Conditions

Condition	Modality	Highest Phase	Product
Alcohol addiction 21 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20089372	Primary	Preclinical	Unknown Approved Use Unknown
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27108932	Primary	Preclinical	Unknown Approved Use Unknown
Convulsions 72 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26471422	Primary	Preclinical	Unknown Approved Use Unknown
Anxiety 267 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18536733	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Characterization of (R,S)-5,7-di-tert-butyl-3-hydroxy-3-trifluoromethyl-3H-benzofuran-2-one as a positive allosteric modulator of GABAB receptors.	2008 Jun	18536733
The positive allosteric modulator of the GABA(B) receptor, rac-BHFF, suppresses alcohol self-administration.	2010 Jun 1	20089372
Discriminative stimulus effects of the GABAB receptor-positive modulator rac-BHFF: comparison with GABAB receptor agonists and drugs of abuse.	2013 Mar	23275067
The positive allosteric GABAB receptor modulator rac-BHFF enhances baclofen-mediated analgesia in neuropathic mice.	2016 Sep	27108932

Patents

Sample Use Guides

In Vivo Use Guide

Infusion volume: 2 ml/kg at the doses of 50, 100, and 200 mg/kg

Route of Administration: Other

In Vitro Use Guide

rac-BHFF does not inhibit major cytochrome P450 isoenzymes (human liver microsomes IC50 values: 3A4 and 2D6: >50 uM; 2C9: 15.5 uM).

Substance Class	Chemical Created by `admin` on `Sat Dec 16 19:04:18 GMT 2023` Edited by `admin` on `Sat Dec 16 19:04:18 GMT 2023`
Record UNII	K3W3822BMV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BHFF

Code

English

5,7-Bis(1,1-dimethylethyl)-3-hydroxy-3(trifluoromethyl)-2(3H)-benzofuranone

Systematic Name

English

Code System Code Type Description

FDA UNII

K3W3822BMV