U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C17H20FNO4S
Molecular Weight 353.408
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AC-261066

SMILES

CCCCOCCOC1=C(C)SC(=N1)C2=CC=C(C(O)=O)C(F)=C2

InChI

InChIKey=HSAOETBFVAWNRP-UHFFFAOYSA-N
InChI=1S/C17H20FNO4S/c1-3-4-7-22-8-9-23-15-11(2)24-16(19-15)12-5-6-13(17(20)21)14(18)10-12/h5-6,10H,3-4,7-9H2,1-2H3,(H,20,21)

HIDE SMILES / InChI

Molecular Formula C17H20FNO4S
Molecular Weight 353.408
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

AC-261066 is an agonist of retinoic acid receptor subtype β isoform 2 (RARβ2). Administration of AC-261066 to either wt mice in a model of HFD-induced T2D or to ob/ob and db/db mice reduces hyperglycaemia, peripheral insulin resistance and body weight. Furthermore, AC-261066 dramatically reduces steatosis, lipid peroxidation and oxidative stress in the liver, pancreas and kidneys of obese, diabetic mice. AC-261066 also lowers levels of mRNAs involved in lipogenesis, such as sterol regulatory element-binding transcription factor 1 (SREBP1) and fatty acid synthase, and increases mRNAs that mediate mitochondrial fatty acid β-oxidation, such as CPT1α, in these organs. AC-261066 lowers triglyceride levels in these organs, and in muscle. AC-261066 should be useful drug for T2D therapy and for treatment of hepatic steatosis.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
8.0 null [pEC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Discovery of a potent, orally available, and isoform-selective retinoic acid beta2 receptor agonist.
2005 Dec 1
Aldo-keto reductases in retinoid metabolism: search for substrate specificity and inhibitor selectivity.
2013 Feb 25
Patents

Sample Use Guides

Mice: AC-261066 was administered in the drinking water of hyperglycemic HFD-fed wt mice for 8 days at a concentration of 0.03 mg/ml water. AC-261066-treated mice had an oral dose of approximately 5.4-mg/kg bw/day.
Route of Administration: Oral
The IC50 of AC-261066 to AKR1B10 is 51 ± 7uM. No inhibition of AC-261066 to AKR1B1 was detected when using up to 100 uM AC-261066 in the enzymatic assay.
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:44:18 GMT 2023
Edited
by admin
on Sat Dec 16 09:44:18 GMT 2023
Record UNII
LGF3F89BZP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AC-261066
Common Name English
BENZOIC ACID, 4-(4-(2-BUTOXYETHOXY)-5-METHYL-2-THIAZOLYL)-2-FLUORO-
Systematic Name English
Code System Code Type Description
CAS
870773-76-5
Created by admin on Sat Dec 16 09:44:18 GMT 2023 , Edited by admin on Sat Dec 16 09:44:18 GMT 2023
PRIMARY
EPA CompTox
DTXSID10236116
Created by admin on Sat Dec 16 09:44:18 GMT 2023 , Edited by admin on Sat Dec 16 09:44:18 GMT 2023
PRIMARY
PUBCHEM
11530459
Created by admin on Sat Dec 16 09:44:18 GMT 2023 , Edited by admin on Sat Dec 16 09:44:18 GMT 2023
PRIMARY
FDA UNII
LGF3F89BZP
Created by admin on Sat Dec 16 09:44:18 GMT 2023 , Edited by admin on Sat Dec 16 09:44:18 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY