ERTIPROTAFIB

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C31H27BrO3S
Molecular Weight	559.513
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=C(C)C2=C(S1)C(Br)=C3C=CC=CC3=C2C4=CC(C)=C(O[C@H](CC5=CC=CC=C5)C(O)=O)C(C)=C4

InChI

InChIKey=FONCZICQWCUXEB-RUZDIDTESA-N

InChI=1S/C31H27BrO3S/c1-17-14-22(15-18(2)29(17)35-25(31(33)34)16-21-10-6-5-7-11-21)27-23-12-8-9-13-24(23)28(32)30-26(27)19(3)20(4)36-30/h5-15,25H,16H2,1-4H3,(H,33,34)/t25-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C31H27BrO3S
Molecular Weight	559.513
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17407812 | https://www.ncbi.nlm.nih.gov/pubmed/15475571 | https://adisinsight.springer.com/drugs/800016671

Ertiprotafib was originally developed as an inhibitor of PTP1B. Multiple targets of ertiprotafib, in addition to PTP1B inhibition, have been suggested including dual PPARalpha/PPARgamma agonism and IKK-beta inhibition. It normalized the plasma glucose and insulin levels in diabetic animal models and progressed to a phase II clinical trial for the treatment of Type 2 diabetes mellitus. Ertiprotafib development has been discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Tyrosine-protein phosphatase non-receptor type 1 4 Target ID: P18031 Gene ID: 5770.0 Gene Symbol: PTPN1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24148325	Inhibitor 8297		0.87 µM [IC50]
Inhibitor of nuclear factor kappa-B kinase subunit beta 5 Target ID: O14920 Gene ID: 3551.0 Gene Symbol: IKBKB Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17407812	Inhibitor 8297		400.0 nM [IC50]

PubMed

Title	Date	PubMed
Ertiprotafib improves glycemic control and lowers lipids via multiple mechanisms.	2005 Jan	15475571
Effects of ertiprotafib on hepatic cytochrome P450 and peroxisomal enzymes in rats and dogs, and in rat and human primary hepatocytes.	2007 Jan	17178630
PTP1B inhibitor Ertiprotafib is also a potent inhibitor of IkappaB kinase beta (IKK-beta).	2007 May 15	17407812
2-Acyl-tetrahydroisoquinoline-3-carboxylic acids: lead compounds with triple actions, peroxisome proliferator-activated receptor α/γ agonist and protein-tyrosine phosphatase 1B inhibitory activities.	2011	21720040
Discovery of novel PTP1B inhibitors via pharmacophore-oriented scaffold hopping from Ertiprotafib.	2013 Dec 1	24148325

Substance Class	Chemical Created by `admin` on `Sat Dec 16 16:50:49 UTC 2023` Edited by `admin` on `Sat Dec 16 16:50:49 UTC 2023`
Record UNII	5TPM2EB426
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ERTIPROTAFIB

Official Name

English

(2R)-2-[4-(9-Bromo-2,3-dimethylnaphtho[2,3-b]thiophen-4-yl)-2,6-dimethylphenoxy]-3-phenylpropionic acid

Systematic Name

English

PTP-112

Code

English

ERTIPROTAFIB [USAN]

Common Name

English

ertiprotafib [INN]

Common Name

English

BENZENEPROPANOIC ACID, .ALPHA.-(4-(9-BROMO-2,3-DIMETHYLNAPHTHO(2,3-B)THIEN-4-YL)-2,6-DIMETHYLPHENOXY)-, (.ALPHA.R)-

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29711