LG 100268

Details

Stereochemistry	ACHIRAL
Molecular Formula	C24H29NO2
Molecular Weight	363.4926
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=C(C=C2C(=C1)C(C)(C)CCC2(C)C)C3(CC3)C4=CC=C(C=N4)C(O)=O

InChI

InChIKey=SLXTWXQUEZSSTJ-UHFFFAOYSA-N

InChI=1S/C24H29NO2/c1-15-12-18-19(23(4,5)9-8-22(18,2)3)13-17(15)24(10-11-24)20-7-6-16(14-25-20)21(26)27/h6-7,12-14H,8-11H2,1-5H3,(H,26,27)

HIDE SMILES / InChI

Molecular Formula	C24H29NO2
Molecular Weight	363.4926
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7636877
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/10951538 | https://www.ncbi.nlm.nih.gov/pubmed/12374698 | https://www.ncbi.nlm.nih.gov/pubmed/18483313

LG 100268 (LGD 1268) is retionid X receptor agonist, originated in Ligand Pharmaceuticals. LG 100268 demonstrated efficacy in preclinical models of obesity, breast and lung cancer.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Retinoid X receptor 4 Target ID: CHEMBL2363070 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7636877	Agonist 2678		3.0 nM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Obesity 203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10951538	Primary	Preclinical	Unknown Approved Use Unknown
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12374698	Primary	Preclinical	Unknown Approved Use Unknown
Lung cancer 69 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18483313	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Synthesis of high specific activity [3H]-9-cis-retinoic acid and its application for identifying retinoids with unusual binding properties.	1994 Feb 4	8308867
Activation of specific RXR heterodimers by an antagonist of RXR homodimers.	1996 Oct 3	8837780
Growth inhibition of myeloid leukemia cells by troglitazone, a ligand for peroxisome proliferator activated receptor gamma, and retinoids.	1999 Nov	10536188
The effects of rexinoids and rosiglitazone on body weight and uncoupling protein isoform expression in the Zucker fa/fa rat.	2000 Dec	11145125
Therapeutic applications for ligands of retinoid receptors.	2000 Jan	10637371
The pregnane X receptor: a promiscuous xenobiotic receptor that has diverged during evolution.	2000 Jan	10628745
Insulin sensitizer, troglitazone, directly inhibits aromatase activity in human ovarian granulosa cells.	2000 May 19	10814527
Prevention and treatment of experimental breast cancer with the combination of a new selective estrogen receptor modulator, arzoxifene, and a new rexinoid, LG 100268.	2002 Oct	12374698
Retinoid X receptor (RXR) agonist-induced antagonism of farnesoid X receptor (FXR) activity due to absence of coactivator recruitment and decreased DNA binding.	2003 Mar 21	12519787
Molecular cloning and characterization of two novel human RXR alpha splice variants.	2004 Sep	15544927
Coactivation of liver receptor homologue-1 by peroxisome proliferator-activated receptor gamma coactivator-1alpha on aromatase promoter II and its inhibition by activated retinoid X receptor suggest a novel target for breast-specific antiestrogen therapy.	2005 Dec 15	16357189
Thiazolidinediones inhibit proliferation of microvascular and macrovascular cells by a PPARgamma-independent mechanism.	2005 Mar	15729575
Trialkyltin compounds bind retinoid X receptor to alter human placental endocrine functions.	2005 Oct	15941851
Organotin compounds enhance 17beta-hydroxysteroid dehydrogenase type I activity in human choriocarcinoma JAr cells: potential promotion of 17beta-estradiol biosynthesis in human placenta.	2006 Apr 28	16513093
Identification of biomarkers modulated by the rexinoid LGD1069 (bexarotene) in human breast cells using oligonucleotide arrays.	2006 Dec 15	17178900
Neu-induced retroviral rat mammary carcinogenesis: a novel chemoprevention model for both hormonally responsive and nonresponsive mammary carcinomas.	2006 Jul 1	16818667
Receptor-selective retinoids inhibit the growth of normal and malignant breast cells by inducing G1 cell cycle blockade.	2006 Mar	16273314
PPARalpha activators and fasting induce the expression of adipose differentiation-related protein in liver.	2006 May	16489205
In silico prediction of pregnane X receptor activators by machine learning approaches.	2007 Jan	17003167
Tributyltin synergizes with 20-hydroxyecdysone to produce endocrine toxicity.	2011 Sep	21673327
Mechanisms of action of hormone-sensitive lipase in mouse Leydig cells: its role in the regulation of the steroidogenic acute regulatory protein.	2013 Mar 22	23362264
Tributyltin engages multiple nuclear receptor pathways and suppresses osteogenesis in bone marrow multipotent stromal cells.	2015 Jun 15	25932594

Patents

Sample Use Guides

In Vivo Use Guide

In obesity studies LG100268 was dosed orally once daily at 20 mg/kg to Zucker rats.

Route of Administration: Oral

In Vitro Use Guide

Receptor binding assays for RXRs were performed using [3H]-9-cis-RA as the radioligand for RXRs. EC50 values we determined by contransfection assay performed with CV-1 cells.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:18:23 GMT 2023` Edited by `admin` on `Fri Dec 15 18:18:23 GMT 2023`
Record UNII	UVU4X1103P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LG 100268

Common Name

English

LG-268

Code

English

AGN-192620

Code

English

6-(1-(3,5,5,8,8-PENTAMETHYL-5,6,7,8-TETRAHYDRONAPHTHALEN-2-YL)CYCLOPROPYL)NICOTINIC ACID

Systematic Name

English

LGD 1268

Code

English

3-PYRIDINECARBOXYLIC ACID, 6-(1-(5,6,7,8-TETRAHYDRO-3,5,5,8,8-PENTAMETHYL-2-NAPHTHALENYL CYCLOPROPYL)-

Common Name

English

CD-3127

Code

English

LGD 100268

Code

English

CD 3127

Code

English

LG100268

Code

English

LG268

Common Name

English

SC-211737

Code

English

LG 268

Code

English

ALRT 268

Code

English

LG-100268

Code

English

LGD-1268

Code

English

AGN 192620

Code

English

ALRT-268

Code

English

LGD-100268

Code

English

Code System Code Type Description

FDA UNII

UVU4X1103P