LX-1031

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C28H25F3N4O4
Molecular Weight	538.5177
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC(=CC=C1)C2=CC=C(C=C2)[C@@H](OC3=CC(=NC(N)=N3)C4=CC=C(C[C@H](N)C(O)=O)C=C4)C(F)(F)F

InChI

InChIKey=XNMUICFMGGQSMZ-WIOPSUGQSA-N

InChI=1S/C28H25F3N4O4/c1-38-21-4-2-3-20(14-21)17-9-11-19(12-10-17)25(28(29,30)31)39-24-15-23(34-27(33)35-24)18-7-5-16(6-8-18)13-22(32)26(36)37/h2-12,14-15,22,25H,13,32H2,1H3,(H,36,37)(H2,33,34,35)/t22-,25+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C28H25F3N4O4
Molecular Weight	538.5177
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21154152
Curator's Comment: Description was created based on several sources, including http://www.lexpharma.com/media-center/news/151-lexicon-initiates-phase-2-clinical-trial-of-lx1031-in-patients-with-irritable-bowel-syndrome-

LX-1031, being developed by Lexicon Pharmaceuticals, is an oral, small-molecule tryptophan 5-hydroxylase (TPH) inhibitor that reduces 5-HT synthesis peripherally. LX-1031 is being developed for the potential treatment of diarrhea-predominant irritable bowel syndrome (IBS-D), which is characterized by excess 5-HT. In preclinical studies, LX-1031 dose-dependently reduced expression of 5-HT in the duodenum, jejunum and ileum, but had no effect on brain 5-HT levels. It was in Phase 2 clinical trial, but later development of LX-1031 was discontinued.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Tryptophan 5-hydroxylase 1 1 Target ID: CHEMBL5689 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21159063 \| https://www.ncbi.nlm.nih.gov/pubmed/21154152	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Irritable bowel syndrome 60 Sources: https://clinicaltrials.gov/ct2/show/NCT00813098	Primary		Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
384 ng/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/21159063	1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered:		LX-1031 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED

T_1/2

Value	Dose	Co-administered	Analyte	Population
20 h REVIEW https://pubmed.ncbi.nlm.nih.gov/21159063	1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered:		LX-1031 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00IIUB	https://www.1pchem.com/search?query=1P00IIUB
AK Scientific	3790AH	https://aksci.com/item_detail.php?cat=3790AH
ApexBio Technology	A3565	https://www.apexbt.com/catalogsearch/result/?q=A3565
BLD Pharm	BD417821	http://www.bldpharm.com/search/Search.html?keyword=BD417821
Debye Scientific	DB-079969	https://www.debyesci.com/index.php?id=product&ext[cno]=DB-079969
MedChem Express	HY-13041	https://www.medchemexpress.com/search.html?q=HY-13041&ft=&fa=&fp=
MolPort	MolPort-039-139-706	https://www.molport.com/shop/molecule-link/MolPort-039-139-706
Molnova	M16780	https://www.molnova.com/en/serch-list.html?keywords=M16780
MuseChem	I005632	https://www.musechem.com/product/I005632.html
eMolecules	275092007	https://orderbb.emolecules.com/search/#?query=275092007
eMolecules	300764699	https://orderbb.emolecules.com/search/#?query=300764699
eMolecules	44811701	https://orderbb.emolecules.com/search/#?query=44811701
mcule	MCULE-2440716989	https://mcule.com/MCULE-2440716989/
mcule	MCULE-4013770264	https://mcule.com/MCULE-4013770264/

PubMed

Title	Date	PubMed
LX-1031, a tryptophan 5-hydroxylase inhibitor that reduces 5-HT levels for the potential treatment of irritable bowel syndrome.	2010 Dec	21154152
LX-1031, a tryptophan 5-hydroxylase inhibitor, and its potential in chronic diarrhea associated with increased serotonin.	2011 Mar	21159063

Patents

Sample Use Guides

In Vivo Use Guide

a 250 mg dose and a 1,000 mg dose, each administered four times daily.

Route of Administration: Oral

In Vitro Use Guide

In vitro, inhibition of TPH1 occurred in 10(-8) -10(-7) M/L range.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 02:48:14 GMT 2023` Edited by `admin` on `Sat Dec 16 02:48:14 GMT 2023`
Record UNII	J08E1J78GK
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

LX-1031

Common Name

English

L-PHENYLALANINE, 4-(2-AMINO-6-((1R)-2,2,2-TRIFLUORO-1-(3'-METHOXY(1,1'-BIPHENYL)-4-YL)ETHOXY)-4-PYRIMIDINYL)-

Systematic Name

English

LX1031

Code

English

Code System Code Type Description

DRUG BANK

DB05199