LX-2931

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C9H15N3O5
Molecular Weight	245.2325
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C\C(=N/O)C1=NC=C(N1)[C@@H](O)[C@H](O)[C@H](O)CO

InChI

InChIKey=AMXVYJYMZLDINS-RSWLNLDNSA-N

InChI=1S/C9H15N3O5/c1-4(12-17)9-10-2-5(11-9)7(15)8(16)6(14)3-13/h2,6-8,13-17H,3H2,1H3,(H,10,11)/b12-4+/t6-,7-,8-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C9H15N3O5
Molecular Weight	245.2325
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21090716 | http://www.lexpharma.com/media-center/news/112-lexicon-initiates-phase-2-clinical-trial-of-lx2931-in-patients-with-rheumatoid-arthritis- | http://www.lexpharma.com/pipeline | https://www.ncbi.nlm.nih.gov/pubmed/31028959 | https://www.ncbi.nlm.nih.gov/pubmed/27663991 | https://www.ncbi.nlm.nih.gov/pubmed/21556483

LX 2931 (LX 3305) is an inhibitor of sphingosine 1-phosphate (S1P) lyase. S1P lyase is an enzyme identified as a promising new target on a pathway associated with regulation of the immune system. Lexicon Pharmaceuticals, Inc. was developing LX 2931 for the treatment of rheumatoid arthritis. LX 2931 has disappeared from the pipeline of Lexicon Pharmaceuticals, Inc. In preclinical studies LX 2931 was effective against experimental cerebral malaria, lung inflammation in a F508del CFTR murine cystic fibrosis model and osteoporosis.

Originator

Approval Year

PubMed

Title	Date	PubMed
Agonist-induced activation of the S1P receptor 2 constitutes a novel osteoanabolic therapy for the treatment of osteoporosis in mice.	2019-08	31028959
Inhibition of sphingosine 1-phosphate lyase for the treatment of rheumatoid arthritis: discovery of (E)-1-(4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl)-1H-imidazol-2-yl)ethanone oxime (LX2931) and (1R,2S,3R)-1-(2-(isoxazol-3-yl)-1H-imidazol-4-yl)butane-1,2,3,4-tetraol (LX2932).	2010-12-23	21090716

Patents

Sample Use Guides

In Vivo Use Guide

Phase I clinical trials indicated that LX 2931, the first clinically studied inhibitor of S1PL, produced a dose-dependent and reversible reduction of circulating lymphocytes and was well tolerated at dose levels of up to 180 mg daily. Lexicon Pharmaceuticals, Inc. was planning the Phase 2 clinical trial is designed as a 12-week, randomized, double-blind, placebo-controlled study to evaluate the safety and tolerability of LX2931 and its effects on symptoms associated with rheumatoid arthritis. Three dose levels will be evaluated: a 70 mg dose, a 110 mg dose and a 150 mg dose, each administered once daily.

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Mon Mar 31 23:11:23 GMT 2025` Edited by `admin` on `Mon Mar 31 23:11:23 GMT 2025`
Record UNII	C5AGI979T7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LX-2931

Common Name

English

LX 2931

Preferred Name

English

1-(4-((1R,2S,3R)-1,2,3,4-TETRAHYDROXYBUTYL)-1H-IMIDAZOL-2-YL)ETHANONE OXIME

Systematic Name

English

LX-3305

Code

English

LX3305

Code

English

LX2931

Code

English

ETHANONE, 1-(5-((1R,2S,3R)-1,2,3,4-TETRAHYDROXYBUTYL)-1H-IMIDAZOL-2-YL)-, OXIME, (1E)-

Systematic Name

English

Code System Code Type Description

PUBCHEM

135564845