LADARIXIN

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C11H12F3NO6S2
Molecular Weight	375.341
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@H](C(=O)NS(C)(=O)=O)C1=CC=C(OS(=O)(=O)C(F)(F)F)C=C1

InChI

InChIKey=DDLPYOCJHQSVSZ-SSDOTTSWSA-N

InChI=1S/C11H12F3NO6S2/c1-7(10(16)15-22(2,17)18)8-3-5-9(6-4-8)21-23(19,20)11(12,13)14/h3-7H,1-2H3,(H,15,16)/t7-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C11H12F3NO6S2
Molecular Weight	375.341
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/mesh/67511776 | https://www.ncbi.nlm.nih.gov/pubmed/16613761 | https://www.ncbi.nlm.nih.gov/pubmed/28129639

LADARIXIN is a dual inhibitor of chemokine receptors CXCR1 and CXCR2. It inhibits human polymorphonuclear leukocyte (PMN) migration to chemokine CXCL8 in vitro and prevents PMN infiltration and tissue damage in several models of cerebral ischemia/reperfusion in vivo. It is under development for the treatment of type 1 diabetes.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
C-X-C chemokine receptor type 1 2 Target ID: P25024\|\|\|Q6IN95 Gene ID: 3577.0 Gene Symbol: CXCR1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21718305 \| https://www.ncbi.nlm.nih.gov/pubmed/16613761	Antagonist 2849
C-X-C chemokine receptor type 2 3 Target ID: P25025 Gene ID: 3579.0 Gene Symbol: CXCR2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21718305 \| https://www.ncbi.nlm.nih.gov/pubmed/16613761	Antagonist 2849

C_max

Value	Dose	Co-administered	Analyte	Population
67.345 μg/mL CLINICAL TRIAL https://classic.clinicaltrials.gov/ct2/show/results/NCT04854642	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		LADARIXIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
95.982 μg/mL CLINICAL TRIAL https://classic.clinicaltrials.gov/ct2/show/results/NCT04854642	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		LADARIXIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
1533.432 μg × h/mL CLINICAL TRIAL https://classic.clinicaltrials.gov/ct2/show/results/NCT04854642	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		LADARIXIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
1677.749 μg × h/mL CLINICAL TRIAL https://classic.clinicaltrials.gov/ct2/show/results/NCT04854642	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		LADARIXIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
16.918 h CLINICAL TRIAL https://classic.clinicaltrials.gov/ct2/show/results/NCT04854642	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		LADARIXIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
17.087 h CLINICAL TRIAL https://classic.clinicaltrials.gov/ct2/show/results/NCT04854642	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		LADARIXIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
0.2% EXPERIMENT https://dom-pubs.onlinelibrary.wiley.com/doi/full/10.1111/dom.14770	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		LADARIXIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

PubMed

Title	Date	PubMed
Ladarixin, a dual CXCR1/2 inhibitor, attenuates experimental melanomas harboring different molecular defects by affecting malignant cells and tumor microenvironment.	2017-02-28	28129639
Receptor binding mode and pharmacological characterization of a potent and selective dual CXCR1/CXCR2 non-competitive allosteric inhibitor.	2012-01	21718305
Design of noncompetitive interleukin-8 inhibitors acting on CXCR1 and CXCR2.	2007-08-23	17665889
Development of a systemically-active dual CXCR1/CXCR2 allosteric inhibitor and its efficacy in a model of transient cerebral ischemia in the rat.	2006-03	16613761
Predicting human serum albumin affinity of interleukin-8 (CXCL8) inhibitors by 3D-QSPR approach.	2005-04-07	15801837

Substance Class	Chemical Created by `admin` on `Mon Mar 31 20:25:02 GMT 2025` Edited by `admin` on `Mon Mar 31 20:25:02 GMT 2025`
Record UNII	DEH7Q6472O
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

METHANESULFONIC ACID, 1,1,1-TRIFLUORO-, 4-((1R)-1-METHYL-2-((METHYLSULFONYL)AMINO)-2-OXOETHYL)PHENYL ESTER

Preferred Name

English

LADARIXIN

Official Name

English

METHANESULFONIC ACID, TRIFLUORO-, 4-((1R)-1-METHYL-2-((METHYLSULFONYL)AMINO)-2-OXOETHYL)PHENYL ESTER

Common Name

English

(R)-(-)-N-(2-(4-(TRIFLUOROMETHANESULFONYLOXY)PHENYL)PROPIONYL)METHANESULFONAMIDE

Systematic Name

English

ladarixin [INN]

Common Name

English

Ladarixin [WHO-DD]

Common Name

English

4-((2R)-1-OXO-1-(METHANESULFONAMIDO)PROPAN-2-YL)PHENYL TRIFLUOROMETHANESULFONATE

Systematic Name

English

Code System Code Type Description

NCI_THESAURUS

C170087