REPARIXIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C14H21NO3S
Molecular Weight	283.386
Optical Activity	( - )
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)CC1=CC=C(C=C1)[C@@H](C)C(=O)NS(C)(=O)=O

InChI

InChIKey=KQDRVXQXKZXMHP-LLVKDONJSA-N

InChI=1S/C14H21NO3S/c1-10(2)9-12-5-7-13(8-6-12)11(3)14(16)15-19(4,17)18/h5-8,10-11H,9H2,1-4H3,(H,15,16)/t11-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C14H21NO3S
Molecular Weight	283.386
Charge	0
Count

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

Description
Sources: https://pubchem.ncbi.nlm.nih.gov/compound/Reparixin | https://www.ncbi.nlm.nih.gov/pubmed/28415590|https://clinicaltrials.gov/ct2/show/NCT01861054

Reparixin is a CXC chemokine receptor type 1 (CXCR1) and type 2 (CXCR2) inhibitor. This compound has potential antineoplastic activity. It can be administered orally, binds to CXCR1 (overexpressed on cancer stem cells) and prevents its activation by its ligand interleukin 8. This might result in the death of cancer cells and inhibition of cell progression and metastasis. Reparixin also inhibits CXCR2 activation, possibly reducing both neutrophil recruitment and vascular permeability during inflammation or injury. A phase II clinical trial evaluating the effects of orally administered reparixin on cancer stem cells in the primary tumor and the tumoral microenvironment in an early breast cancer population was terminated. Reparixin has also been suggested as a novel potential therapeutic strategy for aggressive forms of thyroid cancer, based on results of a xenotransplantation study in mice.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Interleukin-8 receptor A 4 Target ID: CHEMBL4029 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17665889	Inhibitor 8146		5.6 nM [IC50]

PubMed

Title	Date	PubMed
Noncompetitive allosteric inhibitors of the inflammatory chemokine receptors CXCR1 and CXCR2: prevention of reperfusion injury.	2004 Aug 10	15282370
Repertaxin, a novel inhibitor of rat CXCR2 function, inhibits inflammatory responses that follow intestinal ischaemia and reperfusion injury.	2004 Sep	15302676
Inhibition of interleukin-8 (CXCL8/IL-8) responses by repertaxin, a new inhibitor of the chemokine receptors CXCR1 and CXCR2.	2005 Feb 1	15652230
Neutrophil recruitment in the reperfused-injured rat liver was effectively attenuated by repertaxin, a novel allosteric noncompetitive inhibitor of CXCL8 receptors: a therapeutic approach for the treatment of post-ischemic hepatic syndromes.	2005 Jul-Sep	16164828
2-Arylpropionic CXC chemokine receptor 1 (CXCR1) ligands as novel noncompetitive CXCL8 inhibitors.	2005 Jun 30	15974585
Inhibition of the chemokine receptor CXCR2 prevents kidney graft function deterioration due to ischemia/reperfusion.	2005 May	15840022
Down-regulation of CXCR2 on neutrophils in severe sepsis is mediated by inducible nitric oxide synthase-derived nitric oxide.	2007 Mar 1	17138957

Patents

Substance Class	Chemical Created by `admin` on `Sun Dec 18 17:49:42 UTC 2022` Edited by `admin` on `Sun Dec 18 17:49:42 UTC 2022`
Record UNII	U604E1NB3K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

REPARIXIN

Official Name

English

DF 1681Y

Code

English

Reparixin [WHO-DD]

Common Name

English

REPARIXIN [USAN]

Common Name

English

REPARIXIN [MART.]

Common Name

English

BENZENEACETAMIDE, .ALPHA.-METHYL-4-(2-METHYLPROPYL)-N-(METHYLSULFONYL)-, (.ALPHA.R)-

Systematic Name

English

REPERTAXIN

Common Name

English

reparixin [INN]

Common Name

English

DF-1681Y

Code

English

DF1681Y

Code

English

Classification Tree Code System Code

FDA ORPHAN DRUG

373312