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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 of REPARIXIN

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

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

Targets

Primary TargetPharmacologyConditionPotency
5.6 nM [IC50]
PubMed

PubMed

TitleDatePubMed
Inhibition of interleukin-8 (CXCL8/IL-8) responses by repertaxin, a new inhibitor of the chemokine receptors CXCR1 and CXCR2.
2005 Feb 1
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
2-Arylpropionic CXC chemokine receptor 1 (CXCR1) ligands as novel noncompetitive CXCL8 inhibitors.
2005 Jun 30
Down-regulation of CXCR2 on neutrophils in severe sepsis is mediated by inducible nitric oxide synthase-derived nitric oxide.
2007 Mar 1
Patents

Patents

Substance Class Chemical
Created
by admin
on Thu Jul 06 21:30:58 UTC 2023
Edited
by admin
on Thu Jul 06 21:30:58 UTC 2023
Record UNII
U604E1NB3K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
REPARIXIN
INN   MART.   USAN  
INN   USAN  
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
Created by admin on Thu Jul 06 21:30:59 UTC 2023 , Edited by admin on Thu Jul 06 21:30:59 UTC 2023
NCI_THESAURUS C63817
Created by admin on Thu Jul 06 21:30:59 UTC 2023 , Edited by admin on Thu Jul 06 21:30:59 UTC 2023
EU-Orphan Drug EU/3/11/912
Created by admin on Thu Jul 06 21:30:59 UTC 2023 , Edited by admin on Thu Jul 06 21:30:59 UTC 2023
FDA ORPHAN DRUG 162802
Created by admin on Thu Jul 06 21:30:59 UTC 2023 , Edited by admin on Thu Jul 06 21:30:59 UTC 2023
Code System Code Type Description
PUBCHEM
9838712
Created by admin on Thu Jul 06 21:30:59 UTC 2023 , Edited by admin on Thu Jul 06 21:30:59 UTC 2023
PRIMARY
CAS
266359-83-5
Created by admin on Thu Jul 06 21:30:59 UTC 2023 , Edited by admin on Thu Jul 06 21:30:59 UTC 2023
PRIMARY
USAN
RR-70
Created by admin on Thu Jul 06 21:30:59 UTC 2023 , Edited by admin on Thu Jul 06 21:30:59 UTC 2023
PRIMARY
EVMPD
SUB130481
Created by admin on Thu Jul 06 21:30:59 UTC 2023 , Edited by admin on Thu Jul 06 21:30:59 UTC 2023
PRIMARY
EPA CompTox
DTXSID6046509
Created by admin on Thu Jul 06 21:30:59 UTC 2023 , Edited by admin on Thu Jul 06 21:30:59 UTC 2023
PRIMARY
FDA UNII
U604E1NB3K
Created by admin on Thu Jul 06 21:30:59 UTC 2023 , Edited by admin on Thu Jul 06 21:30:59 UTC 2023
PRIMARY
DRUG BANK
DB12614
Created by admin on Thu Jul 06 21:30:59 UTC 2023 , Edited by admin on Thu Jul 06 21:30:59 UTC 2023
PRIMARY
ChEMBL
CHEMBL191413
Created by admin on Thu Jul 06 21:30:59 UTC 2023 , Edited by admin on Thu Jul 06 21:30:59 UTC 2023
PRIMARY
MESH
C490707
Created by admin on Thu Jul 06 21:30:59 UTC 2023 , Edited by admin on Thu Jul 06 21:30:59 UTC 2023
PRIMARY
SMS_ID
100000156558
Created by admin on Thu Jul 06 21:30:59 UTC 2023 , Edited by admin on Thu Jul 06 21:30:59 UTC 2023
PRIMARY
NCI_THESAURUS
C66515
Created by admin on Thu Jul 06 21:30:59 UTC 2023 , Edited by admin on Thu Jul 06 21:30:59 UTC 2023
PRIMARY
INN
8224
Created by admin on Thu Jul 06 21:30:59 UTC 2023 , Edited by admin on Thu Jul 06 21:30:59 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
NONCOMPETIVE BLOCKER OF THE ACTIVATION OF CXCR1 BY IL-8. DOES NOT BLOCK BINDING. PMN MIGRATION ASSAY.
ALLOSTERIC INHIBITOR
IC50
TARGET -> INHIBITOR
NONCOMPETIVE
ALLOSTERIC INHIBITOR
IC50
Related Record Type Details
ACTIVE MOIETY