Details of the Drug

General Information of Drug (ID: DMVBA7I)

Drug Name
Reparixin
Synonyms
reparixin; repertaxin; 266359-83-5; UNII-U604E1NB3K; CHEMBL191413; U604E1NB3K; DF 1681Y; (R)-2-(4-isobutylphenyl)-N-(methylsulfonyl)propanamide; Reparixin [USAN:INN]; (2R)-2-[4-(2-methylpropyl)phenyl]-N-methylsulfonylpropanamide; (2R)-2-(4-(2-Methylpropyl)phenyl)-N-methylsulfonylpropanamide; 2-(4-isobutylphenyl)propionylmethanesulfonamide; Reparixin (USAN/INN); DSSTox_RID_81678; DSSTox_CID_26509; DSSTox_GSID_46509; ZINC8717; SCHEMBL1884299; GTPL8498; DTXSID6046509; EX-A2461; DF-1681Y; BCP10635; Tox21_112272; BDBM50169045; Repertaxin; Reparixin [INN]; Reparixin (INN/USAN); (R)-2-(4-isobutylphenyl)propionylmethanesulfonamide; RAPARIXIN
Indication
Disease Entry ICD 11 Status REF
Pancreatic islet transplantation failure NE84 Phase 3 [1]
Graft rejection in heart transplantation NE84 Phase 2 [2]
Ischemia-reperfusion injury DB98.B Phase 2 [2]
lung transplantation PK80.20 Phase 2 [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 283.39
Logarithm of the Partition Coefficient (xlogp) 2.9
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
Chemical Identifiers
Formula
C14H21NO3S
IUPAC Name
(2R)-2-[4-(2-methylpropyl)phenyl]-N-methylsulfonylpropanamide
Canonical SMILES
C[C@H](C1=CC=C(C=C1)CC(C)C)C(=O)NS(=O)(=O)C
InChI
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
InChIKey
KQDRVXQXKZXMHP-LLVKDONJSA-N
Cross-matching ID
PubChem CID
9838712
ChEBI ID
CHEMBL191413
CAS Number
266359-83-5
UNII
U604E1NB3K
DrugBank ID
DB12614
TTD ID
D0LJ1B
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
C-X-C chemokine receptor type 1 (CXCR1) TTMWT8Z CXCR1_HUMAN Modulator [3]
C-X-C chemokine receptor type 2 (CXCR2) TT30C9G CXCR2_HUMAN Modulator [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Interleukin-8 (CXCL8) OTS7T5VH IL8_HUMAN Gene/Protein Processing [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Pancreatic islet transplantation failure
ICD Disease Classification NE84
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
C-X-C chemokine receptor type 1 (CXCR1) DTT CXCR1 1.29E-01 0.12 0.32
C-X-C chemokine receptor type 1 (CXCR1) DTT CXCR1 1.66E-01 0.07 0.2
C-X-C chemokine receptor type 2 (CXCR2) DTT CXCR2 8.82E-01 -0.23 -0.21
C-X-C chemokine receptor type 2 (CXCR2) DTT CXCR2 1.34E-01 0.21 0.19
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
2 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 8498).
3 2-Arylpropionic CXC chemokine receptor 1 (CXCR1) ligands as novel noncompetitive CXCL8 inhibitors. J Med Chem. 2005 Jun 30;48(13):4312-31.
4 Inhibition of interleukin-8 (CXCL8/IL-8) responses by repertaxin, a new inhibitor of the chemokine receptors CXCR1 and CXCR2. Biochem Pharmacol. 2005 Feb 1;69(3):385-94. doi: 10.1016/j.bcp.2004.10.007. Epub 2004 Dec 9.