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Ladarixin (sodium)

CAT: 0804-HY-19519A-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-19519A-01Size:5 mg
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Description
Ladarixin sodium (DF 2156A) is an orally active, allosteric non-competitive and dual CXCR1 and CXCR2 antagonist. Ladarixin sodium can be used for the research of COPD and asthma[1].
CAS Number
865625-56-5
Product Name Alternative
DF 2156A
UNSPSC
12352005
Target
CXCR
Type
Reference compound
Related Pathways
GPCR/G Protein; Immunology/Inflammation
Applications
COVID-19-immunoregulation
Field of Research
Infection; Inflammation/Immunology; Cancer
Assay Protocol
https://www.medchemexpress.com/ladarixin-sodium.html
Purity
99.84
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
O=S(C(F)(F)F)(OC1=CC=C([C@@H](C)C([N-]S(=O)(C)=O)=O)C=C1)=O.[Na+]
Molecular Formula
C11H11F3NNaO6S2
Molecular Weight
397.32
References & Citations
[1]Matheus Silverio Mattos, et al. CXCR1 and CXCR2 Inhibition by Ladarixin Improves Neutrophil-Dependent Airway Inflammation in Mice. Front Immunol. 2020 Oct 2;11:566953.|[2]Daria Marley Kemp, et al. Ladarixin, a dual CXCR1/2 inhibitor, attenuates experimental melanomas harboring different molecular defects by affecting malignant cells and tumor microenvironment. Oncotarget. 2017 Feb 28;8 (9) :14428-14442.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, sealed storage, away from moisture)
Scientific Category
Reference compound1
Clinical Information
Phase 3
Isoform
CXCR1; CXCR2

Chemical Information

Ladarixin (sodium)

Ladarixin Sodium is the sodium salt form of ladarixin, an orally bioavailable, small molecule, dual inhibitor of C-X-C motif chemokine receptors 1 (CXCR1) and 2 (CXCR2), with potential anti-inflammatory and antineoplastic activities. Upon oral administration, ladarixin selectively targets and allosterically binds to CXCR 1 and 2, thereby preventing CXCR1 and CXCR2 activation by their ligand and pro-inflammatory chemokine interleukin 8 (IL-8 or CXCL8). This inhibits CXCR1/2-mediated signaling, which inhibits inflammatory processes, reduces both the recruitment and migration of immunosuppressive myeloid-derived suppressor cells (MDSCs) and neutrophils in the tumor microenvironment (TME), and abrogates the immunosuppressive-induced nature of the TME. This allows effector cells, such as natural killer (NK) cells and cytotoxic T-lymphocytes (CTLs), to kill and eliminate cancer cells, and inhibits tumor cell migration, metastasis, angiogenesis and tumor cell proliferation. CXCR1 and 2, G protein-coupled receptor proteins located on myeloid cells and certain tumor cells, play key roles in the immunosuppressive nature of the TME, tumor metastasis, resistance to chemotherapeutic agents and myeloid cell suppression. They also play a key role in inflammation and their expression is elevated in several inflammatory-driven diseases.

CAS Number865625-56-5
PubChem CID23709380
IUPAC Namesodium methylsulfonyl-[(2R)-2-[4-(trifluoromethylsulfonyloxy)phenyl]propanoyl]azanide
Molecular FormulaC11H11F3NNaO6S2
Molecular Weight397.3
Topological Polar Surface Area112
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count10
Rotatable Bond Count5
Heavy Atom Count24
Formal Charge0
Complexity630
SMILES
C[C@H](C1=CC=C(C=C1)OS(=O)(=O)C(F)(F)F)C(=O)[N-]S(=O)(=O)C.[Na+]
InChI
InChI=1S/C11H12F3NO6S2.Na/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);/q;+1/p-1/t7-;/m1./s1
InChIKey
QICAUCDBOAKDNS-OGFXRTJISA-M
Chemical Structure
2D Structure
2D structure of Ladarixin (sodium)
CAS: 865625-56-5
CID: 23709380
Formula: C11H11F3NNaO6S2
MW: 397.3
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight397.3
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count10
Rotatable Bond Count5
Exact Mass396.98775819
Monoisotopic Mass396.98775819
Topological Polar Surface Area112 Ų
Heavy Atom Count24
Formal Charge0
Complexity630
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count2
Compound Is CanonicalizedYes

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A24308-100Ladarixin (DF 2156A free base) 100mg
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