AZD5069 - Moligand™, ≥98% , Antagonist of CXCR1;Antagonist of CXCR2, CAS No.878385-84-3, Antagonist of CXCR1;Antagonist of CXCR2

CAS: 878385-84-3 Cat. No.: A413565 Molecular Weight: 476.52 EC Number: 688-153-5

GRADE & PURITY Moligand™, ≥98%

Synonyms

C18H22F2N4O5S2 | N-[2-[[(2,3-Difluorophenyl)methyl]thio]-6-[(1R,2S)-2,3-dihydroxy-1-methylpropoxy]-4-pyrimidinyl]-1-azetidinesulfonamide | HY-19855 | AKOS037649275 | N-(2-((2,3-difluorobenzyl)thio)-6-(((2R,3S)-3,4-dihydroxybutan-2-yl)oxy)pyrimidin-4-yl)az

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Targets

CXCR2

In vitro

AZD5069 is a slowly reversible antagonist of CXCR2 with effects of time and temperature evident on the pharmacology and binding kinetics.

In vivo

In preclinical models, airway neutrophil recruitment in response to inflammatory challenge is abrogated by selective targeting of CXCR2 using AZD5069.

Specifications

Synonyms

C18H22F2N4O5S2 | N-[2-[[(2, 3-Difluorophenyl)methyl]thio]-6-[(1R, 2S)-2, 3-dihydroxy-1-methylpropoxy]-4-pyrimidinyl]-1-azetidinesulfonamide | HY-19855 | AKOS037649275 | N-(2-((2, 3-difluorobenzyl)thio)-6-(((2R, 3S)-3, 4-dihydroxybutan-2-yl)oxy)pyrimidin-4-yl)az

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

AZD5069 is a novel antagonist of CXCR2, which is shown to inhibit binding of CXCL8 to CXCR2 with a pIC50 value of 8.8 and inhibit CXCL8 binding to CXCR1 with pIC50 values of 6.5.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

ANTAGONIST

Mechanism of action

Antagonist of CXCR1;Antagonist of CXCR2

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504771426
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504771426
• Canonical Smiles: CC(C(CO)O)OC1=NC(=NC(=C1)NS(=O)(=O)N2CCC2)SCC3=C(C(=CC=C3)F)F
• IUPAC Name: N-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-[(2R,3S)-3,4-dihydroxybutan-2-yl]oxypyrimidin-4-yl]azetidine-1-sulfonamide
• InChIKey: QZECRCLSIGFCIO-RISCZKNCSA-N
• INCHI: 1S/C18H22F2N4O5S2/c1-11(14(26)9-25)29-16-8-15(23-31(27,28)24-6-3-7-24)21-18(22-16)30-10-12-4-2-5-13(19)17(12)20/h2,4-5,8,11,14,25-26H,3,6-7,9-10H2,1H3,(H,21,22,23)/t11-,14+/m1/s1
• Isomeric SMILES: C[C@H]([C@H](CO)O)OC1=NC(=NC(=C1)NS(=O)(=O)N2CCC2)SCC3=C(C(=CC=C3)F)F
• Alternate CAS: 878385-84-3
• MeSH Entry Terms: AZD5069;N-(2-(2,3-difluoro-6-benzylthio)-6-(3,4-dihydroxybutan-2-yloxy)pyrimidin-4-yl)azetidine-1-sulfonamide
• Molecular Weight: 476.52
• Reaxy-Rn: 49477242
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=49477242&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organosulfur compounds
    • Class Thioethers
      • Subclass Aryl thioethers

• Kingdom: Organic compounds
• Superclass: Organosulfur compounds
• Class: Thioethers
• Subclass: Aryl thioethers
• Intermediate Tree Nodes: Not available
• Direct Parent: Aryl thioethers
• Alternative Parents: Alkyl aryl ethers Alkylarylthioethers Fluorobenzenes Sulfuric acid diamides Pyrimidines and pyrimidine derivatives Aryl fluorides Imidolactams Heteroaromatic compounds 1,2-diols Secondary alcohols Azetidines Sulfenyl compounds Azacyclic compounds Primary alcohols Organofluorides Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Aryl thioether - Halobenzene - Alkyl aryl ether - Fluorobenzene - Alkylarylthioether - Sulfuric acid diamide - Pyrimidine - Aryl fluoride - Benzenoid - Aryl halide - Monocyclic benzene moiety - Imidolactam - Organic sulfuric acid or derivatives - Heteroaromatic compound - Secondary alcohol - 1,2-diol - Azetidine - Azacycle - Organoheterocyclic compound - Ether - Sulfenyl compound - Primary alcohol - Organic oxygen compound - Alcohol - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Organohalogen compound - Organooxygen compound - Organonitrogen compound - Organofluoride - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as aryl thioethers. These are organosulfur compounds containing a thioether group that is substituted by an aryl group.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

CXCR2 Tchem C-X-C chemokine receptor type 2 (1 Activities)

Discover Target: CXCR2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CXCR1 Tchem C-X-C chemokine receptor type 1 (1 Activities)

Discover Target: CXCR1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Associated Targets(non-human)

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solubility (25°C) In vitro DMSO: 95 mg/mL (199.36 mM); Ethanol: 7 mg/mL (14.68 mM); Water: Insoluble
• Molecular Weight: 476.500 g/mol
• XLogP3: 1.500
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 10
• Exact Mass: 476.1 Da
• Monoisotopic Mass: 476.1 Da
• Topological Polar Surface Area: 159.000 Ų
• Heavy Atom Count: 31
• Formal Charge: 0
• Complexity: 670.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1