AMG 487 - ≥98% , CAS No.473719-41-4

CAS: 473719-41-4 Cat. No.: A414114 Molecular Weight: 603.59

GRADE & PURITY ≥98%

Synonyms

(R)-N-(1-(3-(4-ethoxyphenyl)-4-oxo-3,4-dihydropyrido[2,3-d]pyrimidin-2-yl)ethyl)-N-(pyridin-3-ylmethyl)-2-(4-(trifluoromethoxy)phenyl)acetamide | AMG487 | AMG-487 | 355CGR2CBL | Benzeneacetamide, N-((1R)-1-(3-(4-ethoxyphenyl)-3,4-dihydro-4-oxopyrido(2,3-d

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Information

AMG 487 AMG 487 is an orally active and selective CXC chemokine receptor 3 (CXCR3) antagonist that inhibits the binding of IP-10 (CXCL10) and ITAC (CXCL11) to CXCR3 with IC50 of 8.0 nM and 8.2 nM, respectively.

Targets

CXCR3-CXCL10 (Cell-free assay); CXCR3-CXCL11 (Cell-free assay) 8.0 nM; 8.2 nM

In vitro

AMG487 is the targeted blocker of chemokine receptor CXCR3 and improves inflammatory symptoms by blocking the inflammatory cycle. AMG487 significantly affects DC maturity in vitro and function leading to impaired T cell activation, inducing DCs to have characteristics similar to tolerogenic DCs. AMG487 may directly play an immunomodulatory role during DC development and functional shaping.

In vivo

AMG487 exhibits the antiarthritic effects in DBA/1J mice bearing collageninduced arthritis (CIA).

Cell Research(from reference)

Cell lines：Murine bone marrow-derived DCs (BMDCs) 

Concentrations：3 μM, 15 μM, 30 μM, 60 μM 

Incubation Time：over 6 days 

Specifications

Synonyms

(R)-N-(1-(3-(4-ethoxyphenyl)-4-oxo-3, 4-dihydropyrido[2, 3-d]pyrimidin-2-yl)ethyl)-N-(pyridin-3-ylmethyl)-2-(4-(trifluoromethoxy)phenyl)acetamide | AMG487 | AMG-487 | 355CGR2CBL | Benzeneacetamide, N-((1R)-1-(3-(4-ethoxyphenyl)-3, 4-dihydro-4-oxopyrido(2, 3-d

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

AMG 487 is an orally active and selective CXC chemokine receptor 3 (CXCR3) antagonist that inhibits the binding of IP-10 (CXCL10) and ITAC (CXCL11) to CXCR3 with IC50 of 8.0 nM and 8.2 nM, respectively.

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.

Action Type

INHIBITOR

Purity

≥98%

Product Properties

• ALogP: 6.334
• hba_count: 7
• Rotatable Bond: 11

Names and Identifiers

• Pubchem Sid: 504769915
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504769915
• Canonical Smiles: CCOC1=CC=C(C=C1)N2C(=O)C3=C(N=CC=C3)N=C2C(C)N(CC4=CN=CC=C4)C(=O)CC5=CC=C(C=C5)OC(F)(F)F
• IUPAC Name: N-[(1R)-1-[3-(4-ethoxyphenyl)-4-oxopyrido[2,3-d]pyrimidin-2-yl]ethyl]-N-(pyridin-3-ylmethyl)-2-[4-(trifluoromethoxy)phenyl]acetamide
• InChIKey: WQTKNBPCJKRYPA-OAQYLSRUSA-N
• INCHI: 1S/C32H28F3N5O4/c1-3-43-25-14-10-24(11-15-25)40-30(38-29-27(31(40)42)7-5-17-37-29)21(2)39(20-23-6-4-16-36-19-23)28(41)18-22-8-12-26(13-9-22)44-32(33,34)35/h4-17,19,21H,3,18,20H2,1-2H3/t21-/m1/s1
• Isomeric SMILES: CCOC1=CC=C(C=C1)N2C(=O)C3=C(N=CC=C3)N=C2[C@@H](C)N(CC4=CN=CC=C4)C(=O)CC5=CC=C(C=C5)OC(F)(F)F
• Molecular Weight: 603.59
• Reaxy-Rn: 11147940
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=11147940&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Pyridopyrimidines
      • Subclass Pyrido[2,3-d]pyrimidines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Pyridopyrimidines
• Subclass: Pyrido[2,3-d]pyrimidines
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyrido[2,3-d]pyrimidines
• Alternative Parents: Phenylacetamides Phenol ethers Phenoxy compounds Alkyl aryl ethers Pyrimidones Pyridines and derivatives Heteroaromatic compounds Tertiary carboxylic acid amides Lactams Trihalomethanes Azacyclic compounds Organofluorides Organic oxides Hydrocarbon derivatives Carbonyl compounds Organonitrogen compounds Alkyl fluorides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Pyrido[2,3-d]pyrimidine - Phenylacetamide - Phenoxy compound - Phenol ether - Alkyl aryl ether - Pyrimidone - Monocyclic benzene moiety - Pyridine - Pyrimidine - Benzenoid - Tertiary carboxylic acid amide - Heteroaromatic compound - Carboxamide group - Trihalomethane - Lactam - Azacycle - Carboxylic acid derivative - Ether - Organic nitrogen compound - Organonitrogen compound - Organofluoride - Organohalogen compound - Organooxygen compound - Organic oxide - Halomethane - Hydrocarbon derivative - Carbonyl group - Organic oxygen compound - Alkyl halide - Alkyl fluoride - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as pyrido[2,3-d]pyrimidines. These are compounds containing the pyrido[2,3-d]pyrimidine ring system, which is a pyridopyrimidine isomer with three ring nitrogen atoms at the 1-, 3-, and 8- position.
• 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)

CXCR3 Tchem C-X-C chemokine receptor type 3 (17 Activities)

Discover Target: CXCR3

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

CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

Discover Target: CHRM2

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

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

Discover Target: CHRM1

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

CHRM3 Tclin Muscarinic acetylcholine receptor M3 (7750 Activities)

Discover Target: CHRM3

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

CXCR3 Tchem C-X-C chemokine receptor type 3 (2736 Activities)

Discover Target: CXCR3

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

CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

Discover Target: CYP3A4

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

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

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

Canis familiaris (36305 Activities)

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

Mus musculus (284745 Activities)

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

Rattus norvegicus (775804 Activities)

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

Cynomolgus monkey (4946 Activities)

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

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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

Blood (6 Activities)

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

Mechanisms of Action

Chemical and Physical Properties

• DMSO(mg / mL) Max Solubility: 100
• DMSO(mM) Max Solubility: 165.675375668914
• Water(mg / mL) Max Solubility: ＜1
• Molecular Weight: 603.600 g/mol
• XLogP3: 5.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 10
• Exact Mass: 603.209 Da
• Monoisotopic Mass: 603.209 Da
• Topological Polar Surface Area: 97.200 Ų
• Heavy Atom Count: 44
• Formal Charge: 0
• Complexity: 997.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• 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