Pamapimod - Moligand™, ≥99% , MAP kinase p38 alpha inhibitor, CAS No.449811-01-2, MAP kinase p38 alpha inhibitor

CAS: 449811-01-2 Cat. No.: P413914 Molecular Weight: 406.38 PubChem CID: 16220188

GRADE & PURITY Moligand™, ≥99%

Synonyms

AC-33182 | DEGARELIX [USAN] | DTXSID6040244 | FLW | PAMAPIMOD [INN] | 6-(2,4-Difluorophenoxy)-2-{[3-Hydroxy-1-(2-Hydroxyethyl)propyl]amino}-8-Methylpyrido[2,3-D]pyrimidin-7(8h)-One | BCP17491 | 6-(2,4-Difluorophenoxy)-2-((3-hydroxy-1-(2-hydroxyethyl)propy

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Information

Pamapimod (R-1503, Ro4402257) is a novel, selective inhibitor ofp38 mitogen-activated protein kinase. It inhibits p38α and p38β enzymatic activity with IC50 values of 0.014±0.002 and 0.48± 0.04 microM, respectively with no activity against p38delta or p38gamma isoforms.

Targets

p38α (Cell-free assay); p38β (Cell-free assay) 0.014 μM; 0.48 μM

In vitro

Pamapimod inhibited p38, but inhibition of JNK was not detected. Pamapimod also inhibited lipopolysaccharide (LPS)-stimulated tumor necrosis factor (TNF) α production by monocytes, interleukin (IL)-1β production in human whole blood, and spontaneous TNFα production by synovial explants from RA patients.

In vivo

In murine collagen-induced arthritis, pamapimod reduced clinical signs of inflammation and bone loss at 50 mg/kg or greater. In a rat model of hyperalgesia, pamapimod increased tolerance to pressure in a dose-dependent manner, suggesting an important role of p38 in pain associated with inflammation. Pamapimod suppresses spontaneous production of TNFα by synovial explants from RA patients. LPS- and TNFα-stimulated production of TNFα and IL-6 in rodents also was inhibited by pamapimod.

Cell Research(from reference)

Cell lines：Human Monocytic Cell Line, THP-1 

Concentrations：15 μM 

Incubation Time：150 min 

Specifications

Synonyms

AC-33182 | DEGARELIX [USAN] | DTXSID6040244 | FLW | PAMAPIMOD [INN] | 6-(2, 4-Difluorophenoxy)-2-{[3-Hydroxy-1-(2-Hydroxyethyl)propyl]amino}-8-Methylpyrido[2, 3-D]pyrimidin-7(8h)-One | BCP17491 | 6-(2, 4-Difluorophenoxy)-2-((3-hydroxy-1-(2-hydroxyethyl)propy

Specifications & Purity

Moligand™, ≥99%

Biochemical and Physiological Mechanisms

Pamapimod (R-1503, Ro4402257) is a novel, selective inhibitor of p38 mitogen-activated protein kinase. It inhibits p38α and p38β enzymatic activity with IC50 values of 0.014±0.002 and 0.48± 0.04 microM, respectively with no activity against p38delta or p3

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

INHIBITOR

Mechanism of action

MAP kinase p38 alpha inhibitor

Purity

≥99%

Product Properties

• ALogP: 1.298
• HBD Count: 3
• Rotatable Bond: 8

Names and Identifiers

• Pubchem Sid: 504768416
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504768416
• Canonical Smiles: CN1C2=NC(=NC=C2C=C(C1=O)OC3=C(C=C(C=C3)F)F)NC(CCO)CCO
• IUPAC Name: 6-(2,4-difluorophenoxy)-2-(1,5-dihydroxypentan-3-ylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one
• InChIKey: JYYLVUFNAHSSFE-UHFFFAOYSA-N
• INCHI: 1S/C19H20F2N4O4/c1-25-17-11(10-22-19(24-17)23-13(4-6-26)5-7-27)8-16(18(25)28)29-15-3-2-12(20)9-14(15)21/h2-3,8-10,13,26-27H,4-7H2,1H3,(H,22,23,24)
• Isomeric SMILES: CN1C2=NC(=NC=C2C=C(C1=O)OC3=C(C=C(C=C3)F)F)NC(CCO)CCO
• PubChem CID: 16220188
• Molecular Weight: 406.38

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Ethers

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Ethers
• Intermediate Tree Nodes: Not available
• Direct Parent: Diarylethers
• Alternative Parents: Pyrido[2,3-d]pyrimidines Phenoxy compounds Phenol ethers Secondary alkylarylamines Pyridinones Aminopyrimidines and derivatives Fluorobenzenes Aryl fluorides Heteroaromatic compounds Lactams Azacyclic compounds Hydrocarbon derivatives Organic oxides Organofluorides Organopnictogen compounds Primary alcohols
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Diaryl ether - Pyrido[2,3-d]pyrimidine - Pyridopyrimidine - Phenoxy compound - Phenol ether - Aminopyrimidine - Fluorobenzene - Halobenzene - Pyridinone - Secondary aliphatic/aromatic amine - Aryl fluoride - Aryl halide - Monocyclic benzene moiety - Pyridine - Pyrimidine - Benzenoid - Heteroaromatic compound - Lactam - Azacycle - Organoheterocyclic compound - Secondary amine - Primary alcohol - Organonitrogen compound - Organofluoride - Organohalogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic nitrogen compound - Alcohol - Amine - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups.
• 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)

MAPK10 Tchem Mitogen-activated protein kinase 10 (3 Activities)

Discover Target: MAPK10

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

MAPK8 Tchem Mitogen-activated protein kinase 8 (1 Activities)

Discover Target: MAPK8

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

MAPK9 Tchem Mitogen-activated protein kinase 9 (3 Activities)

Discover Target: MAPK9

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

MAPK11 Tchem Mitogen-activated protein kinase 11 (1 Activities)

Discover Target: MAPK11

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

MAPK14 Tchem Mitogen-activated protein kinase 14 (5 Activities)

Discover Target: MAPK14

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

MAPK11 Tchem MAP kinase p38 beta (2785 Activities)

Discover Target: MAPK11

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

MAPK14 Tchem MAP kinase p38 alpha (12866 Activities)

Discover Target: MAPK14

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

RPS6KA4 Tchem Ribosomal protein S6 kinase alpha 4 (2104 Activities)

Discover Target: RPS6KA4

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

CSNK1E Tclin Casein kinase I epsilon (1412 Activities)

Discover Target: CSNK1E

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

CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

Discover Target: CYP2D6

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

MAPK9 Tchem c-Jun N-terminal kinase 2 (4655 Activities)

Discover Target: MAPK9

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

MAPK10 Tchem c-Jun N-terminal kinase 3 (3396 Activities)

Discover Target: MAPK10

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

MAPK8 Tchem c-Jun N-terminal kinase 1 (5038 Activities)

Discover Target: MAPK8

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

CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)

Discover Target: CYP1A2

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

RPS6KA3 Tchem Ribosomal protein S6 kinase alpha 3 (4284 Activities)

Discover Target: RPS6KA3

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

CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

Discover Target: CYP2C9

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

CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

Discover Target: CYP2C19

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

GAK Tchem Serine/threonine-protein kinase GAK (1150 Activities)

Discover Target: GAK

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

STK36 Tbio Serine/threonine-protein kinase 36 (297 Activities)

Discover Target: STK36

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

Caco-2 (12174 Activities)

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

THP-1 (11052 Activities)

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

HEK293 (82097 Activities)

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

DDR1 Tchem Epithelial discoidin domain-containing receptor 1 (1050 Activities)

Discover Target: DDR1

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

NLK Tchem Serine/threonine protein kinase NLK (977 Activities)

Discover Target: NLK

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

COQ8A Tbio Chaperone activity of bc1 complex-like, mitochondrial (552 Activities)

Discover Target: COQ8A

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

Associated Targets(non-human)

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

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

• Solubility: Solubility (25°C) In vitro DMSO: 81 mg/mL (199.32 mM); Ethanol: 28 mg/mL (68.9 mM); Water: Insoluble
• DMSO(mg / mL) Max Solubility: 81
• DMSO(mM) Max Solubility: 199.3208327
• Water(mg / mL) Max Solubility: ＜1
• Molecular Weight: 406.400 g/mol
• XLogP3: 2.400
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 8
• Exact Mass: 406.145 Da
• Monoisotopic Mass: 406.145 Da
• Topological Polar Surface Area: 108.000 Ų
• Heavy Atom Count: 29
• Formal Charge: 0
• Complexity: 591.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• 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