Ritlecitinib (PF-06651600) - Moligand™, 10mM in DMSO , TEC family kinase inhibitor, CAS No.1792180-81-4, TEC family kinase inhibitor

CAS: 1792180-81-4 Cat. No.: R422181 Molecular Weight: 285.34 EC Number: 815-269-7 PubChem CID: 118115473

GRADE & PURITY Moligand™, 10mM in DMSO

Synonyms

DB14924 | Ritlecitinib? | RITLECITINIB [WHO-DD] | PF06651600;PF 06651600 | GTPL9559 | DS-13951 | HY-100754 | AC-35550 | PF 06651600 | ritlecitinib | CCG-267324 | 1-((2S,5R)-5-((7H-Pyrrolo[2,3-d]pyrimidin-4-yl)amino)-2-methylpiperidin-1-yl)prop-2-en-1-one

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Information

Ritlecitinib (PF-06651600) is a potent and irreversibleJAK3-selectiveinhibitor with an IC50 of 33.1 nM but without activity (IC50 > 10 000 nM) against JAK1, JAK2, and TYK2.

Targets

JAK3 (Cell-free assay) 33.1 nM

In vitro

PF-06651600, a newly discovered potent JAK3-selective inhibitor, is highly efficacious at inhibiting γc cytokine signaling, which is dependent on both JAK1 and JAK3. it inhibits Th1 and Th17 cell differentiation and function. In total lymphocytes in human whole blood, PF-06651600 inhibits the phosphorylation of STAT5 elicited by IL-2, IL-4, IL-7, and IL-15 with IC50 values of 244, 340, 407, and 266 nM, respectively, and it inhibits the phosphorylation of STAT3 elicited by IL-21 with an IC50 of 355 nM.

In vivo

PF-06651600 reduces disease pathology in rat adjuvant-induced arthritis as well as in mouse experimental autoimmune encephalomyelitis models. PF-06651600 has suitable pharmacokinetics and pharmacodynamics properties for preclinical and clinical evaluations. Human pharmacokinetics of PF-06651600 are predicted to show approximate values of blood clearance of 5.6 mL/min/kg, a steady state volume of distribution of 1.3 L/kg, oral bioavailability of 90%, and a systemic half-life of 2 h.

Specifications

Synonyms

DB14924 | Ritlecitinib? | RITLECITINIB [WHO-DD] | PF06651600;PF 06651600 | GTPL9559 | DS-13951 | HY-100754 | AC-35550 | PF 06651600 | ritlecitinib | CCG-267324 | 1-((2S, 5R)-5-((7H-Pyrrolo[2, 3-d]pyrimidin-4-yl)amino)-2-methylpiperidin-1-yl)prop-2-en-1-one

Specifications & Purity

Moligand™, 10mM in DMSO

Biochemical and Physiological Mechanisms

Ritlecitinib (PF-06651600) is a potent and irreversible JAK3-selective inhibitor with an IC50 of 33.1 nM but without activity (IC50 > 10 000 nM) against JAK1, JAK2, and TYK2.

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

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

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

TEC family kinase inhibitor

Product Properties

• ALogP: 1.854
• hba_count: 3
• HBD Count: 2
• Rotatable Bond: 3

Names and Identifiers

• Canonical Smiles: C=CC(N1[C@@H](C)CC[C@@H](NC2=C3C(NC=C3)=NC=N2)C1)=O
• IUPAC Name: 1-[(2S,5R)-2-methyl-5-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)piperidin-1-yl]prop-2-en-1-one
• InChIKey: CBRJPFGIXUFMTM-WDEREUQCSA-N
• INCHI: 1S/C15H19N5O/c1-3-13(21)20-8-11(5-4-10(20)2)19-15-12-6-7-16-14(12)17-9-18-15/h3,6-7,9-11H,1,4-5,8H2,2H3,(H2,16,17,18,19)/t10-,11+/m0/s1
• Isomeric SMILES: C[C@H]1CC[C@H](CN1C(=O)C=C)NC2=NC=NC3=C2C=CN3
• PubChem CID: 118115473
• Molecular Weight: 285.34

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Piperidines
      • Subclass N-acylpiperidines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Piperidines
• Subclass: N-acylpiperidines
• Intermediate Tree Nodes: Not available
• Direct Parent: N-acylpiperidines
• Alternative Parents: Pyrrolo[2,3-d]pyrimidines Secondary alkylarylamines Aminopyrimidines and derivatives Aminopiperidines Imidolactams Tertiary carboxylic acid amides Pyrroles Heteroaromatic compounds Acrylic acids and derivatives Amino acids and derivatives Azacyclic compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: N-acyl-piperidine - Pyrrolo[2,3-d]pyrimidine - Pyrrolopyrimidine - 3-aminopiperidine - Aminopyrimidine - Secondary aliphatic/aromatic amine - Pyrimidine - Imidolactam - Acrylic acid or derivatives - Pyrrole - Tertiary carboxylic acid amide - Heteroaromatic compound - Amino acid or derivatives - Carboxamide group - Carboxylic acid derivative - Secondary amine - Azacycle - Hydrocarbon derivative - Organic oxide - Amine - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Carbonyl group - Organic nitrogen compound - Organic oxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as n-acylpiperidines. These are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of a piperidine.
• 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)

ITK Tclin Tyrosine-protein kinase ITK/TSK (1 Activities)

Discover Target: ITK

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

JAK3 Tclin Tyrosine-protein kinase JAK3 (6 Activities)

Discover Target: JAK3

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

JAK1 Tclin Tyrosine-protein kinase JAK1 (1 Activities)

Discover Target: JAK1

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

EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)

Discover Target: EGFR

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

ERBB2 Tclin Receptor protein-tyrosine kinase erbB-2 (7851 Activities)

Discover Target: ERBB2

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

JAK3 Tclin Tyrosine-protein kinase JAK3 (8349 Activities)

Discover Target: JAK3

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

ITK Tclin Tyrosine-protein kinase ITK/TSK (3699 Activities)

Discover Target: ITK

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

JAK1 Tclin Tyrosine-protein kinase JAK1 (8569 Activities)

Discover Target: JAK1

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

JAK2 Tclin Tyrosine-protein kinase JAK2 (12915 Activities)

Discover Target: JAK2

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

BLK Tchem Tyrosine-protein kinase BLK (2498 Activities)

Discover Target: BLK

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

TYK2 Tclin Tyrosine-protein kinase TYK2 (5029 Activities)

Discover Target: TYK2

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

ERBB4 Tclin Receptor protein-tyrosine kinase erbB-4 (2748 Activities)

Discover Target: ERBB4

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

MAP2K7 Tchem Dual specificity mitogen-activated protein kinase kinase 7 (1145 Activities)

Discover Target: MAP2K7

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

BMX Tchem Tyrosine-protein kinase BMX (1995 Activities)

Discover Target: BMX

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

U-937 (7138 Activities)

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

PBMC (10003 Activities)

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

BTK Tclin Tyrosine-protein kinase BTK (8973 Activities)

Discover Target: BTK

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

TXK Tchem Tyrosine-protein kinase TXK (1590 Activities)

Discover Target: TXK

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

Liver (3974 Activities)

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

Associated Targets(non-human)

Tec Tyrosine-protein kinase TEC (25 Activities)

Discover Target: Tec

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

Rhesus monkey (3147 Activities)

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

BaF3 (4657 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

MDCKII-LE (120 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: 57
• DMSO(mM) Max Solubility: 199.7616878
• Molecular Weight: 285.340 g/mol
• XLogP3: 2.100
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 285.159 Da
• Monoisotopic Mass: 285.159 Da
• Topological Polar Surface Area: 73.900 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 402.000
• 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