Orelabrutinib (ICP-022) - Moligand™, ≥98% , Tyrosine-protein kinase BTK inhibitor, CAS No.1655504-04-3, Tyrosine-protein kinase BTK inhibitor

CAS: 1655504-04-3 Cat. No.: O414422 Molecular Weight: 427.49

GRADE & PURITY Moligand™, ≥98%

Synonyms

AC-36680 | ICP022 | ICP-022 | Orelabrutinib | 6-(1-(1-Oxo-2-propen-1-yl)-4-piperidinyl)-2-(4-phenoxyphenyl)-3-pyridinecarboxamide | HY-129390 | F88710 | HY-108451 | NSC826039 | NSC-826039 | ORELABRUTINIB [WHO-DD] | 2-(4-phenoxyphenyl)-6-(1-prop-2-enoylpip

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Information

Orelabrutinib (ICP-022) Orelabrutinib (ICP-022) is a potent, orally active and irreversible inhibitor of Bruton's tyrosine kinase (BTK) . Orelabrutinib has potential antineoplastic activity.

Targets

BTK

In vitro

Orelabrutinib potently inhibits BTK enzymatic activity with an IC50 value of 1.6 nM. In KINOMEscan assay conducted in parallel at 1 μM against a panel of 456 kinases, orelabrutinib only targets BTK with > 90% inhibition while ibrutinib inhibits additional many other kinases including EGFR, TEC and BMX, demonstrating orelabrutinib\'s superior kinase selectivity.

In vivo

Orelabrutinib has a favorable PK profile with an ideal T1/2 (~1.5-4 h) and good oral bioavailability (~20-80%) as well as prolonged BTK target occupancy in preclinical PK/PD studies. The superior selectivity translates into improved safety profile and large safety window in the GLP toxicology studies in rats and dogs.

Specifications

Synonyms

AC-36680 | ICP022 | ICP-022 | Orelabrutinib | 6-(1-(1-Oxo-2-propen-1-yl)-4-piperidinyl)-2-(4-phenoxyphenyl)-3-pyridinecarboxamide | HY-129390 | F88710 | HY-108451 | NSC826039 | NSC-826039 | ORELABRUTINIB [WHO-DD] | 2-(4-phenoxyphenyl)-6-(1-prop-2-enoylpip

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Orelabrutinib (ICP-022) is a potent, orally active and irreversible inhibitor of Bruton's tyrosine kinase (BTK). Orelabrutinib has potential antineoplastic activity.

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

Tyrosine-protein kinase BTK inhibitor

Purity

≥98%

Product Properties

• ALogP: 4.055
• hba_count: 4
• HBD Count: 1
• Rotatable Bond: 6

Names and Identifiers

• Pubchem Sid: 504772644
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504772644
• Canonical Smiles: C=CC(=O)N1CCC(CC1)C2=NC(=C(C=C2)C(=O)N)C3=CC=C(C=C3)OC4=CC=CC=C4
• IUPAC Name: 2-(4-phenoxyphenyl)-6-(1-prop-2-enoylpiperidin-4-yl)pyridine-3-carboxamide
• InChIKey: MZPVEMOYADUARK-UHFFFAOYSA-N
• INCHI: 1S/C26H25N3O3/c1-2-24(30)29-16-14-18(15-17-29)23-13-12-22(26(27)31)25(28-23)19-8-10-21(11-9-19)32-20-6-4-3-5-7-20/h2-13,18H,1,14-17H2,(H2,27,31)
• Isomeric SMILES: C=CC(=O)N1CCC(CC1)C2=NC(=C(C=C2)C(=O)N)C3=CC=C(C=C3)OC4=CC=CC=C4
• Molecular Weight: 427.49
• Reaxy-Rn: 28089169
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=28089169&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Diphenylethers

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Diphenylethers
• Intermediate Tree Nodes: Not available
• Direct Parent: Diphenylethers
• Alternative Parents: Phenylpyridines Diarylethers N-acylpiperidines Nicotinamides Phenoxy compounds Phenol ethers Acrylic acids and derivatives Tertiary carboxylic acid amides Heteroaromatic compounds Primary carboxylic acid amides Azacyclic compounds Hydrocarbon derivatives Carbonyl compounds Organonitrogen compounds Organic oxides Organic anions
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Diphenylether - 2-phenylpyridine - Diaryl ether - N-acyl-piperidine - Nicotinamide - Pyridinecarboxamide - Pyridine carboxylic acid or derivatives - Phenol ether - Phenoxy compound - Piperidine - Pyridine - Tertiary carboxylic acid amide - Acrylic acid or derivatives - Heteroaromatic compound - Carboxamide group - Primary carboxylic acid amide - Organoheterocyclic compound - Carboxylic acid derivative - Azacycle - Ether - Organic oxide - Organic oxygen compound - Organonitrogen compound - Carbonyl group - Organooxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Organic anion - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether 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)

BTK Tclin Tyrosine-protein kinase BTK (0 Activities)

Discover Target: BTK

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

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solubility (25°C) In vitro DMSO: 86 mg/mL (201.17 mM); Ethanol: 10 mg/mL (23.39 mM); Water: Insoluble
• DMSO(mg / mL) Max Solubility: 86
• DMSO(mM) Max Solubility: 201.174296474771
• Water(mg / mL) Max Solubility: ＜1
• Molecular Weight: 427.500 g/mol
• XLogP3: 3.600
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 427.19 Da
• Monoisotopic Mass: 427.19 Da
• Topological Polar Surface Area: 85.500 Ų
• Heavy Atom Count: 32
• Formal Charge: 0
• Complexity: 647.000
• 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