Branebrutinib (BMS-986195) - Moligand™, ≥99% , Inhibitor of Bruton tyrosine kinase, CAS No.1912445-55-6, Inhibitor of Bruton tyrosine kinase

CAS: 1912445-55-6 Cat. No.: B414208 Molecular Weight: 370.42 PubChem CID: 121293929

GRADE & PURITY Moligand™, ≥99%

Synonyms

4-((3S)-3-(2-Butynoylamino)-1-piperidinyl)-5-fluoro-2,3-dimethyl-1H-indole-7-carboxamide | 4-((3S)-3-(2-BUTYNOYLAMINO)-1-PIPERIDINYL)-5-FLUORO-2,3-DIMETHYL-1HINDOLE-7-CARBOXAMIDE | (S)-4-(3-(2-BUTYNOYLAMINO)PIPERIDIN-1-YL)-5-FLUORO-2,3-DIMETHYL-1H-INDOLE-

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Information

Branebrutinib (BMS-986195) Branebrutinib (BMS-986195) is a potent inhibitor of BTK with IC50 values of 0.1 nM, 0.9 nM, 1.5 nM, 5 nM for BTK, TEC, BMX, TXK, respectively.

Targets

BTK (Cell-free assay); TEC (Cell-free assay); BMX (Cell-free assay); TXK (Cell-free assay) 0.1 nM; 0.9 nM ;1.5 nM; 5 nM

In vitro

In human whole blood assays, BMS-986195 potently inhibited BCR-stimulated expression of CD69 on B cells with an IC50 of 11 nM. BMS-986195 is highly selective, providing >5,000-fold selectivity for BTK over 240 kinases with only the 4 related Tec family kinases demonstrating less than 5000-fold selectivity (9 - 1,000-fold).

In vivo

In multi-species pharmacokinetic studies, the absolute oral bioavailability of BMS-986195 is 100% in mice, 74% in rats, 46% in cynomolgus monkeys, and 81% in dogs. The total body plasma clearance of BMS-986195 is low in all species. The steadystate volume of distribution observed is greater than the plasma volume but less than the total body water, indicative of extravascular distribution, in spite of the high protein binding (free fraction: 0.2-1.2%). Brain penetration is very low in mice, rats, and dogs (<5% of plasma concentration). Both the plasma T_1/2 (i.v.) and Tmax (p.o.) values were short across species (0.46-4.3 h and 0.58-1.0 h, respectively）.

Specifications

Synonyms

4-((3S)-3-(2-Butynoylamino)-1-piperidinyl)-5-fluoro-2, 3-dimethyl-1H-indole-7-carboxamide | 4-((3S)-3-(2-BUTYNOYLAMINO)-1-PIPERIDINYL)-5-FLUORO-2, 3-DIMETHYL-1HINDOLE-7-CARBOXAMIDE | (S)-4-(3-(2-BUTYNOYLAMINO)PIPERIDIN-1-YL)-5-FLUORO-2, 3-DIMETHYL-1H-INDOLE-

Specifications & Purity

Moligand™, ≥99%

Biochemical and Physiological Mechanisms

Branebrutinib (BMS-986195) is a potent inhibitor of BTK with IC50 values of 0.1 nM, 0.9 nM, 1.5 nM, 5 nM for BTK, TEC, BMX, TXK, 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.

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

Inhibitor of Bruton tyrosine kinase

Purity

≥99%

Product Properties

• ALogP: 2.8

Names and Identifiers

• Canonical Smiles: CC#CC(=O)NC1CCCN(C1)C2=C(C=C(C3=C2C(=C(N3)C)C)C(=O)N)F
• IUPAC Name: 4-[(3S)-3-(but-2-ynoylamino)piperidin-1-yl]-5-fluoro-2,3-dimethyl-1H-indole-7-carboxamide
• InChIKey: VJPPLCNBDLZIFG-ZDUSSCGKSA-N
• INCHI: 1S/C20H23FN4O2/c1-4-6-16(26)24-13-7-5-8-25(10-13)19-15(21)9-14(20(22)27)18-17(19)11(2)12(3)23-18/h9,13,23H,5,7-8,10H2,1-3H3,(H2,22,27)(H,24,26)/t13-/m0/s1
• Isomeric SMILES: CC#CC(=O)N[C@H]1CCCN(C1)C2=C(C=C(C3=C2C(=C(N3)C)C)C(=O)N)F
• Alternate CAS: 1912445-55-6
• PubChem CID: 121293929
• MeSH Entry Terms: 4-((3S)-3-(2-Butynoylamino)-1-piperidinyl)-5-fluoro-2,3-dimethyl-1H-indole-7-carboxamide;BMS-986195;branebrutinib
• Molecular Weight: 370.42

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Indoles and derivatives
      • Subclass Indolecarboxylic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Indoles and derivatives
• Subclass: Indolecarboxylic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Indolecarboxamides and derivatives
• Alternative Parents: Aminobenzamides 3-methylindoles Dialkylarylamines Substituted pyrroles Piperidines N-acyl amines Aryl fluorides Vinylogous amides Heteroaromatic compounds Secondary carboxylic acid amides Primary carboxylic acid amides Amino acids and derivatives Azacyclic compounds Organopnictogen compounds Organofluorides Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Indolecarboxamide derivative - 3-methylindole - 3-alkylindole - Aminobenzoic acid or derivatives - Aminobenzamide - Indole - Dialkylarylamine - Tertiary aliphatic/aromatic amine - Benzenoid - Substituted pyrrole - Piperidine - N-acyl-amine - Aryl halide - Aryl fluoride - Heteroaromatic compound - Vinylogous amide - Pyrrole - Tertiary amine - Secondary carboxylic acid amide - Primary carboxylic acid amide - Carboxamide group - Amino acid or derivatives - Azacycle - Carboxylic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organofluoride - Organohalogen compound - Carbonyl group - Amine - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as indolecarboxamides and derivatives. These are compounds containing a carboxamide group attached to an indole.
• 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)

TXK Tchem Tyrosine-protein kinase TXK (1 Activities)

Discover Target: TXK

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

TEC Tchem Tyrosine-protein kinase Tec (2 Activities)

Discover Target: TEC

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

BTK Tclin Tyrosine-protein kinase BTK (10 Activities)

Discover Target: BTK

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

BMX Tchem Cytoplasmic tyrosine-protein kinase BMX (2 Activities)

Discover Target: BMX

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

KCNH2 Tclin HERG (29587 Activities)

Discover Target: KCNH2

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

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

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

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

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

Mus musculus (284745 Activities)

Explore this target

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

Cynomolgus monkey (4946 Activities)

Explore this target

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

SARS-CoV-2 (38078 Activities)

Explore this target

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: 74 mg/mL (199.77 mM); Ethanol: 38 mg/mL (102.58 mM); Water: Insoluble
• Molecular Weight: 370.400 g/mol
• XLogP3: 2.800
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 370.181 Da
• Monoisotopic Mass: 370.181 Da
• Topological Polar Surface Area: 91.200 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 657.000
• 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