OSI-906 (Linsitinib) - Moligand™, ≥99% , Inhibitor of Insulin-like growth factor I receptor;Inhibitor of Insulin receptor;Inhibitor of Insulin receptor-related receptor, CAS No.867160-71-2, Inhibitor of Insulin-like growth factor I receptor;Inhibitor of Insulin receptor;Inhibitor of Insulin receptor-related receptor

CAS: 867160-71-2 Cat. No.: L126224 Molecular Weight: 421.51

GRADE & PURITY Moligand™, ≥99%

Synonyms

Linsitinib (USAN/INN) | Cis-3-(8-Amino-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl)-1-methylcyclobutan-1-ol | HMS3295G15 | Kinome_3532 | CHEBI:91402 | (1s,3s)-3-(8-amino-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl)-1-methylcyclobutanol | S

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Linsitinib is a potent, selective insulin-like growth factor-1 receptor (IGF-1R, IC50 = 35 nM) and insulin receptor (IR, IC50 = 75 nM) kinase inhibitor which works to block the autophosphorylation of IGF-1R and IR. Additionally, in vitro studies of Linsitinib have demonstrated its ability to inhibit the proliferation of multiple tumor cell lines.Linsitinib is a selective inhibitor of IGF-1R with IC50 of 35 nM, and modestly potent to InsR with IC50 of 75 nM, and has no activity towards Abl, ALK, BTK, EGFR, FGFR1/2, PKA etc.

Specifications

Synonyms

Linsitinib (USAN/INN) | Cis-3-(8-Amino-1-(2-phenylquinolin-7-yl)imidazo[1, 5-a]pyrazin-3-yl)-1-methylcyclobutan-1-ol | HMS3295G15 | Kinome_3532 | CHEBI:91402 | (1s, 3s)-3-(8-amino-1-(2-phenylquinolin-7-yl)imidazo[1, 5-a]pyrazin-3-yl)-1-methylcyclobutanol | S

Specifications & Purity

Moligand™, ≥99%

Biochemical and Physiological Mechanisms

Linsitinib is highly potent, orally efficacious and highly selective, dual ATP-competitive tyrosine kinase inhibitor of insulin-like growth factor-1 receptor (IGF-1R) (IC50: 35 nM) and insulin receptor (IR) (IC50: 75 nM).Potent and selective dual IGF-1R (

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 Insulin-like growth factor I receptor;Inhibitor of Insulin receptor;Inhibitor of Insulin receptor-related receptor

Note

Refer to SDS for further information Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥99%

Names and Identifiers

• Pubchem Sid: 504766617
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504766617
• Canonical Smiles: CC1(CC(C1)C2=NC(=C3N2C=CN=C3N)C4=CC5=C(C=C4)C=CC(=N5)C6=CC=CC=C6)O
• IUPAC Name: 3-[8-amino-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]-1-methylcyclobutan-1-ol
• InChIKey: PKCDDUHJAFVJJB-UHFFFAOYSA-N
• INCHI: 1S/C26H23N5O/c1-26(32)14-19(15-26)25-30-22(23-24(27)28-11-12-31(23)25)18-8-7-17-9-10-20(29-21(17)13-18)16-5-3-2-4-6-16/h2-13,19,32H,14-15H2,1H3,(H2,27,28)
• Isomeric SMILES: CC1(CC(C1)C2=NC(=C3N2C=CN=C3N)C4=CC5=C(C=C4)C=CC(=N5)C6=CC=CC=C6)O
• Molecular Weight: 421.51
• Reaxy-Rn: 25747541
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25747541&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Quinolines and derivatives
      • Subclass Phenylquinolines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Quinolines and derivatives
• Subclass: Phenylquinolines
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenylquinolines
• Alternative Parents: Phenylpyridines Imidazo[1,5-a]pyrazines Aminopyrazines N-substituted imidazoles Imidolactams Benzene and substituted derivatives Tertiary alcohols Heteroaromatic compounds Cyclic alcohols and derivatives Azacyclic compounds Primary amines Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Phenylquinoline - 2-phenylpyridine - Imidazo[1,5-a]pyrazine - Aminopyrazine - Monocyclic benzene moiety - Imidolactam - Benzenoid - Pyridine - Pyrazine - N-substituted imidazole - Azole - Heteroaromatic compound - Imidazole - Tertiary alcohol - Cyclobutanol - Azacycle - Organonitrogen compound - Primary amine - Alcohol - Hydrocarbon derivative - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Amine - Organooxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as phenylquinolines. These are heterocyclic compounds containing a quinoline moiety substituted with a phenyl 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)

IGF1R Tclin Insulin-like growth factor 1 receptor (10 Activities)

Discover Target: IGF1R

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

INSRR Tchem Insulin receptor-related protein (1 Activities)

Discover Target: INSRR

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

INSR Tclin Insulin receptor (3 Activities)

Discover Target: INSR

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

Chemical and Physical Properties

• Solubility: DMSO 84 mg/mL Water <1 mg/mL Ethanol <1 mg/mL
• Molecular Weight: 421.500 g/mol
• XLogP3: 4.200
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 421.19 Da
• Monoisotopic Mass: 421.19 Da
• Topological Polar Surface Area: 89.300 Ų
• Heavy Atom Count: 32
• Formal Charge: 0
• Complexity: 663.000
• 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