LINSITINIB

Details

Stereochemistry	ACHIRAL
Molecular Formula	C26H23N5O
Molecular Weight	421.4937
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@]1(O)C[C@@H](C1)C2=NC(=C3N2C=CN=C3N)C4=CC=C5C=CC(=NC5=C4)C6=CC=CC=C6

InChI

InChIKey=PKCDDUHJAFVJJB-VLZXCDOPSA-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)/t19-,26+

HIDE SMILES / InChI

Molecular Formula	C26H23N5O
Molecular Weight	421.4937
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.cancer.gov/publications/dictionaries/cancer-drug?cdrid=566191
Curator's Comment: description was created based on several sources, including: http://adisinsight.springer.com/drugs/800026466 | http://www.pharmacodia.com/yaodu/html/v1/chemicals/571e646d4ea4d46a8fde33d07167efe5.html | https://www.ncbi.nlm.nih.gov/pubmed/25795408 | https://www.ncbi.nlm.nih.gov/pubmed/25335932

Linsitinib is an inhibitor of the insulin receptor and the insulin-like growth factor 1 receptor, which may result in the inhibition of tumor cell proliferation and the induction of tumor cell apoptosis. Linsitinib is in phase II clinical trials for the treatment of metastatic prostate carcinoma, gastrointestinal stromal tumors and other cancers. Common adverse events included fatigue, nausea hyperglycaemia and anorexia.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Insulin receptor 13 Target ID: CHEMBL1981 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21425998	Inhibitor 8297	0.075 µM [IC50]
Insulin-like growth factor I receptor 6 Target ID: CHEMBL1957 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21425998	Inhibitor 8297	0.035 µM [IC50]
Insulin receptor-related protein 1 Target ID: CHEMBL5483 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21425998	Inhibitor 8297	0.075 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Adrenocortical carcinoma 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25795408	Primary	Phase III 656	Unknown Approved Use Unknown
Colorectal cancer 101 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25335932	Primary	Phase I 428	Unknown Approved Use Unknown
Ovarian cancer 157 Sources: https://clinicaltrials.gov/ct2/show/NCT00889382 http://adisinsight.springer.com/drugs/800026466	Primary	Phase II 1132	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
AK Scientific	SYN5696	https://aksci.com/item_detail.php?cat=SYN5696
Excenen	EX-A719	http://www.excenen.com/searchresultlist.php?id=EX-A719
KeyOrganics	AS-16999	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-16999
MolPort	MolPort-044-181-468	https://www.molport.com/shop/molecule-link/MolPort-044-181-468
Molcore	MC105320	http://www.molcore.com/CatMC105320.html
MuseChem	I005217	https://www.musechem.com/product/I005217.html
ShangHai Biochempartner	BCP000133	http://www.biochempartner.com/search_BCP000133
TargetMol	T6017	https://www.targetmol.com/search?keyword=T6017
Toronto Research Chemicals	L469020	https://www.trc-canada.com/product-detail/?CatNum=L469020
Toronto Research Chemicals	P274355	https://www.trc-canada.com/product-detail/?CatNum=P274355
eMolecules	252367884	https://orderbb.emolecules.com/search/#?query=252367884
eMolecules	300581920	https://orderbb.emolecules.com/search/#?query=300581920
eMolecules	50894623	https://orderbb.emolecules.com/search/#?query=50894623
eMolecules	85147652	https://orderbb.emolecules.com/search/#?query=85147652

PubMed

Title	Date	PubMed
		252160378
Discovery of OSI-906: a selective and orally efficacious dual inhibitor of the IGF-1 receptor and insulin receptor.	2009 Sep	21425998
Insulin-like modulation of Akt/FoxO signaling by copper ions is independent of insulin receptor.	2014 Sep 15	24933099

Patents

Sample Use Guides

In Vivo Use Guide

150 mg twice daily

Route of Administration: Oral

In Vitro Use Guide

Different concentrations of linsitinib (2 nM, 5 nM, 10 nM, 20 nM, 40 nM, 60 nM) did not inhibit PC-3 cell proliferation after 48 h at 37°C in CCK-8 assay.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:04:07 GMT 2023` Edited by `admin` on `Sat Dec 16 17:04:07 GMT 2023`
Record UNII	15A52GPT8T
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LINSITINIB

Official Name

English

cis-3-[8-amino-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]-1-methylcyclobutanol

Systematic Name

English

LINSITINIB [USAN]

Common Name

English

CYCLOBUTANOL, 3-(8-AMINO-1-(2-PHENYL-7-QUINOLINYL)IMIDAZO(1,5-A)PYRAZIN-3-YL)-1-METHYL-, CIS-

Systematic Name

English

CIS-3-(8-AMINO-1-(2-PHENYLQUINOLIN-7-YL)IMIDAZO(1,5-A)PYRAZIN-3-YL)-1-METHYLCYCLOBUTAN-1-OL

Common Name

English

Linsitinib [WHO-DD]

Common Name

English

linsitinib [INN]

Common Name

English

ASP-7487

Code

English

CIS-3-(8-AMINO-1-(2-PHENYL-7-QUINOLINYL)IMIDAZO(1,5-A)PYRAZIN-3-YL)-1-METHYLCYCLOBUTANOL

Systematic Name

English

OSI-906AA

Code

English

OSI-906

Code

English

Classification Tree Code System Code

EU-Orphan Drug

EU/3/12/977