LINSITINIB

Investigational

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 8504	0.075 µM [IC50]
Insulin-like growth factor I receptor 6 Target ID: CHEMBL1957 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21425998	Inhibitor 8504	0.035 µM [IC50]
Insulin receptor-related protein 1 Target ID: CHEMBL5483 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21425998	Inhibitor 8504	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 665	Unknown Approved Use Unknown
Colorectal cancer 102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25335932	Primary	Phase I 438	Unknown Approved Use Unknown
Ovarian cancer 160 Sources: https://clinicaltrials.gov/ct2/show/NCT00889382 http://adisinsight.springer.com/drugs/800026466	Primary	Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
1705 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/25212606	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	LINSITINIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
3110 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/25212606	150 mg 2 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	LINSITINIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
2580 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26831715	150 mg 2 times / day multiple, oral dose: 150 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LINSITINIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
9475 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/25212606	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	LINSITINIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
24747 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/25212606	150 mg 2 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	LINSITINIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
17906 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26831715	150 mg 2 times / day multiple, oral dose: 150 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LINSITINIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.93 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/25212606	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:		LINSITINIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
5.03 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/25212606	150 mg 2 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		LINSITINIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

Sourcing

Vendor/Aggregator	ID	URL
AK Scientific	SYN5696	https://aksci.com/item_detail.php?cat=SYN5696
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
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
Molcore	MC105320	http://www.molcore.com/CatMC105320.html
MolPort	MolPort-044-181-468	https://www.molport.com/shop/molecule-link/MolPort-044-181-468
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

PubMed

Title	Date	PubMed
Insulin-like modulation of Akt/FoxO signaling by copper ions is independent of insulin receptor.	2014-09-15	24933099
Discovery of OSI-906: a selective and orally efficacious dual inhibitor of the IGF-1 receptor and insulin receptor.	2009-09	21425998

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 `Wed Apr 02 08:44:18 GMT 2025` Edited by `admin` on `Wed Apr 02 08:44:18 GMT 2025`
Record UNII	15A52GPT8T
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

linsitinib [INN]

Preferred Name

English

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

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