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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 of LINSITINIB

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
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

CNS Penetrant
2554
Curator's Comment: Known to be CNS penetrant in mouse. Human data not available.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 0.075 µM [IC50]
Inhibitor
8297
 0.035 µM [IC50]
Inhibitor
8297
 0.075 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
656
Unknown

Approved Use

Unknown
Primary
Phase I
428
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
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

PubMed

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

Patents

20060235031
1
20080267957
1

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 UTC 2023
Edited
by admin
on Sat Dec 16 17:04:07 UTC 2023
Record UNII
15A52GPT8T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LINSITINIB
INN   USAN   WHO-DD  
INN   USAN  
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
Created by admin on Sat Dec 16 17:04:08 UTC 2023 , Edited by admin on Sat Dec 16 17:04:08 UTC 2023
FDA ORPHAN DRUG 362311
Created by admin on Sat Dec 16 17:04:08 UTC 2023 , Edited by admin on Sat Dec 16 17:04:08 UTC 2023
NCI_THESAURUS C1967
Created by admin on Sat Dec 16 17:04:08 UTC 2023 , Edited by admin on Sat Dec 16 17:04:08 UTC 2023
NCI_THESAURUS C129825
Created by admin on Sat Dec 16 17:04:08 UTC 2023 , Edited by admin on Sat Dec 16 17:04:08 UTC 2023
Code System Code Type Description
DRUG BANK
DB06075
Created by admin on Sat Dec 16 17:04:08 UTC 2023 , Edited by admin on Sat Dec 16 17:04:08 UTC 2023
PRIMARY
ChEMBL
CHEMBL1091644
Created by admin on Sat Dec 16 17:04:08 UTC 2023 , Edited by admin on Sat Dec 16 17:04:08 UTC 2023
PRIMARY
EVMPD
SUB35196
Created by admin on Sat Dec 16 17:04:08 UTC 2023 , Edited by admin on Sat Dec 16 17:04:08 UTC 2023
PRIMARY
NCI_THESAURUS
C70982
Created by admin on Sat Dec 16 17:04:08 UTC 2023 , Edited by admin on Sat Dec 16 17:04:08 UTC 2023
PRIMARY
EPA CompTox
DTXSID401007055
Created by admin on Sat Dec 16 17:04:08 UTC 2023 , Edited by admin on Sat Dec 16 17:04:08 UTC 2023
PRIMARY
SMS_ID
100000128316
Created by admin on Sat Dec 16 17:04:08 UTC 2023 , Edited by admin on Sat Dec 16 17:04:08 UTC 2023
PRIMARY
CAS
867160-71-2
Created by admin on Sat Dec 16 17:04:08 UTC 2023 , Edited by admin on Sat Dec 16 17:04:08 UTC 2023
PRIMARY
WIKIPEDIA
LINSITINIB
Created by admin on Sat Dec 16 17:04:08 UTC 2023 , Edited by admin on Sat Dec 16 17:04:08 UTC 2023
PRIMARY
INN
9357
Created by admin on Sat Dec 16 17:04:08 UTC 2023 , Edited by admin on Sat Dec 16 17:04:08 UTC 2023
PRIMARY
FDA UNII
15A52GPT8T
Created by admin on Sat Dec 16 17:04:08 UTC 2023 , Edited by admin on Sat Dec 16 17:04:08 UTC 2023
PRIMARY
USAN
WW-16
Created by admin on Sat Dec 16 17:04:08 UTC 2023 , Edited by admin on Sat Dec 16 17:04:08 UTC 2023
PRIMARY
Related Record Type Details
INSULIN RECEPTOR
TARGET -> INHIBITOR
INSULIN-LIKE GROWTH FACTOR 1 RECEPTOR
TARGET -> INHIBITOR
MULTIDRUG RESISTANCE-ASSOCIATED PROTEIN 7
TRANSPORTER -> INHIBITOR
Related Record Type Details
Structure of LINSITINIB
ACTIVE MOIETY
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