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Details

Stereochemistry ABSOLUTE
Molecular Formula C30H38ClN7O3
Molecular Weight 580.121
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEP-37440

SMILES

CNC(=O)C1=C(NC2=NC(NC3=CC=C4C[C@H](CCCC4=C3OC)N5CCN(CCO)CC5)=NC=C2Cl)C=CC=C1

InChI

InChIKey=BCSHRERPHLTPEE-NRFANRHFSA-N
InChI=1S/C30H38ClN7O3/c1-32-29(40)23-7-3-4-9-25(23)34-28-24(31)19-33-30(36-28)35-26-11-10-20-18-21(6-5-8-22(20)27(26)41-2)38-14-12-37(13-15-38)16-17-39/h3-4,7,9-11,19,21,39H,5-6,8,12-18H2,1-2H3,(H,32,40)(H2,33,34,35,36)/t21-/m0/s1

HIDE SMILES / InChI
Molecular Formula C30H38ClN7O3
Molecular Weight 580.121
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/27009091 | https://www.ncbi.nlm.nih.gov/pubmed/26753004

CEP-37440 is a potent ATP-competitive, highly kinase selective, and orally active inhibitor of FAK1 and anaplastic lymphoma kinase (ALK). In addition to a favorable metabolic stability and pharmacokinetic profile preclinically, CEP-37440 is also a brain penetrant. CEP-37440 was able to inhibit the proliferation of certain IBC cells by decreasing the levels of phospho-FAK1 (Tyr 397); none of the cells expressed ALK. Studies using IBC xenograft models showed that CEP-37440 also effectively reduces the growth of the primary tumor xenografts and inhibits the development of brain metastases in mice.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 2.0 nM [IC50]
Inhibitor
8297
 3.1 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase I
428
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1533 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/27527804
10 mg/kg single, oral
dose: 10 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
CEP-37440 plasma
Mus musculus
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1612 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/27527804
1 mg/kg single, intravenous
dose: 1 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CEP-37440 plasma
Mus musculus
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
16429 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/27527804
10 mg/kg single, oral
dose: 10 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
CEP-37440 plasma
Mus musculus
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/27527804
1 mg/kg single, intravenous
dose: 1 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CEP-37440 plasma
Mus musculus
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P009CR5
https://www.1pchem.com/search?query=1P009CR5
ApexBio Technology
B3271
https://www.apexbt.com/catalogsearch/result/?q=B3271
AstaTech
F13321
http://astatechinc.com/CPSResult.php?CRNO=F13321
Cayman Chemical
21278
http://www.caymanchem.com/app/template/Product.vm/catalog/21278
Chem Scene
CS-2684
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-2684
ChemShuttle
157280
https://www.chemshuttle.com/catalogsearch/result/?q=157280
Combi-Blocks
QV-7347
http://www.combi-blocks.com/cgi-bin/find.cgi?QV-7347
Excenen
EX-A1543
http://www.excenen.com/searchresultlist.php?id=EX-A1543
Excenen
EX-A1625
http://www.excenen.com/searchresultlist.php?id=EX-A1625
MedChem Express
HY-15841
https://www.medchemexpress.com/search.html?q=HY-15841&ft=&fa=&fp=
MolPort
MolPort-042-676-269
https://www.molport.com/shop/molecule-link/MolPort-042-676-269
MolPort
MolPort-044-561-845
https://www.molport.com/shop/molecule-link/MolPort-044-561-845
Molnova
M17273
https://www.molnova.com/en/serch-list.html?keywords=M17273
MuseChem
I001499
https://www.musechem.com/product/I001499.html
TargetMol
T2655
https://www.targetmol.com/search?keyword=T2655
eMolecules
108759164
https://orderbb.emolecules.com/search/#?query=108759164
eMolecules
301191637
https://orderbb.emolecules.com/search/#?query=301191637
eMolecules
50282356
https://orderbb.emolecules.com/search/#?query=50282356
mcule
MCULE-3401000639
https://mcule.com/MCULE-3401000639/
mcule
MCULE-8370728429
https://mcule.com/MCULE-8370728429/
PubMed

PubMed

TitleDatePubMed
ALK inhibitors in non-small cell lung cancer: crizotinib and beyond.
2014 Jul
Discovery of Clinical Candidate CEP-37440, a Selective Inhibitor of Focal Adhesion Kinase (FAK) and Anaplastic Lymphoma Kinase (ALK).
2016 Aug 25
Patents

Patents

20150011561
2
US9339502
2

Sample Use Guides

In Vivo Use Guide
CEP-37440 supplied as 25 mg and 100 mg capsules and orally administered daily.
Route of Administration: Oral
In Vitro Use Guide
CEP-37440 was screened against both NPM-ALK+ ALCL cell lines (Sup-M2 and Karpas-299) and NPM-ALK− hematologic cell lines (Hut-102 and K562) and demonstrated selective cytotoxicity in the oncogene-addicted cell lines in nanomolar range
Substance Class Chemical
Created
by admin
on Sat Dec 16 05:50:13 UTC 2023
Edited
by admin
on Sat Dec 16 05:50:13 UTC 2023
Record UNII
O3MNS8782H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEP-37440
Common Name English
BENZAMIDE, 2-((5-CHLORO-2-(((6S)-6,7,8,9-TETRAHYDRO-6-(4-(2-HYDROXYETHYL)-1-PIPERAZINYL)-1-METHOXY-5H-BENZOCYCLOHEPTEN-2-YL)AMINO)-4-PYRIMIDINYL)AMINO)-N-METHYL-
Systematic Name English
ALK-FAK INHIBITOR CEP-37440
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C129825
Created by admin on Sat Dec 16 05:50:13 UTC 2023 , Edited by admin on Sat Dec 16 05:50:13 UTC 2023
NCI_THESAURUS C141136
Created by admin on Sat Dec 16 05:50:13 UTC 2023 , Edited by admin on Sat Dec 16 05:50:13 UTC 2023
Code System Code Type Description
CAS
1609103-92-5
Created by admin on Sat Dec 16 05:50:13 UTC 2023 , Edited by admin on Sat Dec 16 05:50:13 UTC 2023
NO STRUCTURE GIVEN
PUBCHEM
71721648
Created by admin on Sat Dec 16 05:50:13 UTC 2023 , Edited by admin on Sat Dec 16 05:50:13 UTC 2023
PRIMARY
NCI_THESAURUS
C111685
Created by admin on Sat Dec 16 05:50:13 UTC 2023 , Edited by admin on Sat Dec 16 05:50:13 UTC 2023
PRIMARY
CAS
1391712-60-9
Created by admin on Sat Dec 16 05:50:13 UTC 2023 , Edited by admin on Sat Dec 16 05:50:13 UTC 2023
PRIMARY
DRUG BANK
DB13060
Created by admin on Sat Dec 16 05:50:13 UTC 2023 , Edited by admin on Sat Dec 16 05:50:13 UTC 2023
PRIMARY
EPA CompTox
DTXSID301025939
Created by admin on Sat Dec 16 05:50:13 UTC 2023 , Edited by admin on Sat Dec 16 05:50:13 UTC 2023
PRIMARY
FDA UNII
O3MNS8782H
Created by admin on Sat Dec 16 05:50:13 UTC 2023 , Edited by admin on Sat Dec 16 05:50:13 UTC 2023
PRIMARY
ChEMBL
CHEMBL3545051
Created by admin on Sat Dec 16 05:50:13 UTC 2023 , Edited by admin on Sat Dec 16 05:50:13 UTC 2023
PRIMARY
Related Record Type Details
FOCAL ADHESION KINASE 1
TARGET -> INHIBITOR
INHIBITOR
IC50
ANAPLASTIC LYMPHOMA KINASE
TARGET -> INHIBITOR
INHIBITOR
IC50
Structure of CEP-37440 TRIHYDROCHLORIDE DIHYDRATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of CEP-37440
ACTIVE MOIETY
NIH
NCATS
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