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Details

Stereochemistry ACHIRAL
Molecular Formula C21H27N5O3
Molecular Weight 397.4708
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ONATASERTIB

SMILES

CO[C@H]1CC[C@@H](CC1)N2C(=O)CNC3=C2N=C(C=N3)C4=CN=C(C=C4)C(C)(C)O

InChI

InChIKey=UFKLYTOEMRFKAD-SHTZXODSSA-N
InChI=1S/C21H27N5O3/c1-21(2,28)17-9-4-13(10-22-17)16-11-23-19-20(25-16)26(18(27)12-24-19)14-5-7-15(29-3)8-6-14/h4,9-11,14-15,28H,5-8,12H2,1-3H3,(H,23,24)/t14-,15-

HIDE SMILES / InChI

Molecular Formula C21H27N5O3
Molecular Weight 397.4708
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

CC-223 is an orally available inhibitor of the mammalian target of rapamycin (mTOR) with potential antineoplastic activity. mTOR kinase inhibitor CC-223 inhibits the activity of mTOR, which may result in the induction of tumor cell apoptosis and a decrease in tumor cell proliferation. CC-223 disrupted mitochondrial function, and induced mitochondrial permeability transition pore (mPTP) opening and reactive oxygen species (ROS) production. CC-223 is currently in phase II clinical trials for the treatment of Multiple myeloma; Non-Hodgkin's lymphoma; Solid tumours. The most common treatment-related adverse events were hyperglycemia, fatigue and rash.

CNS Activity

Sources: DOI: 10.1200/jco.2013.31.15_suppl.2606

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
16.0 nM [IC50]
4.0 µM [IC50]
0.84 µM [IC50]
Conditions
PubMed

PubMed

TitleDatePubMed
Discovery and SAR exploration of a novel series of imidazo[4,5-b]pyrazin-2-ones as potent and selective mTOR kinase inhibitors.
2011 Nov 15
Mammalian target of rapamycin inhibition in hepatocellular carcinoma.
2014 Nov 27
Discovery of mammalian target of rapamycin (mTOR) kinase inhibitor CC-223.
2015 Jul 9
CC-223, a Potent and Selective Inhibitor of mTOR Kinase: In Vitro and In Vivo Characterization.
2015 Jun
A phase I dose-escalation study to assess safety, tolerability, pharmacokinetics, and preliminary efficacy of the dual mTORC1/mTORC2 kinase inhibitor CC-223 in patients with advanced solid tumors or multiple myeloma.
2015 Oct 1
Patents

Sample Use Guides

20 mg or 30 mg once daily.
Route of Administration: Oral
CC-223 showed a concentration-dependent reduction in each marker, with IC50 values of 31 nmol/L for pS6RP, 405 47 nmol/L for p4EBP1, and 11 10 nmol/L for pAKT(S473). CC-223 inhibited both mTORC1 (S6RP and 4EBP1) and mTORC2 [AKT(S473)] markers across the panel with IC50 ranges of 27 to 184 nmol/L for pS6RP, 120 to 1,050 nmol/L for p4EBP1 and 11 to 150 nmol/L for pAKT (S473).
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:00:26 GMT 2023
Edited
by admin
on Sat Dec 16 11:00:26 GMT 2023
Record UNII
I8RA3543SY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ONATASERTIB
INN   USAN  
Official Name English
CC-223
WHO-DD  
Preferred Name English
ONATASERTIB [USAN]
Common Name English
ATG008
Code English
CC223
Code English
ONATASERTIB [WHO-DD]
Common Name English
7-[6-(2-Hydroxypropan-2-yl)pyridin-3-yl]-1-(trans-4-methoxycyclohexyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one
Systematic Name English
PYRAZINO(2,3-B)PYRAZIN-2(1H)-ONE, 3,4-DIHYDRO-7-(6-(1-HYDROXY-1-METHYLETHYL)-3-PYRIDINYL)-1-(TRANS-4-METHOXYCYCLOHEXYL)-
Systematic Name English
ATG-008
Code English
3,4-DIHYDRO-7-(6-(1-HYDROXY-1-METHYLETHYL)-3-PYRIDINYL)-1-(TRANS-4-METHOXYCYCLOHEXYL)PYRAZINO(2,3-B)PYRAZIN-2(1H)-ONE
Systematic Name English
onatasertib [INN]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 407913
Created by admin on Sat Dec 16 11:00:26 GMT 2023 , Edited by admin on Sat Dec 16 11:00:26 GMT 2023
Code System Code Type Description
INN
11237
Created by admin on Sat Dec 16 11:00:26 GMT 2023 , Edited by admin on Sat Dec 16 11:00:26 GMT 2023
PRIMARY
DRUG BANK
DB12570
Created by admin on Sat Dec 16 11:00:26 GMT 2023 , Edited by admin on Sat Dec 16 11:00:26 GMT 2023
PRIMARY
ChEMBL
CHEMBL3545151
Created by admin on Sat Dec 16 11:00:26 GMT 2023 , Edited by admin on Sat Dec 16 11:00:26 GMT 2023
PRIMARY
USAN
GH-13
Created by admin on Sat Dec 16 11:00:26 GMT 2023 , Edited by admin on Sat Dec 16 11:00:26 GMT 2023
PRIMARY
NCI_THESAURUS
C92575
Created by admin on Sat Dec 16 11:00:26 GMT 2023 , Edited by admin on Sat Dec 16 11:00:26 GMT 2023
PRIMARY
SMS_ID
300000023876
Created by admin on Sat Dec 16 11:00:26 GMT 2023 , Edited by admin on Sat Dec 16 11:00:26 GMT 2023
PRIMARY
CAS
1228013-30-6
Created by admin on Sat Dec 16 11:00:26 GMT 2023 , Edited by admin on Sat Dec 16 11:00:26 GMT 2023
PRIMARY
PUBCHEM
58298316
Created by admin on Sat Dec 16 11:00:26 GMT 2023 , Edited by admin on Sat Dec 16 11:00:26 GMT 2023
PRIMARY
FDA UNII
I8RA3543SY
Created by admin on Sat Dec 16 11:00:26 GMT 2023 , Edited by admin on Sat Dec 16 11:00:26 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY