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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
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
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 Thu Jul 06 16:35:34 UTC 2023
Edited
by admin
on Thu Jul 06 16:35:34 UTC 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 Thu Jul 06 16:35:34 UTC 2023 , Edited by admin on Thu Jul 06 16:35:34 UTC 2023
Code System Code Type Description
INN
11237
Created by admin on Thu Jul 06 16:35:34 UTC 2023 , Edited by admin on Thu Jul 06 16:35:34 UTC 2023
PRIMARY
DRUG BANK
DB12570
Created by admin on Thu Jul 06 16:35:34 UTC 2023 , Edited by admin on Thu Jul 06 16:35:34 UTC 2023
PRIMARY
ChEMBL
CHEMBL3545151
Created by admin on Thu Jul 06 16:35:34 UTC 2023 , Edited by admin on Thu Jul 06 16:35:34 UTC 2023
PRIMARY
USAN
GH-13
Created by admin on Thu Jul 06 16:35:34 UTC 2023 , Edited by admin on Thu Jul 06 16:35:34 UTC 2023
PRIMARY
NCI_THESAURUS
C92575
Created by admin on Thu Jul 06 16:35:34 UTC 2023 , Edited by admin on Thu Jul 06 16:35:34 UTC 2023
PRIMARY
SMS_ID
300000023876
Created by admin on Thu Jul 06 16:35:34 UTC 2023 , Edited by admin on Thu Jul 06 16:35:34 UTC 2023
PRIMARY
CAS
1228013-30-6
Created by admin on Thu Jul 06 16:35:34 UTC 2023 , Edited by admin on Thu Jul 06 16:35:34 UTC 2023
PRIMARY
PUBCHEM
58298316
Created by admin on Thu Jul 06 16:35:34 UTC 2023 , Edited by admin on Thu Jul 06 16:35:34 UTC 2023
PRIMARY
FDA UNII
I8RA3543SY
Created by admin on Thu Jul 06 16:35:34 UTC 2023 , Edited by admin on Thu Jul 06 16:35:34 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY