U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C18H18FN5O2S
Molecular Weight 387.431
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ATUVECICLIB

SMILES

COC1=CC(F)=CC=C1C2=NC=NC(NC3=CC=CC(C[S@](C)(=N)=O)=C3)=N2

InChI

InChIKey=ACWKGTGIJRCOOM-HHHXNRCGSA-N
InChI=1S/C18H18FN5O2S/c1-26-16-9-13(19)6-7-15(16)17-21-11-22-18(24-17)23-14-5-3-4-12(8-14)10-27(2,20)25/h3-9,11,20H,10H2,1-2H3,(H,21,22,23,24)/t27-/m1/s1

HIDE SMILES / InChI

Molecular Formula C18H18FN5O2S
Molecular Weight 387.431
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Atuveciclib (previously known as BAY 1143572) was developed as a highly selective inhibitor of positive transcription elongation factor b (PTEFb) /CDK9 for the treatment of cancer. PTEFb is a heterodimer of CDK9 and one of four cyclin partners, cyclin T1, cyclin K, cyclin T2a or cyclin T2b. Atuveciclib also inhibits RNA polymerase II (Ser2) phosphorylation and downregulate MYC protein expression in hematologic malignancies. The drug participated in phase I clinical trials in subjects with advanced acute leukemia and for patients with advanced malignancies. Information about further studies for these types of cancer is not available. Recently published article has shown that atuveciclib enhanced the antineoplastic effects of cisplatin and promoted inhibitory effects on breast cancer stem-like cells grown as mammospheres. In addition, was suggested that CDK9 could be a potential therapeutic target in aggressive forms of CDK9-high triple-negative breast cancer (TNBC).

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
13.0 nM [IC50]
PubMed

PubMed

TitleDatePubMed
Novel Pieces for the Emerging Picture of Sulfoximines in Drug Discovery: Synthesis and Evaluation of Sulfoximine Analogues of Marketed Drugs and Advanced Clinical Candidates.
2017 Apr 6
Identification of Atuveciclib (BAY 1143572), the First Highly Selective, Clinical PTEFb/CDK9 Inhibitor for the Treatment of Cancer.
2017 Nov 8
Antineoplastic effects of selective CDK9 inhibition with atuveciclib on cancer stem-like cells in triple-negative breast cancer.
2018 Dec 18

Sample Use Guides

Subjects received 20, 40, 80, 120, 160 or 200 mg tablet orally once daily from Cycle 1 Day 1 of each cycle.
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:29:20 UTC 2023
Edited
by admin
on Sat Dec 16 08:29:20 UTC 2023
Record UNII
63Q7F59W0V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ATUVECICLIB
INN  
INN  
Official Name English
atuveciclib [INN]
Common Name English
Atuveciclib [WHO-DD]
Common Name English
1,3,5-TRIAZIN-2-AMINE, 4-(4-FLUORO-2-METHOXYPHENYL)-N-(3-((S-METHYLSULFONIMIDOYL)METHYL)PHENYL)-, (+)-
Systematic Name English
Code System Code Type Description
FDA UNII
63Q7F59W0V
Created by admin on Sat Dec 16 08:29:20 UTC 2023 , Edited by admin on Sat Dec 16 08:29:20 UTC 2023
PRIMARY
CAS
1414943-94-4
Created by admin on Sat Dec 16 08:29:20 UTC 2023 , Edited by admin on Sat Dec 16 08:29:20 UTC 2023
PRIMARY
INN
10373
Created by admin on Sat Dec 16 08:29:20 UTC 2023 , Edited by admin on Sat Dec 16 08:29:20 UTC 2023
PRIMARY
PUBCHEM
121488167
Created by admin on Sat Dec 16 08:29:20 UTC 2023 , Edited by admin on Sat Dec 16 08:29:20 UTC 2023
PRIMARY
NCI_THESAURUS
C121456
Created by admin on Sat Dec 16 08:29:20 UTC 2023 , Edited by admin on Sat Dec 16 08:29:20 UTC 2023
PRIMARY
SMS_ID
100000174620
Created by admin on Sat Dec 16 08:29:20 UTC 2023 , Edited by admin on Sat Dec 16 08:29:20 UTC 2023
PRIMARY
Related Record Type Details
TARGET->WEAK INHIBITOR
IC50
TARGET -> INHIBITOR
IC50
Related Record Type Details
ACTIVE MOIETY