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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H30FN7O.C7H6O2
Molecular Weight 573.661
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CENISERTIB BENZOATE

SMILES

OC(=O)C1=CC=CC=C1.CN2CCN(CC2)C3=C(C)C=C(NC4=NC=C(F)C(N[C@@H]5[C@@H]6C[C@@H](C=C6)[C@@H]5C(N)=O)=N4)C=C3

InChI

InChIKey=MZPZKZPRYUOUIW-MCOAATBNSA-N
InChI=1S/C24H30FN7O.C7H6O2/c1-14-11-17(5-6-19(14)32-9-7-31(2)8-10-32)28-24-27-13-18(25)23(30-24)29-21-16-4-3-15(12-16)20(21)22(26)33;8-7(9)6-4-2-1-3-5-6/h3-6,11,13,15-16,20-21H,7-10,12H2,1-2H3,(H2,26,33)(H2,27,28,29,30);1-5H,(H,8,9)/t15-,16+,20+,21-;/m1./s1

HIDE SMILES / InChI

Molecular Formula C7H6O2
Molecular Weight 122.1213
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C24H30FN7O
Molecular Weight 451.5397
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Cenisertib (also known as R763) is water-soluble, synthetic small molecule aurora kinase inhibitor with potential antineoplastic activity. Cenisertib is a potent adenine triphosphate-competitive inhibitor of Aurora kinase isoforms A–C, disrupting mitotic spindle activity, blocking cell separation, and leading to polyploidy and cell death. At low nanomolar concentrations, Cenisertib also inhibits other kinases involved in cell survival and proliferation including FLT3, BCR-ABL1, and BCR-ABL1 with T315I mutation. It also inhibits JAK2 kinase, but at higher concentrations. Preclinically, Cenisertib has demonstrated potent antitumor activity as a single agent and in combination treatment in leukemia cell lines, freshly isolated leukemia cells, and leukemia xenograft models. Toxicities appear to be related mainly to the gastrointestinal and hematopoietic systems. In animal models, activity and toxicity depend not only on dose but also on the schedule of administration.

Approval Year

PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

Patients received escalating doses either on days 1–3 and 8–10 (n = 36) or on days 1–6 (n = 39) of a 21-day cycle. The maximum tolerated doses were 37 and 28 mg/m2/day, respectively.
Route of Administration: Intravenous
Substance Class Chemical
Created
by admin
on Thu Jul 06 08:32:42 UTC 2023
Edited
by admin
on Thu Jul 06 08:32:42 UTC 2023
Record UNII
S68QU67MAZ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CENISERTIB BENZOATE
Common Name English
R-763 BENZOATE
Code English
AS-703569 BENZOATE
Code English
(1S,2S,3R,4R)-3-(5-FLUORO-2-(3-METHYL-4-(4-METHYLPIPERAZIN-1-YL)-PHENYLAMINO)-PYRIMIDIN-4-YLAMINO)BICYCLE(2.2.1)HEPT-5-ENE-2-CARBOXAMIDE BENZOATE
Common Name English
MSC-1992371A
Common Name English
BICYCLO(2.2.1)HEPT-5-ENE-2-CARBOXAMIDE, 3-((5-FLUORO-2-((3-METHYL-4-(4-METHYL-1-PIPERAZINYL)PHENYL)AMINO)-4-PYRIMIDINYL)AMINO)-, (1S,2S,3R,4R)-, BENZOATE
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 299109
Created by admin on Thu Jul 06 08:32:42 UTC 2023 , Edited by admin on Thu Jul 06 08:32:42 UTC 2023
Code System Code Type Description
SMS_ID
100000181838
Created by admin on Thu Jul 06 08:32:42 UTC 2023 , Edited by admin on Thu Jul 06 08:32:42 UTC 2023
PRIMARY
FDA UNII
S68QU67MAZ
Created by admin on Thu Jul 06 08:32:42 UTC 2023 , Edited by admin on Thu Jul 06 08:32:42 UTC 2023
PRIMARY
CAS
1145859-64-8
Created by admin on Thu Jul 06 08:32:42 UTC 2023 , Edited by admin on Thu Jul 06 08:32:42 UTC 2023
PRIMARY
EPA CompTox
DTXSID10150787
Created by admin on Thu Jul 06 08:32:42 UTC 2023 , Edited by admin on Thu Jul 06 08:32:42 UTC 2023
PRIMARY
EU-Orphan Drug
EU/3/10/729 WITHDRAWN
Created by admin on Thu Jul 06 08:32:42 UTC 2023 , Edited by admin on Thu Jul 06 08:32:42 UTC 2023
PRIMARY Please note that this product was withdrawn from the Community Register of designated orphan medicinal products in October 2011 on request of the sponsor.
PUBCHEM
66872873
Created by admin on Thu Jul 06 08:32:42 UTC 2023 , Edited by admin on Thu Jul 06 08:32:42 UTC 2023
PRIMARY
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