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Details

Stereochemistry ACHIRAL
Molecular Formula C25H21FN2O.ClH
Molecular Weight 420.906
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CP-461

SMILES

Cl.CC1=C(CC(=O)NCC2=CC=CC=C2)C3=C(C=CC(F)=C3)\C1=C/C4=CC=NC=C4

InChI

InChIKey=KGXPDNOBLLACKL-BWLGBDCWSA-N
InChI=1S/C25H21FN2O.ClH/c1-17-22(13-18-9-11-27-12-10-18)21-8-7-20(26)14-24(21)23(17)15-25(29)28-16-19-5-3-2-4-6-19;/h2-14H,15-16H2,1H3,(H,28,29);1H/b22-13-;

HIDE SMILES / InChI

Molecular Formula C25H21FN2O
Molecular Weight 384.4454
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

CP-461 is an orally bioavailable second-generation apoptotic antineoplastic drug and analog of the nonsteroidal anti-inflammatory drug sulindac. CP-461 is an inhibitor of monophosphate-phosphodiesterase, an enzyme that inhibits the normal apoptosis signal pathway. Inhibition of cGMP-PDE permits the apoptotic signal pathway to proceed unopposed, resulting in apoptotic cell death. CP-461 was initially developed by OSI Pharmaceuticals, and in the early 2000s, CP-461 was investigated in phase I and phase 2 clinical trials for the treatment of chronic lymphocytic leukemia, Crohn's disease, malignant melanoma, renal cell carcinoma, and prostate cancer, both alone and in combination with other chemotherapeutic agents. The coadministration of CP-461 with other agents, however, did not increase the response rate. CP-461 was licensed to Celek Pharmaceuticals, where the compound was repurposed for the treatment of bladder cancer, but no development was reported.

Approval Year

PubMed

PubMed

TitleDatePubMed
Cyclic GMP mediates apoptosis induced by sulindac derivatives via activation of c-Jun NH2-terminal kinase 1.
2000 Oct
Cyclic GMP-dependent protein kinase activation and induction by exisulind and CP461 in colon tumor cells.
2001 Nov
Pro-apoptotic actions of exisulind and CP461 in SW480 colon tumor cells involve beta-catenin and cyclin D1 down-regulation.
2002 Nov 1
Synergistic effects of acyclic retinoid and OSI-461 on growth inhibition and gene expression in human hepatoma cells.
2004 Oct 1
Activation of protein kinase G up-regulates expression of 15-lipoxygenase-1 in human colon cancer cells.
2005 Sep 15
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:07:01 GMT 2023
Edited
by admin
on Fri Dec 15 16:07:01 GMT 2023
Record UNII
68OJX9I7DT
Record Status Validated (UNII)
Record Version
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Name Type Language
CP-461
Common Name English
CP 461 [WHO-DD]
Common Name English
1H-INDENE-3-ACETAMIDE, 5-FLUORO-2-METHYL-N-(PHENYLMETHYL)-1-(4-PYRIDINYLMETHYLENE)-, HYDROCHLORIDE (1:1), (1Z)-
Common Name English
OSI-461
Code English
Code System Code Type Description
DRUG BANK
DB05415
Created by admin on Fri Dec 15 16:07:01 GMT 2023 , Edited by admin on Fri Dec 15 16:07:01 GMT 2023
PRIMARY
PUBCHEM
6445781
Created by admin on Fri Dec 15 16:07:01 GMT 2023 , Edited by admin on Fri Dec 15 16:07:01 GMT 2023
PRIMARY
NCI_THESAURUS
C133019
Created by admin on Fri Dec 15 16:07:01 GMT 2023 , Edited by admin on Fri Dec 15 16:07:01 GMT 2023
PRIMARY
FDA UNII
68OJX9I7DT
Created by admin on Fri Dec 15 16:07:01 GMT 2023 , Edited by admin on Fri Dec 15 16:07:01 GMT 2023
PRIMARY
CAS
227619-96-7
Created by admin on Fri Dec 15 16:07:01 GMT 2023 , Edited by admin on Fri Dec 15 16:07:01 GMT 2023
PRIMARY
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ACTIVE MOIETY