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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H16ClN3O2
Molecular Weight 365.813
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PELABRESIB ANHYDROUS

SMILES

CC1=NOC2=C1C3=C(C=CC=C3)C(=N[C@H]2CC(N)=O)C4=CC=C(Cl)C=C4

InChI

InChIKey=GCWIQUVXWZWCLE-INIZCTEOSA-N
InChI=1S/C20H16ClN3O2/c1-11-18-14-4-2-3-5-15(14)19(12-6-8-13(21)9-7-12)23-16(10-17(22)25)20(18)26-24-11/h2-9,16H,10H2,1H3,(H2,22,25)/t16-/m0/s1

HIDE SMILES / InChI
Molecular Formula C20H16ClN3O2
Molecular Weight 365.813
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26815195

CPI-0610 is a small molecule inhibitor of the Bromodomain and Extra-Terminal (BET) family of proteins, with potential antineoplastic activity. Upon administration, the BET inhibitor CPI-0610 binds to the acetylated lysine recognition motifs on the bromodomain of BET proteins, thereby preventing the interaction between the BET proteins and acetylated histone peptides. This disrupts chromatin remodeling and gene expression. Prevention of the expression of certain growth-promoting genes may lead to an inhibition of tumor cell growth. CPI-0610 is currently being evaluated in three Phase 1 clinical trials in the U.S.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 0.039 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase I
428
Unknown

Approved Use

Unknown
Primary
Phase I
428
Unknown

Approved Use

Unknown
Primary
Phase I
428
Unknown

Approved Use

Unknown
Primary
Phase I
428
Unknown

Approved Use

Unknown
Primary
Phase I
428
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
5.9 μM
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26815195
300 mg 1 times / day steady-state, oral
dose: 300 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CPI-0610 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1.8 μM
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26815195
5 mg/kg single, oral
dose: 5 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
CPI-0610 plasma
Rattus norvegicus
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
49 μM × h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26815195
300 mg 1 times / day steady-state, oral
dose: 300 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CPI-0610 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
9.1 μM × h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26815195
5 mg/kg single, oral
dose: 5 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
CPI-0610 plasma
Rattus norvegicus
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
23 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26815195
300 mg 1 times / day steady-state, oral
dose: 300 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CPI-0610 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
7%
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26815195
5 mg/kg single, oral
dose: 5 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
CPI-0610 plasma
Rattus norvegicus
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P0018A5
https://www.1pchem.com/search?query=1P0018A5
AKOS
AKOS028109790
http://akoscompounds.de/catalogue/AKosSamplesiSSretrieval.php?GUID=4e4caa52-3dca-4da0-b75a-caeae59e1096&IDNUMBERS=AKOS028109790
Ambeed
A137689
http://www.ambeed.com/search/Search.html?keyword=A137689
ApexBio Technology
B5887
https://www.apexbt.com/catalogsearch/result/?q=B5887
AstaTech
C72527
http://astatechinc.com/CPSResult.php?CRNO=C72527
Axon MedChem
2594
https://www.axonmedchem.com/product/2594
BLD Pharm
BD630200
http://www.bldpharm.com/search/Search.html?keyword=BD630200
Cayman Chemical
21680
http://www.caymanchem.com/app/template/Product.vm/catalog/21680
ChemShuttle
185549
https://www.chemshuttle.com/catalogsearch/result/?q=185549
Excenen
EX-A1612
http://www.excenen.com/searchresultlist.php?id=EX-A1612
KeyOrganics
AS-73876
http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-73876
Lab Network
LN01350020
https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01350020
MolPort
MolPort-042-665-896
https://www.molport.com/shop/molecule-link/MolPort-042-665-896
Molnova
M11568
https://www.molnova.com/en/serch-list.html?keywords=M11568
MuseChem
I006253
https://www.musechem.com/product/I006253.html
ShangHai Biochempartner
BCP001268
http://www.biochempartner.com/search_BCP001268
eMolecules
84836344
https://orderbb.emolecules.com/search/#?query=84836344
eMolecules
93430713
https://orderbb.emolecules.com/search/#?query=93430713
mcule
MCULE-5899904676
https://mcule.com/MCULE-5899904676/
PubMed

PubMed

TitleDatePubMed
Identification of a Benzoisoxazoloazepine Inhibitor (CPI-0610) of the Bromodomain and Extra-Terminal (BET) Family as a Candidate for Human Clinical Trials.
2016 Feb 25
Patents

Patents

US20150087636
2

Sample Use Guides

In Vivo Use Guide
In an ongoing study, CPI-0610 has been administered to patients with progressive lymphoma once daily orally for fourteen consecutive days, followed by a seven-day period without treatment. Cycles are repeated, at escalating doses, as tolerated by the patients. Dosing at three representative levels (24 mg, 120 mg, and 300 mg).
Route of Administration: Oral
In Vitro Use Guide
A panel of MM cell lines was cultured in the presence of increasing doses of CPI-0610 (0-1500 nM) for 72 h. CPI-0610 treatment resulted in dose-dependent cytotoxicity with EC50 ranging between 200 and 900 nM at 72 h for BET-sensitive cell lines (INA6, RPMI-8226, LR5, H929, MM.1S, MM.1R, U266).
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:31:52 UTC 2023
Edited
by admin
on Sat Dec 16 10:31:52 UTC 2023
Record UNII
U4017GUQ06
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PELABRESIB ANHYDROUS
Common Name English
pelabresib [INN]
Common Name English
CPI-232
Code English
CPI-267232
Code English
2-((4S)-6-(4-CHLOROPHENYL)-1-METHYL-4H-ISOXAZOLO(5,4-D)(2)BENZAZEPIN-4-YL)ACETAMIDE
Systematic Name English
4H-ISOXAZOLO(5,4-D)(2)BENZAZEPINE-4-ACETAMIDE, 6-(4-CHLOROPHENYL)-1-METHYL-, (4S)
Systematic Name English
CPI-0610 ANHYDROUS
Common Name English
Code System Code Type Description
WIKIPEDIA
CPI-0610
Created by admin on Sat Dec 16 10:31:52 UTC 2023 , Edited by admin on Sat Dec 16 10:31:52 UTC 2023
PRIMARY
PUBCHEM
57389999
Created by admin on Sat Dec 16 10:31:52 UTC 2023 , Edited by admin on Sat Dec 16 10:31:52 UTC 2023
PRIMARY
INN
11382
Created by admin on Sat Dec 16 10:31:52 UTC 2023 , Edited by admin on Sat Dec 16 10:31:52 UTC 2023
PRIMARY
EPA CompTox
DTXSID201022544
Created by admin on Sat Dec 16 10:31:52 UTC 2023 , Edited by admin on Sat Dec 16 10:31:52 UTC 2023
PRIMARY
MANUFACTURER PRODUCT INFORMATION
CPI-0610 ANHYDROUS
Created by admin on Sat Dec 16 10:31:52 UTC 2023 , Edited by admin on Sat Dec 16 10:31:52 UTC 2023
PRIMARY MedKoo CAT NO.: 206117, CAS NO.: 1380087-89-7Description: CPI-0610 is a small molecule inhibitor of the Bromodomain and Extra-Terminal (BET) family of proteins, with potential antineoplastic activity. Upon administration, the BET inhibitor CPI-0610 binds to the acetylated lysine recognition motifs on the bromodomain of BET proteins, thereby preventing the interaction between the BET proteins and acetylated histone peptides. This disrupts chromatin remodeling and gene expression. Prevention of the expression of certain growth-promoting genes may lead to an inhibition of tumor cell growth. (Last updated: 5/18/2016).
SMS_ID
300000007881
Created by admin on Sat Dec 16 10:31:52 UTC 2023 , Edited by admin on Sat Dec 16 10:31:52 UTC 2023
PRIMARY
NCI_THESAURUS
C111901
Created by admin on Sat Dec 16 10:31:52 UTC 2023 , Edited by admin on Sat Dec 16 10:31:52 UTC 2023
PRIMARY
FDA UNII
U4017GUQ06
Created by admin on Sat Dec 16 10:31:52 UTC 2023 , Edited by admin on Sat Dec 16 10:31:52 UTC 2023
PRIMARY
CAS
1380087-89-7
Created by admin on Sat Dec 16 10:31:52 UTC 2023 , Edited by admin on Sat Dec 16 10:31:52 UTC 2023
PRIMARY
Related Record Type Details
BROMODOMAIN-CONTAINING PROTEIN 4
TARGET -> INHIBITOR
IC50
Structure of PELABRESIB
SOLVATE->ANHYDROUS
BROMODOMAIN-CONTAINING PROTEIN 3
TARGET -> INHIBITOR
IC50
BROMODOMAIN-CONTAINING PROTEIN 2
TARGET -> INHIBITOR
IC50
BROMODOMAIN TESTIS-SPECIFIC PROTEIN
TARGET -> INHIBITOR
IC50
Related Record Type Details
Structure of PELABRESIB ANHYDROUS
ACTIVE MOIETY
In recent years, inhibition of the interaction between the bromodomain and extra-terminal domain (BET) family of chromatin adaptors and acetyl-lysine residues on chromatin has emerged as a promising approach to regulate the expression of important disease-relevant genes, including MYC, BCL-2, and NF-.KAPPA.B. Here we describe the identification and characterization of a potent and selective benzoisoxazoloazepine BET bromodomain inhibitor that attenuates BET-dependent gene expression in vivo, demonstrates antitumor efficacy in an MV-4-11 mouse xenograft model, and is currently undergoing human clinical trials for hematological malignancies (CPI-0610).
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