PELABRESIB

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H16ClN3O2.H2O
Molecular Weight	383.828
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=LXMGXMQQJNULPR-NTISSMGPSA-N

InChI=1S/C20H16ClN3O2.H2O/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);1H2/t16-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27890933
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

Targets

Primary Target	Pharmacology	Condition	Potency
Bromodomain-containing protein 4 13 Target ID: CHEMBL1163125 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27890933	Inhibitor 8297		0.039 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Multiple myeloma 159 Sources: https://clinicaltrials.gov/ct2/show/NCT02157636	Primary	Phase I 428	Unknown Approved Use Unknown
Lymphoma 58 Sources: https://clinicaltrials.gov/ct2/show/NCT02157636	Primary	Phase I 428	Unknown Approved Use Unknown
Acute myeloid leukemia 136 Sources: https://clinicaltrials.gov/ct2/show/NCT02157636	Primary	Phase I 428	Unknown Approved Use Unknown
Myelodysplastic syndromes 58 Sources: https://clinicaltrials.gov/ct2/show/NCT02157636	Primary	Phase I 428	Unknown Approved Use Unknown
Myelofibrosis 15 Sources: https://clinicaltrials.gov/ct2/show/NCT02157636	Primary	Phase I 428	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
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

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

F_unbound

Value	Dose	Co-administered	Analyte	Population
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

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
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	26815195
Preclinical activity of CPI-0610, a novel small-molecule bromodomain and extra-terminal protein inhibitor in the therapy of multiple myeloma.	2017 Aug	27890933

Patents

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 10:55:23 UTC 2023` Edited by `admin` on `Sat Dec 16 10:55:23 UTC 2023`
Record UNII	306QR91I9R
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PELABRESIB

Official Name

English

PELABRESIB [USAN]

Common Name

English

PELABRESIB MONOHYDRATE

Common Name

English

Pelabresib [WHO-DD]

Common Name

English

CPI-0610

Code

English

4H-ISOXAZOLO(5,4-D)(2)BENZAZEPINE-4-ACETAMIDE, 6-(4-CHLOROPHENYL)-1-METHYL-, HYDRATE (1:1), (4S)-

Systematic Name

English

2-((4S)-6-(4-CHLOROPHENYL)-1-METHYL-4H-ISOXAZOLO(5,4-D)(2)BENZAZEPIN-4-YL)ACETAMIDE MONOHYDRATE

Systematic Name

English

2-((4S)-6-(4-CHLOROPHENYL)-1-METHYL-4H-BENZO(C)ISOXAZOLO(4,5-E)AZEPIN-4-YL)ACETAMIDE MONOHYDRATE

Systematic Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

710219