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
SMILES
CC1=NOC2=C1C3=CC=CC=C3C(=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
| 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 |
DescriptionCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/26815195
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 |
|---|---|---|---|
Target ID: CHEMBL1163125 |
0.039 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1210 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/36923307/ |
125 mg single, oral dose: 125 mg route of administration: Oral experiment type: SINGLE co-administered: |
CPI-0610 ANHYDROUS plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
2052 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/36923307/ |
125 mg 1 times / day multiple, oral dose: 125 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CPI-0610 ANHYDROUS plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
5.9 μM EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/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: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
10500 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/36923307/ |
125 mg 1 times / day multiple, oral dose: 125 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CPI-0610 ANHYDROUS plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
11950 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/36923307/ |
125 mg single, oral dose: 125 mg route of administration: Oral experiment type: SINGLE co-administered: |
CPI-0610 ANHYDROUS plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
19734 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/36923307/ |
125 mg 1 times / day multiple, oral dose: 125 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CPI-0610 ANHYDROUS plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
49 μM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/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: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
15.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/36923307/ |
125 mg 1 times / day multiple, oral dose: 125 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CPI-0610 ANHYDROUS plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
6.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/36923307/ |
125 mg single, oral dose: 125 mg route of administration: Oral experiment type: SINGLE co-administered: |
CPI-0610 ANHYDROUS plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
15.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/36923307/ |
125 mg 1 times / day multiple, oral dose: 125 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CPI-0610 ANHYDROUS plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
10.7 h |
230 mg 1 times / day steady-state, oral dose: 230 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CPI-0610 plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
23 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/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: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Preclinical activity of CPI-0610, a novel small-molecule bromodomain and extra-terminal protein inhibitor in the therapy of multiple myeloma. | 2017-08 |
|
| Identification of a Benzoisoxazoloazepine Inhibitor (CPI-0610) of the Bromodomain and Extra-Terminal (BET) Family as a Candidate for Human Clinical Trials. | 2016-02-25 |
Patents
Sample Use Guides
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
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
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U4017GUQ06
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| Record Status |
Validated (UNII)
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CPI-0610
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CPI-0610 ANHYDROUS
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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). | ||
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| Related Record | Type | Details | ||
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TARGET -> INHIBITOR |
IC50
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SOLVATE->ANHYDROUS | |||
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TARGET -> INHIBITOR |
IC50
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TARGET -> INHIBITOR |
IC50
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TARGET -> INHIBITOR |
IC50
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| Related Record | Type | Details | ||
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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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