Details
Stereochemistry | ACHIRAL |
Molecular Formula | C21H26N6O2 |
Molecular Weight | 394.4701 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1C=C(CNCC2CCN(CC2)C3=NC=C(C=N3)C(=O)NO)C4=C1C=CC=C4
InChI
InChIKey=PAWIYAYFNXQGAP-UHFFFAOYSA-N
InChI=1S/C21H26N6O2/c1-26-14-17(18-4-2-3-5-19(18)26)11-22-10-15-6-8-27(9-7-15)21-23-12-16(13-24-21)20(28)25-29/h2-5,12-15,22,29H,6-11H2,1H3,(H,25,28)
Molecular Formula | C21H26N6O2 |
Molecular Weight | 394.4701 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Quisinostat is an orally bioavailable potent histone deacetylase inhibitor, specifically selected due to its sustained inhibition of HDAC1 in solid tumor tissues and prolonged period of half-elimination from tissues. Phase 2 clinical trials are ongoing in patients with platinum-resistant ovarian cancer and non-small cell lung cancer (NSCLC). Quisinostat is active in the treatment of patients with relapsed or refractory Sézary syndrome. The most common drug-related adverse events reported in this trial were: nausea, diarrhea, asthenia. Grade 3 adverse events were also reported: hypertension, lethargy and pruritus.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL325 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19861438 |
0.11 nM [IC50] | ||
Target ID: CHEMBL1937 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19861438 |
0.33 nM [IC50] | ||
Target ID: CHEMBL3310 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19861438 |
0.37 nM [IC50] | ||
Target ID: CHEMBL5103 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19861438 |
0.46 nM [IC50] | ||
Target ID: CHEMBL3524 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19861438 |
0.64 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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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 |
---|---|---|---|---|
0.828 ng/mL |
6 mg 1 times / day steady-state, oral dose: 6 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
QUISINOSTAT plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
1.24 ng/mL |
8 mg 1 times / day steady-state, oral dose: 8 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
QUISINOSTAT plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
2.155 ng/mL |
12 mg 1 times / day steady-state, oral dose: 12 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
QUISINOSTAT plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.62 ng × h/mL |
6 mg 1 times / day steady-state, oral dose: 6 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
QUISINOSTAT plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
9.77 ng × h/mL |
8 mg 1 times / day steady-state, oral dose: 8 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
QUISINOSTAT plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
12.91 ng × h/mL |
12 mg 1 times / day steady-state, oral dose: 12 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
QUISINOSTAT plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2 h |
6 mg 1 times / day steady-state, oral dose: 6 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
QUISINOSTAT plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
4.08 h |
8 mg 1 times / day steady-state, oral dose: 8 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
QUISINOSTAT plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
2.76 h |
12 mg 1 times / day steady-state, oral dose: 12 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
QUISINOSTAT plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
PubMed
Title | Date | PubMed |
---|---|---|
Bortezomib alone or in combination with the histone deacetylase inhibitor JNJ-26481585: effect on myeloma bone disease in the 5T2MM murine model of myeloma. | 2009 Jul 1 |
|
Acquired vorinostat resistance shows partial cross-resistance to 'second-generation' HDAC inhibitors and correlates with loss of histone acetylation and apoptosis but not with altered HDAC and HAT activities. | 2009 Jun |
|
JNJ-26481585, a novel "second-generation" oral histone deacetylase inhibitor, shows broad-spectrum preclinical antitumoral activity. | 2009 Nov 15 |
|
The effects of JNJ-26481585, a novel hydroxamate-based histone deacetylase inhibitor, on the development of multiple myeloma in the 5T2MM and 5T33MM murine models. | 2009 Oct |
|
Preclinical antileukemia activity of JNJ-26481585, a potent second-generation histone deacetylase inhibitor. | 2010 Feb |
|
Preclinical anti-myeloma activity of the novel HDAC-inhibitor JNJ-26481585. | 2010 May |
|
Optimization of the in vitro cardiac safety of hydroxamate-based histone deacetylase inhibitors. | 2011 Jul 14 |
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT01486277
12 mg capsule on days 1, 3, and 5 of each week in a 21-day treatment cycle
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19861438
Quisinostat inhibited cell proliferation in all lung, breast, colon, prostate, brain, and ovarian tumor cell lines tested, with IC50 values ranging from 3.1 to 246 nM/L.
Substance Class |
Chemical
Created
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admin
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Edited
Mon Mar 31 20:57:22 GMT 2025
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Mon Mar 31 20:57:22 GMT 2025
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Record UNII |
9BJ85K1J8S
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Record Status |
Validated (UNII)
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NCI_THESAURUS |
C1946
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C77912
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9BJ85K1J8S
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CHEMBL2105763
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Quisinostat
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DB12985
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875320-29-9
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XX-125
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Related Record | Type | Details | ||
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TARGET -> INHIBITOR |
IC50
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TARGET -> INHIBITOR |
IC50
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TARGET -> INHIBITOR |
It is approximately 500-fold more potent than vorinostat at inhibiting HDAC1.
IC50
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TARGET->WEAK INHIBITOR |
IC50
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TARGET->WEAK INHIBITOR |
IC50
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TARGET -> INHIBITOR |
IC50
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TARGET ORGANISM->INHIBITOR |
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TARGET->WEAK INHIBITOR |
IC50
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TARGET -> INHIBITOR |
IC50
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TARGET -> INHIBITOR |
IC50
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SALT/SOLVATE -> PARENT | |||
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TARGET -> INHIBITOR |
IC50
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Related Record | Type | Details | ||
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ACTIVE MOIETY |