Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C18H20N2O3 |
Molecular Weight | 312.363 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)[C@H](C(=O)NC1=CC=C(C=C1)C(=O)NO)C2=CC=CC=C2
InChI
InChIKey=LAMIXXKAWNLXOC-INIZCTEOSA-N
InChI=1S/C18H20N2O3/c1-12(2)16(13-6-4-3-5-7-13)18(22)19-15-10-8-14(9-11-15)17(21)20-23/h3-12,16,23H,1-2H3,(H,19,22)(H,20,21)/t16-/m0/s1
Molecular Formula | C18H20N2O3 |
Molecular Weight | 312.363 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
AR-42, also known as (S)-HDAC-42, is a phenylbutyrate-based histone deacetylase (HDAC) inhibitor. HDACs are enzymes that determine acetylation status of histones, thereby affecting chromatin structure and regulating the expression and activity of numerous proteins involved in both cancer initiation and cancer progression. AR-42 possesses antitumor activity at multiple cellular levels. It is currently in Phase I/Ib trials for hematological malignancies and solid tumors.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22109824
Curator's Comment: Human data unavailable, known CNS penetrant in mice.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2093865 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16107152 |
16.0 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 |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Structure-based optimization of phenylbutyrate-derived histone deacetylase inhibitors. | 2005 Aug 25 |
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AR-42, a novel HDAC inhibitor, exhibits biologic activity against malignant mast cell lines via down-regulation of constitutively activated Kit. | 2010 May 27 |
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Preclinical validation of AR42, a novel histone deacetylase inhibitor, as treatment for vestibular schwannomas. | 2012 Jan |
Patents
Sample Use Guides
Patients receive AR-42 daily on days 1, 3, and 5 or 1, 3, 4, 5. Treatment repeats every 28 days for up to 3 courses in the absence of disease progression or unacceptable toxicity.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16107152
AR-42 treatment induces histone hyperacetylation and p21WAF/CIP1 overexpression and inhibits the growth of human prostate cancer DU-145 cells with IC50 of 0.11 uM.
Substance Class |
Chemical
Created
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admin
on
Edited
Fri Dec 15 15:21:27 GMT 2023
by
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on
Fri Dec 15 15:21:27 GMT 2023
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Record UNII |
E0GG29V0AQ
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Record Status |
Validated (UNII)
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FDA ORPHAN DRUG |
355611
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EU-Orphan Drug |
EU/3/12/996
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admin on Fri Dec 15 15:21:27 GMT 2023 , Edited by admin on Fri Dec 15 15:21:27 GMT 2023
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FDA ORPHAN DRUG |
355511
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admin on Fri Dec 15 15:21:27 GMT 2023 , Edited by admin on Fri Dec 15 15:21:27 GMT 2023
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6918848
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100000182442
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C116850
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935881-37-1
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DB12707
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SUB196585
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E0GG29V0AQ
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Related Record | Type | Details | ||
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TARGET -> INHIBITOR |
IC50
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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