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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
Structure of REC-2282

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

HIDE SMILES / InChI

Molecular Formula C18H20N2O3
Molecular Weight 312.363
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
16.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
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
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
Record UNII
E0GG29V0AQ
Record Status Validated (UNII)
Record Version