U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
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

Curator's Comment: Human data unavailable, known CNS penetrant in mice.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
16.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 1.4818 uM]
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Structure-based optimization of phenylbutyrate-derived histone deacetylase inhibitors.
2005 Aug 25
Evaluation of the effects of histone deacetylase inhibitors on cells from canine cancer cell lines.
2008 Jul
AR-42, a novel HDAC inhibitor, exhibits biologic activity against malignant mast cell lines via down-regulation of constitutively activated Kit.
2010 May 27
Patents

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
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
by admin
on Wed Jul 05 22:51:59 UTC 2023
Edited
by admin
on Wed Jul 05 22:51:59 UTC 2023
Record UNII
E0GG29V0AQ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
REC-2282
Common Name English
(S)-HDAC-42
Code English
BENZENEACETAMIDE, N-(4-((HYDROXYAMINO)CARBONYL)PHENYL)-.ALPHA.-(1-METHYLETHYL)-, (.ALPHA.S)-
Common Name English
AR-42
Code English
(S)-(+)-N-HYDROXY-4-(3-METHYL-2-PHENYL-BUTYRYLAMINO)-BENZAMIDE
Systematic Name English
AR42
Code English
N-HYDROXY-4-(3-METHYL-2-(S)PHENYL-BUTYRYLAMINO)BENZAMIDE
Systematic Name English
N-HYDROXY-4-(3-METHYL-2-(S)-PHENYL-BUTYRYLAMINO) BENZAMIDE
Systematic Name English
OSU-HDAC 42
Common Name English
(S)-HDAC 42
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 355611
Created by admin on Wed Jul 05 22:51:59 UTC 2023 , Edited by admin on Wed Jul 05 22:51:59 UTC 2023
EU-Orphan Drug EU/3/12/996
Created by admin on Wed Jul 05 22:51:59 UTC 2023 , Edited by admin on Wed Jul 05 22:51:59 UTC 2023
FDA ORPHAN DRUG 355511
Created by admin on Wed Jul 05 22:51:59 UTC 2023 , Edited by admin on Wed Jul 05 22:51:59 UTC 2023
Code System Code Type Description
PUBCHEM
6918848
Created by admin on Wed Jul 05 22:51:59 UTC 2023 , Edited by admin on Wed Jul 05 22:51:59 UTC 2023
PRIMARY
SMS_ID
100000182442
Created by admin on Wed Jul 05 22:51:59 UTC 2023 , Edited by admin on Wed Jul 05 22:51:59 UTC 2023
PRIMARY
NCI_THESAURUS
C116850
Created by admin on Wed Jul 05 22:51:59 UTC 2023 , Edited by admin on Wed Jul 05 22:51:59 UTC 2023
PRIMARY
CAS
935881-37-1
Created by admin on Wed Jul 05 22:51:59 UTC 2023 , Edited by admin on Wed Jul 05 22:51:59 UTC 2023
PRIMARY
DRUG BANK
DB12707
Created by admin on Wed Jul 05 22:51:59 UTC 2023 , Edited by admin on Wed Jul 05 22:51:59 UTC 2023
PRIMARY
EVMPD
SUB196585
Created by admin on Wed Jul 05 22:51:59 UTC 2023 , Edited by admin on Wed Jul 05 22:51:59 UTC 2023
PRIMARY
FDA UNII
E0GG29V0AQ
Created by admin on Wed Jul 05 22:51:59 UTC 2023 , Edited by admin on Wed Jul 05 22:51:59 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
IC50
Related Record Type Details
ACTIVE MOIETY