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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
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

CNS Penetrant
2554
Curator's Comment: Human data unavailable, known CNS penetrant in mice.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 16.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase I
428
Unknown

Approved Use

Unknown
Primary
Phase I
428
Unknown

Approved Use

Unknown
Primary
Phase I
428
Unknown

Approved Use

Unknown
Primary
Phase I
428
Unknown

Approved Use

Unknown
Primary
Phase I
428
Unknown

Approved Use

Unknown
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
P-gp
1461
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
P-gp
1650
 yes [IC50 1.4818 uM]
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P0062G5
https://www.1pchem.com/search?query=1P0062G5
AK Scientific
X7576
https://aksci.com/item_detail.php?cat=X7576
AOBIOUS INC
AOB3995
http://aobious.com/aobious/search?search_query=AOB3995
Angene
AGN-PC-0WH9N6
http://www.angenechemical.com/productshow/AGN-PC-0WH9N6.html
ApexBio Technology
A4104
https://www.apexbt.com/catalogsearch/result/?q=A4104
AstaTech
C77219
http://astatechinc.com/CPSResult.php?CRNO=C77219
Axon MedChem
2394
https://www.axonmedchem.com/product/2394
BLD Pharm
BD237364
http://www.bldpharm.com/search/Search.html?keyword=BD237364
BOC Sciences
935881-37-1
http://www.bocsci.com/description.asp?cas=935881-37-1
ChemShuttle
111845
https://www.chemshuttle.com/catalogsearch/result/?q=111845
KeyOrganics
AS-16777
http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-16777
Lab Network
LN01267313
https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01267313
Matrix Scientific
147193
http://www.matrixscientific.com/147193.html
MolPort
MolPort-009-019-571
https://www.molport.com/shop/molecule-link/MolPort-009-019-571
Molnova
M17674
https://www.molnova.com/en/serch-list.html?keywords=M17674
MuseChem
I011413
https://www.musechem.com/product/I011413.html
Selleck Chemicals
S2244
http://www.selleckchem.com/search.html?searchDTO.searchParam=S2244
ShangHai Biochempartner
BCP26343
http://www.biochempartner.com/search_BCP26343
TargetMol
T6392
https://www.targetmol.com/search?keyword=T6392
Toronto Research Chemicals
A735450
https://www.trc-canada.com/product-detail/?CatNum=A735450
Toronto Research Chemicals
P990500
https://www.trc-canada.com/product-detail/?CatNum=P990500
eMolecules
275064480
https://orderbb.emolecules.com/search/#?query=275064480
eMolecules
300480667
https://orderbb.emolecules.com/search/#?query=300480667
eMolecules
30497473
https://orderbb.emolecules.com/search/#?query=30497473
eNovation Chemicals
D372407
https://www.enovationchem.com/Products.asp?SEARCHTEXT=D372407&searchbtn.x=0&searchbtn.y=0
mcule
MCULE-4403250568
https://mcule.com/MCULE-4403250568/
PubMed

PubMed

TitleDatePubMed
Structure-based optimization of phenylbutyrate-derived histone deacetylase inhibitors.
2005 Aug 25
Antitumor effects of a novel phenylbutyrate-based histone deacetylase inhibitor, (S)-HDAC-42, in prostate cancer.
2006 Sep 1
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
Preclinical validation of AR42, a novel histone deacetylase inhibitor, as treatment for vestibular schwannomas.
2012 Jan
Patents

Patents

WO2014164784
1

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
Created
by admin
on Fri Dec 15 15:21:27 GMT 2023
Edited
by admin
on Fri Dec 15 15:21:27 GMT 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 Fri Dec 15 15:21:27 GMT 2023 , Edited by admin on Fri Dec 15 15:21:27 GMT 2023
EU-Orphan Drug EU/3/12/996
Created by admin on Fri Dec 15 15:21:27 GMT 2023 , Edited by admin on Fri Dec 15 15:21:27 GMT 2023
FDA ORPHAN DRUG 355511
Created by admin on Fri Dec 15 15:21:27 GMT 2023 , Edited by admin on Fri Dec 15 15:21:27 GMT 2023
Code System Code Type Description
PUBCHEM
6918848
Created by admin on Fri Dec 15 15:21:27 GMT 2023 , Edited by admin on Fri Dec 15 15:21:27 GMT 2023
PRIMARY
SMS_ID
100000182442
Created by admin on Fri Dec 15 15:21:27 GMT 2023 , Edited by admin on Fri Dec 15 15:21:27 GMT 2023
PRIMARY
NCI_THESAURUS
C116850
Created by admin on Fri Dec 15 15:21:27 GMT 2023 , Edited by admin on Fri Dec 15 15:21:27 GMT 2023
PRIMARY
CAS
935881-37-1
Created by admin on Fri Dec 15 15:21:27 GMT 2023 , Edited by admin on Fri Dec 15 15:21:27 GMT 2023
PRIMARY
DRUG BANK
DB12707
Created by admin on Fri Dec 15 15:21:27 GMT 2023 , Edited by admin on Fri Dec 15 15:21:27 GMT 2023
PRIMARY
EVMPD
SUB196585
Created by admin on Fri Dec 15 15:21:27 GMT 2023 , Edited by admin on Fri Dec 15 15:21:27 GMT 2023
PRIMARY
FDA UNII
E0GG29V0AQ
Created by admin on Fri Dec 15 15:21:27 GMT 2023 , Edited by admin on Fri Dec 15 15:21:27 GMT 2023
PRIMARY
Related Record Type Details
HISTONE DEACETYLASE 1
TARGET -> INHIBITOR
IC50
Related Record Type Details
Structure of REC-2282
ACTIVE MOIETY
NIH
NCATS
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