REC-2282

Investigational

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16951239 | https://www.ncbi.nlm.nih.gov/pubmed/28829799

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 Target	Pharmacology	Condition	Potency
Histone deacetylase 23 Target ID: CHEMBL2093865 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16107152	Inhibitor 8297		16.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Vestibular schwannoma 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28829799	Primary	Phase I 428	Unknown Approved Use Unknown
Acute myeloid leukemia 136 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28829799	Primary	Phase I 428	Unknown Approved Use Unknown
Meningioma 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28829799	Primary	Phase I 428	Unknown Approved Use Unknown
Acoustic neuroma 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28829799	Primary	Phase I 428	Unknown Approved Use Unknown
Neurofibromatosis type 2 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28829799	Primary	Phase I 428	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1461

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1650	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346987#sid=174007070	yes [IC50 1.4818 uM]

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	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 Created by `admin` on `Fri Dec 15 15:21:27 UTC 2023` Edited by `admin` on `Fri Dec 15 15:21:27 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