TACEDINALINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H15N3O2
Molecular Weight	269.2985
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)NC1=CC=C(C=C1)C(=O)NC2=C(N)C=CC=C2

InChI

InChIKey=VAZAPHZUAVEOMC-UHFFFAOYSA-N

InChI=1S/C15H15N3O2/c1-10(19)17-12-8-6-11(7-9-12)15(20)18-14-5-3-2-4-13(14)16/h2-9H,16H2,1H3,(H,17,19)(H,18,20)

HIDE SMILES / InChI

Molecular Formula	C15H15N3O2
Molecular Weight	269.2985
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17018703
Curator's Comment: description was created based on several sources, including: http://adisinsight.springer.com/drugs/800002525 http://en.pharmacodia.com/web/drug/1_1986.html http://www.apexbt.com/ci994-tacedinaline.html

A second generation of HDACs, synthetic benzamide-containing HDACs such as Tacedinaline (CI-994), have reached phase I and II clinical trials. It has been investigated for its applications to the treatment of cancers such as Breast cancer and Colorectal cancer. Tacedinaline has been in phase III clinical trials by Pfizer for the treatment of advanced non-small cell lung cancer and pancreatic cancer combined with gemcitabine. However, this research has been discontinued. Mechanism of Action: Angiogenesis inhibitors; Histone deacetylase inhibitors. Pharmacokinetics showed that CI-994 absorption and disposition were unaffected by carboplatin and paclitaxel coadministration.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Histone deacetylase 1 51 Target ID: CHEMBL325 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24780082	Inhibitor 8297	0.045 nM [IC50]
Histone deacetylase 2 37 Target ID: CHEMBL1937 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24780082	Inhibitor 8297	0.031 nM [IC50]
Histone deacetylase 3 35 Target ID: CHEMBL1829 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24780082	Inhibitor 8297	0.02 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Multiple myeloma 159 Sources: https://clinicaltrials.gov/ct2/show/NCT00005624	Primary	Phase II 1132	Unknown Approved Use Unknown
Non-small cell lung cancer 206 Sources: http://en.pharmacodia.com/web/drug/1_1986.html	Primary	Phase III 656	Unknown Approved Use Unknown
Pancreatic cancer 97 Sources: http://en.pharmacodia.com/web/drug/1_1986.html https://www.ncbi.nlm.nih.gov/pubmed/16641168	Primary	Phase II 1132	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=363677293	inconclusive [IC50 8.9285 uM]

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY106700	https://www.001chemical.com/chem/search?q=DY106700
1PlusChem LLC	1P007B8O	https://www.1pchem.com/search?query=1P007B8O
A2B Chem	AD40360	http://a2bchem.com/prod/AD40360
AChemBlock	O33971	http://www.achemblock.com/catalogsearch/result/?q=O33971
AK Scientific	Y0359	https://aksci.com/item_detail.php?cat=Y0359
AOBIOUS INC	AOB2104	http://aobious.com/aobious/search?search_query=AOB2104
Aceschem	ACS019850	https://www.aceschem.com/catalog/search.do?q=ACS019850
Achemo Scientific Limited	AC-24128	http://www.achemo.com/search/?Keyword=AC-24128
Ambeed	A132717	http://www.ambeed.com/search/Search.html?keyword=A132717
Angene	AGN-PC-0JK6C6	http://www.angenechemical.com/productshow/AGN-PC-0JK6C6.html
ApexBio Technology	A4102	https://www.apexbt.com/catalogsearch/result/?q=A4102
Axon MedChem	2014	https://www.axonmedchem.com/product/2014
BOC Sciences	112522-64-2	http://www.bocsci.com/description.asp?cas=112522-64-2
Capot Chemical	33974	https://www.capotchem.com/search.do?q=33974
Cayman Chemical	12084	http://www.caymanchem.com/app/template/Product.vm/catalog/12084
Chem Scene	CS-1280	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-1280
ChemShuttle	106192	https://www.chemshuttle.com/catalogsearch/result/?q=106192
Debye Scientific	DB-006613	https://www.debyesci.com/index.php?id=product&ext[cno]=DB-006613
Enamine	BBV-95343848	http://www.enaminestore.com/catalog/BBV-95343848
Enamine	Z2393493967	https://www.enaminestore.com/blog/real/?codes=Z2393493967
Enamine	EN300-1270468	https://www.enaminestore.com/catalog/EN300-1270468
Enamine	EN300-657160	https://www.enaminestore.com/catalog/EN300-657160
Excenen	EX-A224	http://www.excenen.com/searchresultlist.php?id=EX-A224
Exclusive Chemistry	2116	http://www.exchemistry.com/chem-catalog/product-2116.html
Fluorochem	50680	http://www.fluorochem.co.uk/Products/Product?code=050680
Hairui	HR33003	http://www.hairuichem.com/en/product/search.do?q=HR33003
KeyOrganics	AS-19557	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-19557
Lab Network	LN00334571	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00334571
Matrix Scientific	131998	http://www.matrixscientific.com/131998.html
MedChem Express	HY-50934	https://www.medchemexpress.com/search.html?q=HY-50934&ft=&fa=&fp=
MolPort	MolPort-009-197-463	https://www.molport.com/shop/molecule-link/MolPort-009-197-463
MolPort	MolPort-028-767-188	https://www.molport.com/shop/molecule-link/MolPort-028-767-188
Molcore	MC106700	http://www.molcore.com/CatMC106700.html
Molnova	M10439	https://www.molnova.com/en/serch-list.html?keywords=M10439
MuseChem	I000472	https://www.musechem.com/product/I000472.html
Otava	6478459	https://search.otavachemicals.com/#!/search?query=6478459&type=code
PI Chemicals	PI-38522	http://www.pipharm.com/catalog_products/PI-38522.html
Princeton BioMolecular Research	PBMR221732	http://www.princetonbio.com/order_online?common_id=PBMR221732
Ryan Scientific	101-94004	https://ryansci.com/products?q=101-94004&list_q=&search_type=exact
ShangHai Biochempartner	BCP000424	http://www.biochempartner.com/search_BCP000424
ShangHai Biochempartner	BCP02577	http://www.biochempartner.com/search_BCP02577
TargetMol	T1888	https://www.targetmol.com/search?keyword=T1888
Tetrahedron	TS02946	http://www.thsci.com/search.do?q=TS02946
TimTec	ST51052145	http://www.echemstore.com/catalogsearch/result/?q=ST51052145
Tocris	2952	https://www.tocris.com/search.php?Type=QuickSearch&Value=2952
Toronto Research Chemicals	T004000	https://www.trc-canada.com/product-detail/?CatNum=T004000
eMolecules	1986168	https://orderbb.emolecules.com/search/#?query=1986168
eMolecules	48788750	https://orderbb.emolecules.com/search/#?query=48788750
eNovation Chemicals	D320146	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D320146&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-6069634534	https://mcule.com/MCULE-6069634534/
mcule	MCULE-7745808196	https://mcule.com/MCULE-7745808196/

PubMed

Title	Date	PubMed
		252160654
Preclinical antitumor activity of CI-994.	1996	9157069
Modulation of histone acetylation by [4-(acetylamino)-N-(2-amino-phenyl) benzamide] in HCT-8 colon carcinoma.	2003 Apr	12700284
Epigenetic treatment of myelodysplastic syndromes and acute myeloid leukemias.	2008	18537607
Improved synthesis of histone deacetylase inhibitors (HDIs) (MS-275 and CI-994) and inhibitory effects of HDIs alone or in combination with RAMBAs or retinoids on growth of human LNCaP prostate cancer cells and tumor xenografts.	2008 Mar 15	18166465
Combined inhibition of DNA methyltransferase and histone deacetylase restores caspase-8 expression and sensitizes SCLC cells to TRAIL.	2011 Oct	21771726

Patents

Sample Use Guides

In Vivo Use Guide

6 mg/m(2)/day during 21 days

Route of Administration: Oral

In Vitro Use Guide

The half-dose once daily treatment with Acetyldinaline (11.85 mg/kg) for 1 or 2 cycles resulted in about a 4.5 or > 8-log leukemic cell kill, respectively.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:40:22 UTC 2023` Edited by `admin` on `Fri Dec 15 15:40:22 UTC 2023`
Record UNII	UMF554N5FG
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TACEDINALINE

Official Name

English

GOE 5549

Code

English

TACEDINALINE [USAN]

Common Name

English

Tacedinaline [WHO-DD]

Common Name

English

CI-994

Code

English

PD-123654

Code

English

tacedinaline [INN]

Common Name

English

PD 123654

Code

English

4-(Acetylamino)-N-(2-aminophenyl)benzamide

Systematic Name

English

GOE-5549

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C1946