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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 of TACEDINALINE

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.045 nM [IC50]
0.031 nM [IC50]
0.02 nM [IC50]
Conditions

Conditions

Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
inconclusive [IC50 8.9285 uM]
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
A novel histone deacetylase inhibitor Chidamide induces apoptosis of human colon cancer cells.
2010 Feb 5
Patents

Sample Use Guides

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 GMT 2023
Edited
by admin
on Fri Dec 15 15:40:22 GMT 2023
Record UNII
UMF554N5FG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TACEDINALINE
INN   USAN  
USAN   INN  
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
Created by admin on Fri Dec 15 15:40:22 GMT 2023 , Edited by admin on Fri Dec 15 15:40:22 GMT 2023
Code System Code Type Description
PUBCHEM
2746
Created by admin on Fri Dec 15 15:40:22 GMT 2023 , Edited by admin on Fri Dec 15 15:40:22 GMT 2023
PRIMARY
SMS_ID
100000155280
Created by admin on Fri Dec 15 15:40:22 GMT 2023 , Edited by admin on Fri Dec 15 15:40:22 GMT 2023
PRIMARY
FDA UNII
UMF554N5FG
Created by admin on Fri Dec 15 15:40:22 GMT 2023 , Edited by admin on Fri Dec 15 15:40:22 GMT 2023
PRIMARY
DRUG BANK
DB12291
Created by admin on Fri Dec 15 15:40:22 GMT 2023 , Edited by admin on Fri Dec 15 15:40:22 GMT 2023
PRIMARY
USAN
NN-16
Created by admin on Fri Dec 15 15:40:22 GMT 2023 , Edited by admin on Fri Dec 15 15:40:22 GMT 2023
PRIMARY
CAS
112522-64-2
Created by admin on Fri Dec 15 15:40:22 GMT 2023 , Edited by admin on Fri Dec 15 15:40:22 GMT 2023
PRIMARY
ChEMBL
CHEMBL235191
Created by admin on Fri Dec 15 15:40:22 GMT 2023 , Edited by admin on Fri Dec 15 15:40:22 GMT 2023
PRIMARY
CHEBI
90195
Created by admin on Fri Dec 15 15:40:22 GMT 2023 , Edited by admin on Fri Dec 15 15:40:22 GMT 2023
PRIMARY
INN
8328
Created by admin on Fri Dec 15 15:40:22 GMT 2023 , Edited by admin on Fri Dec 15 15:40:22 GMT 2023
PRIMARY
EVMPD
SUB129288
Created by admin on Fri Dec 15 15:40:22 GMT 2023 , Edited by admin on Fri Dec 15 15:40:22 GMT 2023
PRIMARY
EPA CompTox
DTXSID60150095
Created by admin on Fri Dec 15 15:40:22 GMT 2023 , Edited by admin on Fri Dec 15 15:40:22 GMT 2023
PRIMARY
NCI_THESAURUS
C2202
Created by admin on Fri Dec 15 15:40:22 GMT 2023 , Edited by admin on Fri Dec 15 15:40:22 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
IC50
Related Record Type Details
ACTIVE MOIETY