TUCIDINOSTAT

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H19FN4O2
Molecular Weight	390.4103
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=CC(F)=CC=C1NC(=O)C2=CC=C(CNC(=O)\C=C\C3=CC=CN=C3)C=C2

InChI

InChIKey=SZMJVTADHFNAIS-BJMVGYQFSA-N

InChI=1S/C22H19FN4O2/c23-18-8-9-20(19(24)12-18)27-22(29)17-6-3-16(4-7-17)14-26-21(28)10-5-15-2-1-11-25-13-15/h1-13H,14,24H2,(H,26,28)(H,27,29)/b10-5+

HIDE SMILES / InChI

Molecular Formula	C22H19FN4O2
Molecular Weight	390.4103
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: http://www.epidaza.com/doc/%E8%A5%BF%E8%BE%BE%E6%9C%AC%E8%83%BA%E7%89%87%E8%8D%AF%E5%93%81%E8%AF%B4%E6%98%8E%E4%B9%A6.pdf | https://www.ncbi.nlm.nih.gov/pubmed/27672541 | https://www.ncbi.nlm.nih.gov/pubmed/27647973 | https://www.ncbi.nlm.nih.gov/pubmed/26105599 | https://newdrugapprovals.org/tag/chidamide/

Chidamide (CS055) is a novel and orally active benzamide class of histone deacetylase (HDAC) inhibitor that selectively inhibits activity of HDAC1, 2, 3 and 10, the enzymes that are involved and play an important role in tumor initiation and development in both tumor cells and their surrounding micro-environment. It was approved by the CFDA in December 2014 for the treatment of recurrent of refractory peripheral T-cell lymphoma. Reported hematological adverse events are: neutropenia, thrombocytopenia, leukopenia. Chidamide is under investigation as a potential agent for the treatment of other types of tumors.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Histone deacetylase 1 51 Target ID: CHEMBL325 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22080169	Inhibitor 8297	0.095 µM [IC50]
Histone deacetylase 2 37 Target ID: CHEMBL1937 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22080169	Inhibitor 8297	0.16 µM [IC50]
Histone deacetylase 3 35 Target ID: CHEMBL1829 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22080169	Inhibitor 8297	0.067 µM [IC50]
Histone deacetylase 8 17 Target ID: CHEMBL3192 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22080169	Inhibitor 8297	0.733 µM [IC50]
Histone deacetylase 10 10 Target ID: CHEMBL5103 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22080169	Inhibitor 8297	0.078 µM [IC50]
Histone deacetylase 11 8 Target ID: CHEMBL3310 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22080169	Inhibitor 8297	0.432 µM [IC50]
Histone deacetylase 23 Target ID: CHEMBL2093865 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20060381	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Peripheral T-cell lymphoma 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26105599 http://adisinsight.springer.com/drugs/800025931	Primary	Approved 8429	Epidaza Approved Use Epidaza tablets are indicated for patients with recurrent or refractory peripheral T-cell lymphoma (PTCL) who have received at least one systemic chemotherapy. Launch Date 1.35613435E12
Breast cancer 434 Sources: http://adisinsight.springer.com/drugs/800025931	Primary	Phase III 656	Unknown Approved Use Unknown
Chronic HIV infection 2 Sources: http://adisinsight.springer.com/drugs/800025931	Primary	Phase III 656	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Complete molecular remission in relapsed and refractory acute myeloid leukaemia with MLL-AF9 treated with chidamide-based chemotherapy.	2017 Dec	28646565
Chidamide in FLT3-ITD positive acute myeloid leukemia and the synergistic effect in combination with cytarabine.	2017 Jun	28419965
Chidamide tablets: HDAC inhibition to treat lymphoma.	2017 Mar	28447074
Chidamide in relapsed or refractory peripheral T cell lymphoma: a multicenter real-world study in China.	2017 Mar 15	28298231
Synergistic antitumor effect of histone deacetylase inhibitor and Doxorubicin in peripheral T-cell lymphoma.	2017 May	28171799

Patents

Sample Use Guides

In Vivo Use Guide

30 mg (6 tablets) twice a week. The interval should not be less than 3 days, 30 min after breakfast.

Route of Administration: Oral

In Vitro Use Guide

At low concentrations (<1 uM), Chidamide induced G1 arrest in human leukaemia cell lines and primary myeloid leukaemia cells. At moderate concentrations (0.5 uM-2 uM), Chidamide induced differentiation, as determined by the increased expression of the myeloid differentiation marker CD11b. At relatively high concentrations (2 uM-4 uM), Chidamide potently induced caspase-dependent apoptosis.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 07:49:13 UTC 2023` Edited by `admin` on `Sat Dec 16 07:49:13 UTC 2023`
Record UNII	87CIC980Y0
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TUCIDINOSTAT

Official Name

English

EPIDAZA

Brand Name

English

Tucidinostat [WHO-DD]

Common Name

English

Chidamide [WHO-DD]

Common Name

English

tucidinostat [INN]

Common Name

English

N-(2-AMINO-4-FLUOROPHENYL)-4-(((2E)-3-(PYRIDIN-3-YL)PROP- 2-ENAMIDO)METHYL)BENZAMIDE

Systematic Name

English

CS055

Code

English

TUCIDINOSTAT [JAN]

Common Name

English

N-(2-AMINO-4-FLUOROPHENYL)-4-(((1-OXO-3-(3-PYRIDINYL)-2-PROPEN-1-YL)AMINO)METHYL)BENZAMIDE

Systematic Name

English

CS-055

Code

English

BENZAMIDE, N-(2-AMINO-4-FLUOROPHENYL)-4-((((2E)-1-OXO-3-(3-PYRIDINYL)-2-PROPEN-1-YL)AMINO)METHYL)-

Systematic Name

English

CHIDAMIDE

Common Name

English

BENZAMIDE, N-(2-AMINO-4-FLUOROPHENYL)-4-(((1-OXO-3-(3-PYRIDINYL)-2-PROPEN-1-YL)AMINO)METHYL)-

Systematic Name

English

TUCIDINOSTAT [USAN]

Common Name

English

HBI-8000

Code

English

Classification Tree Code System Code

FDA ORPHAN DRUG

867121