CAS 112522-64-2 Tacedinaline (HCID 2746)

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Basic information

CAS: 112522-64-2
Standard SMILES: CC(=O)Nc1ccc(C(=O)Nc2ccccc2N)cc1
InChIKey: VAZAPHZUAVEOMC-UHFFFAOYSA-N
Molecular formula: C15H15N3O2
Average molar mass: 269.3 g/mol
Monoisotopic mass: 269.11642673

Overview

Tacedinaline is a benzamide obtained by formal condensation of the carboxy group of 4-acetamidobenzoic acid with one of the amino groups of 1,2-phenylenediamine. An oral cytostatic drug with impressive differential activity against leukemic cells and normal stem-cells. Also used in combination therapy for selected tumors including non-smoll cell lung, pancreatic, breast, and colorectal cancers. It has a role as an antineoplastic agent and an EC 3.5.1.98 (histone deacetylase) inhibitor. It is a member of acetamides, a member of benzamides and a substituted aniline. It is functionally related to a 1,2-phenylenediamine.

Names & identifiers

Preferred name: Tacedinaline
IUPAC: 4-acetamido-N-(2-aminophenyl)benzamide
English name: Tacedinaline
Molecular formula: C15H15N3O2
Molecular weight: 269.3

Names & synonyms

Tacedinaline112522-64-2ci-9944-acetamido-N-(2-aminophenyl)benzamideCI 994Tacedinalina4-(Acetylamino)-N-(2-aminophenyl)benzamideN-acetyldinalineGoe 5549Goe-5549PD-123654PD 123654

Show more names

acetyldinalineCS-617Cl-994CI994, >=99%

C.I. 994UMF554N5FGN-(2-aminophenyl)-4-acetamidobenzamideCHEBI:90195DTXSID60150095tacedinalinumN-acetyl DinalineRefChem:890200

Database identifiers

CAS: 112522-64-2、58338-59-3
PubChem CID: 2746
DTXSID: DTXSID60150095
ChEMBL: CHEMBL235191
ChEBI: CHEBI:90195
UNII: UMF554N5FG
EC Number: 631-226-3
Nikkaji: J545.180I

Properties

Computed structural properties

XLogP: 1.3
Topological polar surface area: 84.2 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 3
Rotatable bonds: 3
Heavy atoms: 20
Formal charge: 0
Complexity: 351

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

LogP0.82

Physicochemical properties

Melting point: 216.1 °C · 216.1 °C
Boiling point: 450.6 · 450.6±30.0 °C(Predicted)
Density: 1.322 · 1.322±0.06 g/cm3(Predicted)
RTECS: 8702023 · CU8702023
storage temp.: 2 · Keep in dark place,Inert atmosphere,2-8°C
solubility: Soluble in DMSO
pka: 13.15 · 13.15±0.70(Predicted)
form: powder
color: off-white
Sensitive: Air Sensitive
Stability: 1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
InChI

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)

Aggregated GHS information provided per 67 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesEye Irrit. 2 (100%)

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
hs_code: 2924.29.7790
risk_code: 36
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26
Storage Class: 11 - Combustible Solids
Hazard statements: H319
Hazard Classifications: Eye Irrit. 2
Precautionary statements: P305+P351+P338

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

Substances that inhibit or prevent the proliferation of NEOPLASMS.

Compounds that inhibit HISTONE DEACETYLASES. This class of drugs may influence gene expression by increasing the level of acetylated HISTONES in specific CHROMATIN domains.

Applications · 2 items

DescriptionCI-994 (112522-64-2) is an orally active histone deacetylase (HDAC) inhibitor, IC50 = 0.9, 0.9, 1.2 and >20 μM for HDAC1, HDAC2, HDAC3 and HDAC8 respectively.1 Mediates G1 cell cycle arrest, inhibits proliferation and induces apoptosis in vitro and in vivo.2,3 Increases neuroplasticity during memory extinction.4 Protects beta cells from cytokine-induced apoptosis.4

UsesTacedinaline is a histone deacetylase (HDAC) inhibitor. Tacedinaline is an anti-cancer agent as HDAC inhibitors block angiogenesis, arrest cell growth, and lead to differentiation and apoptosis in tumor cells. Studies show Tacedinaline to be effective against acute myeloid leukemia in vitro and in vivo when used in combination with conventional anti-cancer agents.