N-(2-aminophenyl)-4-acetamidobenzamide

• ChemBase ID: 154450
• Molecular Formular: C15H15N3O2
• Molecular Mass: 269.2985
• Monoisotopic Mass: 269.11642674
• SMILES: CC(=O)Nc1ccc(cc1)C(=O)Nc1ccccc1N
• Canonical SMILES: CC(=O)Nc1ccc(cc1)C(=O)Nc1ccccc1N
• InChI: 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)
• InChIKey: VAZAPHZUAVEOMC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(2-aminophenyl)-4-acetamidobenzamide
• IUPAC Traditional name: tacedinaline
• Synonyms: 4-Acetylamino-N-(2′-aminophenyl)benzamide; Acetyldinaline; Tacedinaline; CI-994; PD-123654; CI994 (Tacedinaline)

Database IDs

• CAS Number: 112522-64-2
• MDL Number: MFCD00866266
• PubChem SID: 162248589
• PubChem CID: 2746

CALCULATED PROPERTIES

• Acid pKa: 13.475711
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 1.4715471
• LogD (pH = 7.4): 1.4738848
• Log P: 1.473915
• Molar Refractivity: 81.1549 cm^3
• Polarizability: 28.955147 Å^3
• Polar Surface Area: 84.22 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: off-white powder

Safety Information

• Storage Condition: under inert gas
• RTECS: CU8702023
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: room temp

Pharmacology Properties

• Target: HDAC

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C15H15N3O2

DETAILS

Sigma Aldrich - C0621

Biochem/physiol Actions
CI-994 is the acetylated derivative form of the original compound Dinaline (PD 104 208). It is an oral cytostatic drug with impressive differential activity against leukemic cells & normal stem-cells. It is used for combination therapy for selected tumors including non-small cell lung, pancreatic, breast, and colorectal cancers. It acts as a histone deacetylase inhibitor. CI-994 blocks cells in the G1-S phase of the cell cycle. The 16 kDa phosphoprotein is confined to the nuclear compartment. Loss of the 16-kDa nuclear phosphoprotein appears to be a direct effect of CI-994 treatment and that the inhibition of this phosphoprotein may play a critical role in the mechanism of action of CI-994.