104206-65-7

Basic information

• Product Name: 2-(2-nitro-4-trifluoromethylbenzoyl)-1,3-cyclohexanedione
• Synonyms: 2-(2-nitro-4-trifluoromethylbenzoyl)-1,3-cyclohexanedione;2-[2-Nitro-4-(trifluoroMethyl)benzoyl]-;1,3-Cyclohexanedione,2-[2-nitro-4-(trifluoroMethyl)benzoyl]-;Nitisinone 2-(2-nitro-4-trifluoroMethylbenzoyl)-1,3-cyclohexanedione;Nitisone;NTBC;SC 0735
• CAS NO: 104206-65-7
• Molecular Formula: C14H10F3NO5
• Molecular Weight: 329.23
• EINECS: 1592732-453-0
• Product Categories: Miscellaneous Compounds;Aromatics;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 104206-65-7.mol
• Article Data: 0

Chemical Properties

• Melting Point: 129-131°C
• Boiling Point: 486.2 °C at 760 mmHg
• Flash Point: 247.9 °C
• Appearance: white to brown/Solid
• Density: 1.484 g/cm³
• Vapor Pressure: 1.32E-09mmHg at 25°C
• Refractive Index: 1.535
• Storage Temp.: -20°C Freezer
• Solubility: DMSO: ≥5mg/mL
• PKA: 3.13±0.50(Predicted)
• CAS DataBase Reference: 2-(2-nitro-4-trifluoromethylbenzoyl)-1,3-cyclohexanedione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-nitro-4-trifluoromethylbenzoyl)-1,3-cyclohexanedione(104206-65-7)
• EPA Substance Registry System: 2-(2-nitro-4-trifluoromethylbenzoyl)-1,3-cyclohexanedione(104206-65-7)

Safety Data

• WGK Germany: 3
• RTECS: GV0766666
• Hazardous Substances Data: 104206-65-7(Hazardous Substances Data)

Usage

Description

2-(2-nitro-4-trifluoromethylbenzoyl)-1,3-cyclohexanedione, also known as Orfadin, is a pharmaceutical compound that belongs to the class of cyclohexanone derivatives. It is characterized by its light brown solid appearance and is primarily used in the treatment of hereditary tyrosinemia type 1.

Uses

Used in Pharmaceutical Industry:
2-(2-nitro-4-trifluoromethylbenzoyl)-1,3-cyclohexanedione is used as a therapeutic agent for the treatment of hereditary tyrosinemia type 1. It functions by inhibiting the enzyme 4-hydroxyphenylpyruvate dioxygenase (HPPD), which is involved in the tyrosine catabolic pathway. This inhibition prevents the accumulation of toxic metabolites, such as succinylacetoacetate, in the liver, thereby reducing the risk of liver failure and hepatocellular carcinoma associated with the disease.
Used in Quality Control:
2-(2-nitro-4-trifluoromethylbenzoyl)-1,3-cyclohexanedione serves as a pharmaceutical secondary standard, providing a convenient and cost-effective alternative for the preparation of in-house working standards in pharmaceutical laboratories and manufacturing facilities. This application ensures the quality and efficacy of the compound in the development and production of medications for hereditary tyrosinemia type 1.

Originator

AstraZeneca (UK)

Biochem/physiol Actions

Nitisinone is a competitive inhibitor that reversibly inhibits 4-Hydroxyphenylpyruvate oxidase (dioxygenase). Nitisinone is used in the treatment of hereditary tyrosinemia type 1, where it blocks the degradation of tyrosine into harmful substances.

InChI:InChI=1/C14H10F3NO5/c15-14(16,17)7-4-5-8(9(6-7)18(22)23)13(21)12-10(19)2-1-3-11(12)20/h4-6,12H,1-3H2