199191-67-8

Basic information

• Product Name: 2-[[Methyl[(3S)-3-(1-naphthalenyloxy)-3-(2-thienyl)propyl]aMino]carbonyl]benzoic Acid
• Synonyms: (S)-Duloxetine PhthalaMide;2-[[Methyl[(3S)-3-(1-naphthalenyloxy)-3-(2-thienyl)propyl]aMino]carbonyl]benzoic Acid;(S)-Duloxetine PhtalaMide;(S)-2-(methyl(3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propyl)carbamoyl)benzoic acid
• CAS NO: 199191-67-8
• Molecular Formula: C26H23NO4S
• Molecular Weight: 445.53012
• Product Categories: Aromatics, Heterocycles, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds
• Mol File: 199191-67-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 695.1±55.0 °C(Predicted)
• Appearance: /
• Density: 1.296±0.06 g/cm3(Predicted)
• Storage Temp.: -86°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.58±0.36(Predicted)
• CAS DataBase Reference: 2-[[Methyl[(3S)-3-(1-naphthalenyloxy)-3-(2-thienyl)propyl]aMino]carbonyl]benzoic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[[Methyl[(3S)-3-(1-naphthalenyloxy)-3-(2-thienyl)propyl]aMino]carbonyl]benzoic Acid(199191-67-8)
• EPA Substance Registry System: 2-[[Methyl[(3S)-3-(1-naphthalenyloxy)-3-(2-thienyl)propyl]aMino]carbonyl]benzoic Acid(199191-67-8)

Safety Data

• Hazardous Substances Data: 199191-67-8(Hazardous Substances Data)

Usage

Uses

(S)-Duloxetine Phthalamide is an impurity of (S)-Duloxetine present with enteric polymer hydroxypropylmethylcellulose phthalate (HPMCP) in dosage formulations.

Upstream product

• 85-44-9 phthalic anhydride 
• 136434-34-9 duloxetine hydrochloride 

Relevant articles and documents

Characterization of impurities formed by interaction of duloxetine HCl with enteric polymers hydroxypropyl methylcellulose acetate succinate and hydroxypropyl methylcellulose phthalate

Duloxetine hydrochloride ((S)-N-methyl-3-(1-naphthalenyloxy)-2- thiophenepropanamine hydrochloride) has been found to react with polymer degradation products or residual free acids present in the enteric polymers hydroxypropyl methylcellulose acetate succinate (HPMCAS) and hydroxypropyl methylcellulose phthalate (HPMCP) in dosage formulations to form succinamide and phthalamide impurities, respectively. The rate of formation of the impurities is accelerated by heat and humidity. The structures were deduced using molecular weights obtained from LC-MS experiments and confirmed by comparison of UV spectra, HPLC retention times, and electrospray mass spectra to independently synthesized material. It is proposed that polymer-bound succinic and phthalic substituents can be cleaved from the polymer, resulting in the formulation of either the free acids or the anhydrides. It is postulated that the reaction is enabled by migration of either (1) the free acid or anhydride or (2) the parent drug through the formulation. The formation of these impurities was minimized by increasing the thickness of the physical barrier separating the enteric coating from the drug.