15935-54-3

Basic information

• Product Name: CARBOXYIBUPROFEN
• Synonyms: CARBOXYIBUPROFEN;IBUPROFEN CARBOXYLIC ACID (MIXTURE OF DIASTERIOMERS);CARBOXYIBUPROFEN (MIXTURE OF STEREOISOMERS);2,4(2-Carboxypropyl)phenylpropionic Acid;2-[4-(2-Carboxypropyl)phenyl]propionic Acid;4-(1-Carboxyethyl)-methyl-benzenepropanoic Acid;4-(1-Carboxyethyl)-a-methyl-benzenepropanoic Acid;Ibuprofen Carboxylic Acid(Mixture of Diastereomers)
• CAS NO: 15935-54-3
• Molecular Formula: C₁₃H₁₆O₄
• Molecular Weight: 236.26
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Metabolite Reference Standard
• Mol File: 15935-54-3.mol
• Article Data: 1

Chemical Properties

• Melting Point: 114-116°C
• Boiling Point: 416.2±25.0 °C(Predicted)
• Appearance: /
• Density: 1.211±0.06 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 4.39±0.10(Predicted)
• CAS DataBase Reference: CARBOXYIBUPROFEN(CAS DataBase Reference)
• NIST Chemistry Reference: CARBOXYIBUPROFEN(15935-54-3)
• EPA Substance Registry System: CARBOXYIBUPROFEN(15935-54-3)

Safety Data

• Hazardous Substances Data: 15935-54-3(Hazardous Substances Data)

Usage

Description

Ibuprofen carboxylic acid is a major metabolite of ibuprofen (Item Nos. 70280 | 16793 | 16794). It prevents fructose-, cyanate-, and prednisolone-induced inactivation of catalase and fructose- and cyanate-induced inactivation of fumarase when used at a concentration of 2 mM and penetrates into the lens of isolated bovine eyes. Ibuprofen carboxylic acid has been found in bank filtrate and surface water, as well as influent and effluent wastewater, and is considered a micropollutant.

Chemical Properties

White Solid

Uses

The major metabolite of Ibuprofen; may reduce the risk of cataract by protecting lenticular enzymes.

Definition

ChEBI: A dicarboxylic acid that is ibuprofen in which one of the methyl groups in the isobutyl portion has been converted to the corresponding carboxylic acid.

Upstream product

• 1346752-29-1 C₂₁H₃₃O₈P 

Relevant articles and documents

Phospho-ibuprofen (MDC-917) is a novel agent against colon cancer: Efficacy, metabolism, and pharmacokinetics in mouse models

We have developed a novel chemical modification of conventional nonsteroidal anti-inflammatory drugs to reduce their toxicity and enhance their efficacy. Phospho-ibuprofen [(PI) 2-(4-isobutyl-phenyl)-propionic acid-4-(diethoxy-phosphoryloxy)-butyl ester (MDC-917)], a novel derivative of ibuprofen, strongly inhibited the growth of human colon cancer cells in vitro and SW480 human colon cancer xenografts in nude mice. PI was metabolized minimally by cultured cells, but extensively by liver microsomes and mice, undergoing regioselective oxidation to produce 1-OH-PI and carboxyl-PI, which can be hydrolyzed to 1-OH-ibuprofen and carboxyl-ibuprofen, respectively. PI also can be hydrolyzed to release ibuprofen, which can generate 2-OH-ibuprofen, carboxyl-ibuprofen, and ibuprofen glucuronide. After a single oral administration (400 mg/kg) of PI, ibuprofen and ibuprofen glucuronide are the main plasma metabolites of PI; they have, respectively, Cmax of 530 and 215 μM, Tmax of 1 and 2 h, elimination t1/2 of 7.7 and 5.3 h, and area under the concentration-time curve (0-24 h) of 1816 and 832 μM X h. Intact PI was detected in several tissues but not in plasma; at a higher PI dose (1200 mg/kg), PI plasma levels were 12.4 μM. PI generated the same metabolites in mouse plasma as conventional ibuprofen, but with much lower levels, perhaps accounting for the enhanced safety of PI. The antitumor effect of PI was significantly associated with plasma ibuprofen levels (p = 0.016) but not with xenograft ibuprofen levels (p = 0.08), suggesting a complex anticancer effect. These results provide a pharmacological basis to explain, at least in part, the anticancer efficacy and safety of this promising compound and indicate that PI merits further evaluation as an anticancer agent.