953817-12-4

Basic information

• Product Name: C₁₂H₁₇NO₅
• Synonyms: C₁₂H₁₇NO₅
• CAS NO: 953817-12-4
• Molecular Weight: 255.271
• Mol File: 953817-12-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: C₁₂H₁₇NO₅(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₂H₁₇NO₅(953817-12-4)
• EPA Substance Registry System: C₁₂H₁₇NO₅(953817-12-4)

Safety Data

• Hazardous Substances Data: 953817-12-4(Hazardous Substances Data)

Upstream product

• 108-31-6 maleic anhydride 
• 1197-18-8 trans-4-aminomethyl-cyclohexyl-carboxylic acid 

Downstream Products

• 108-31-6 maleic anhydride 
• 1197-18-8 trans-4-aminomethyl-cyclohexyl-carboxylic acid 
• 1337538-63-2 trans-2,5-dioxo-1-pyrrolidinyl 4-{[[(2E)-4-[(2,5-dioxo-1-pyrrolidinyl)oxy]-1,4-dioxo-2-buten-1-yl]amino]methyl}tranexamate 
• 69907-67-1 (1r,4r)-4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexane-1-carboxylic acid 
• 71875-81-5 4-(N-maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester 

Relevant articles and documents

Design, synthesis and in vitro kinetic study of tranexamic acid prodrugs for the treatment of bleeding conditions

Based on density functional theory (DFT) calculations for the acid-catalyzed hydrolysis of several maleamic acid amide derivatives four tranexamic acid prodrugs were designed. The DFT results on the acid catalyzed hydrolysis revealed that the reaction rate-limiting step is determined on the nature of the amine leaving group. When the amine leaving group was a primary amine or tranexamic acid moiety, the tetrahedral intermediate collapse was the rate-limiting step, whereas in the cases by which the amine leaving group was aciclovir or cefuroxime the rate-limiting step was the tetrahedral intermediate formation. The linear correlation between the calculated DFT and experimental rates for N-methylmaleamic acids 1-7 provided a credible basis for designing tranexamic acid prodrugs that have the potential to release the parent drug in a sustained release fashion. For example, based on the calculated B3LYP/6-31G(d,p) rates the predicted t1/2 (a time needed for 50 % of the prodrug to be converted into drug) values for tranexamic acid prodrugs ProD 1-ProD 4 at pH 2 were 556 h [50.5 h as calculated by B3LYP/311+G(d,p)] and 6.2 h as calculated by GGA: MPW1K), 253 h, 70 s and 1.7 h, respectively. Kinetic study on the interconversion of the newly synthesized tranexamic acid prodrug ProD 1 revealed that the t1/2 for its conversion to the parent drug was largely affected by the pH of the medium. The experimental t1/2 values in 1 N HCl, buffer pH 2 and buffer pH 5 were 54 min, 23.9 and 270 h, respectively. Graphical Abstract: [Figure not available: see fulltext.]

PHARMACEUTICAL COMPOSITIONS COMPRISING MACROLIDE DIASTEREOMERS, METHODS OF THEIR SYNTHESIS AND THERAPEUTIC USES

The disclosure relates to compositions comprising diastereomer of a macrolide exhibiting improved therapeutic profile in the context of inhibiting cell proliferation compared to the corresponding compositions comprising mixture of diastereomers. The discl