26689-55-4

Basic information

• Product Name: N-acetyl carbamazepine
• Synonyms: N-acetyl carbamazepine
• CAS NO: 26689-55-4
• Molecular Weight: 278.31
• Mol File: 26689-55-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-acetyl carbamazepine(CAS DataBase Reference)
• NIST Chemistry Reference: N-acetyl carbamazepine(26689-55-4)
• EPA Substance Registry System: N-acetyl carbamazepine(26689-55-4)

Safety Data

• Hazardous Substances Data: 26689-55-4(Hazardous Substances Data)

Upstream product

• 256-96-2 dibenzoazepine 
• 3998-25-2 acetyl isocyanate 

Downstream Products

• 298-46-4 carbamazepin 
• 256-96-2 dibenzoazepine 

Relevant articles and documents

Preparation and physicochemical characterization of a novel water-soluble prodrug of carbamazepine

N-Acyl-urea derivatives of carbamazepine (CBZ) were synthesized through the reactions of iminostilbene with acyl-isocyanates to form N-glycyl-carbamazepine (N-Gly-CBZ, after a deprotection step) or N-acetyl-carbamazepine (N-acetyl-CBZ). N-Gly-CBZ was isolated as its water-soluble HCl salt and was designed to act as a prodrug and convert to CBZ and glycine in vivo by enzymatic cleavage of the acyl-urea bond. The stability pH-rate profiles for N-Gly-CBZ and N-acetyl-CBZ were determined. The stability of N-Gly-CBZ was found to range over four orders of magnitude with its greatest stability at pH 3-4 and a t 90 value of 5.9 day at pH 4 at 25°C. From the fit of the pH rate profile two pKa values were estimated to be 7.2 (terminal amine) and 10.0 (imide), which were independently verified using UV-visible spectroscopic analysis. The solubility of N-Gly-CBZ in aqueous solution was determined in the range of pH 5.5-7.5. The intrinsic solubility of the neutral form of the prodrug was found to be 4.4 mg/mL, and the solubility of the prodrug increased exponentially (log linear) as pH was decreased below its pKa1 value. N-Gly-CBZ was found to have an aqueous solubility in excess of 50 mg/mL at pH 4. The presence of N-Gly-CBZ was found to increase the aqueous solubility of CBZ, a degradation product. CBZ showed an 8.6-fold greater solubility in an aqueous solution containing 23 mg/mL of N-Gly-CBZ than in water alone. The solubilization of CBZ by N-Gly-CBZ was investigated by examining the diffusion coefficients of the predominant species in D2O and was found to be more consistent with stacking complex formation than micelle formation. The stability ofN-Gly-CBZ makes a ready-to-use parenteral formulation impractical, but a freeze-dried preparation for reconstitution appears to be feasible.