2066-89-9

Usage

Originator

Pasinazid, Yick-Vic Chemicals

Manufacturing Process

10 parts by weight of isonicotinoyl hydrazine was dissolved in 200 by volume of methanol by stirring at 60°C. Then 11.2 parts 4-aminosalycylic acid was added at 60°C. On cooling a salt of both compounds crystallized as yellow prisms with MP: 135°-140°C (decomposed).Isonicotinic acid hydrazide compound with 4-aminosalicylic acid may be prepared from the same components by using 750 parts of water by volume as a solvent. 10 parts 4-aminosalicylic acid was dissolved in 600 volume parts of water containing 39 parts by volume 2 N ammonium hydroxide. 9 parts by weight isonicotinoyl hydrazide was added and the mixture was heated to 30°C. The solution was acidified with 49 parts by volume of 2 N acetic acid. On cooling isonicotinic acid hydrazide compound with 4-amino-salicylic acid crystallized, which decomposed at 135°-140°C. The yield was almost quantitative

Therapeutic Function

Antitubercular

InChI:InChI=1/C7H7NO3.C6H7N3O/c8-4-1-2-5(7(10)11)6(9)3-4;7-9-6(10)5-1-3-8-4-2-5/h1-3,9H,8H2,(H,10,11);1-4H,7H2,(H,9,10)

Upstream product

• 54-85-3 isoniazid 
• 65-49-6 4-Aminosalicylic acid 

Relevant academic research and scientific papers

Conformations and interactions in pasiniazid: A spectroscopic and computational characterization

In this work, the conformations of isonicotinic acid hydrazide 4-aminosalicylate (pasiniazid) has been comprehensively investigated by analyzing the potential binding site on isoniazid and para-aminosalicylic acid. The powder X-ray diffraction and vibrational spectroscopy analysis with quantum chemical calculation are utilized to characterize the appropriate conformation of pasiniazid. Two hydrogen-bond systems are found in pasiniazid and the relevant vibrational modes have been assigned with the help of potential energy distribution analysis. Natural bond orbital analysis is implemented for evaluating interactions in pasiniazid. The result indicates that the intermolecular interaction is responsible for the stabilization of this complex. Furthermore, molecular electrostatic potential provides an intuitive vision for intermolecular interaction between isoniazid and para-aminosalicylic acid. The chemical stability is estimated by the frontier molecular orbitals analysis.

Drug-drug co-crystals: Temperature-dependent proton mobility in the molecular complex of isoniazid with 4-aminosalicylic acid

Two drug-drug co-crystals of the anti-tuberculosis drugs isoniazid (INH), pyrazinamide (PYR) and 4-aminosalicylic acid (PAS) are reported. The first is the 1:1 molecular complex of INH and PAS. The second is the monohydrate of the 1:1 complex of PYR and PAS. The crystal structures of both co-crystals are characterized by a number of hydrogen bonded synthons. Hydrogen bonding of the COOH...Npyridine type is found in both cases. In the INH:PAS co-crystal, there are two symmetry independent COOH...Npyridine hydrogen bonds. In one of these, the H-atom is located on the carboxylic group and is indicative of a co-crystal. In the second case, partial proton transfer occurs across the hydrogen bond, and the extent of proton transfer depends on the temperature. This is more indicative of a salt. Drug-drug co-crystals may have some bearing in the treatment of tuberculosis.