Multicomponent system of NPS-1034, an orally administered lung cancer drug candidate, with sulfonic acids and solid state characterization

Jangmi Lee, Suzie Park, Seon Joo Yoon, Yong Woo Jung, Youngjoo Byun, Soon Hong Yuk, Min Keyong Jeon, Sung Kwon Kang, Eun Hee Lee

Research output: Contribution to journalArticlepeer-review

1 Scopus citations


NPS-1034 is a drug candidate targeted for the regulation of c-MET/AXL receptor tyrosin kinase activity. NPS-1034 was developed to improve efficacy and reduce toxicity by targeting c-MET/AXL related signaling pathways. However, NPS-1034 is practically insoluble in almost all organic solvents as well as aqueous media (pH 1, 4.5, and 7.5). We attempted to improve the physicochemical properties of NPS-1034 by forming multicomponent systems with a wide variety of sulfonic acids including methanesulfonic acid, 1,2-ethanedisulfonic acid, p-toluenesulfonic acid, and camphorsulfonic acid. Solid state characterization of NPS-1034 salts and amorphous with sulfonic acids was conducted, and the crystal structures of four salts and NPS-1034 were compared and investigated. Sulfonic acid salts of NPS-1034 decreased the melting point of NPS-1034 as much as -155.43 C. Solubilities of NPS-1034 and salts of NPS-1034 were measured to develop lipid-based formulation for the GLP toxicity study. Solvents studied include oleic acid, poly(ethylene glycol) 400, and ethanol. Solubility of amorphous of NPS-1034 with camphorsulfonic acid showed a significant increase in all three solvents. This work will give some insight into how various types of sulfonic acids interact with pharmaceutically important compounds containing the pyrrolepyridine moiety.

Original languageEnglish (US)
Pages (from-to)3958-3968
Number of pages11
JournalCrystal Growth and Design
Issue number9
StatePublished - Sep 4 2013
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)
  • Condensed Matter Physics


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