Haloprogin is a topical antifungal agent. Its structure does not contain any of the functional groups typically exploited in hydrogen bond based co-crystal design. On the other hand, its 1-iodoalkyne moiety is nicely tailored to a crystal engineering strategy based on halogen bonding. Here we describe the formation of three polymorphs of haloprogin and of three co-crystals that this active pharmaceutical ingredient forms with both neutral and ionic co-crystal formers. The halogen bond plays a major role in all of the six structures and the interaction is thus confirmed to be a valuable tool which may complement the hydrogen bond when polymorphs and co-crystals of active pharmaceutical ingredients are pursued.

Polymorphs and co-crystals of haloprogin: an antifungal agent

BALDRIGHI, MICHELE;CAVALLO, GABRIELLA;METRANGOLO, PIERANGELO;PILATI, TULLIO MARIA;RESNATI, GIUSEPPE;TERRANEO, GIANCARLO
2014-01-01

Abstract

Haloprogin is a topical antifungal agent. Its structure does not contain any of the functional groups typically exploited in hydrogen bond based co-crystal design. On the other hand, its 1-iodoalkyne moiety is nicely tailored to a crystal engineering strategy based on halogen bonding. Here we describe the formation of three polymorphs of haloprogin and of three co-crystals that this active pharmaceutical ingredient forms with both neutral and ionic co-crystal formers. The halogen bond plays a major role in all of the six structures and the interaction is thus confirmed to be a valuable tool which may complement the hydrogen bond when polymorphs and co-crystals of active pharmaceutical ingredients are pursued.
File in questo prodotto:
File Dimensione Formato  
c4ce00367e.pdf

Accesso riservato

: Publisher’s version
Dimensione 1.72 MB
Formato Adobe PDF
1.72 MB Adobe PDF   Visualizza/Apri
Polymorphs and co-crystals of haloprogin_11311-844600_Metrangolo.pdf

accesso aperto

: Post-Print (DRAFT o Author’s Accepted Manuscript-AAM)
Dimensione 1.65 MB
Formato Adobe PDF
1.65 MB Adobe PDF Visualizza/Apri

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11311/844600
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 44
  • ???jsp.display-item.citation.isi??? 42
social impact