Abafungin

Abafungin
Clinical data
Trade names	Abasol
Routes of; administration	Topical (cream)
ATC code	none;
Identifiers
	IUPAC name N-[4-[2-(2,4-dimethylphenoxy)phenyl]-1,3-thiazol-2-yl]-1,4,5,6-tetrahydropyrimidin-2-amine;
CAS Number	129639-79-8 ;
PubChem CID	159326;
ChemSpider	140124 ;
UNII	11DI31LWXF;
ChEBI	CHEBI:76005 ;
ECHA InfoCard	100.125.129
Chemical and physical data
Formula	C21H22N4OS
Molar mass	378.491 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=CC(=C(C=C1)OC2=CC=CC=C2C3=CSC(=N3)NC4=NCCCN4)C;
	InChI InChI=1S/C21H22N4OS/c1-14-8-9-18(15(2)12-14)26-19-7-4-3-6-16(19)17-13-27-21(24-17)25-20-22-10-5-11-23-20/h3-4,6-9,12-13H,5,10-11H2,1-2H3,(H2,22,23,24,25) ; Key:TYBHXIFFPVFXQW-UHFFFAOYSA-N ;
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Abafungin (INN) is a broad-spectrum antifungal agent with a novel mechanism of action for the treatment of dermatomycoses.

Abasol is a topical cream formulation of abafungin by York Pharma.[1]

History

Abafungin was first synthesized at Bayer AG, Leverkusen, Germany. A study of H₂-antagonists related to famotidine, resulted in the discovery of its antifungal properties.[2]

Mechanism of action

Unlike imidazole- and triazole-class antifungals, abafungin directly impairs the fungal cell membrane.[2]

In addition, abafungin inhibits the enzyme sterol 24-C-methyltransferase, modifying the composition of the fungal membrane.[3]

Abafungin has antibiotic activity against gram-positive bacteria as well as sporicidal activity.[4]

References

York Pharma: Regulatory Update – Abasol Archived September 27, 2007, at the Wayback Machine
Borelli, C.; Schaller, M.; Niewerth, M.; Baasner, B.; Berg, D.; Tiemann, R.; Tietjen, K.; Fugmann, B.; Lang-Fugmann, S.; Korting, H. C. (August 2008). "Modes of action of the new arylguanidine abafungin beyond interference with ergosterol biosynthesis and in vitro activity against medically important fungi". Chemotherapy. 54 (4): 245–59. doi:10.1159/000142334. PMC 2818358. Retrieved 10 December 2018 – via Karger.
Borelli C1, Schaller M, Niewerth M, Nocker K, Baasner B, Berg D, Tiemann R, Tietjen K, Fugmann B, Lang-Fugmann S, Korting HC. "Modes of action of the new arylguanidine abafungin beyond interference with ergosterol biosynthesis and in vitro activity against medically important fungi". Chemotherapy. 2008;54(4):245-59
Ginter-Hanselmayer, Gabriele (March 2009), Arbeitsunterlagen zur 42. wissenschaftlichen Fortbildungsveranstaltung für Apothekerinnen und Apotheker: Infektionskrankheiten, Österreichische Apothekerkammer, p. 103

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[1] York Pharma: Regulatory Update – Abasol Archived September 27, 2007, at the Wayback Machine

[BorelliEtAl2008-2] Borelli, C.; Schaller, M.; Niewerth, M.; Baasner, B.; Berg, D.; Tiemann, R.; Tietjen, K.; Fugmann, B.; Lang-Fugmann, S.; Korting, H. C. (August 2008). "Modes of action of the new arylguanidine abafungin beyond interference with ergosterol biosynthesis and in vitro activity against medically important fungi". Chemotherapy. 54 (4): 245–59. doi:10.1159/000142334. PMC 2818358. Retrieved 10 December 2018 – via Karger.

[3] Borelli C1, Schaller M, Niewerth M, Nocker K, Baasner B, Berg D, Tiemann R, Tietjen K, Fugmann B, Lang-Fugmann S, Korting HC. "Modes of action of the new arylguanidine abafungin beyond interference with ergosterol biosynthesis and in vitro activity against medically important fungi". Chemotherapy. 2008;54(4):245-59

[4] Ginter-Hanselmayer, Gabriele (March 2009), Arbeitsunterlagen zur 42. wissenschaftlichen Fortbildungsveranstaltung für Apothekerinnen und Apotheker: Infektionskrankheiten, Österreichische Apothekerkammer, p. 103