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^N
PubChem CID	159326
ChemSpider	140124^Y
UNII	11DI31LWXF
ChEBI	CHEBI:76005^N
ECHA InfoCard	100.125.129
Chemical and physical data
Formula	C₂₁H₂₂N₄OS
Molar mass	378.491 g/mol
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)^Y Key:TYBHXIFFPVFXQW-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

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]

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]

↑ York Pharma: Regulatory Update – Abasol Archived September 27, 2007, at the Wayback Machine.
↑ 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
↑ 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

Wall/
membrane

Ergosterol
inhibitors

Imidazoles	Topical: bifonazole^‡ butoconazole chlormidazole^‡ clotrimazole^# croconazole^‡ eberconazole econazole fenticonazole^‡ flutrimazole isoconazole^‡ ketoconazole luliconazole miconazole^# neticonazole^‡ omoconazole^‡ oxiconazole sertaconazole sulconazole tioconazole Systemic: ketoconazole
Triazoles	Topical: efinaconazole fluconazole^# fosfluconazole terconazole Systemic: fluconazole^# hexaconazole^‡ isavuconazole itraconazole posaconazole voriconazole Unknown: albaconazole^‡ ravuconazole^†
Thiazoles	Topical: abafungin^‡

Allylamines	Topical: naftifine terbinafine Systemic: terbinafine
Benzylamines	Topical: butenafine

Others

Intracellular

Pyrimidine analogues/ thymidylate synthase inhibitors	flucytosine^#
Mitotic inhibitors	griseofulvin^#
Aminoacyl tRNA synthetase inhibitors	tavaborole

Others

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