Abafungin

Abafungin
Systematic (IUPAC) name


N-[4-[2-(2,4-dimethylphenoxy)phenyl]-1,3-thiazol-2-yl]-1,4,5,6-tetrahydropyrimidin-2-amine
Clinical data
Routes of administration	topical
Identifiers
CAS Number	129639-79-8
ATC code	None
PubChem	CID 159326
ChemSpider	140124^Y
UNII	11DI31LWXF^Y
ChEBI	CHEBI:76005
Chemical data
Formula	C₂₁H₂₂N₄OS
Molar mass	378.491 g/mol
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
(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]

References

↑ York Pharma: Regulatory Update – Abasol
↑ 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

Antifungals (D01 and J02)

Wall/
membrane

Ergosterol
inhibitors

Azoles
(lanosterol 14
alpha-demethylase inhibitors)

Imidazoles	Topical: bifonazole^‡ chlormidazole^‡ croconazole^‡ fenticonazole^‡ isoconazole^‡ luliconazole neticonazole^‡ omoconazole^‡ butoconazole clotrimazole^# econazole ketoconazole miconazole^# oxiconazole sertaconazole sulconazole tioconazole

Triazoles	Topical: fluconazole^#, fosfluconazole efinaconazole terconazole Systemic: hexaconazole^‡ isavuconazole fluconazole itraconazole posaconazole voriconazole Unknown: albaconazole^‡

Thiazoles	Topical: abafungin^‡

Polyene antimycotics
(ergosterol binding)

Topical: hamycin^‡
natamycin
nystatin^#
Systemic: amphotericin B^#, hamycin^‡

Allylamines
(squalene monooxygenase
inhibitors)

Topical: amorolfine^‡
butenafine
naftifine
terbinafine
Systemic: terbinafine

β-glucan synthase
inhibitors

Intracellular

Pyrimidine analogues/ thymidylate synthase inhibitors	flucytosine^#

Mitotic inhibitors	griseofulvin^#

Aminoacyl tRNA synthetase inhibitors	tavaborole

Others

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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