Abafungin

Chemical compound

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

DrugBank

DB06395^Y

ChemSpider

140124^Y

UNII

11DI31LWXF

ChEBI

CHEBI:76005^N

CompTox Dashboard (EPA)

DTXSID60869776

ECHA InfoCard100.125.129

Chemical and physical dataFormulaC₂₁H₂₂N₄OSMolar mass378.49 g·mol⁻¹3D 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]

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]

Its development seems to have been discontinued in 2009.^[3]

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.^[4]

Abafungin has antibiotic activity against gram-positive bacteria as well as sporicidal activity.^[5]

References

^ "Regulatory Update – Abasol" (PDF). York Pharma. Archived from the original (PDF) on September 27, 2007.
^ ^a ^b Borelli C, Schaller M, Niewerth M, Nocker K, Baasner B, Berg D, et al. (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. PMID 18587237.
^ "Abafungin". AdisInsight. Retrieved 5 May 2021.
^ Ruiz-Ortega M, González S, Serón D, Condom E, Bustos C, Largo R, González E, Ortiz A, Egido J (December 1995). "ACE inhibition reduces proteinuria, glomerular lesions and extracellular matrix production in a normotensive rat model of immune complex nephritis". Kidney International. 48 (6): 1778–91. doi:10.1038/ki.1995.476. PMID 8587237.
^ Ginter-Hanselmayer G (March 2009). Arbeitsunterlagen zur 42. wissenschaftlichen Fortbildungsveranstaltung für Apothekerinnen und Apotheker: Infektionskrankheiten. Österreichische Apothekerkammer. p. 103.

External links

Media related to Abafungin at Wikimedia Commons

Antifungals (D01 and J02)

Wall/
membrane

Ergosterol
inhibitors

Azoles (lanosterol 14α-
demethylase inhibitors)

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

Polyene antimycotics
(ergosterol binding)

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

Squalene monooxygenase
inhibitors

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

Others

Topical: amorolfine

β-glucan synthase
inhibitors

Intracellular

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