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;
DrugBank	DB06395 ;
ChemSpider	140124 ;
UNII	11DI31LWXF;
ChEBI	CHEBI:76005 ;
CompTox Dashboard (EPA)	DTXSID60869776 ;
ECHA InfoCard	100.125.129
Chemical and physical data
Formula	C21H22N4OS
Molar mass	378.49 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 ;
	(what is this?) (verify)

Abafungin (INN) is a broad-spectrum arylguanidines-class antifungal agent with a novel mechanism of action for the treatment of dermatomycoses.^[1]

Abasol is a topical cream formulation of abafungin by York Pharma.^[2]

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.^[3]

Its development seems to have been discontinued in 2009.^[4]

Mechanism of action

Unlike imidazole- and triazole-class antifungals, abafungin directly impairs the fungal cell membrane.^[3]

In addition, abafungin inhibits the enzyme sterol 24-C-methyltransferase, modifying the composition of the fungal membrane.^[5]

Abafungin has antibiotic activity against gram-positive bacteria as well as sporicidal activity.^[6]

References

^ Borelli C, Schaller M, Niewerth M, Nocker K, Baasner B, Berg D, et al. (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): 245–259. doi:10.1159/000142334. PMC 2818358. PMID 18587237.
^ "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): 245–259. 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, et al. (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): 1778–1791. doi:10.1038/ki.1995.476. PMID 8587237.
^ Ginter-Hanselmayer G (March 2009). Arbeitsunterlagen zur 42. wissenschaftlichen Fortbildungsveranstaltung für Apothekerinnen und Apotheker: Infektionskrankheiten [Working documents for the 42nd scientific training event for pharmacists: Infectious diseases] (in German). Österreichische Apothekerkammer (Austrian Chamber of Pharmacists). p. 103.

External links

Media related to Abafungin at Wikimedia Commons

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[1] Borelli C, Schaller M, Niewerth M, Nocker K, Baasner B, Berg D, et al. (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): 245–259. doi:10.1159/000142334. PMC 2818358. PMID 18587237.

[2] "Regulatory Update – Abasol" (PDF). York Pharma. Archived from the original (PDF) on September 27, 2007.

[BorelliEtAl2008-3] 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): 245–259. doi:10.1159/000142334. PMC 2818358. PMID 18587237.

[4] "Abafungin". AdisInsight. Retrieved 5 May 2021.

[pmid8587237-5] Ruiz-Ortega M, González S, Serón D, Condom E, Bustos C, Largo R, et al. (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): 1778–1791. doi:10.1038/ki.1995.476. PMID 8587237.

[6] Ginter-Hanselmayer G (March 2009). Arbeitsunterlagen zur 42. wissenschaftlichen Fortbildungsveranstaltung für Apothekerinnen und Apotheker: Infektionskrankheiten [Working documents for the 42nd scientific training event for pharmacists: Infectious diseases] (in German). Österreichische Apothekerkammer (Austrian Chamber of Pharmacists). p. 103.

[1]

[2]

[3]

[4]

[5]

[6]

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
DrugBank	DB06395^Y
ChemSpider	140124^Y
UNII	11DI31LWXF
ChEBI	CHEBI:76005^N
CompTox Dashboard (EPA)	DTXSID60869776
ECHA InfoCard	100.125.129
Chemical and physical data
Formula	C₂₁H₂₂N₄OS
Molar mass	378.49 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)^Y Key:TYBHXIFFPVFXQW-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)