abafungin

{{Short description|Chemical compound}}

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{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477236893

| IUPAC_name = N-[4-[2-(2,4-dimethylphenoxy)phenyl]-1,3-thiazol-2-yl]-1,4,5,6-tetrahydropyrimidin-2-amine

| image = Abafungin.svg

| alt = Structural formula of abafungin

| width = 175

| image2 = Abafungin 3D spacefill.png

| alt2 = Space-filling model of the abafungin molecule

| width2 = 150

| tradename = Abasol

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| routes_of_administration = Topical (cream)

| bioavailability =

| protein_bound =

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| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 129639-79-8

| ATC_prefix = none

| ATC_suffix =

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| PubChem = 159326

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 76005

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB06395

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 140124

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 11DI31LWXF

| chemical_formula =

| C=21 | H=22 | N=4 | O=1 | S=1

| smiles = CC1=CC(=C(C=C1)OC2=CC=CC=C2C3=CSC(=N3)NC4=NCCCN4)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = TYBHXIFFPVFXQW-UHFFFAOYSA-N

}}

Abafungin (INN) is a broad-spectrum arylguanidines-class antifungal agent with a novel mechanism of action for the treatment of dermatomycoses.{{cite journal | vauthors = Borelli C, Schaller M, Niewerth M, Nocker K, Baasner B, Berg D, Tiemann R, Tietjen K, Fugmann B, Lang-Fugmann S, Korting HC | title = Modes of action of the new arylguanidine abafungin beyond interference with ergosterol biosynthesis and in vitro activity against medically important fungi | journal = Chemotherapy | volume = 54 | issue = 4 | pages = 245–259 | date = 2008 | pmid = 18587237 | pmc = 2818358 | doi = 10.1159/000142334 }}

Abasol is a topical cream formulation of abafungin by York Pharma.{{cite web | url = http://www.yorkpharma.com/media/YRK-Update_Abasol_061002-FN.pdf | publisher = York Pharma | title = Regulatory Update – Abasol | archive-url = https://web.archive.org/web/20070927102715/http://www.yorkpharma.com/media/YRK-Update_Abasol_061002-FN.pdf | archive-date=September 27, 2007 }}

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.{{cite journal | vauthors = Borelli C, Schaller M, Niewerth M, Nocker K, Baasner B, Berg D, Tiemann R, Tietjen K, Fugmann B, Lang-Fugmann S, Korting HC | title = Modes of action of the new arylguanidine abafungin beyond interference with ergosterol biosynthesis and in vitro activity against medically important fungi | journal = Chemotherapy | volume = 54 | issue = 4 | pages = 245–259 | date = August 2008 | pmid = 18587237 | pmc = 2818358 | doi = 10.1159/000142334 }}

Its development seems to have been discontinued in 2009.{{cite web|url=https://adisinsight.springer.com/drugs/800022887|title=Abafungin|publisher=AdisInsight|access-date=5 May 2021}}

Mechanism of action

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

In addition, abafungin inhibits the enzyme sterol 24-C-methyltransferase, modifying the composition of the fungal membrane.{{cite journal | vauthors = Ruiz-Ortega M, González S, Serón D, Condom E, Bustos C, Largo R, González E, Ortiz A, Egido J | title = ACE inhibition reduces proteinuria, glomerular lesions and extracellular matrix production in a normotensive rat model of immune complex nephritis | journal = Kidney International | volume = 48 | issue = 6 | pages = 1778–1791 | date = December 1995 | pmid = 8587237 | doi = 10.1038/ki.1995.476 | doi-access = free }}

Abafungin has antibiotic activity against gram-positive bacteria as well as sporicidal activity.{{cite book | vauthors = Ginter-Hanselmayer G |date=March 2009|title=Arbeitsunterlagen zur 42. wissenschaftlichen Fortbildungsveranstaltung für Apothekerinnen und Apotheker: Infektionskrankheiten | trans-title = Working documents for the 42nd scientific training event for pharmacists: Infectious diseases | language = de |publisher=Österreichische Apothekerkammer (Austrian Chamber of Pharmacists) |page=103}}

References

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