Fusafungine

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 447387050

| IUPAC_name = cyclo[N-oxa-DL-valyl-N-methyl-L-valyl-N-oxa-DL-valyl-N-methyl-L-valyl-N-oxa-DL-valyl-N-methyl-L-valyl]

| image =Fusafungine structure.svg

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| Drugs.com = {{drugs.com|international|fusafungine}}

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 1393-87-9

| ATC_prefix = R02

| ATC_suffix = AB03

| PubChem = 3084092

| DrugBank_Ref = {{drugbankcite|changed|drugbank}}

| DrugBank = DB08965

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

| UNII = 65DD690W0C

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = D08002

| C=33 | H=57 | N=3 | O=9

| synonyms = Fusafungin

| SMILES = CC(C)[C@H]1C(=O)OC(C(=O)N([C@H](C(=O)OC(C(=O)N([C@H](C(=O)OC(C(=O)N1C)C(C)C)C(C)C)C)C(C)C)C(C)C)C)C(C)C

| melting_point = 125

| melting_high = 129

}}

Fusafungine (INN), also known as fusafungin, is an active agent used in antibiotics for treatment of nasal and throat infection. It also possesses anti-inflammatory properties. Fusafungine is a mixture of enniatin cyclohexadepsipeptides made up of alternating D-α-hydroxyvaleric acid and L-N-methylamino acid residues,{{cite journal | vauthors = Levy D, Bluzat A, Seigneuret M, Rigaud JL | title = Alkali cation transport through liposomes by the antimicrobial fusafungine and its constitutive enniatins | journal = Biochemical Pharmacology | volume = 50 | issue = 12 | pages = 2105–7 | date = December 1995 | pmid = 8849339 | doi = 10.1016/0006-2952(95)02045-4 }} produced by the ascomycete Fusarium lateritium, and marketed by Servier under the trade names Locabiotal, Bioparox, and Locabiosol.

According to a pooled analysis study done in the UK for the efficacy of fusafungine in rhinopharingitis, it was found that the proportion of patients who showed an improvement in symptoms from Day 0 to Day 4 of infection was 61.5% with fusafungine vs. 46.8% when compared to a placebo.{{cite journal | vauthors = Lund VJ, Grouin JM, Eccles R, Bouter C, Chabolle F | title = Efficacy of fusafungine in acute rhinopharyngitis: a pooled analysis | journal = Rhinology | volume = 42 | issue = 4 | pages = 207–12 | date = December 2004 | pmid = 15626253 }}

In February 2016, the European Medicines Agency recommended the withdrawal of fusafungine from the market due to rare but severe allergic reactions (mainly bronchospasms).{{cite web | url = http://www.ema.europa.eu/ema/index.jsp?curl=pages/medicines/human/referrals/Fusafungine_for_oromucosal_and_nasal_use/human_referral_prac_000054.jsp&mid=WC0b01ac05805c516f | title = CMDh endorses revocation of authorisations for fusafungine sprays used to treat airway infections | date = 17 September 2018 | publisher = European Medicines Agency | access-date = 18 February 2022 | archive-date = 20 June 2018 | archive-url = https://web.archive.org/web/20180620220021/http://www.ema.europa.eu/ema//index.jsp?curl=pages%2Fmedicines%2Fhuman%2Freferrals%2FFusafungine_for_oromucosal_and_nasal_use%2Fhuman_referral_prac_000054.jsp&mid=WC0b01ac05805c516f | url-status = dead }}