AM-2-19

AM-2-19
Legal status
Legal status	In general: unscheduled;
Identifiers
CAS Number	2761794-74-3;
PubChem CID	170453316;
Chemical and physical data
3D model (JSmol)	Interactive image;
	SMILES [C@H]1[C@H](C)OC(C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O2)(O)C[C@H](O)[C@@H](C(NC(CO)CO)=O)[C@@H]2C[C@@H](O[C@@H]3O[C@H](C)[C@@H](O)[C@H](N)[C@H]3O)/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@H]1O)=O;
	InChI InChI=1S/C50H80N2O18/c1-29-17-15-13-11-9-7-5-6-8-10-12-14-16-18-37(69-49-47(64)44(51)46(63)32(4)68-49)24-41-43(48(65)52-33(27-53)28-54)40(60)26-50(66,70-41)25-36(57)22-39(59)38(58)20-19-34(55)21-35(56)23-42(61)67-31(3)30(2)45(29)62/h5-18,29-41,43-47,49,53-60,62-64,66H,19-28,51H2,1-4H3,(H,52,65)/b6-5+,9-7+,10-8+,13-11+,14-12+,17-15+,18-16+/t29-,30-,31-,32+,34+,35+,36-,37-,38+,39+,40-,41-,43+,44-,45+,46+,47+,49-,50+/m0/s1; Key:DYFDQVUOYRWTOB-JYUTVPRCSA-N;

AM-2-19 is an experimental antifungal drug based on amphotericin B (AmB) that is engineered to be less toxic to the kidneys.^[1]^[2]^[3]

Amphotericin B is a polyene that targets fungal ergosterol as well as human cholesterol, which results in kidney damage. AM-2-19 (also known as SF001) instead is selective to fungal ergosterol and also draws out fungal ergosterol more effectively. The investigational new drug (IND) application was filed in May 2023. SF001 received Qualified Infectious Disease Product (QIDP) for invasive aspergillosis and Fast Track designations from the FDA in 2023. It is now under phase I trial. An oral formulation is currently in the feasibility phase.

References

^ "New antifungal kills without toxic side effects". Science.org. Retrieved 19 November 2023.
^ Maji, Arun; Soutar, Corinne P.; Zhang, Jiabao; Lewandowska, Agnieszka; Uno, Brice E.; Yan, Su; Shelke, Yogesh; Murhade, Ganesh; Nimerovsky, Evgeny; Borcik, Collin G.; Arango, Andres S.; Lange, Justin D.; Marin-Toledo, Jonnathan P.; Lyu, Yinghuan; Bailey, Keith L.; Roady, Patrick J.; Holler, Jordan T.; Khandelwal, Anuj; SantaMaria, Anna M.; Sanchez, Hiram; Juvvadi, Praveen R.; Johns, Gina; Hageman, Michael J.; Krise, Joanna; Gebremariam, Teclegiorgis; Youssef, Eman G.; Bartizal, Ken; Marr, Kieren A.; Steinbach, William J.; Ibrahim, Ashraf S.; Patterson, Thomas F.; Wiederhold, Nathan P.; Andes, David R.; Pogorelov, Taras V.; Schwieters, Charles D.; Fan, Timothy M.; Rienstra, Chad M.; Burke, Martin D. (8 November 2023). "Tuning sterol extraction kinetics yields a renal-sparing polyene antifungal". Nature. 623 (7989): 1079–1085. Bibcode:2023Natur.623.1079M. doi:10.1038/s41586-023-06710-4. ISSN 1476-4687. PMC 10883201. PMID 37938782. S2CID 265048011.
^ "Antifungal analog offers reduced toxicity". Chemical & Engineering News. Retrieved 19 November 2023.

[1] "New antifungal kills without toxic side effects". Science.org. Retrieved 19 November 2023.

[2] Maji, Arun; Soutar, Corinne P.; Zhang, Jiabao; Lewandowska, Agnieszka; Uno, Brice E.; Yan, Su; Shelke, Yogesh; Murhade, Ganesh; Nimerovsky, Evgeny; Borcik, Collin G.; Arango, Andres S.; Lange, Justin D.; Marin-Toledo, Jonnathan P.; Lyu, Yinghuan; Bailey, Keith L.; Roady, Patrick J.; Holler, Jordan T.; Khandelwal, Anuj; SantaMaria, Anna M.; Sanchez, Hiram; Juvvadi, Praveen R.; Johns, Gina; Hageman, Michael J.; Krise, Joanna; Gebremariam, Teclegiorgis; Youssef, Eman G.; Bartizal, Ken; Marr, Kieren A.; Steinbach, William J.; Ibrahim, Ashraf S.; Patterson, Thomas F.; Wiederhold, Nathan P.; Andes, David R.; Pogorelov, Taras V.; Schwieters, Charles D.; Fan, Timothy M.; Rienstra, Chad M.; Burke, Martin D. (8 November 2023). "Tuning sterol extraction kinetics yields a renal-sparing polyene antifungal". Nature. 623 (7989): 1079–1085. Bibcode:2023Natur.623.1079M. doi:10.1038/s41586-023-06710-4. ISSN 1476-4687. PMC 10883201. PMID 37938782. S2CID 265048011.

[3] "Antifungal analog offers reduced toxicity". Chemical & Engineering News. Retrieved 19 November 2023.

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