eAmSPC 2593

Class: Aminoglycoside

Spectrum of activity:	Gram-positive  &  Gram-negative
Details of activity:	Active against Mycobacterium abscessus, Mycobacterium tuberculosis, Mycobacterium avium, Streptococcus sp., methicillin-resistant Staphylococcus aureus, and Escherichia coli; protein synthesis inhibitor
Description:	Synthetic compound; derived from spectinomycin (N-ethylene linked aminomethyl spectinomycin); shows synergistic effect with clarithromycin, linezolid, bedaquiline, and clofazimine; efficacious in reducing bacterial burden in Mycobacterium abscessus infection in immunocompromised mouse
Institute where first reported:	Department of Chemical Biology and Therapeutics, St. Jude Children’s Research Hospital, Memphis
Year first mentioned:	2024
Development status:	Experimental

Chemical structure(s):
Canonical SMILES:	C[C@@H]1C[C@@](CNCCC2=CC=C(C=C2)F)([C@]3([C@@H](O1)O[C@@H]4[C@H]([C@@H]([C@@H]([C@@H]([C@H]4O3)NC)O)NC)O)O)O
Isomeric SMILES:	C[C@@H]1C[C@]([C@]2([C@@H](O1)O[C@@H]3[C@H]([C@@H]([C@@H]([C@@H]([C@H]3O2)NC)O)NC)O)O)(CNCCC4=CC=C(C=C4)F)O
InChI:	InChI=1S/C23H36FN3O7/c1-12-10-22(30,11-27-9-8-13-4-6-14(24)7-5-13)23(31)21(32-12)33-20-18(29)15(25-2)17(28)16(26-3)19(20)34-23/h4-7,12,15-21,25-31H,8-11H2,1-3H3/t12-,15-,16+,17+,18+,19-,20-,21+,22-,23-/m1/s1
InChI Key:	KRCLSDQUEUBIKY-LLHOOWCXSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/117986569

External links:
Guide to Pharmacology:	eAmSPC 2593
Main Source:	https://www.pnas.org/doi/10.1073/pnas.2314101120