Neamine

Neamine
Clinical data
Other names	Neomycin A
Identifiers
	IUPAC name (1R,2R,3S,4R,6S)-4,6-Diamino-2,3-dihydroxycyclohexyl 2,6-diamino-2,6-dideoxy-α-D-glucopyranoside;
CAS Number	3947-65-7;
PubChem CID	72392;
DrugBank	DB04808;
ChemSpider	65325;
UNII	5981U00LY0;
CompTox Dashboard (EPA)	DTXSID7023358 ;
Chemical and physical data
Formula	C12H26N4O6
Molar mass	322.362 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O([C@H]1[C@H](O)[C@@H](O)[C@H](N)C[C@@H]1N)[C@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2N)CN;
	InChI InChI=1S/C12H26N4O6/c13-2-5-8(18)9(19)6(16)12(21-5)22-11-4(15)1-3(14)7(17)10(11)20/h3-12,17-20H,1-2,13-16H2/t3-,4+,5-,6-,7+,8-,9-,10-,11-,12-/m1/s1; Key:SYJXFKPQNSDJLI-HKEUSBCWSA-N;

Neamine (neomycin A) is a degradation product of the aminoglycoside antibiotic neomycin.^[1] Several derivatives of neamine are active against susceptible and resistant Gram-positive and Gram-negative bacteria.^[2]

References

^ Leach BE, Teeters CM (June 1951). "Neamine, an Antibacterial Degradation Product of Neomycin". Journal of the American Chemical Society. 73 (6): 2794–2797. doi:10.1021/ja01150a107.
^ Zimmermann L, Bussière A, Ouberai M, Baussanne I, Jolivalt C, Mingeot-Leclercq MP, et al. (October 2013). "Tuning the antibacterial activity of amphiphilic neamine derivatives and comparison to paromamine homologues". Journal of Medicinal Chemistry. 56 (19): 7691–7705. doi:10.1021/jm401148j. PMID 24083676.