Micronomicin sulfate

S01AA15(WHO)QA07AA90(WHO)QJ01GA90(WHO)QJ51GA90(WHO) WIthdrawn 2-[(1S,2R,3R,4S,5R,6R)-5-(Diaminomethylideneamino)-2-[(2R,3R,4R,5S)-3-[(2S,3S,4S,5R,6S)- 4,5-dihydroxy-6-(hydroxymethyl)-3-methylaminooxan-2-yl]oxy-4-hydroxy-4-(hydroxymethyl)- 5-methyloxolan-2-yl]oxy-3,4,6-trihydroxycyclohexyl]guanidine 128-46-1 439369 DB11512Y 388489 P2I6R8W6UA ChEMBL1950576 DTXSID0022937 Interactive image C[C@H]1[C@@]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H]([C@@H]([C@H]2O)O)NC(=N)N)O)NC(=N)N)O[C@H]3[C@H]([C@@H]([C@H]([C@@H](O3)CO)O)O)NC)(CO)O InChI=1S/C21H41N7O12/c1-5-21(36,4-30)16(40-17-9(26-2)13(34)10(31)6(3-29)38-17)1​​​‍​​‍​​​​‍​​‍‍8(37-5)39-15-8(28-20(24)25)11(32)7(27-19(22)23)12(33)14(15)35/h5-18,26,29-36H,3-4H2,1-2H3,(H4,22,23,27)(H4,24,25,28)/t5-,6-,7+,8-,9-,10-,11+,12-,13-,14+,15+,16-,17-,18-,21+/m0/s1Key:ASXBYYWOLISCLQ-HZYVHMACSA-N Dihydrostreptomycinissemisyntheticaminoglycosideantibioticwithbactericidalproperties.It is thedihydroderivativeofstreptomycin, and was formerly used in the treatment oftuberculosis. It acts by irreversibly binding the S12 protein in the bacterial30Sribosomal subunit, after being actively transported across thecell membrane, which interferes with theinitiation complexbetween themRNAand the bacterialribosome. This leads to the synthesis of defective, nonfunctional proteins, which results in the bacterial cell's death. Dihydrostreptomycin is moreototoxicthan streptomycin with a significantly higher risk of causing irreversiblehearing loss, since streptomycin primarily affectsvestibular systemwhile dihydrostreptomycin primarily affects thecochlea.This lead to it being gradully pulled from market from 1959 and fully withdrawn from human use globally in 1970s.It remains a commonly usedveterinary drug(usually in combination withpenicillin Gas an alternative to streptomycin) and agricultural bactericide.