Dihydrostreptomycin

Dihydrostreptomycin is a derivative of streptomycin that has a bactericidal properties.^[1] It is a semisynthetic aminoglycoside antibiotic used in the treatment of tuberculosis.^[2]

Dihydrostreptomycin

Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	S01AA15 (WHO) QA07AA90 (WHO) QJ01GA90 (WHO) QJ51GA90 (WHO)
Identifiers
IUPAC name 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
CAS Number	128-46-1
PubChem CID	439369
ChemSpider	388489
UNII	P2I6R8W6UA
ChEMBL	ChEMBL1950576
CompTox Dashboard (EPA)	DTXSID0022937
ECHA InfoCard	100.004.445
Chemical and physical data
Formula	C21H41N7O12
Molar mass	583.596 g·mol−1
3D model (JSmol)	Interactive image
SMILES 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 InChI=1S/C21H41N7O12/c1-5-21(36,4-30)16(40-17-9(26-2)13(34)10(31)6(3-29)38-17)18(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/s1 Key:ASXBYYWOLISCLQ-HZYVHMACSA-N
(verify)

It acts by irreversibly binding the S12 protein in the bacterial 30S ribosomal subunit, after being actively transported across the cell membrane, which interferes with the initiation complex between the mRNA and the bacterial ribosome. This leads to the synthesis of defective, nonfunctional proteins, which results in the bacterial cell's death.^[1]

It causes ototoxicity,^[3] which is why it is no longer used in humans.^{[citation needed]}