Dihydrostreptomycin

Dihydrostreptomycin is a semisynthetic aminoglycoside antibiotic with bactericidal properties.^[1] It is the dihydro derivative of streptomycin, and was formerly used in the treatment of tuberculosis.^[2]

AHFS/Drugs.comInternational Drug Names

ATC code

• S01AA15 (WHO) QA07AA90 (WHO) QJ01GA90 (WHO) QJ51GA90 (WHO)

Legal status

• WIthdrawn

CAS Number

• 128-46-1

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Dihydrostreptomycin

Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	S01AA15 (WHO) QA07AA90 (WHO) QJ01GA90 (WHO) QJ51GA90 (WHO)
Legal status
Legal status	WIthdrawn
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
DrugBank	DB11512 Y
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
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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.^[2]

Dihydrostreptomycin is more ototoxic than streptomycin, with a significantly higher risk of causing irreversible hearing loss, since streptomycin primarily affects the vestibular system while dihydrostreptomycin primarily affects the cochlea.^[3][4] This led to it being gradully pulled from the market in 1959, and fully, globally withdrawn from human use in 1970s.^[5][6] It remains a commonly used veterinary drug (usually in combination with penicillin G as an alternative to streptomycin) and agricultural bactericide.^[7][8]