:Dihydrostreptomycin

{{Short description|Chemical compound}}

{{Drugbox

| verifiedrevid = 443991243

| 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

| image = Dihydrostreptomycin.svg

| tradename =

| Drugs.com = {{drugs.com|international|dihydrostreptomycin}}

| pregnancy_AU =

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| legal_AU =

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| bioavailability =

| protein_bound =

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| CAS_number = 128-46-1

| CAS_supplemental =

| ATC_prefix = S01

| ATC_suffix = AA15

| ATC_supplemental = {{ATCvet|A07|AA90}} {{ATCvet|J01|GA90}} {{ATCvet|J51|GA90}}

| PubChem = 439369

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| ChEMBL = 1950576

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = P2I6R8W6UA

| ChemSpiderID = 388489

| chemical_formula =

| C=21 | H=41 | N=7 | O=12

| 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

| StdInChI = 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

| StdInChIKey = ASXBYYWOLISCLQ-HZYVHMACSA-N

}}

Dihydrostreptomycin is a derivative of streptomycin that has a bactericidal properties.{{cite web | url=https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=NCI_Thesaurus&code=C61724 | title=Dihydrostreptomycin (Code C61724) - NCI Thesaurus | access-date=July 7, 2016}} It is a semisynthetic aminoglycoside antibiotic used in the treatment of tuberculosis.{{cite web | url=https://www.ncbi.nlm.nih.gov/mesh/68004096 | title=Dihydrostreptomycin Sulfate - MeSH - NCBI | access-date=July 7, 2016}}

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.

It causes ototoxicity,{{cite journal | vauthors = Harrison WH | title = Ototoxicity of dihydrostreptomycin | journal = Quarterly Bulletin. Northwestern University | volume = 28 | issue = 3 | pages = 271–3 | year = 1954 | pmid = 13186082 | pmc = 3803976 }} which is why it is no longer used in humans.{{cn|date=March 2023}}