Dihydrostreptomycin: Difference between revisions

{{Short description|Chemical compound}}

{{Drugbox

| verifiedrevid = 443991243

| IUPAC_name = 2-[(1''S'',2''R'',3''R'',4''S'',5''R'',6''R'')-5-(Diaminomethylideneamino)-2-[(2''R'',3''R'',4''R'',5''S'')-3-[(2''S'',3''S'',4''S'',5''R'',6''S'')- 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

<!--Clinical data-->

| tradename =

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

| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->

| pregnancy_US = <!-- A / B / C / D / X -->

| pregnancy_category =

| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->

| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->

| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->

| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->

| legal_status =

| routes_of_administration =

<!--Pharmacokinetic data-->

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

<!--Identifiers-->

| 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

| ChemSpiderID = 388489

<!--Chemical data-->

| chemical_formula =

| 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.<ref name="ncit">{{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}}</ref> It is a [[semisynthetic]] [[aminoglycoside]] antibiotic used in the treatment of [[tuberculosis]].<ref name="mesh">{{cite web | url=https://www.ncbi.nlm.nih.gov/mesh/68004096 | title=Dihydrostreptomycin Sulfate - MeSH - NCBI | access-date=July 7, 2016}}</ref>

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 [[bacterial translation|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.<ref name="ncit" />

It causes [[ototoxicity]],<ref>{{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 }}</ref> which is why it is no longer used in humans.{{cn|date=March 2023}}

== See also ==

* [[Translation (biology)]]

== References ==

{{Reflist}}

== External links ==

* [https://pubchem.ncbi.nlm.nih.gov/compound/DIHYDROSTREPTOMYCIN Dihydrostreptomycin | C21H41N7O12 - PubChem]

{{Protein synthesis inhibitor antibiotics|state=collapsed}}