Dihydrostreptomycin
- S01AA15 (WHO) QA07AA90 (WHO) QJ01GA90 (WHO) QJ51GA90 (WHO)
- 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
- 388489
- P2I6R8W6UA
- ChEMBL1950576
- DTXSID0022937
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- 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)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
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]
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]
See also
- Translation (biology)
References
- ^ a b "Dihydrostreptomycin (Code C61724) - NCI Thesaurus". Retrieved July 7, 2016.
- ^ "Dihydrostreptomycin Sulfate - MeSH - NCBI". Retrieved July 7, 2016.
- ^ Harrison WH (1954). "Ototoxicity of dihydrostreptomycin". Quarterly Bulletin. Northwestern University. 28 (3): 271–3. PMC 3803976. PMID 13186082.
External links
- Dihydrostreptomycin | C21H41N7O12 - PubChem
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Aminoglycosides (initiation inhibitors) |
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Tetracycline antibiotics (tRNA binding) |
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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