Dihydrostreptomycin

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Dihydrostreptomycin
Dihydrostreptomycin.svg
Clinical data
AHFS/Drugs.com International Drug Names
ATC code
Legal status
Legal status
  • WIthdrawn
Identifiers
  • 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
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
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ECHA InfoCard 100.004.445 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C21H41N7O12
Molar mass 583.596 g·mol−1
3D model (JSmol)
  • 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
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Dihydrostreptomycin is semisynthetic aminoglycoside antibiotic with bactericidal properties. [1] It is the dihydro derivative of streptomycin, and was formerly 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. [2]

Dihydrostreptomycin is more ototoxic than streptomycin with a significantly higher risk of causing irreversible hearing loss, since streptomycin primarily affects vestibular system while dihydrostreptomycin primarily affects the cochlea. [3] [4] This lead to it being gradully pulled from market from 1959 and fully withdrawn from human use globally in 1970s.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]

References

  1. ↑ "Dihydrostreptomycin Sulfate - MeSH - NCBI" . Retrieved July 7, 2016.
  2. 1 2 "Dihydrostreptomycin (Code C61724) - NCI Thesaurus" . Retrieved July 7, 2016.
  3. ↑ Harrison WH (1954). "Ototoxicity of dihydrostreptomycin". Quarterly Bulletin. Northwestern University. 28 (3): 271–273. PMC   3803976 . PMID   13186082.
  4. ↑ Chen, Yang; Huang, Wei-Guo; Zha, Ding-Jun; Qiu, Jian-Hua; Wang, Jin-Ling; Sha, Su-Hua; Schacht, Jochen (2007). "Aspirin attenuates gentamicin ototoxicity: From the laboratory to the clinic". Hearing Research. 226 (1–2): 178–182. doi:10.1016/j.heares.2006.05.008 . Retrieved 2026-03-19.
  5. ↑ Sheehy, J. L. (1961). "OTOTOXIC ANTIBIOTICS". California Medicine. 94 (6): 363–365. ISSN   0008-1264. PMC   1574403 . PMID   18732406 . Retrieved 2026-03-19.
  6. ↑ Fung, M.; Thornton, A.; Mybeck, K.; Wu, J. H.-h.; Hornbuckle, K.; Muniz, E. (1 January 2001). "Evaluation of the Characteristics of Safety Withdrawal of Prescription Drugs from Worldwide Pharmaceutical Markets-1960 to 1999". Therapeutic Innovation & Regulatory Science. 35 (1): 293–317. doi:10.1177/009286150103500134. S2CID   73036562.
  7. ↑ Whittem, T.; Hanlon, D. (1997-01-10). "Dihydrostreptomycin or streptomycin in combination with penicillin G in dairy cattle therapeutics: A review and re-analysis of published data Part 1: Clinical pharmacology". New Zealand Veterinary Journal. 45 (5): 178–184. doi:10.1080/00480169.1997.36022. ISSN   0048-0169 . Retrieved 2026-04-03.
  8. ↑ Khalifa, Hazim O.; Shikoray, Lamek; Mohamed, Mohamed-Yousif Ibrahim; Habib, Ihab; Matsumoto, Tetsuya (2024-05-23). "Veterinary Drug Residues in the Food Chain as an Emerging Public Health Threat: Sources, Analytical Methods, Health Impacts, and Preventive Measures". Foods. 13 (11): 1629. doi: 10.3390/foods13111629 . ISSN   2304-8158. PMC   11172309 . PMID   38890858.


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