Dihydrostreptomycin

Dihydrostreptomycin
Clinical data
AHFS/Drugs.comInternational 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  • WIthdrawn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
CompTox Dashboard (EPA)
ECHA InfoCard100.004.445
Chemical and physical data
FormulaC21H41N7O12
Molar mass583.596 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
  (verify)

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primarily affects the cochlea.[3][4] This lead to it being gradully pulled from market from 1959 and fully withdrawn from human use globally in 1970s.[5][6] It remains a commonly used veterinary drug (usually in combination with penicillin G as an alternative to streptomycin)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. ^ a b "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 Y, Huang WG, Zha DJ, Qiu JH, Wang JL, Sha SH, et al. (April 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. PMID 16844331.
  5. ^ Sheehy JL (June 1961). "Ototoxic Antibiotics". California Medicine. 94 (6): 363–365. PMC 1574403. PMID 18732406.
  6. ^ Fung M, Thornton A, Mybeck K, Wu JH, 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 (October 1997). "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. PMID 16031982.
  8. ^ Khalifa HO, Shikoray L, Mohamed MI, Habib I, Matsumoto T (May 2024). "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. PMC 11172309. PMID 38890858.
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