Compound ID | 1855

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Dihydrostreptomycin

Class: Aminoglycoside

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Protein synthesis inhibitor. Binds to the bacterial 30S ribosomal subunit
Target Pathogen: Active against Gram-positive and Gram-negative bacteria
Description: Semisynthetic, derived from streptomycin. Used in veterinary medicine
Year first mentioned: 1949
Highest development stage: Approved
Development status: Withdrawn
Reason dropped: Risk of ototoxicity/ irreversible hearing loss
Chemical structure(s):
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Molecular weight: 583.59
Iso. 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)N=C(N)N)O)N=C(N)N)O[C@H]3[C@H]([C@@H]([C@H]([C@@H](O3)CO)O)O)NC)(CO)O
InChI Key: ASXBYYWOLISCLQ-HZYVHMACSA-N
Can. SMILES: C[C@H]1[C@](CO)([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H]([C@@H]([C@H]2O)O)N=C(N)N)O)N=C(N)N)O[C@H]3[C@H]([C@@H]([C@H]([C@H](CO)O3)O)O)NC)O
InChI: 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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/439369
Guide to Pharmacology: dihydrostreptomycin
Citation: https://www.nejm.org/doi/full/10.1056/NEJM194905052401810

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