Stereochemistry | ABSOLUTE |
Molecular Formula | C21H41N7O12 |
Molecular Weight | 583.5899 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 15 / 15 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@H]2[C@H](O[C@H]3[C@H](O)[C@@H](O)[C@H](NC(N)=N)[C@@H](O)[C@@H]3NC(N)=N)O[C@@H](C)[C@]2(O)CO
InChI
InChIKey=ASXBYYWOLISCLQ-HZYVHMACSA-N
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
Molecular Formula | C21H41N7O12 |
Molecular Weight | 583.5899 |
Charge | 0 |
Count |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 15 / 15 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Dihydrostreptomycin is an antibiotic compound derived from streptomycin by reduction with hydrogen. The primary mechanism of action of the antibiotic dihydrostreptomycin is binding to and modifying the function of the bacterial ribosome, thus leading to decreased and aberrant translation of proteins, in addition it binds mechanosensitive channel of large conductance (MscL) and modifies its conformation, thus allowing the passage of K+ and glutamate out of, and dihydrostreptomycin into, the cell. It has about the same degree of antibacterial activity as streptomycin, but it is less effective against some gram-negative microorganisms. Because it has a higher risk of irreversible deafness, and its effectiveness is no greater that that of streptomycin, dihydrostreptomycin is no longer used clinically. To date dihydrostreptomycin is approved for veterinary use to treat bacterial infections.
CNS Activity
Approval Year
Doses
AEs
Sourcing
PubMed
Patents
Sample Use Guides
Treatment of leptospirosis in dogs, horses and swine: 5 mg per pound of body weight.
Dihydrostreptomycin is used for intramammary use to reduce the frequency of existing infection and to prevent new infections with Staphylococcus aureus in dry cows.
Route of Administration:
Other
minimal inhibiting concentrations (MIC) of pure dihydrostreptomycin trihydrochloride against Mycobacterium smegmatis, Aerobacter aerogenes, Bacillus subtilis, Klebsiella pneumoniae, Serratia marcescens, Staphylococcus aureus, Pseudomonas aeruginosa, Bacillus subtilis, Mycobacterium tuberculosis, and Bacillus sp. range from 0.036 to 5.66 ug/ml depending on species