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Details

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
Structure of DIHYDROSTREPTOMYCIN

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

HIDE SMILES / InChI

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

Description

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

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
94.0 nM [Kd]
9.81 mM [Kd]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Doses

AEs

Sourcing

PubMed

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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
Substance Class Chemical
Record UNII
P2I6R8W6UA
Record Status Validated (UNII)
Record Version