Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H41N7O12.C9H17NO5 |
| Molecular Weight | 802.8249 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 16 / 16 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)(CO)[C@@H](O)C(=O)NCCC(O)=O.[H][C@@]3(O[C@H]1[C@H](O[C@@]2([H])[C@H](O)[C@@H](O)[C@H](NC(N)=N)[C@@H](O)[C@@H]2NC(N)=N)O[C@@H](C)[C@]1(O)CO)O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]3NC
InChI
InChIKey=BCYSNOFYSIJRNM-FGZKHVCBSA-N
InChI=1S/C21H41N7O12.C9H17NO5/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;1-9(2,5-11)7(14)8(15)10-4-3-6(12)13/h5-18,26,29-36H,3-4H2,1-2H3,(H4,22,23,27)(H4,24,25,28);7,11,14H,3-5H2,1-2H3,(H,10,15)(H,12,13)/t5-,6-,7+,8-,9-,10-,11+,12-,13-,14+,15+,16-,17-,18-,21+;7-/m00/s1
DescriptionCurator's Comment: Description was created based on several sources, including
http://link.springer.com/chapter/10.1007%2F978-3-642-46304-4_36 | https://www.ncbi.nlm.nih.gov/pubmed/4133236 | https://www.ncbi.nlm.nih.gov/pubmed/27280286 |
https://www.ncbi.nlm.nih.gov/pubmed/13186082 | https://www.ncbi.nlm.nih.gov/pubmed/14925346 | https://www.ncbi.nlm.nih.gov/pubmed/13459234 | https://www.drugs.com/international/dihydrostreptomycin.html
Curator's Comment: Description was created based on several sources, including
http://link.springer.com/chapter/10.1007%2F978-3-642-46304-4_36 | https://www.ncbi.nlm.nih.gov/pubmed/4133236 | https://www.ncbi.nlm.nih.gov/pubmed/27280286 |
https://www.ncbi.nlm.nih.gov/pubmed/13186082 | https://www.ncbi.nlm.nih.gov/pubmed/14925346 | https://www.ncbi.nlm.nih.gov/pubmed/13459234 | https://www.drugs.com/international/dihydrostreptomycin.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14925346 | https://www.ncbi.nlm.nih.gov/pubmed/13459234
Curator's Comment: Dihydrostreptomycin is oto- and neurotoxic.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2363135 |
94.0 nM [Kd] | ||
Target ID: P0A742 Gene ID: 947787.0 Gene Symbol: mscL Target Organism: Escherichia coli (strain K12) |
9.81 mM [Kd] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | Unknown Approved UseUnknown |
Doses
| Dose | Population | Adverse events |
|---|---|---|
1 g 1 times / day multiple, oral Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: |
unhealthy, 21-64 years n = 3 Health Status: unhealthy Age Group: 21-64 years Sex: M+F Population Size: 3 Sources: |
Disc. AE: Hearing loss... AEs leading to discontinuation/dose reduction: Hearing loss (severe, 3 patients) Sources: |
2 g 1 times / day multiple, oral Dose: 2 g, 1 times / day Route: oral Route: multiple Dose: 2 g, 1 times / day Sources: |
unhealthy, 29 years n = 1 Health Status: unhealthy Age Group: 29 years Sex: F Population Size: 1 Sources: |
Disc. AE: Hearing loss... AEs leading to discontinuation/dose reduction: Hearing loss (severe, 1 patient) Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Hearing loss | severe, 3 patients Disc. AE |
1 g 1 times / day multiple, oral Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: |
unhealthy, 21-64 years n = 3 Health Status: unhealthy Age Group: 21-64 years Sex: M+F Population Size: 3 Sources: |
| Hearing loss | severe, 1 patient Disc. AE |
2 g 1 times / day multiple, oral Dose: 2 g, 1 times / day Route: oral Route: multiple Dose: 2 g, 1 times / day Sources: |
unhealthy, 29 years n = 1 Health Status: unhealthy Age Group: 29 years Sex: F Population Size: 1 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Developing a dynamic pharmacophore model for HIV-1 integrase. | 2000 Jun 1 |
|
| [Determination of streptomycin and dihydrostreptomycin in meat by liquid chromatography/mass spectrometry]. | 2001 Dec |
|
| Detection of streptomycin residues in whole milk using an optical immunobiosensor. | 2001 Jul |
|
| Antimicrobial susceptibilities of Erysipelothrix rhusiopathiae isolated from pigs with swine erysipelas in Japan, 1988-1998. | 2001 Mar |
|
| Improved agar diffusion method for detecting residual antimicrobial agents. | 2001 Mar |
|
| Evaluation of antibiotics for treatment of cattle infected with Leptospira borgpetersenii serovar hardjo. | 2001 Sep 1 |
|
| Detection of streptomycin and dihydrostreptomycin residues in milk, honey and meat samples using an optical biosensor. | 2002 Jul |
|
| Minimum inhibitory concentrations of 20 antimicrobial agents against Staphylococcus aureus isolated from bovine intramammary infections in Japan. | 2002 Nov |
|
| Pharmacological and toxicological aspects of combination of beta-lactam and aminoglycoside antibiotic, prednisolone and procaine hydrochloride on the example of Vetramycin. | 2003 |
|
| A national surveillance of antimicrobial resistance in Escherichia coli isolated from food-producing animals in Japan. | 2003 Feb |
|
| Interleukin-1 (IL-1) system gene expression in granulosa cells: kinetics during terminal preovulatory follicle maturation in the mare. | 2003 May 16 |
|
| Antimicrobial susceptibility of Salmonella isolated from cattle, swine and poultry (2001-2002): report from the Japanese Veterinary Antimicrobial Resistance Monitoring Program. | 2004 Feb |
|
| Capillary electrophoresis method for simultaneous determination of penicillin G, procaine and dihydrostreptomycin in veterinary drugs. | 2004 Feb 5 |
|
| New agents active against Mycobacterium avium complex selected by molecular topology: a virtual screening method. | 2004 Jan |
|
| Tonic mechanosensitivity of outer hair cells after loss of tip links. | 2005 Apr |
|
| Enzyme immunoassays for the analysis of streptomycin in milk, serum and water: development and assessment of a polyclonal antiserum and assay procedures using novel streptomycin derivatives. | 2005 Jun |
|
| Role of coresistance in the development of resistance to chloramphenicol in Escherichia coli isolated from sick cattle and pigs. | 2006 Feb |
|
| Development of a novel method based on liquid chromatography-evaporative light scattering detection for the direct determination of streptomycin and dihydrostreptomycin in raw materials, pharmaceutical formulations, culture media and plasma. | 2006 Jul 28 |
|
| Depolarization of cochlear outer hair cells evokes active hair bundle motion by two mechanisms. | 2006 Mar 8 |
|
| Quantitative determination of dihydrostreptomycin in bovine tissues and milk by liquid chromatography-electrospray ionization-tandem mass spectrometry. | 2007 May |
|
| Changes of multi-drug resistance pattern in Salmonella enterica subspecies enterica serovar typhimurium isolates from food-producing animals in Japan. | 2007 Nov |
|
| Dihydrostreptomycin goes through the mechano-electric transduction channel in chick cochlear hair cells. | 2009 |
|
| Treatment of mastitis during lactation. | 2009 Apr 1 |
|
| National surveillance of Salmonella enterica in food-producing animals in Japan. | 2009 Aug 25 |
|
| Phenotypic characterization of Salmonella typhimurium isolates from food-animals and abattoir drains in Buea, Cameroon. | 2009 Oct |
|
| Giardiavirus internal ribosome entry site has an apparently unique mechanism of initiating translation. | 2009 Oct 14 |
|
| An atypical case of respiratory actinobacillosis in a cow. | 2009 Sep |
|
| Role of antimicrobial selective pressure and secondary factors on antimicrobial resistance prevalence in Escherichia coli from food-producing animals in Japan. | 2010 |
|
| Monoclonal antibody-based ELISA and colloidal gold-based immunochromatographic assay for streptomycin residue detection in milk and swine urine. | 2010 Jan |
|
| Hydrophilic interaction vs ion pair liquid chromatography for the determination of streptomycin and dihydrostreptomycin residues in milk based on mass spectrometric detection. | 2010 Oct 22 |
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
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222-637-5
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4A47J84Y2K
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100000087488
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m4467
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DTXSID30957018
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SUB01724MIG
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ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
