Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H41N7O12.2ClH |
| Molecular Weight | 656.512 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 15 / 15 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.Cl.[H][C@@]2(O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1NC)[C@@H](O[C@@]3([H])[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=IONSYBIUIGVTJV-JOMTZEKMSA-N
InChI=1S/C21H41N7O12.2ClH/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);2*1H/t5-,6-,7-,8+,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,21+;;/m1../s1
| Molecular Formula | C21H41N7O12 |
| Molecular Weight | 583.5899 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 15 / 15 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|
| Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production. | 1993 Sep 24 |
|
| [Determination of streptomycin and dihydrostreptomycin in meat by liquid chromatography/mass spectrometry]. | 2001 Dec |
|
| Antimicrobial susceptibilities of Erysipelothrix rhusiopathiae isolated from pigs with swine erysipelas in Japan, 1988-1998. | 2001 Mar |
|
| Membrane current possessing the properties of a mechano-electric transducer current in inner hair cells of guinea-pig cochlea. | 2001 Oct 5 |
|
| Differences in mechano-transducer channel kinetics underlie tonotopic distribution of fast adaptation in auditory hair cells. | 2002 Apr |
|
| Fm1-43 reveals membrane recycling in adult inner hair cells of the mammalian cochlea. | 2002 May 15 |
|
| Minimum inhibitory concentrations of 20 antimicrobial agents against Staphylococcus aureus isolated from bovine intramammary infections in Japan. | 2002 Nov |
|
| Simulation of concentration-time profiles of benzyl-penicillin, enrofloxacin and dihydrostreptomycin in tissue cages in calves. | 2002 Oct |
|
| Pharmacological and toxicological aspects of combination of beta-lactam and aminoglycoside antibiotic, prednisolone and procaine hydrochloride on the example of Vetramycin. | 2003 |
|
| Potassium currents in vestibular type II hair cells activated by hydrostatic pressure. | 2003 |
|
| In vitro antimicrobial susceptibility of Escherichia coli isolates from clinical bovine mastitis in Finland and Israel. | 2003 Dec |
|
| A national surveillance of antimicrobial resistance in Escherichia coli isolated from food-producing animals in Japan. | 2003 Feb |
|
| Intramammary treatment of clinical mastitis of dairy cows with a combination of lincomycin and neomycin, or penicillin and dihydrostreptomycin. | 2003 Jun |
|
| Prioritisation of veterinary medicines in the UK environment. | 2003 May 15 |
|
| Cumulus expansion, nuclear maturation and connexin 43, cyclooxygenase-2 and FSH receptor mRNA expression in equine cumulus-oocyte complexes cultured in vitro in the presence of FSH and precursors for hyaluronic acid synthesis. | 2004 Jun 22 |
|
| Determination of streptomycin and dihydrostreptomycin in milk and honey by liquid chromatography with tandem mass spectrometry. | 2004 Nov 26 |
|
| Tonic mechanosensitivity of outer hair cells after loss of tip links. | 2005 Apr |
|
| Antimicrobial susceptibility of pathogenic Escherichia coli isolated from sick cattle and pigs in Japan. | 2005 Oct |
|
| The aminoglycoside antibiotic dihydrostreptomycin rapidly enters mouse outer hair cells through the mechano-electrical transducer channels. | 2005 Sep 1 |
|
| Antimicrobial resistance in Salmonella isolates from apparently healthy food-producing animal from 2000 to 2003: the first stage of Japanese veterinary antimicrobial resistance monitoring (JVARM). | 2006 Aug |
|
| Antimicrobial resistance types and genes in Salmonella enterica infantis isolates from retail raw chicken meat and broiler chickens on farms. | 2006 Jan |
|
| 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 |
|
| Prioritizing genomic drug targets in pathogens: application to Mycobacterium tuberculosis. | 2006 Jun 9 |
|
| Depolarization of cochlear outer hair cells evokes active hair bundle motion by two mechanisms. | 2006 Mar 8 |
|
| Liquid chromatography on an amide stationary phase with post-column derivatization and fluorimetric detection for the determination of streptomycin and dihydrostreptomycin in foods. | 2007 Apr 30 |
|
| Clinical and bacteriological response to treatment of clinical mastitis with one of three intramammary antibiotics. | 2007 Aug |
|
| Changes of multi-drug resistance pattern in Salmonella enterica subspecies enterica serovar typhimurium isolates from food-producing animals in Japan. | 2007 Nov |
|
| The actions of calcium on hair bundle mechanics in mammalian cochlear hair cells. | 2008 Apr 1 |
|
| [Simultaneous determination of aminoglycoside antibiotics in milk by liquid chromatography with tandem mass spectrometry]. | 2008 Jun |
|
| [Simple and rapid microbiological method for determination of residual antibacterials in meat]. | 2008 Jun |
|
| Monitoring of streptomycin and dihydrostreptomycin residual levels in porcine meat press juice and muscle via solid-phase fluorescence immunoassay and confirmatory analysis by liquid chromatography after post-column derivatization. | 2008 Mar |
|
| Farm-level impact of therapeutic antimicrobial use on antimicrobial-resistant populations of Escherichia coli isolates from pigs. | 2008 Sep |
|
| Toxin detection by surface plasmon resonance. | 2009 |
|
| Treatment of mastitis during lactation. | 2009 Apr 1 |
|
| National surveillance of Salmonella enterica in food-producing animals in Japan. | 2009 Aug 25 |
|
| Analysis of impurities in streptomycin and dihydrostreptomycin by hydrophilic interaction chromatography/electrospray ionization quadrupole ion trap/time-of-flight mass spectrometry. | 2009 Mar |
|
| Development and validation of an LC-APCI-MS-MS analytical method for the determination of streptomycin and dihydrostreptomycin residues in milk. | 2009 Oct |
|
| Microbial screening methods for detection of antibiotic residues in slaughter animals. | 2009 Oct |
|
| Role of antimicrobial selective pressure and secondary factors on antimicrobial resistance prevalence in Escherichia coli from food-producing animals in Japan. | 2010 |
|
| Stallion Sperm Viability, as Measured by the Nucleocounter SP-100, Is Affected by Extender and Enhanced by Single Layer Centrifugation. | 2010 |
|
| Reproductive performance, udder health, and antibiotic resistance in mastitis bacteria isolated from Norwegian Red cows in conventional and organic farming. | 2010 Feb 8 |
|
| Staphylococcus aureus sigma B-dependent emergence of small-colony variants and biofilm production following exposure to Pseudomonas aeruginosa 4-hydroxy-2-heptylquinoline-N-oxide. | 2010 Jan 30 |
|
| WD-repeat instability and diversification of the Podospora anserina hnwd non-self recognition gene family. | 2010 May 6 |
|
| Nationwide survey of salmonella prevalence in environmental dust from layer farms in Japan. | 2010 Nov |
|
| 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
| Substance Class |
Chemical
Created
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admin
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Edited
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on
Fri Dec 15 15:02:55 GMT 2023
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| Record UNII |
F08EJ7FH4R
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| Record Status |
Validated (UNII)
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| Record Version |
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NON-SPECIFIC STOICHIOMETRY |
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |