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 |
|---|---|---|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| An indirect conductimetric screening method for the detection of antibiotic residues in bovine kidneys. | 2002 Sep |
|
| Potassium currents in vestibular type II hair cells activated by hydrostatic pressure. | 2003 |
|
| A national surveillance of antimicrobial resistance in Escherichia coli isolated from food-producing animals in Japan. | 2003 Feb |
|
| Isolation and characterization of bluensomycin biosynthetic genes from Streptomyces bluensis. | 2003 Feb 28 |
|
| Intramammary treatment of clinical mastitis of dairy cows with a combination of lincomycin and neomycin, or penicillin and dihydrostreptomycin. | 2003 Jun |
|
| 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 |
|
| New agents active against Mycobacterium avium complex selected by molecular topology: a virtual screening method. | 2004 Jan |
|
| 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 |
|
| Treatment of persistent intramammary infections with Streptococcus uberis in dairy cows. | 2005 Aug 27 |
|
| In vivo effect of interleukin-1beta and interleukin-1RA on oocyte cytoplasmic maturation, ovulation, and early embryonic development in the mare. | 2005 Jun 22 |
|
| Antimicrobial susceptibility of pathogenic Escherichia coli isolated from sick cattle and pigs in Japan. | 2005 Oct |
|
| A high-throughput analytical method for determination of aminoglycosides in veal tissues by liquid chromatography/tandem mass spectrometry with automated cleanup. | 2007 Sep-Oct |
|
| Susceptibility of bacterial pathogens against lincomycin/spectinomycin (1/2), penicillin G/neomycin (1/1), and penicillin G/dihydrostreptomycin (1/1) as determined in the BfT-GermVet monitoring program 2004-2006. | 2007 Sep-Oct |
|
| Multi-residue quantitation of aminoglycoside antibiotics in kidney and meat by liquid chromatography with tandem mass spectrometry. | 2008 Dec |
|
| Sperm morphology and chromatin integrity in Swedish warmblood stallions and their relationship to pregnancy rates. | 2008 Jan 7 |
|
| Clinical effects of transcatheter hepatic arterial embolization with holmium-166 poly(L-lactic acid) microspheres in healthy pigs. | 2008 Jul |
|
| Phage type and antimicrobial susceptibility of Salmonella enterica serovar Enteritidis from food-producing animals in Japan between 1976 and 2004. | 2008 Oct |
|
| Occurrence of antimicrobial residues in pasteurized milk commercialized in the state of Paraná, Brazil. | 2009 Apr |
|
| The chlamydial functional homolog of KsgA confers kasugamycin sensitivity to Chlamydia trachomatis and impacts bacterial fitness. | 2009 Dec 31 |
|
| Changing prevalence of O-serogroups and antimicrobial susceptibility among STEC strains isolated from healthy dairy cows over a decade in Japan between 1998 and 2007. | 2009 Mar |
|
| Relationships between multidrug-resistant Salmonella enterica Serovar Schwarzengrund and both broiler chickens and retail chicken meats in Japan. | 2009 May |
|
| Microbial screening methods for detection of antibiotic residues in slaughter animals. | 2009 Oct |
|
| Defining features of the hair cell mechanoelectrical transducer channel. | 2009 Oct |
|
| Antimicrobial resistance and genetic characterization of fluoroquinolone-resistant Mannheimia haemolytica isolates from cattle with bovine pneumonia. | 2009 Oct 20 |
|
| Stallion Sperm Viability, as Measured by the Nucleocounter SP-100, Is Affected by Extender and Enhanced by Single Layer Centrifugation. | 2010 |
|
| Monoclonal antibody-based ELISA and colloidal gold-based immunochromatographic assay for streptomycin residue detection in milk and swine urine. | 2010 Jan |
|
| Isolation of meticillin-resistant Staphylococcus aureus (MRSA) from swine in Japan. | 2010 Oct |
|
| Antibiotic use, resistance development and environmental factors: a qualitative study among healthcare professionals in Orissa, India. | 2010 Oct 21 |
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
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
222-637-5
Created by
admin on Fri Dec 15 18:05:30 GMT 2023 , Edited by admin on Fri Dec 15 18:05:30 GMT 2023
|
PRIMARY | |||
|
4A47J84Y2K
Created by
admin on Fri Dec 15 18:05:30 GMT 2023 , Edited by admin on Fri Dec 15 18:05:30 GMT 2023
|
PRIMARY | |||
|
107411
Created by
admin on Fri Dec 15 18:05:30 GMT 2023 , Edited by admin on Fri Dec 15 18:05:30 GMT 2023
|
PRIMARY | |||
|
100000087488
Created by
admin on Fri Dec 15 18:05:30 GMT 2023 , Edited by admin on Fri Dec 15 18:05:30 GMT 2023
|
PRIMARY | |||
|
m4467
Created by
admin on Fri Dec 15 18:05:30 GMT 2023 , Edited by admin on Fri Dec 15 18:05:30 GMT 2023
|
PRIMARY | Merck Index | ||
|
DTXSID30957018
Created by
admin on Fri Dec 15 18:05:30 GMT 2023 , Edited by admin on Fri Dec 15 18:05:30 GMT 2023
|
PRIMARY | |||
|
3563-84-6
Created by
admin on Fri Dec 15 18:05:30 GMT 2023 , Edited by admin on Fri Dec 15 18:05:30 GMT 2023
|
PRIMARY | |||
|
SUB01724MIG
Created by
admin on Fri Dec 15 18:05:30 GMT 2023 , Edited by admin on Fri Dec 15 18:05:30 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
