U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula 2C21H41N7O12.3H2O4S
Molecular Weight 1461.4204
Optical Activity UNSPECIFIED
Defined Stereocenters 30 / 30
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIHYDROSTREPTOMYCIN SULFATE

SMILES

C[C@@]1([H])[C@](CO)([C@]([H])([C@@]([H])(O1)O[C@]2([H])[C@]([H])([C@@]([H])([C@]([H])([C@@]([H])([C@@]2([H])O)O)NC(=N)N)O)NC(=N)N)O[C@@]3([H])[C@]([H])([C@@]([H])([C@]([H])([C@]([H])(CO)O3)O)O)NC)O.C[C@@]1([H])[C@](CO)([C@]([H])([C@@]([H])(O1)O[C@]2([H])[C@]([H])([C@@]([H])([C@]([H])([C@@]([H])([C@@]2([H])O)O)NC(=N)N)O)NC(=N)N)O[C@@]3([H])[C@]([H])([C@@]([H])([C@]([H])([C@]([H])(CO)O3)O)O)NC)O.OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O

InChI

InChIKey=CZWJCQXZZJHHRH-YCRXJPFRSA-N
InChI=1S/2C21H41N7O12.3H2O4S/c2*1-5-21(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;3*1-5(2,3)4/h2*5-18,26,29-36H,3-4H2,1-2H3,(H4,22,23,27)(H4,24,25,28);3*(H2,1,2,3,4)/t2*5-,6-,7+,8-,9-,10-,11+,12-,13-,14+,15+,16-,17-,18-,21+;;;/m00.../s1

HIDE SMILES / InChI

Molecular Formula H2O4S
Molecular Weight 98.0796
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C21H41N7O12
Molecular Weight 583.5908
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 15 / 15
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: 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

Curator's Comment:: Dihydrostreptomycin is oto- and neurotoxic.

Originator

Curator's Comment:: Peck et al., 1946; Fried and Wintersteiner, 1947; Bartz et al., 1946

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
94 nM [Kd]
Target ID: P0A742
Gene ID: 947787
Gene Symbol: mscL
Target Organism: Escherichia coli (strain K12)
9.8100000000000005 mM [Kd]
Conditions
Doses

Doses

DosePopulationAdverse 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
Health Status: unhealthy
Age Group: 21-64 years
Sex: M+F
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
Health Status: unhealthy
Age Group: 29 years
Sex: F
Sources:
Disc. AE: Hearing loss...
AEs leading to
discontinuation/dose reduction:
Hearing loss (severe, 1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
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
Health Status: unhealthy
Age Group: 21-64 years
Sex: M+F
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
Health Status: unhealthy
Age Group: 29 years
Sex: F
Sources:
Sourcing
PubMed

PubMed

TitleDatePubMed
Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production.
1993 Sep 24
Pharmacological and toxicological aspects of combination of beta-lactam and aminoglycoside antibiotic, prednisolone and procaine hydrochloride on the example of Vetramycin.
2003
In vitro antimicrobial susceptibility of Escherichia coli isolates from clinical bovine mastitis in Finland and Israel.
2003 Dec
[Interaction of aminoglycosides and the other antibiotic on selected bacterial strains].
2004
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
Antimicrobial susceptibilities of Campylobacter isolated from food-producing animals on farms (1999-2001): results from the Japanese Veterinary Antimicrobial Resistance Monitoring Program.
2004 Sep
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
Antimicrobial susceptibility of Mannheimia haemolytica isolates from cattle in Japan from 2001 to 2002.
2005 Jan
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
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
The aminoglycoside antibiotic dihydrostreptomycin rapidly enters mouse outer hair cells through the mechano-electrical transducer channels.
2005 Sep 1
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
[Present situation of national surveillance of antimicrobial resistance in bacteria isolated from farm animals in Japan and correspondence to the issue].
2006 May
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
Characterization of Klebsiella pneumoniae isolates from New Zealand sea lion (Phocarctos hookeri) pups during and after the epidemics on Enderby Island, Auckland Islands.
2007 May 16
Changes of multi-drug resistance pattern in Salmonella enterica subspecies enterica serovar typhimurium isolates from food-producing animals in Japan.
2007 Nov
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
The actions of calcium on hair bundle mechanics in mammalian cochlear hair cells.
2008 Apr 1
Multi-residue quantitation of aminoglycoside antibiotics in kidney and meat by liquid chromatography with tandem mass spectrometry.
2008 Dec
Reaching activity in parietal area V6A of macaque: eye influence on arm activity or retinocentric coding of reaching movements?
2008 Feb
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
[Simultaneous determination of aminoglycoside antibiotics in milk by liquid chromatography with tandem mass spectrometry].
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
Occurrence of antimicrobial residues in pasteurized milk commercialized in the state of Paraná, Brazil.
2009 Apr
Treatment of mastitis during lactation.
2009 Apr 1
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
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
Antimicrobial resistance and genetic characterization of fluoroquinolone-resistant Mannheimia haemolytica isolates from cattle with bovine pneumonia.
2009 Oct 20
An atypical case of respiratory actinobacillosis in a cow.
2009 Sep
Epidemiology of plasmid-mediated quinolone resistance in salmonella enterica serovar typhimurium isolates from food-producing animals in Japan.
2010 Dec 7
Reproductive performance, udder health, and antibiotic resistance in mastitis bacteria isolated from Norwegian Red cows in conventional and organic farming.
2010 Feb 8
Monoclonal antibody-based ELISA and colloidal gold-based immunochromatographic assay for streptomycin residue detection in milk and swine urine.
2010 Jan
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
Determination of aminoglycoside and macrolide antibiotics in meat by pressurized liquid extraction and LC-ESI-MS.
2010 Mar
WD-repeat instability and diversification of the Podospora anserina hnwd non-self recognition gene family.
2010 May 6
Nano-vectors for the Ocular Delivery of Nucleic Acid-based Therapeutics.
2010 Nov
Nationwide survey of salmonella prevalence in environmental dust from layer farms in Japan.
2010 Nov
CLIMP-63 is a gentamicin-binding protein that is involved in drug-induced cytotoxicity.
2010 Nov 18
Tissue distribution of cloxacillin after intramammary administration in the isolated perfused bovine udder.
2010 Oct 6
Patents

Sample Use Guides

Treatment of leptospirosis in dogs, horses and swine: 5 mg per pound of body weight.
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
by admin
on Fri Jun 25 20:35:20 UTC 2021
Edited
by admin
on Fri Jun 25 20:35:20 UTC 2021
Record UNII
T7D4876IUE
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIHYDROSTREPTOMYCIN SULFATE
GREEN BOOK   MART.   USP   USP-RS   WHO-DD  
Common Name English
DIHYDROSTREPTOMYCIN SULFATE (2:3)(SALT)
Common Name English
DIHYDROSTREPTOMYCIN SULPHATE
Common Name English
DIHYDROSTREPTOMYCIN SESQUISULFATE
MI  
Common Name English
DIHYDROSTREPTOMYCIN SESQUISULFATE [MI]
Common Name English
DIHYDROSTREPTOMYCIN SULFATE [WHO-DD]
Common Name English
DIHYDROSTREPTOMYCIN SULFATE [USP-RS]
Common Name English
NSC-756739
Code English
DIHYDROSTREPTOMYCIN SULFATE [GREEN BOOK]
Common Name English
DIHYDROSTREPTOMYCIN SULPHATE (2:3)(SALT)
Common Name English
DIHYDROSTREPTOMYCIN SULFATE [USP MONOGRAPH]
Common Name English
DIHYDROSTREPTOMYCIN SULFATE [MART.]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 522.650
Created by admin on Fri Jun 25 20:35:20 UTC 2021 , Edited by admin on Fri Jun 25 20:35:20 UTC 2021
NCI_THESAURUS C2363
Created by admin on Fri Jun 25 20:35:20 UTC 2021 , Edited by admin on Fri Jun 25 20:35:20 UTC 2021
CFR 21 CFR 526.1696C
Created by admin on Fri Jun 25 20:35:20 UTC 2021 , Edited by admin on Fri Jun 25 20:35:20 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL1950576
Created by admin on Fri Jun 25 20:35:20 UTC 2021 , Edited by admin on Fri Jun 25 20:35:20 UTC 2021
PRIMARY
PUBCHEM
21653
Created by admin on Fri Jun 25 20:35:20 UTC 2021 , Edited by admin on Fri Jun 25 20:35:20 UTC 2021
PRIMARY
EVMPD
SUB01725MIG
Created by admin on Fri Jun 25 20:35:20 UTC 2021 , Edited by admin on Fri Jun 25 20:35:20 UTC 2021
PRIMARY
EPA CompTox
5490-27-7
Created by admin on Fri Jun 25 20:35:20 UTC 2021 , Edited by admin on Fri Jun 25 20:35:20 UTC 2021
PRIMARY
MERCK INDEX
M4467
Created by admin on Fri Jun 25 20:35:20 UTC 2021 , Edited by admin on Fri Jun 25 20:35:20 UTC 2021
PRIMARY Merck Index
CAS
1425-61-2
Created by admin on Fri Jun 25 20:35:20 UTC 2021 , Edited by admin on Fri Jun 25 20:35:20 UTC 2021
NON-SPECIFIC STOICHIOMETRY
MESH
D004096
Created by admin on Fri Jun 25 20:35:20 UTC 2021 , Edited by admin on Fri Jun 25 20:35:20 UTC 2021
PRIMARY
CAS
5490-27-7
Created by admin on Fri Jun 25 20:35:20 UTC 2021 , Edited by admin on Fri Jun 25 20:35:20 UTC 2021
PRIMARY
RXCUI
1549556
Created by admin on Fri Jun 25 20:35:20 UTC 2021 , Edited by admin on Fri Jun 25 20:35:20 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C47492
Created by admin on Fri Jun 25 20:35:20 UTC 2021 , Edited by admin on Fri Jun 25 20:35:20 UTC 2021
PRIMARY
USP_CATALOG
1203008
Created by admin on Fri Jun 25 20:35:20 UTC 2021 , Edited by admin on Fri Jun 25 20:35:20 UTC 2021
PRIMARY USP-RS
ECHA (EC/EINECS)
226-823-7
Created by admin on Fri Jun 25 20:35:20 UTC 2021 , Edited by admin on Fri Jun 25 20:35:20 UTC 2021
PRIMARY
FDA UNII
T7D4876IUE
Created by admin on Fri Jun 25 20:35:20 UTC 2021 , Edited by admin on Fri Jun 25 20:35:20 UTC 2021
PRIMARY
DRUG BANK
DBSALT001676
Created by admin on Fri Jun 25 20:35:20 UTC 2021 , Edited by admin on Fri Jun 25 20:35:20 UTC 2021
PRIMARY
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