Dihydrostreptomycin

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Dihydrostreptomycin
Accession Number
DB11512
Type
Small Molecule
Groups
Investigational, Vet approved
Description

Dihydrostreptomycin is an antibiotic.

Structure
Thumb
Synonyms
  • DHMS
  • DST
  • N,N'''-[(1R,2R,3S,4R,5R,6S)-4-({5-deoxy-2-O-[2-deoxy-2-(methylamino)-a-L-glucopyranosyl]-3-C-(hydroxymethyl)-a-L-lyxofuranosyl}oxy)-2,5,6-trihydroxycyclohexane-1,3-diyl]diguanidine
  • N,N'''-[(1R,2R,3S,4R,5R,6S)-4-({5-deoxy-2-O-[2-deoxy-2-(methylamino)-alpha-L-glucopyranosyl]-3-C-(hydroxymethyl)-alpha-L-lyxofuranosyl}oxy)-2,5,6-trihydroxycyclohexane-1,3-diyl]diguanidine
  • N,N'''-[(1R,2R,3S,4R,5R,6S)-4-({5-deoxy-2-O-[2-deoxy-2-(methylamino)-α-L-glucopyranosyl]-3-C-(hydroxymethyl)-α-L-lyxofuranosyl}oxy)-2,5,6-trihydroxycyclohexane-1,3-diyl]diguanidine
Product Ingredients
IngredientUNIICASInChI Key
Dihydrostreptomycin sulfateT7D4876IUE5490-27-7Not applicable
Categories
UNII
P2I6R8W6UA
CAS number
128-46-1
Weight
Average: 583.596
Monoisotopic: 583.281319788
Chemical Formula
C21H41N7O12
InChI Key
ASXBYYWOLISCLQ-HZYVHMACSA-N
InChI
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
IUPAC Name
N-[(1R,2R,3S,4R,5R,6S)-3-carbamimidamido-4-{[(2R,3R,4R,5S)-3-{[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy}-4-hydroxy-4-(hydroxymethyl)-5-methyloxolan-2-yl]oxy}-2,5,6-trihydroxycyclohexyl]guanidine
SMILES
CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@H]1[C@H](O[C@H]2[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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AcetaminophenDihydrostreptomycin may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Dihydrostreptomycin.
AcetyldigitoxinThe risk or severity of adverse effects can be decreased when Dihydrostreptomycin is combined with Acetyldigitoxin.
AcetyldigoxinThe risk or severity of adverse effects can be decreased when Dihydrostreptomycin is combined with Acetyldigoxin.
AcyclovirThe risk or severity of nephrotoxicity can be increased when Acyclovir is combined with Dihydrostreptomycin.
AdefovirThe risk or severity of nephrotoxicity can be increased when Dihydrostreptomycin is combined with Adefovir.
Adefovir DipivoxilThe risk or severity of nephrotoxicity can be increased when Adefovir Dipivoxil is combined with Dihydrostreptomycin.
AlaproclateThe risk or severity of adverse effects can be increased when Dihydrostreptomycin is combined with Alaproclate.
AlcuroniumDihydrostreptomycin may increase the respiratory depressant activities of Alcuronium.
AlcuroniumThe therapeutic efficacy of Alcuronium can be increased when used in combination with Dihydrostreptomycin.
Food Interactions
Not Available

References

General References
  1. CURCI G: [Dihydrostreptomycin]. Arch Tisiol Mal Appar Respir. 1951 Mar;6(3):Varia, 104-6. [PubMed:14830485]
  2. Midtvedt T: [Dihydrostreptomycin]. Tidsskr Nor Laegeforen. 1970 Apr 15;90(8):791. [PubMed:4194808]
  3. BARTZ QR, CONTROULIS J, et al.: Dihydrostreptomycin. J Am Chem Soc. 1946 Nov;68(11):2163-6. [PubMed:21002218]
  4. HARRISON WH: Dihydrostreptomycin deafness. Antibiot Annu. 1959-1960;7:549-51. [PubMed:14400056]
  5. SHAMBAUGH GE Jr, DERLACKI EL, HARRISON WH, HOUSE H, HOUSE W, HILDYARD V, SCHUKNECHT H, SHEA JJ: Dihydrostreptomycin deafness. J Am Med Assoc. 1959 Aug 1;170(14):1657-60. [PubMed:13672753]
  6. MAHADY SC, ARMSTRONG FL, MONROE J: Purified dihydrostreptomycin. Am Rev Tuberc. 1956 May;73(5):776-8. [PubMed:13313964]
  7. AGOPSOWICZ G, BEKIERKUNST A, HOCHBERGER B, JEDRZEJEWSKA A, KOSSOWSKI S: [Dihydrostreptomycin and dihydrostreptomycin-penicillin therapy of ozena]. Arch Immunol Ther Exp (Warsz). 1955;3:239-47. [PubMed:13395829]
  8. LEES JK, MARKLE DM: Dihydrostreptomycin and deafness. N Y State J Med. 1953 Dec 15;53(24):2997-9. [PubMed:13111505]
  9. Authors unspecified: [Dihydrostreptomycin in pulmonary tuberculosis]. Dia Med. 1951 Sep 24;23(64):2861; passim. [PubMed:14879647]
  10. SHANE SJ, LAURIE JH: Neurotoxicity of dihydrostreptomycin. Can Med Assoc J. 1950 Sep;63(3):277-9. [PubMed:15434767]
External Links
KEGG Drug
D07840
KEGG Compound
C01023
ChemSpider
388489
ChEBI
38291
ChEMBL
CHEMBL1950576
HET
71R
Wikipedia
Dihydrostreptomycin
ATC Codes
S01AA15 — Dihydrostreptomycin
PDB Entries
5lpa

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4RecruitingTreatmentBMI >30 kg/m2 / Metabolic Syndromes1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility16.0 mg/mLALOGPS
logP-3ALOGPS
logP-7.3ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)12.11ChemAxon
pKa (Strongest Basic)11.31ChemAxon
Physiological Charge3ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count15ChemAxon
Polar Surface Area334.59 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity150.45 m3·mol-1ChemAxon
Polarizability56.06 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-0001090000-e5c939b16a98cbc76e8f
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-0001090000-f492efdcf9b73dccff78
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-0110090000-a21d136fb6ad87c99c54
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03di-1290020000-c272561234831b3053da
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03ka-1190000000-4c31681402bf294549fd
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-0090000000-094483dbe63a6b4a3a35
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0bvi-3940300000-adca1fa480c33dd8c023
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-01w1-9570000000-da64f1603c2c8b791414
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0fki-9340000000-915a5b4c2e2c08346763
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0fgx-9010000000-0d0be639d3cdcb114f75
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-03di-0090010000-2014c0916e72e16177f4

Taxonomy

Description
This compound belongs to the class of organic compounds known as aminocyclitol glycosides. These are organic compounds containing an amicocyclitol moiety glycosidically linked to a carbohydrate moiety. There are two major classes of aminoglycosides containing a 2-streptamine core. They are called 4,5- and 4,6-disubstituted 2-deoxystreptamines.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Aminocyclitol glycosides
Alternative Parents
O-glycosyl compounds / Cyclohexanols / Oxanes / Monosaccharides / Cyclitols and derivatives / Tetrahydrofurans / Tertiary alcohols / Guanidines / 1,2-aminoalcohols / Propargyl-type 1,3-dipolar organic compounds
show 8 more
Substituents
Amino cyclitol glycoside / Glycosyl compound / O-glycosyl compound / Cyclohexanol / Cyclitol or derivatives / Monosaccharide / Oxane / Cyclic alcohol / Tertiary alcohol / Tetrahydrofuran
show 20 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
streptomycins (CHEBI:38291)

Drug created on February 26, 2016 10:29 / Updated on October 01, 2018 16:41