Paromomycin sulfate (CHEM019637)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:21:27 UTC
Update Date2016-11-09 01:16:02 UTC
Accession NumberCHEM019637
Identification
Common NameParomomycin sulfate
ClassSmall Molecule
DescriptionParomomycin is an antimicrobial used to treat a number of parasitic infections including amebiasis, giardiasis, leishmaniasis, and tapeworm infection. It is a first line treatment for amebiasis or giardiasis during pregnancy. Otherwise it is generally a second line treatment option. It is used by mouth, applied to the skin, or by injection into a muscle.Common side effects when taken by mouth include loss of appetite, vomiting, abdominal pain, and diarrhea. When applied to the skin side effects include itchiness, redness, and blisters. When given by injection there may be fever, liver problems, or hearing loss. Use during breastfeeding appears to be safe. Paromomycin is in the aminoglycoside family of medications and causes microbe death by stopping the creation of bacterial proteins.Paromomycin was discovered in the 1950s from a type of streptomyces and came into medical use in 1960. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. Paromomycin is available as a generic medication. In India the injectable form is about 4.19 to 8.38 pounds for a course of treatment as of 2007. In the United States a typical course of treatment is more than US$200 as of 2015.
Contaminant Sources
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
HumatinKegg
Paromomycin sulfuric acidGenerator
Paromomycin sulphateGenerator
Paromomycin sulphuric acidGenerator
EstomycinMeSH
Paromomycin sulfate (2:5)MeSH
Paromomycin IMeSH
ParamomycinMeSH
ParomomycinMeSH
Paromomycin phosphateMeSH
AminosidineMeSH
CatenulinMeSH
Paromomycin, beta-D-glucopyranosyl-isomerMeSH
Neomycin eMeSH
HydroxymycinMeSH
Paromomycin, beta D glucopyranosyl isomerMeSH
beta-D-Glucopyranosyl-isomer paromomycinMeSH
Paromomycin sulfate (1:1)MeSH
GabbromycinMeSH
Monarch brand OF paromomycin sulfateMeSH
Parke davis brand OF paromomycin sulfateMeSH
Cheminova brand OF paromomycin sulfateMeSH
Phosphate, paromomycinMeSH
Sulfate, paromomycinMeSH
Pfizer brand OF paromomycin sulfateMeSH
(2S,3S,4R,5R,6R)-5-Amino-2-(aminomethyl)-6-{[(2R,3S,4R,5S)-5-{[(1R,2R,3S,5R,6S)-3,5-diamino-2-{[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxycyclohexyl]oxy}-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}oxane-3,4-diol; sulfateGenerator
(2S,3S,4R,5R,6R)-5-Amino-2-(aminomethyl)-6-{[(2R,3S,4R,5S)-5-{[(1R,2R,3S,5R,6S)-3,5-diamino-2-{[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxycyclohexyl]oxy}-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}oxane-3,4-diol; sulphateGenerator
(2S,3S,4R,5R,6R)-5-Amino-2-(aminomethyl)-6-{[(2R,3S,4R,5S)-5-{[(1R,2R,3S,5R,6S)-3,5-diamino-2-{[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxycyclohexyl]oxy}-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}oxane-3,4-diol; sulphuric acidGenerator
Chemical FormulaC23H47N5O18S
Average Molecular Mass713.707 g/mol
Monoisotopic Mass713.264 g/mol
CAS Registry Number1263-89-4
IUPAC Name(2R,3S,4R,5R,6S)-5-amino-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-2-{[(2S,3R,4S,5R)-4-{[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy}-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxycyclohexyl]oxy}-2-(hydroxymethyl)oxane-3,4-diol; sulfuric acid
Traditional Name(2R,3S,4R,5R,6S)-5-amino-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-2-{[(2S,3R,4S,5R)-4-{[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy}-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxycyclohexyl]oxy}-2-(hydroxymethyl)oxane-3,4-diol; sulfuric acid
SMILESOS(O)(=O)=O.[H][C@]1(CO)O[C@@]([H])(O[C@]2([H])[C@@]([H])(O)[C@]([H])(N)C[C@]([H])(N)[C@@]2([H])O[C@@]2([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])N)[C@]([H])(O)[C@]1([H])O[C@@]1([H])O[C@@]([H])(CN)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])N
InChI IdentifierInChI=1S/C23H45N5O14.H2O4S/c24-2-7-13(32)15(34)10(27)21(37-7)41-19-9(4-30)39-23(17(19)36)42-20-12(31)5(25)1-6(26)18(20)40-22-11(28)16(35)14(33)8(3-29)38-22;1-5(2,3)4/h5-23,29-36H,1-4,24-28H2;(H2,1,2,3,4)/t5-,6+,7+,8-,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+;/m1./s1
InChI KeyLJRDOKAZOAKLDU-UDXJMMFXSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 4,5-disubstituted 2-deoxystreptamines. These are 2-deoxystreptamine aminoglycosides that are glycosidically linked to a pyranose of furanose unit at the C4- and C5-positions.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct Parent4,5-disubstituted 2-deoxystreptamines
Alternative Parents
Substituents
  • 4,5-disubstituted 2-deoxystreptamine
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Aminocyclitol or derivatives
  • Cyclohexanol
  • Cyclohexylamine
  • Sulfuric acid
  • Cyclitol or derivatives
  • Oxane
  • Cyclic alcohol
  • Tetrahydrofuran
  • Organic sulfuric acid or derivatives
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Alcohol
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Amine
  • Organonitrogen compound
  • Primary amine
  • Primary alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility79.7 g/LALOGPS
logP-2.9ALOGPS
logP-8.3ChemAxon
logS-0.89ALOGPS
pKa (Strongest Acidic)12.23ChemAxon
pKa (Strongest Basic)9.94ChemAxon
Physiological Charge5ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area347.32 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity134.24 m³·mol⁻¹ChemAxon
Polarizability60.89 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000900-7130007640a1ca30ed13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000900-7130007640a1ca30ed13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0000000900-7130007640a1ca30ed13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000900-8d4420a214ad3487c89cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000000900-8d4420a214ad3487c89cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0000000900-8d4420a214ad3487c89cSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDBSALT000265
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkParomomycin
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID441375
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available