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Identification
NameParomomycin
Accession NumberDB01421
TypeSmall Molecule
GroupsApproved, Investigational
Description

An oligosaccharide antibiotic produced by various streptomyces. [PubChem]

Structure
Thumb
Synonyms
(1R,2R,3S,4R,6S)-4,6-Diamino-2-{[3-O-(2,6-diamino-2,6-dideoxy-beta-L-idopyranosyl)-beta-D-ribofuranosyl]oxy}-3-hydroxycyclohexyl 2-amino-2-deoxy-alpha-D-glucopyranoside
Aminosidin
Aminosidine
Catenulin
Crestomycin
Estomycin
Hydroxymycin
Monomycin a
Neomycin e
Paromomicina
PAROMOMYCIN
Paromomycin i
Paromomycine
Paromomycinum
Paucimycin
Paucimycinum
R 400
R-400
Zygomycin a1
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Humatin Cap 250mgcapsule250 mgoralErfa Canada 2012 Inc1994-12-31Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Paromomycin Sulfatecapsule250 mg/1oralHeritage Pharmaceuticals Inc.2009-10-22Not applicableUs
Paromomycin Sulfatecapsule250 mg/1oralSun Pharmaceutical Industries, Inc.1997-06-30Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
HumatinParke Davis (now Pfizer)
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Paromomycin sulfate
1263-89-4
Thumb
  • InChI Key: LJRDOKAZOAKLDU-UDXJMMFXSA-N
  • Monoisotopic Mass: 713.263680415
  • Average Mass: 713.707
DBSALT000265
Categories
UNII61JJC8N5ZK
CAS number7542-37-2
WeightAverage: 615.6285
Monoisotopic: 615.296301173
Chemical FormulaC23H45N5O14
InChI KeyInChIKey=UOZODPSAJZTQNH-LSWIJEOBSA-N
InChI
InChI=1S/C23H45N5O14/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/h5-23,29-36H,1-4,24-28H2/t5-,6+,7+,8-,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+/m1/s1
IUPAC Name
(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
SMILES
NC[C@@H]1O[[email protected]](O[C@@H]2[C@@H](CO)O[C@@H](O[C@@H]3[C@@H](O)[[email protected]](N)C[[email protected]](N)[[email protected]]3O[[email protected]]3O[[email protected]](CO)[C@@H](O)[[email protected]](O)[[email protected]]3N)[C@@H]2O)[[email protected]](N)[C@@H](O)[C@@H]1O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as amino sugars. These are sugars having one alcoholic hydroxy group replaced by an amino group; systematically known as x-amino-x-deoxymonosaccharides. These compounds do not include Glycosylamines.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassAminosaccharides
Direct ParentAmino sugars
Alternative Parents
Substituents
  • 4,5-disubstituted 2-deoxystreptamine
  • Aminoglycoside core
  • 2-deoxystreptamine aminoglycoside
  • Glucosamine
  • Amino sugar
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • Cyclohexylamine
  • Cyclohexanol
  • Oxane
  • Oxolane
  • Cyclic alcohol
  • Secondary alcohol
  • 1,2-diol
  • 1,2-aminoalcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of acute and chronic intestinal amebiasis (it is not effective in extraintestinal amebiasis). Also for the management of hepatic coma as adjunctive therapy.
PharmacodynamicsParomomycin is a broad spectrum aminoglycoside antibiotic produced by Streptomyces rimosus var. paromomycinus. The in vitro and in vivo antibacterial action of paromomycin closely parallels that of neomycin.
Mechanism of actionParomomycin inhibits protein synthesis by binding to 16S ribosomal RNA. Bacterial proteins are synthesized by ribosomal RNA complexes which are composed of 2 subunits, a large subunit (50s) and small (30s) subunit, which forms a 70s ribosomal subunit. tRNA binds to the top of this ribosomal structure. Paramomycin binds to the A site, which causes defective polypeptide chains to be produced. Continuous production of defective proteins eventually leads to bacterial death.
Related Articles
AbsorptionPoorly absorbed after oral administration, with almost 100% of the drug recoverable in the stool.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways
PathwayCategorySMPDB ID
Paromomycin Action PathwayDrug actionSMP00714
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8617
Blood Brain Barrier-0.9659
Caco-2 permeable-0.7502
P-glycoprotein substrateNon-substrate0.5164
P-glycoprotein inhibitor INon-inhibitor0.8023
P-glycoprotein inhibitor IINon-inhibitor0.8764
Renal organic cation transporterNon-inhibitor0.7886
CYP450 2C9 substrateNon-substrate0.8231
CYP450 2D6 substrateNon-substrate0.8041
CYP450 3A4 substrateNon-substrate0.6473
CYP450 1A2 substrateNon-inhibitor0.9157
CYP450 2C9 inhibitorNon-inhibitor0.9147
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9034
CYP450 3A4 inhibitorNon-inhibitor0.9471
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8446
Ames testNon AMES toxic0.6934
CarcinogenicityNon-carcinogens0.9505
BiodegradationNot ready biodegradable0.8587
Rat acute toxicity1.4850 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9728
hERG inhibition (predictor II)Non-inhibitor0.81
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Capsuleoral250 mg
Capsuleoral250 mg/1
Prices
Unit descriptionCostUnit
Paromomycin 250 mg capsule5.67USD capsule
Humatin 250 mg capsule2.67USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility79.7 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity134.24 m3·mol-1ChemAxon
Polarizability60.4 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Federico Arcamone, Giuseppe Cassinelli, “Paromomycin derivatives and process for the preparation thereof.” U.S. Patent US4021601, issued October, 1967.

US4021601
General References
  1. Vicens Q, Westhof E: Crystal structure of paromomycin docked into the eubacterial ribosomal decoding A site. Structure. 2001 Aug;9(8):647-58. [PubMed:11587639 ]
External Links
ATC CodesA07AA06
AHFS Codes
  • 08:30.04
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNo interactions found.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Thermus thermophilus (strain HB8 / ATCC 27634 / DSM 579)
Pharmacological action
yes
Actions
inhibitor
General Function:
Trna binding
Specific Function:
Part of the top of the 30S subunit head.
Gene Name:
rpsJ
Uniprot ID:
Q5SHN7
Molecular Weight:
11929.82 Da
References
  1. Dlugosz M, Trylska J: Aminoglycoside association pathways with the 30S ribosomal subunit. J Phys Chem B. 2009 May 21;113(20):7322-30. doi: 10.1021/jp8112914. [PubMed:19438282 ]
2. 16S rRNA
Kind
Nucleotide
Organism
Enteric bacteria and other eubacteria
Pharmacological action
yes
Actions
inhibitor
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Konno T, Kurita D, Takahashi T, Muto A, Himeno H: Initiation-shift of trans-translation by aminoglycosides. Nucleic Acids Symp Ser (Oxf). 2004;(48):299-300. [PubMed:17150597 ]
  4. Chao PW, Chow CS: Monitoring aminoglycoside-induced conformational changes in 16S rRNA through acrylamide quenching. Bioorg Med Chem. 2007 Jun 1;15(11):3825-31. Epub 2007 Mar 13. [PubMed:17399988 ]
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Drug created on July 24, 2007 04:03 / Updated on August 17, 2016 12:23