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Sodium stibogluconate

July 24, 2017
Common Name

Sodium stibogluconate Description

Sodium stibogluconate is a medicine used to treat leishmaniasis and is only available for administration by injection. It belongs to the class of medicines known as the pentavalent antimonials. Sodium stibogluconate is sold in the UK as Pentostam (manufactured by GlaxoSmithKline). Widespread resistance has limited the utility of sodium stibogluconate, and in many parts of the world, amphotericin or miltefosine are used instead. It is also being investigated as an anti-tumor agent. Structure

MOLSDFPDBSMILESInChI

Synonyms

Value Source Antimony (V) derivative OF sodium gluconateChEBI Antimony sodium gluconateChEBI estibogluconato SodicoChEBI MyostibinChEBI Natrii stibogluconasChEBI PentostamChEBI StibanateChEBI StibanoseChEBI StibatinChEBI StibinolChEBI Stibogluconate de sodiumChEBI Trisodium 1-{[3-carboxylato-5-(1,2-dihydroxyethyl)-1-hydroxy-2,6,7-trioxa-1lambda(5)-stibabicyclo[2.2.1]hept-1-yl]oxy}-5-(1,2-dihydroxyethyl)-1-oxido-2,6,7-trioxa-1lambda(5)-stibabicyclo[2.2.1]heptane-3-carboxylate nonahydrateChEBI Antimony (V) derivative OF sodium gluconic acidGenerator Sodium stibogluconic acidGenerator Antimony sodium gluconic acidGenerator Stibanic acidGenerator Stibogluconic acid de sodiumGenerator Trisodium 1-{[3-carboxylato-5-(1,2-dihydroxyethyl)-1-hydroxy-2,6,7-trioxa-1lambda(5)-stibabicyclo[2.2.1]hept-1-yl]oxy}-5-(1,2-dihydroxyethyl)-1-oxido-2,6,7-trioxa-1lambda(5)-stibabicyclo[2.2.1]heptane-3-carboxylic acid nonahydric acidGenerator

Chemical Formlia

C12H35Na3O26Sb2 Average Molecliar Weight

907.88 Monoisotopic Molecliar Weight

905.918601405 IUPAC Name

trisodium (3R,4S,5R)-1-{[(3R,4S,5R)-3-carboxylato-5-[(1R)-1,2-dihydroxyethyl]-1-oxido-2,6,7-trioxa-1-stibabicyclo[2.2.1]heptan-1-yl]oxy}-5-[(1R)-1,2-dihydroxyethyl]-1-hydroxy-2,6,7-trioxa-1-stibabicyclo[2.2.1]heptane-3-carboxylate nonahydrate Traditional Name

trisodium (3R,4S,5R)-1-{[(3R,4S,5R)-3-carboxylato-5-[(1R)-1,2-dihydroxyethyl]-1-oxido-2,6,7-trioxa-1-stibabicyclo[2.2.1]heptan-1-yl]oxy}-5-[(1R)-1,2-dihydroxyethyl]-1-hydroxy-2,6,7-trioxa-1-stibabicyclo[2.2.1]heptane-3-carboxylate nonahydrate CAS Registry Number

16037-91-5 SMILES

O.O.O.O.O.O.O.O.O.[Na+].[Na+].[Na+].[H][C@@]1(O[Sb]2(O)(O[Sb]34([O-])O[C@@H](C([O-])=O)[C@@]([H])(O3)[C@]([H])(O4)[C@H](O)CO)O[C@@H](C([O-])=O)[C@@]1([H])O2)[C@H](O)CO

InChI Identifier

InChI=1S/2C6H9O7.3Na.10H2O.2O.2Sb/c2*7-1-2(8)3(9)4(10)5(11)6(12)13;;;;;;;;;;;;;;;;;/h2*2-5,7-8H,1H2,(H,12,13);;;;10*1H2;;;;/q2*-3;3*+1;;;;;;;;;;;;-1;+3;+4/p-3/t2*2-,3-,4+,5-;;;;;;;;;;;;;;;;;/m11……………../s1

InChI Key

YQDGWZZYGYKDLR-UZVLBLASSA-K Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic acids and derivatives Sub Class

Carboxylic acids and derivatives Direct Parent

Dicarboxylic acids and derivatives Alternative Parents

  • Secondary alcohols
  • Organic antimony salts
  • Carboxylic acid salts
  • Oxacyclic compounds
  • Metalloheterocyclic compounds
  • Carboxylic acids
  • Primary alcohols
  • Organic zwitterions
  • Organic sodium salts
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • Substituents

  • Dicarboxylic acid or derivatives
  • Carboxylic acid salt
  • Secondary alcohol
  • Organic antimony salt
  • Organic alkali metal salt
  • Oxacycle
  • Organic metal salt
  • Organic metalloid salt
  • Carboxylic acid
  • Organoheterocyclic compound
  • Metalloheterocycle
  • Organic oxide
  • Organic zwitterion
  • Primary alcohol
  • Organooxygen compound
  • Organic salt
  • Organic oxygen compound
  • Organic sodium salt
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound

    • Molecliar Framework

    Aliphatic heteropolycyclic compounds External Descriptors

  • D-gluconate adduct (CHEBI:28148 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anticancer Agents
  • Antiparasitic Agents

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source logP-3.4ChemAxon pKa (Strongest Acidic)2.29ChemAxon pKa (Strongest Basic)-3ChemAxon Physiological Charge-2ChemAxon Hydrogen Acceptor Count17ChemAxon Hydrogen Donor Count5ChemAxon Polar Surface Area269.08 Å2ChemAxon Rotatable Bond Count8ChemAxon Refractivity96.29 m3·mol-1ChemAxon Polarizability39.78 Å3ChemAxon Number of Rings4ChemAxon Bioavailability0ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Not Available Biological Properties Cellliar Locations

  • Cytoplasm

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB05630

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB05630

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB05630 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    27471272 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Sodium_stibogluconate NuGOwiki Link

    HMDB15617 Metagene Link

    HMDB15617 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    28148

    Product: Sulfamerazine

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Murray HW, Berman JD, Davies CR, Saravia NG: Advances in leishmaniasis. Lancet. 2005 Oct 29-Nov 4;366(9496):1561-77. [PubMed:16257344 ]

    PMID: 17660385

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