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Identification
Name Sodium stibogluconate
Accession Number DB05630
Type small molecule
Groups approved
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 Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Brand names
  • Lenocta
  • Myostibin
  • Pentostam (GlaxoSmithKline)
  • Stibanate
  • Stibanose
  • Stibatin
  • Stibinol
Brand name mixtures Not Available
Categories
  • Antiparasitic Agents
  • Anticancer Agents
CAS number 16037-91-5
Weight Average: 907.88
Monoisotopic: 905.918601405
Chemical Formula C12H35Na3O26Sb2
InChI Key InChIKey=YQDGWZZYGYKDLR-UHFFFAOYSA-K
InChI
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
Plain Text
IUPAC Name
trisodium 1-{[3-carboxylato-5-(1,2-dihydroxyethyl)-1-oxido-2,6,7-trioxa-1$l^{5}-stibabicyclo[2.2.1]heptan-1-yl]oxy}-5-(1,2-dihydroxyethyl)-1-hydroxy-2,6,7-trioxa-1$l^{5}-stibabicyclo[2.2.1]heptane-3-carboxylate nonahydrate
SMILES
O.O.O.O.O.O.O.O.O.[Na+].[Na+].[Na+].OCC(O)C1O[Sb]2(O)(O[Sb]34([O-])OC(C(O)CO)C(O3)C(O4)C([O-])=O)OC1C(O2)C([O-])=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication For the treatment of various types of a protozoal infection called leishmaniasis, which may result from sandfly bites in tropical and temperate parts of the world. Also investigated for use/treatment in cancer/tumors (unspecified) and solid tumors.
Pharmacodynamics The mode of action of sodium stibogluconate is not clearly understood. In vitro exposure of amastigotes to 500 mg pentavalent antimony/ml results in a greater than 50% decrease in parasite DNA, RNA protein and purine nucleoside triphosphate levels. It has been postulated that the reduction in ATP (adenosine triphosphate) and GTP (guanosine triphosphate) synthesis contributes to decreased macromolecular synthesis.
Mechanism of action Sodium stibogluconate directly inhibits DNA topoisomerase I leading to inhibition of both DNA replication and transcription.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity The main symptoms of antimony overdosage are gastro-intestinal disturbances (nausea, vomiting and severe diarrhoea). Haemorrhagic nephritis and hepatitis may also occur.
Affected organisms
  • Humans and other mammals
  • Protozoa
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers Not Available
Dosage forms
Form Route Strength
Solution Intravenous
Prices Not Available
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties Not Available
Predicted Properties
Property Value Source
water solubility ALOGPS
logP ALOGPS
logP -3.43 ChemAxon Molconvert
logS ALOGPS
pKa 2.96 ChemAxon Molconvert
hydrogen acceptor count 17 ChemAxon Molconvert
hydrogen donor count 5 ChemAxon Molconvert
polar surface area 269.08 ChemAxon Molconvert
rotatable bond count 8 ChemAxon Molconvert
refractivity 96.29 ChemAxon Molconvert
polarizability 39.67 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. Murray HW, Berman JD, Davies CR, Saravia NG: Advances in leishmaniasis. Lancet. 2005 Oct 29-Nov 4;366(9496):1561-77. Pubmed
External Links
Resource Link
KEGG Drug D00582 Link_out
PubChem Compound 16685683 Link_out
PubChem Substance 99443233 Link_out
ChemSpider 21864906 Link_out
ChEBI 28148 Link_out
ChEMBL 28148 Link_out
Therapeutic Targets Database DCL000001 Link_out
Drug Product Database 0 Link_out
Wikipedia http://en.wikipedia.org/wiki/Sodium_stibogluconate Link_out
ATC Codes
  • P01CB02
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Food Interactions Not Available
Targets

1. DNA topoisomerase 1

Pharmacological action: yes
Actions: inhibitor

The reaction catalyzed by topoisomerases leads to the conversion of one topological isomer of DNA to another

Organism class: human
UniProt ID: P11387 Link_out
Gene: TOP1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Walker J, Saravia NG: Inhibition of Leishmania donovani promastigote DNA topoisomerase I and human monocyte DNA topoisomerases I and II by antimonial drugs and classical antitopoisomerase agents. J Parasitol. 2004 Oct;90(5):1155-62. Pubmed
  2. Chakraborty AK, Majumder HK: Mode of action of pentavalent antimonials: specific inhibition of type I DNA topoisomerase of Leishmania donovani. Biochem Biophys Res Commun. 1988 Apr 29;152(2):605-11. Pubmed
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed
Comments
Drug created on November 18, 2007 11:26 / Updated on January 09, 2011 09:34

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.