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

• ChemBase ID: 4413
• Molecular Formular: C12H35Na3O26Sb2
• Molecular Mass: 907.88001
• Monoisotopic Mass: 905.91859408
• SMILES: C(O)C(O)C1O[Sb]2(OC(C1O2)C(=O)[O-])(O[Sb]12(OC(C(C(CO)O)O1)C(O2)C(=O)[O-])[O-])O.[Na+].[Na+].[Na+].O.O.O.O.O.O.O.O.O
• Canonical SMILES: OCC(C1O[Sb]2(OC1C(O2)C(=O)[O-])([O-])O[Sb]12(O)OC(C(O2)C(O1)C(=O)[O-])C(CO)O)O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[Na+]
• 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
• InChIKey: YQDGWZZYGYKDLR-UHFFFAOYSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: trisodium 1-{[3-carboxylato-5-(1,2-dihydroxyethyl)-1-oxido-2,6,7-trioxa-1-stibabicyclo[2.2.1]heptan-1-yl]oxy}-5-(1,2-dihydroxyethyl)-1-hydroxy-2,6,7-trioxa-1-stibabicyclo[2.2.1]heptane-3-carboxylate nonahydrate
• IUPAC Traditional name: tripotassium 1-{[3-carboxylato-5-(1,2-dihydroxyethyl)-1-oxido-2,6,7-trioxa-1-stibabicyclo[2.2.1]heptan-1-yl]oxy}-5-(1,2-dihydroxyethyl)-1-hydroxy-2,6,7-trioxa-1-stibabicyclo[2.2.1]heptane-3-carboxylate nonahydrate
• Brand Name: Lenocta; Pentostam; Stibanate; Stibanose; Stibatin; Stibinol; Myostibin
• Synonyms: Sodium stibogluconate

Database IDs

• CAS Number: 16037-91-5
• PubChem SID: 160967845
• PubChem CID: 16685683

CALCULATED PROPERTIES

• Acid pKa: 2.289914
• H Acceptors: 17
• H Donor: 5
• LogD (pH = 5.5): -9.043909
• LogD (pH = 7.4): -10.716197
• Log P: -3.4262
• Molar Refractivity: 96.2875 cm^3
• Polarizability: 43.117653 Å^3
• Polar Surface Area: 269.08 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

DrugBank - DB05630

• Drug Groups: approved; investigational
• 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.
• 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.
• Pharmacology: 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.
• 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
• References: Murray HW, Berman JD, Davies CR, Saravia NG: Advances in leishmaniasis. Lancet. 2005 Oct 29-Nov 4;366(9496):1561-77. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Murray HW, Berman JD, Davies CR, Saravia NG: Advances in leishmaniasis. Lancet. 2005 Oct 29-Nov 4;366(9496):1561-77. Pubmed