Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C12H16O17Sb2.3Na.H.9H2O |
Molecular Weight | 907.88 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 8 / 8 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H+].O.O.O.O.O.O.O.O.O.[Na+].[Na+].[Na+].[H][C@@]1(O[Sb]4([O-])(O[Sb]23([O-])O[C@H]([C@@H](O2)[C@]([H])(O3)[C@H](O)CO)C([O-])=O)O[C@H]([C@H]1O4)C([O-])=O)[C@H](O)CO
InChI
InChIKey=NTHCIZIBFDGPFR-UZVLBLASSA-M
InChI=1S/2C6H9O7.3Na.9H2O.3O.2Sb/c2*7-1-2(8)3(9)4(10)5(11)6(12)13;;;;;;;;;;;;;;;;;/h2*2-5,7-8H,1H2,(H,12,13);;;;9*1H2;;;;;/q2*-3;3*+1;;;;;;;;;;;2*-1;2*+3/p-1/t2*2-,3-,4+,5-;;;;;;;;;;;;;;;;;/m11................./s1
Stibogluconic acid (Sodium stibogluconate) is the pentavalent antimonial compound used to treat leishmaniasis and is only available for administration by injection. Sodium stibogluconate is sold in the UK as Pentostam (manufactured by GlaxoSmithKline). Sodium stibogluconate was granted orphan drug designation for the treatment of cutaneous leishmaniasis by the US FDA in January 2007. It is available in the United States only through the Centers for Disease Control. Sodium stibogluconate is indicated 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. It is also investigated for use/treatment in cancer. 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. Sodium stibogluconate was shown to specifically inhibit type I DNA topoisomerase from Leishmania donovani through the inhibition of the unwinding and cleavage of the supercoiled plasmid pBR322, and to stabilize topoisomerase and DNA covalent complexes but not calf-thymus topoisomerase I and Escherichia coli DNA gyrase. Sodium stibogluconate is also a potent inhibitor of PTPases Src homology PTPase1 (SHP-1), SHP-2, and PTP1B but not the dual-specificity phosphatase mitogen-activated protein kinase phosphatase 1. Sodium stibogluconate combined with IFN-alpha-2b (IFN-α) inhibited solid tumor cell line growth in vitro, in vivo it was well tolerated and augmented cellular immune parameters.
Approval Year
Sample Use Guides
Dosage Forms & Strengths
injectable solution
100mg Sb/mL
Leishmaniasis (Orphan)
20 mg Sb/kg/day (maximum 850 mg) IV/IM for 20-28 days
Available in the United States only from CDC
Route of Administration:
Parenteral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11544330
Sodium stibogluconate inhibited 99% of SHP-1 activity at 10 ug/ml, a therapeutic concentration of the drug for leishmaniasis. Similar degrees of inhibition of SHP-2 and PTP1B required 100 ug/ml sodium stibogluconate, demonstrating differential sensitivities of PTPases to the inhibitor.
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16037-91-5
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28148
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DB05630
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DTXSID50894911
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m1962
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APJ6285Y89
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admin on Sat Dec 16 10:13:33 GMT 2023 , Edited by admin on Sat Dec 16 10:13:33 GMT 2023
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ACTIVE MOIETY
SUBSTANCE RECORD