Sodium stibogluconate

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Sodium Stibogluconate (Pentostam)









Effective Against

Leishmaniasis. It is only available for administration by injection.

Pentavalent antimony (Sb) in differential complex formation with gluconic acid with leishmanicidal and potential antineoplastic activities. The Sb moiety of sodium stibogluconate (SSG) may inhibit protein tyrosine phophorylases (PTPases) by covalently modifying sulfhydryl groups in PTPase cysteine residues, resulting in specific inactivation of SH2 domain-containing tyrosine phosphatases-1 and -2 (SHP-1 and SHP-2), PTPases which negatively regulate interferon (IFN) signaling; enhancement of IFN-induced Stat1 tyrosine phosphorylation; and induction of cellular protein tyrosine phosphorylation. SSG in combination with IFN-alpha may synergize to overcome tumor cell resistance to IFN-alpha-mediated apoptosis.

Cost

From Sigma-Aldrich: 501 USD (500mg)

Reported Route of Synthesis

Image:313769-01-a.jpg

Reaction of D-gluconic acid with HSb(OH)6 (Hexahydroxoantimonic acid) in the presence of NaOH affords the anhydrous form of the title compound (I). (1)

Vardnayan, R. Drugs for treating protozoan infections. Synthesis of essential drugs, Ruben Vardanya, Elsevier, Tucson, Arizona , 2006, 559

Cost of Starting Materials and Reagents:
D-Gluconic acid sodium salt from Sigma-Aldrich: 15.5 USD (500g)
Antimony Acid must be freshly precipitated

Submitted Syntheses