CHEBI:28148 - sodium stibogluconate

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ChEBI Name sodium stibogluconate
ChEBI ID CHEBI:28148
Definition A D-gluconate adduct of indefinite composition containing between 30 and 34% of antimony(V), calculated with reference to dried and methanol-free substance. It is used as a treatment for leishmaniasis.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:9181, CHEBI:26716
Supplier Information No supplier information found for this compound.
Download Molfile XML SDF
Formulae C12H17O17Sb2.9H2O.3Na
C12H35Na3O26Sb2
Net Charge 0
Average Mass 907.88000
Monoisotopic Mass 905.91858
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/t2*2-,3-,4+,5-;;;;;;;;;;;;;;;;;/m11................./s1
InChIKey YQDGWZZYGYKDLR-UZVLBLASSA-K
SMILES O.O.O.O.O.O.O.O.O.[Na+].[Na+].[Na+].[H][C@@]1(O[Sb]2(O)(O[C@@H](C([O-])=O)[C@@]1([H])O2)O[Sb]12([O-])O[C@@H](C([O-])=O)[C@@]([H])(O1)[C@]([H])(O2)[C@H](O)CO)[C@H](O)CO
Roles Classification
Biological Role(s): antileishmanial agent
An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
antileishmanial agent
An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing sodium stibogluconate (CHEBI:28148) has role antileishmanial agent (CHEBI:70868)
sodium stibogluconate (CHEBI:28148) has role antineoplastic agent (CHEBI:35610)
sodium stibogluconate (CHEBI:28148) is a D-gluconate adduct (CHEBI:20984)
IUPAC Name
trisodium 1-{[3-carboxylato-5-(1,2-dihydroxyethyl)-1-hydroxy-2,6,7-trioxa-1λ5-stibabicyclo[2.2.1]hept-1-yl]oxy}-5-(1,2-dihydroxyethyl)-1-oxido-2,6,7-trioxa-1λ5-stibabicyclo[2.2.1]heptane-3-carboxylate—water (1/9)
INNs Sources
estibogluconato sodico ChemIDplus
natrii stibogluconas ChemIDplus
sodium stibogluconate ChemIDplus
stibogluconate de sodium ChemIDplus
Synonyms Sources
Antimony (V) derivative of sodium gluconate ChemIDplus
Antimony sodium gluconate ChemIDplus
Antimony sodium gluconate KEGG COMPOUND
Myostibin ChemIDplus
Sodium stibogluconate KEGG DRUG
Stibanate ChemIDplus
Stibanose ChemIDplus
Stibatin ChemIDplus
Stibinol ChemIDplus
trisodium 1-{[3-carboxylato-5-(1,2-dihydroxyethyl)-1-hydroxy-2,6,7-trioxa-1λ5-stibabicyclo[2.2.1]hept-1-yl]oxy}-5-(1,2-dihydroxyethyl)-1-oxido-2,6,7-trioxa-1λ5-stibabicyclo[2.2.1]heptane-3-carboxylate nonahydrate IUPAC
Brand Name Source
Pentostam KEGG DRUG
Manual Xrefs Databases
C07638 KEGG COMPOUND
D00582 KEGG DRUG
DB05630 DrugBank
View more database links
Registry Numbers Types Sources
16037-91-5 CAS Registry Number KEGG DRUG
16037-91-5 CAS Registry Number ChemIDplus
Last Modified
22 February 2017
General Comment
2012-03-06 An alternative structure commonly used for this substance is that of the trisodium salt, nonahydrate of 2,4:2',4'-O-(oxydistibylidyne)bis-D-gluconic acid, Sb,Sb'-dioxide.