Legend: drug field target field enzyme field
| Version | 2.5 | ||||
| Creation Date | 2007-11-18 18:26:35 | ||||
| Update Date | 2008-08-27 22:06:06 | ||||
| Primary Accession Number | DB05630 | ||||
| Secondary Accession Number | Not Available | ||||
| Name | Sodium stibogluconate | ||||
| Drug Type |
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| 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. | ||||
| Synonyms |
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| Brand Names |
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| Brand Mixtures | Not Available | ||||
| Chemical IUPAC Name | trisodium 1-[[3-carboxylato-5-(1,2-dihydroxyethyl)-2,6,7-trioxa-1$l^{4}-stibabicyclo[2.2.1]heptan-1-yl]oxy]-5-(1,2-dihydroxyethyl)-2,6,7-trioxa-1$l^{4}-stibabicyclo[2.2.1]heptane-3-carboxylate hydroxide decahydrate | ||||
| Chemical Formula | C12H35Na3O26Sb2 | ||||
| Chemical Structure | |||||
| CAS Registry Number | 16037-91-5 | ||||
| InChI Identifier | InChI=1/2C6H9O7.3Na.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/f2C6H8O7.3Na.9H2O.HO.2O.2Sb/h;;;;;;;;;;;;;;1h;;;;/q2*-4;3m;;;;;;;;;;-1;;3m/rC12H19O17Sb2.3Na.9H2O/c13-1-3(15)5-7-9(11(17)18)27-30(21,23-5,25-7)29-31(22)24-6(4(16)2-14)8(26-31)10(28-31)12(19)20;;;;;;;;;;;;/h3-10,13-16,21H,1-2H2,(H,17,18)(H,19,20);;;;9*1H2/q-1;3*+1;;;;;;;;;/p-2/fC12H17O17Sb2.3Na.9H2O/q-3;3m;;;;;;;;; | ||||
| InChI Key | YQDGWZZYGYKDLR-PJXBVMCRCH | ||||
| KEGG Drug | D00582 ![]() |
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| KEGG Compound | Not Available | ||||
| PubChem Compound | 16685683 ![]() |
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| PubChem Substance | Not Available | ||||
| ChEBI ID | 28148 ![]() |
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| PharmGKB ID | Not Available | ||||
| HET ID | Not Available | ||||
| GenBank ID | Not Available | ||||
| Drug ID Number [DIN] | Not Available | ||||
| RxList Link | Not Available | ||||
| PDRhealth Link | Not Available | ||||
| Wikipedia Link | http://en.wikipedia.org/wiki/Sodium_stibogluconate ![]() |
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| FDA Label | Not Available | ||||
| Material Safety Data Sheet (MSDS) | Not Available | ||||
| Synthesis Reference | Not Available | ||||
| Average Molecular Weight | 907.8800 | ||||
| Monoisotopic Molecular Weight | 905.9186 | ||||
| State | Solid | ||||
| Melting Point | Not Available | ||||
| Experimental Water Solubility | Not Available Source: PhysProp | ||||
| Predicted Water Solubility | Not Available Calculated using ALOGPS | ||||
| Experimental LogP/Hydrophobicity | Not Available Source: PhysProp | ||||
| Predicted LogP | Not Available Calculated using ALOGPS | ||||
| Experimental LogS | Not Available | ||||
| Predicted LogS | Not Available Calculated using ALOGPS | ||||
| Experimental Caco2 Permeability | Not Available | ||||
| pKa/Isoelectric Point | Not Available | ||||
| Mass Spectrum | Not Available | ||||
| MOL File | Show | Download ![]() |
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| SDF File | Show | Download ![]() |
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| PDB File | Show | Download ![]() |
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| 2D Structure | |||||
| 3D Structure | |||||
| Experimental PDB ID | Not Available | ||||
| Isomeric SMILES | Not Available | ||||
| Canonical SMILES | Not Available | ||||
| Drug Category |
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| ATC Codes | |||||
| AHFS Codes | Not Available | ||||
| 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. | ||||
| Mechanism of Action | Sodium stibogluconate directly inhibits DNA topoisomerase I leading to inhibition of both DNA replication and transcription. | ||||
| Absorption | 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. | ||||
| Protein Binding | Not Available | ||||
| Biotransformation | Not Available | ||||
| Half Life | Not Available | ||||
| Dosage Forms |
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| Patient Information | Not Available | ||||
| Contraindications | Show ![]() |
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| Interactions | Show ![]() |
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| Drug Interactions | Not Available | ||||
| Food Interactions | Not Available | ||||
| Pathways | Not Available | ||||
| General References | |||||
| Organisms Affected |
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| Targets |
| Drug Target 1 [top] | |||||||
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| Target 1 ID | 1353 | ||||||
| Target 1 Name | DNA topoisomerase 1 | ||||||
| Target 1 Synonyms |
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| Target 1 Gene Name | TOP1 | ||||||
| Target 1 Protein Sequence |
>DNA topoisomerase 1
MSGDHLHNDSQIEADFRLNDSHKHKDKHKDREHRHKEHKKEKDREKSKHSNSEHKDSEKK HKEKEKTKHKDGSSEKHKDKHKDRDKEKRKEEKVRASGDAKIKKEKENGFSSPPQIKDEP EDDGYFVPPKEDIKPLKRPRDEDDADYKPKKIKTEDTKKEKKRKLEEEEDGKLKKPKNKD KDKKVPEPDNKKKKPKKEEEQKWKWWEEERYPEGIKWKFLEHKGPVFAPPYEPLPENVKF YYDGKVMKLSPKAEEVATFFAKMLDHEYTTKEIFRKNFFKDWRKEMTNEEKNIITNLSKC DFTQMSQYFKAQTEARKQMSKEEKLKIKEENEKLLKEYGFCIMDNHKERIANFKIEPPGL FRGRGNHPKMGMLKRRIMPEDIIINCSKDAKVPSPPPGHKWKEVRHDNKVTWLVSWTENI QGSIKYIMLNPSSRIKGEKDWQKYETARRLKKCVDKIRNQYREDWKSKEMKVRQRAVALY FIDKLALRAGNEKEEGETADTVGCCSLRVEHINLHPELDGQEYVVEFDFLGKDSIRYYNK VPVEKRVFKNLQLFMENKQPEDDLFDRLNTGILNKHLQDLMEGLTAKVFRTYNASITLQQ QLKELTAPDENIPAKILSYNRANRAVAILCNHQRAPPKTFEKSMMNLQTKIDAKKEQLAD ARRDLKSAKADAKVMKDAKTKKVVESKKKAVQRLEEQLMKLEVQATDREENKQIALGTSK LNYLDPRITVAWCKKWGVPIEKIYNKTQREKFAWAIDMADEDYEF |
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| Target 1 Number of Residues | 777 | ||||||
| Target 1 Molecular Weight | 90726 | ||||||
| Target 1 Theoretical pI | 9.95 | ||||||
| Target 1 GO Classification |
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| Target 1 General Function | Replication, recombination and repair | ||||||
| Target 1 Specific Function | The reaction catalyzed by topoisomerases leads to the conversion of one topological isomer of DNA to another | ||||||
| Target 1 Pathways | Not Available | ||||||
| Target 1 Reactions |
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| Target 1 Pfam Domain Function | |||||||
| Target 1 Signals |
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| Target 1 Transmembrane Regions |
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| Target 1 Essentiality | Non-Essential | ||||||
| Target 1 GenBank ID Protein | 339806 ![]() |
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| Target 1 UniProtKB/Swiss-Prot ID | P11387 ![]() |
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| Target 1 UniProtKB/Swiss-Prot Entry Name | TOP1_HUMAN ![]() |
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| Target 1 PDB ID | 1A36 ![]() |
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| Target 1 PDB File | Show | ||||||
| Target 1 3D Structure | |||||||
| Target 1 Cellular Location |
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| Target 1 Gene Sequence |
>2298 bp
ATGAGTGGGGACCACCTCCACAACGATTCCCAGATCGAAGCGGATTTCCGATTGAATGAT TCTCATAAACACAAAGATAAACACAAAGATCGAGAACACCGGCACAAAGAACACAAGAAG GAGAAGGACCGGGAAAAGTCCAAGCATAGCAACAGTGAACATAAAGATTCTGAAAAGAAA CACAAAGAGAAGGAGAAGACCAAACACAAAGATGGAAGCTCAGAAAAGCATAAAGACAAA CATAAAGACAGAGACAAGGAAAAACGAAAAGAGGAAAAGGTTCGAGCCTCTGGGGATGCA AAAATAAAGAAGGAGAAGGAAAATGGCTTCTCTAGTCCACCACAAATTAAAGATGAACCT GAAGATGATGGCTATTTTGTTCCTCCTAAAGAGGATATAAAGCCATTAAAGAGACCTCGA GATGAGGATGATGTTGATTATAAACCTAAGAAAATTAAAACAGAAGATACCAAGAAGGAG AAGAAAAGAAAACTAGAAGAAGAAGAGGATGGTAAATTGAAAAAACCCAAGAATAAAGAT AAAGATAAAAAAGTTCCTGAGCCAGATAACAAGAAAAAGAAGCCGAAGAAAGAAGAGGAA CAGAAGTGGAAATGGTGGGAAGAAGAGCGCTATCCTGAAGGCATCAAGTGGAAATTCCTA GAACATAAAGGTCCAGTATTTGCCCCACCATATGAGCCTCTTCCAGAGAATGTCAAGTTT TATTATGATGGTAAAGTCATGAAGCTGAGCCCCAAAGCAGAGGAAGTAGCTACGTTCTTT GCAAAAATGCTCGACCATGAATATACTACCAAGGAAATATTTAGGAAAAATTTCTTTAAA GACTGGAGAAAGGAAATGACTAATGAAGAGAAGAATATTATCACCAACCTAAGCAAATGT GATTTTACCCAGATGAGCCAGTATTTCAAAGCCCAGACGGAAGCTCGGAAACAGATGAGC AAGGAAGAGAAACTGAAAATCAAAGAGGAGAATGAAAAATTACTGAAAGAATATGGATTC TGTATTATGGATAACCACAAAGAGAGGATTGCTAACTTCAAGATAGAGCCTCCTGGACTT TTCCGTGGCCGCGGCAACCACCCCAAGATGGGCATGCTGAAGAGACGAATCATGCCCGAG GATATAATCATCAACTGTAGCAAAGATGCCAAGGTTCCTTCTCCTCCTCCAGGACATAAG TGGAAAGAAGTCCGGCATGATAACAAGGTTACTTGGCTGGTTTCCTGGACAGAGAACATC CAAGGTTCCATTAAATACATCATGCTTAACCCTAGTTCACGAATCAAGGGTGAGAAGGAC TGGCAGAAATACGAGACTGCTCGGCGGCTGAAAAAATGTGTGGACAAGATCCGGAACCAG TATCGAGAAGACTGGAAGTCCAAAGAGATGAAAGTCCGGCAGAGAGCTGTAGCCCTGTAC TTCATCGACAAGCTTGCTCTGAGAGCAGGCAATGAAAAGGAGGAAGGAGAAACAGCGGAC ACTGTGGGCTGCTGCTCACTTCGTGTGGAGCACATCAATCTACACCCAGAGTTGGATGGT CAGGAATATGTGGTAGAGTTTGACTTCCTCGGGAAGGACTCCATCAGATACTATAACAAG GTCCCTGTTGAGAAACGAGTTTTTAAGAACCTACAACTATTTATGGAGAACAAGCAGCCC GAGGATGATCTTTTTGATAGACTCAATACTGGTATTCTGAATAAGCATCTTCAGGATCTC ATGGAGGGCTTGACAGCCAAGGTATTCCGTACGTACAATGCCTCCATCACGCTACAGCAG CAGCTAAAAGAACTGACAGCCCCGGATGAGAACATCCCAGCGAAGATCCTTTCTTATAAC CGTGCCAATCGAGCTGTTGCAATTCTTTGTAACCATCAGAGGGCACCACCAAAAACTTTT GAGAAGTCTATGATGAACTTGCAAACTAAGATTGATGCCAAGAAGGAACAGCTAGCAGAT GCCCGGAGAGACCTGAAAAGTGCTAAGGCTGATGCCAAGGTCATGAAGGATGCAAAGACG AAGAAGGTAGTAGAGTCAAAGAAGAAGGCTGTTCAGAGACTGGAGGAACAGTTGATGAAG CTGGAAGTTCAAGCCACAGACCGAGAGGAAAATAAACAGATTGCCCTGGGAACCTCCAAA CTCAATTATCTGGACCCTAGGATCACAGTGGCTTGGTGCAAGAAGTGGGGTGTCCCAATT GAGAAGATTTACAACAAAACCCAGCGGGAGAAGTTTGCCTGGGCCATTGACATGGCTGAT GAAGACTATGAGTTTTAG |
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| Target 1 GenBank Gene ID | |||||||
| Target 1 GeneCard ID | TOP1 ![]() |
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| Target 1 GenAtlas ID | TOP1 ![]() |
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| Target 1 HGNC ID | HGNC:11986 ![]() |
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| Target 1 Chromosome Location | 20 | ||||||
| Target 1 Locus | 20q12-q13.1 | ||||||
| Target 1 SNPs | SNPJam Report ![]() |
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| Target 1 General References |
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| Target 1 Drug References |
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| Drug Target 2 [top] | |||||||
| Target 2 ID | 5989 | ||||||
| Target 2 Name | DNA topoisomerase I | ||||||
| Target 2 Synonyms | Not Available | ||||||
| Target 2 Gene Name | TOP1 | ||||||
| Target 2 Protein Sequence |
>DNA topoisomerase I
MPLPGGGTEVLKGITLLTQHHGLKPVQPMSFCYLSFLNRHTHEHHLRLHCCRPHAYARAH PCTCLIDFPLTSYPISQQCAPRLLPLPRQPPLSSQPAEAPSQIGTKDGLLLFRVSNRPQW VFCVCVCVRACPSFPLPRSCDFNRRGAVSPLSSPPRRAPVCCWRFFFHSCSFFFLVLYLL SAPYFCSLWARCANEEDKQNKLRIKQHETKKETPFRVCGGDCPSCCVGLSSHLFFPRWRL LVPPLPYTLDSNNSIFCVFHLFIYFLVCLFVSLAPSTYPFVPLCQLRTLHLYEPRPHIGT PLRCFCCHRDSIRRIMKVENSKMGVKREQSHSNEDEEINEEDLNWWEQENLRIAMKGERR WETLAHNGVLFPPEYEPHGIPIFYDGREFKMTPEEEEVATMFAVMKEHDYYRMEVFRRNF FESWREILDKRQHPIRRLELCDFEPIYQWHLVQREKKLSRTKEEKKAIKEKQDAEAEPYR YCVWDGRREQVANFRVEPPGLFRGRGKHPLMGKLKVRVQPEDITINIGETAEVPVPPAGH KWAAVQHDHTVTWLAMWRDSVAGNMKYVMLAPSSSVKGQSDMVKFEKARKLKDKVDDIRA SYMEDFKSNDLHVAQRAVAMYIDRLALRVGNEKGEDEADTVGCCSLRVEHIQLMPDNIVR FDFLGKDSIRYQNDVAVLPEVYALLQRFTRRKSPGMDIFDQLNPTQLNDHLKSFMDGLSA KVFRTYNASITLDRWFKEKPVDPKWSTADKLAYFNKANTEVAILCNHQKSVSKNFKLQMM QLTTKSEYTRKTIELLEKAEVTAKKKSVEEAAKEFLEEQDRMQREWLESYGTEEQKKEFE EIVAKRAAPRVRSEKKKSTSGAKKAESASGKKRAAKKKKSAKKGGKMLSKKAASKSSKKA PKKLKEEDEDDVPLVSVAAKTKKTAGVKRQRANKVVSDDDDVPLAALRV |
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| Target 2 Number of Residues | 964 | ||||||
| Target 2 Molecular Weight | 109573 | ||||||
| Target 2 Theoretical pI | 9.41 | ||||||
| Target 2 GO Classification |
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| Target 2 General Function | Replication, recombination and repair | ||||||
| Target 2 Specific Function | Not Available | ||||||
| Target 2 Pathways | Not Available | ||||||
| Target 2 Reactions | Not Available | ||||||
| Target 2 Pfam Domain Function | |||||||
| Target 2 Signals |
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| Target 2 Transmembrane Regions |
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| Target 2 Essentiality | Essential | ||||||
| Target 2 GenBank ID Protein | Not Available | ||||||
| Target 2 UniProtKB/Swiss-Prot ID | Q9NJG8 ![]() |
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| Target 2 UniProtKB/Swiss-Prot Entry Name | Q9NJG8_LEIDO ![]() |
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| Target 2 PDB ID | Not Available | ||||||
| Target 2 Cellular Location |
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| Target 2 Gene Sequence | Not Available | ||||||
| Target 2 GenBank Gene ID | |||||||
| Target 2 GeneCard ID | Not Available | ||||||
| Target 2 GenAtlas ID | Not Available | ||||||
| Target 2 HGNC ID | Not Available | ||||||
| Target 2 Chromosome Location | Not Available | ||||||
| Target 2 Locus | Not Available | ||||||
| Target 2 SNPs | SNPJam Report ![]() |
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| Target 2 General References |
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| Target 2 Drug References |
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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.