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Revision as of 12:39, 15 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 473571622 of page Sodium_stibogluconate for the Chem/Drugbox validation project (updated: 'UNII', 'ChEMBL', 'CAS_number').  Latest revision as of 02:21, 27 May 2024 edit 2600:1700:25e0:5fb0:d597:9ab9:6aa7:b535 (talk) Corrected paramycin to paromomycinTags: Visual edit Mobile edit Mobile web edit 
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{{Short description|Pharmaceutical drug}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 464404127 | verifiedrevid = 476995418
| IUPAC_name = 2,4:2',4'-O-(oxydistibylidyne)bis | IUPAC_name = 2,4:2',4'-''O''-(oxydistibylidyne)bis
| image = Sodium Stibogluconate.png
| image =ImprovedSbgluconicAcid.png
| width = 300px | width = 300px


<!--Clinical data--> <!--Clinical data-->
| tradename = Pentostam, Stiboson, others<ref>{{cite web|title=Sodium Stibogluconate | work = Drugs.com|url=https://www.drugs.com/international/sodium-stibogluconate.html |access-date=7 December 2016|url-status=live|archive-url=https://web.archive.org/web/20161220222926/https://www.drugs.com/international/sodium-stibogluconate.html|archive-date=20 December 2016}}</ref>
| tradename =
| Drugs.com = {{drugs.com|international|sodium-stibogluconate}} | Drugs.com = {{drugs.com|international|sodium-stibogluconate}}
| pregnancy_category = | pregnancy_category =
| legal_UK = POM | legal_status = Rx-only
⚫ | routes_of_administration = intravenous, intramusclar<ref name=WHO2010/>
| legal_status =
⚫ | routes_of_administration = IV only


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = | bioavailability =
| metabolism = | metabolism =
| excretion = | excretion =


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}} | CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = <!-- blanked - oldvalue: 16037-91-5 --> | CAS_number = 219717-42-7
| ATC_prefix = P01 | ATC_prefix = P01
| ATC_suffix = CB02 | ATC_suffix = CB02
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| ChemSpiderID = 21106382 | ChemSpiderID = 21106382
| UNII_Ref = {{fdacite|changed|FDA}} | UNII_Ref = {{fdacite|changed|FDA}}
| UNII = <!-- blanked - oldvalue: V083S0159D --> | UNII = V083S0159D
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00582 | KEGG = D00582
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 367144 --> | ChEMBL = 367144
| NIAID_ChemDB = 007935 | NIAID_ChemDB = 007935
| index2_label = nonhydrate

| CAS_number2_Ref = {{cascite|correct|CAS}}
| CAS_number2 = 16037-91-5
| UNII2_Ref = {{fdacite|correct|FDA}}
| UNII2 = APJ6285Y89
<!--Chemical data--> <!--Chemical data-->
| chemical_formula = | chemical_formula =
| C=12 | H=38 | Na=3 | O=26 | C=2 | C=12 | H=38 | Na=3 | O=26 | Sb=2
| molecular_weight = 910.9
| smiles = ...O=2(O1(=O)OC((O)CO)(O)(O1)C()=O)O((O)(O2)C()=O)(O)CO | smiles = ...O=2(O1(=O)OC((O)CO)(O)(O1)C()=O)O((O)(O2)C()=O)(O)CO
| InChI = 1/2C6H10O7.3Na.3O.2Sb/c2*7-1-2(8)3(9)4(10)5(11)6(12)13;;;;;;;;/h2*2-5,7-8,10H,1H2,(H,12,13);;;;;;;;/q2*-2;3*+1;;;;2*+2/p-2/t2-,3?,4+,5-;2-,3-,4+,5-;;;;;;;;/m11......../s1/rC12H20O17Sb2.3Na/c13-1-3(15)7-5(17)9(11(19)20)27-30(23,25-7)29-31(24)26-8(4(16)2-14)6(18)10(28-31)12(21)22;;;/h3-10,13-18H,1-2H2,(H,19,20)(H,21,22);;;/q;3*+1/p-2/t3-,4-,5+,6+,7-,8?,9-,10-;;;/m1.../s1
| InChIKey = RTLKTTNTVTVWPV-CIGDLYFHBG
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/2C6H10O7.3Na.3O.2Sb/c2*7-1-2(8)3(9)4(10)5(11)6(12)13;;;;;;;;/h2*2-5,7-8,10H,1H2,(H,12,13);;;;;;;;/q2*-2;3*+1;;;;2*+2/p-2/t2-,3?,4+,5-;2-,3-,4+,5-;;;;;;;;/m11......../s1 | StdInChI = 1S/2C6H10O7.3Na.3O.2Sb/c2*7-1-2(8)3(9)4(10)5(11)6(12)13;;;;;;;;/h2*2-5,7-8,10H,1H2,(H,12,13);;;;;;;;/q2*-2;3*+1;;;;2*+2/p-2/t2-,3?,4+,5-;2-,3-,4+,5-;;;;;;;;/m11......../s1
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| StdInChIKey = RTLKTTNTVTVWPV-UQCYVGCHSA-L | StdInChIKey = RTLKTTNTVTVWPV-UQCYVGCHSA-L
}} }}
<!-- Definition and medical uses -->
'''Sodium stibogluconate''', sold under the brand name '''Pentostam''' among others, is a medication used to treat ].<ref name=CDC2016>{{cite web|title=Our Formulary Infectious Diseases Laboratories CDC|url=https://www.cdc.gov/laboratory/drugservice/formulary.html#tmelarsoprol|website=www.cdc.gov|access-date=7 December 2016|date=22 September 2016|url-status=live|archive-url=https://web.archive.org/web/20161216173833/https://www.cdc.gov/laboratory/drugservice/formulary.html#tmelarsoprol|archive-date=16 December 2016}}</ref> This includes leishmaniasis of the cutaneous, visceral, and mucosal types.<ref name=Bar1992>{{cite journal | vauthors = Herwaldt BL, Berman JD | title = Recommendations for treating leishmaniasis with sodium stibogluconate (Pentostam) and review of pertinent clinical studies | journal = The American Journal of Tropical Medicine and Hygiene | volume = 46 | issue = 3 | pages = 296–306 | date = March 1992 | pmid = 1313656 | doi = 10.4269/ajtmh.1992.46.296 }}</ref> Some combination of ], ] and ], however, may be recommended due to issues with ].<ref name=WHO2010/><ref name=Or2016>{{cite journal | vauthors = Oryan A, Akbari M | title = Worldwide risk factors in leishmaniasis | journal = Asian Pacific Journal of Tropical Medicine | volume = 9 | issue = 10 | pages = 925–932 | date = October 2016 | pmid = 27794384 | doi = 10.1016/j.apjtm.2016.06.021 | doi-access = free }}</ref> It is given by injection.<ref name="BNF">{{cite web |last1=Joint Formulary Committee |title=Sodium Stibogluconate |url=https://bnf.nice.org.uk/drug/sodium-stibogluconate.html |website=British National Formulary |publisher=BMJ Group and Pharmaceutical Press |access-date=29 December 2020}}</ref>

<!-- Side effects and mechanism -->
Side effects are common and include loss of appetite, nausea, muscle pains, headache, and feeling tired.<ref name=WHO2010>{{cite book|title=Control of the leishmaniasis: report of a meeting of the WHO Expert Committee on the Control of Leishmaniases|date=March 2010|publisher=World Health Organization|isbn=9789241209496|page=55,186|url=http://apps.who.int/iris/bitstream/10665/44412/1/WHO_TRS_949_eng.pdf?ua=1|url-status=live|archive-url=https://web.archive.org/web/20160608074251/http://apps.who.int/iris/bitstream/10665/44412/1/WHO_TRS_949_eng.pdf?ua=1|archive-date=2016-06-08|hdl=10665/44412|last1=Organization|first1=World Health}}</ref><ref name=Or2016/> Serious side effect may include an ] or ].<ref name=Or2016/> Sodium stibogluconate is less safe than some other options during ].<ref name=WHO2010/> It is not believed to result in any problems if used during ].<ref>{{cite web|title=Sodium Stibogluconate use while Breastfeeding | work = Drugs.com |url= https://www.drugs.com/breastfeeding/sodium-stibogluconate.html |access-date=7 December 2016|url-status=live|archive-url=https://web.archive.org/web/20161220223351/https://www.drugs.com/breastfeeding/sodium-stibogluconate.html|archive-date=20 December 2016}}</ref> Sodium stibogluconate is in the ]s class of medication.<ref name=Or2016/>

<!-- Society and culture -->
Sodium stibogluconate has been studied as early as 1937 and has been in medical use since the 1940s.<ref>{{cite book| vauthors = Sneader W | chapter = Legacies of the Past: Chemical Medicines |title=Drug Discovery: A History|date=2005|publisher=John Wiley & Sons|isbn=9780470015520|page=58| chapter-url= https://books.google.com/books?id=jglFsz5EJR8C&pg=PA58 |language=en|url-status=live|archive-url= https://web.archive.org/web/20161220080740/https://books.google.com/books?id=jglFsz5EJR8C&pg=PA58 |archive-date=2016-12-20}}</ref><ref>{{cite book| vauthors = Jäger T, Koch O, Flohé L | chapter = Foreward |title=Trypanosomatid Diseases: Molecular Routes to Drug Discovery|date=2013|publisher=John Wiley & Sons |isbn=9783527670406|page=17| chapter-url=https://books.google.com/books?id=4iSH9g4sJc4C&pg=PP17|language=en|url-status=live|archive-url=https://web.archive.org/web/20161220074335/https://books.google.com/books?id=4iSH9g4sJc4C&pg=PP17|archive-date=2016-12-20}}</ref> It is on the ].<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref> In the United States, it is available from the ].<ref name=CDC2016/>

==Side effects==
Sodium stibogluconate is exceedingly toxic to ]. One of the practical problems is that after a few doses it can become exceedingly difficult to find a vein in which to inject the drug. The insertion of a ] (PICC) does not prevent the problem and can instead exacerbate it: the entire vein along the course of the PICC line can become inflamed and ]. Large doses of sodium stibogluconate are often administered as dilute solutions.{{cn|date=December 2022}}

] is a common deleterious effect of the drug, and the ] ] or ] should be monitored twice weekly; there is no need to stop treatment if the amylase remains less than four times the upper limit of normal; if the amylase rises above the cut-off, then treatment should be interrupted until the amylase falls to less than twice the upper limit of normal, whereupon treatment can be resumed. Cardiac conduction disturbances are less common, but ] (ECG) monitoring while the medicine is injected is advisable and changes quickly reverse after the drug is stopped or the infusion rate is decreased.{{cn|date=December 2022}}

The drug can be given intramuscularly but is exceedingly painful when given by this route. It can also be given intralesionally when treating ] (i.e., injected directly into the area of infected skin) and again, this is exceedingly painful and does not give results superior to intravenous administration.{{cn|date=December 2022}}

Sodium stibogluconate can also cause a reduced appetite, metallic taste in mouth, ], ], ], headache, tiredness, joint pains, muscle aches, dizziness, and ].{{cn|date=December 2022}}

==Dosing==
Sodium stibogluconate is available in the ] as Pentostam, where it is manufactured by ]. It is available in the ] on a named-patient basis from the ] (CDC).{{cn|date=December 2022}}

As dosage regimens for treating leishmaniasis have evolved, the daily dose of antimony and the duration of therapy have been progressively increased to combat unresponsiveness to therapy. In the 1980s, the use of 20&nbsp;mg/kg/day (instead of 10&nbsp;mg/kg/day) of antimony was recommended, but only to a maximum daily dose of 850&nbsp;mg. Recent research has suggested on the basis of recent efficacy and toxicity data that this 850-mg restriction should be removed. The evidence to date, which is in their research, suggests that a regimen of 20&nbsp;mg/kg/day of pentavalent antimony, without an upper limit on the daily dose, is more efficacious and is not substantially more toxic than regimens with lower daily doses. It is recommend treating all forms of leishmaniasis with a full 20&nbsp;mg/kg/day of pentavalent antimony. Treatment of cutaneous leishmaniasis usually lasts for 20 days and visceral and mucosal leishmaniasis for 28 days.<ref>{{cite journal | vauthors = Herwaldt BL, Berman JD | title = Recommendations for treating leishmaniasis with sodium stibogluconate (Pentostam) and review of pertinent clinical studies | journal = The American Journal of Tropical Medicine and Hygiene | volume = 46 | issue = 3 | pages = 296–306 | date = March 1992 | pmid = 1313656 | doi = 10.4269/ajtmh.1992.46.296 }}</ref>

The dose of sodium stibogluconate is by slow intravenous infusion (at least five minutes with cardiac monitoring). The injection are stopped if there is ]ing or central chest pain. The chemotherapeutic index was established by ] during the Second World War when a treatment was urgently required for Allied troops during the ].<ref name="tel">{{cite news|url=https://www.telegraph.co.uk/news/obituaries/4241645/Leonard-Goodwin.html|title=Leonard Goodwin |date=14 January 2009|newspaper=The Daily Telegraph|access-date=2009-01-18|url-status=live|archive-url=https://web.archive.org/web/20090420055410/http://www.telegraph.co.uk/news/obituaries/4241645/Leonard-Goodwin.html|archive-date=20 April 2009}}</ref>

The duration of treatment is usually 10 to 21 days and depends on the species of '']'' and the type of infection (] or ]).{{cn|date=February 2023}}

==Chemical structure==
The chemical structure of sodium stibogluconate is somewhat ambiguous, and the structure shown above is idealized. Its solutions may contain multiple antimony compounds, although this heterogeneity may be unimportant. It has been speculated that the active species contains only a single antimony centre.<ref>{{cite journal | vauthors = Frézard F, Demicheli C, Ribeiro RR | title = Pentavalent antimonials: new perspectives for old drugs | journal = Molecules | volume = 14 | issue = 7 | pages = 2317–2336 | date = June 2009 | pmid = 19633606 | pmc = 6254722 | doi = 10.3390/molecules14072317 | doi-access = free }}</ref>

==Pharmacokinetics==
Pentavalent antimony does not appear to accumulate in the body and is excreted by the kidneys.<ref>{{cite journal | vauthors = Rees PH, Keating MI, Kager PA, Hockmeyer WT | title = Renal clearance of pentavalent antimony (sodium stibogluconate) | journal = Lancet | volume = 2 | issue = 8188 | pages = 226–229 | date = August 1980 | pmid = 6105394 | doi = 10.1016/s0140-6736(80)90120-8 | s2cid = 23764245 }}</ref>

==Mechanism of action==
The mechanism of sodium stibogluconate is poorly understood, but is thought to stem from the inhibition of macromolecular synthesis via a reduction in available ] and ], likely secondary to inhibition of the ] and ]. Bermann et al. studied the effects of stibogluconate on '']'' and demonstrated a 56–65% reduction in incorporation of a label into ] nucleoside ]s (ATP and GTP) as well as between a 34–60% increase of label incorporation into purine ] mono- and ]s (], ], ], and ]) following 4 hour exposure to stibogluconate.<ref>{{cite journal | vauthors = Berman JD, Waddell D, Hanson BD | title = Biochemical mechanisms of the antileishmanial activity of sodium stibogluconate | journal = Antimicrobial Agents and Chemotherapy | volume = 27 | issue = 6 | pages = 916–920 | date = June 1985 | pmid = 2411217 | pmc = 180186 | doi = 10.1128/aac.27.6.916 }}</ref>

== References ==
{{Reflist}}

{{Excavata antiparasitics}}

{{Portal bar|Medicine}}

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