Sodium stibogluconate: Difference between revisions

Jump to navigation Jump to search
No edit summary
No edit summary
 
Line 4: Line 4:
| verifiedrevid = 476995418
| verifiedrevid = 476995418
| IUPAC_name = 2,4:2',4'-O-(oxydistibylidyne)bis[D-gluconic acid]
| IUPAC_name = 2,4:2',4'-O-(oxydistibylidyne)bis[D-gluconic acid]
| image =ImprovedSbgluconicAcid.png
| image =gluconicAcid.png
| width = 300px
| width = 300px


Line 51: Line 51:
| StdInChIKey = RTLKTTNTVTVWPV-UQCYVGCHSA-L
| StdInChIKey = RTLKTTNTVTVWPV-UQCYVGCHSA-L
}}
}}
              __NOTOC__
{{SI}}
{{CMG}}
==Overview==
   
'''Sodium stibogluconate''' is a medicine used to treat [[leishmaniasis]] and is only available for administration by injection.  It belongs to the class of drugs known as the [[pentavalent antimonial]]s because they contain antimony in its [[oxidation state]] of 5.  Sodium stibogluconate is marketed under the name '''Pentostam'''.  In parts of the world resistance has limited the utility of sodium stibogluconate,<ref>{{ cite journal | author = Mukhopadhyay R, Dey S, Xu N, Gage D, Lightbody J, Ouellette M, Rosen BP | title = Trypanothione Overproduction and Resistance to Antimonials and Arsenicals in Leishmania | journal = PNAS | year = 1996 | volume = 93 | issue = 19 | pages = 10383–10387 | pmid =    8816809 | pmc = 38393 | url = http://www.ncbi.nlm.nih.gov/pmc/articles/PMC38393/pdf/pnas01523-0401.pdf | format = pdf | doi=10.1073/pnas.93.19.10383}}</ref> in which cases [[amphotericin]] or [[miltefosine]] is used instead.
'''Sodium stibogluconate''' is a medicine used to treat [[leishmaniasis]] and is only available for administration by injection.  It belongs to the class of drugs known as the [[pentavalent antimonial]]s because they contain antimony in its [[oxidation state]] of 5.  Sodium stibogluconate is marketed under the name '''Pentostam'''.  In parts of the world resistance has limited the utility of sodium stibogluconate,<ref>{{ cite journal | author = Mukhopadhyay R, Dey S, Xu N, Gage D, Lightbody J, Ouellette M, Rosen BP | title = Trypanothione Overproduction and Resistance to Antimonials and Arsenicals in Leishmania | journal = PNAS | year = 1996 | volume = 93 | issue = 19 | pages = 10383–10387 | pmid =    8816809 | pmc = 38393 | url = http://www.ncbi.nlm.nih.gov/pmc/articles/PMC38393/pdf/pnas01523-0401.pdf | format = pdf | doi=10.1073/pnas.93.19.10383}}</ref> in which cases [[amphotericin]] or [[miltefosine]] is used instead.


<!-- Society and culture -->
<!-- Society and culture -->
It is on the [[World Health Organization's List of Essential Medicines]], a list of the most important medication needed in a basic [[health system]].<ref>{{cite web|title=WHO Model List of EssentialMedicines|url=http://apps.who.int/iris/bitstream/10665/93142/1/EML_18_eng.pdf?ua=1|work=World Health Organization|accessdate=22 April 2014|date=October 2013}}</ref>
It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic [[health system]].<ref>{{cite web|title=WHO Model List of EssentialMedicines|url=http://apps.who.int/iris/bitstream/10665/93142/1/EML_18_eng.pdf?ua=1|work=World Health Organization|accessdate=22 April 2014|date=October 2013}}</ref>


==Side effects==
==Side effects==
Line 79: Line 85:


==References==
==References==
{{reflist}}
{{reflist|2}}
{{refbegin}}
{{refbegin}}
*[http://www.bnf.org British National Formulary]
*[http://www.bnf.org British National Formulary]
Line 85: Line 91:
{{refend}}
{{refend}}


{{Excavata antiparasitics}}
 


[[Category:Orphan drugs]]
[[Category:Orphan drugs]]
[[Category:Antiprotozoal agents]]
[[Category:Antiprotozoal agents]]
[[Category:World Health Organization essential medicines]]
[[Category:Drug]]
[[Category:Antimony heterocycles]]

Latest revision as of 16:14, 13 April 2015

Sodium stibogluconate
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration
IV only
ATC code
Legal status
Legal status
  • UK: POM (Prescription only)
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
NIAID ChemDB
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC12H38Na3O26Sb2
Molar mass910.9 g/mol
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

WikiDoc Resources for Sodium stibogluconate

Articles

Most recent articles on Sodium stibogluconate

Most cited articles on Sodium stibogluconate

Review articles on Sodium stibogluconate

Articles on Sodium stibogluconate in N Eng J Med, Lancet, BMJ

Media

Powerpoint slides on Sodium stibogluconate

Images of Sodium stibogluconate

Photos of Sodium stibogluconate

Podcasts & MP3s on Sodium stibogluconate

Videos on Sodium stibogluconate

Evidence Based Medicine

Cochrane Collaboration on Sodium stibogluconate

Bandolier on Sodium stibogluconate

TRIP on Sodium stibogluconate

Clinical Trials

Ongoing Trials on Sodium stibogluconate at Clinical Trials.gov

Trial results on Sodium stibogluconate

Clinical Trials on Sodium stibogluconate at Google

Guidelines / Policies / Govt

US National Guidelines Clearinghouse on Sodium stibogluconate

NICE Guidance on Sodium stibogluconate

NHS PRODIGY Guidance

FDA on Sodium stibogluconate

CDC on Sodium stibogluconate

Books

Books on Sodium stibogluconate

News

Sodium stibogluconate in the news

Be alerted to news on Sodium stibogluconate

News trends on Sodium stibogluconate

Commentary

Blogs on Sodium stibogluconate

Definitions

Definitions of Sodium stibogluconate

Patient Resources / Community

Patient resources on Sodium stibogluconate

Discussion groups on Sodium stibogluconate

Patient Handouts on Sodium stibogluconate

Directions to Hospitals Treating Sodium stibogluconate

Risk calculators and risk factors for Sodium stibogluconate

Healthcare Provider Resources

Symptoms of Sodium stibogluconate

Causes & Risk Factors for Sodium stibogluconate

Diagnostic studies for Sodium stibogluconate

Treatment of Sodium stibogluconate

Continuing Medical Education (CME)

CME Programs on Sodium stibogluconate

International

Sodium stibogluconate en Espanol

Sodium stibogluconate en Francais

Business

Sodium stibogluconate in the Marketplace

Patents on Sodium stibogluconate

Experimental / Informatics

List of terms related to Sodium stibogluconate

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Sodium stibogluconate is a medicine used to treat leishmaniasis and is only available for administration by injection. It belongs to the class of drugs known as the pentavalent antimonials because they contain antimony in its oxidation state of 5. Sodium stibogluconate is marketed under the name Pentostam. In parts of the world resistance has limited the utility of sodium stibogluconate,[1] in which cases amphotericin or miltefosine is used instead.

It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.[2]

Side effects

Sodium stibogluconate is exceedingly phlebotoxic. 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 thrombose. Large doses of sodium stibogluconate are often administered as dilute solutions

Pancreatitis is a common problem and the serum amylase or lipase 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.

The drug can be given intramuscularly but is exceedingly painful when given by this route. It can also be given intralesionally when treating cutaneous leishmaniasis (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.

Sodium stibogluconate can also cause a reduced appetite, metallic taste in mouth, nausea, vomiting, diarrhoea, headache, tiredness, joint pains, muscle aches, dizziness, and anaphylaxis.

Dosing

Sodium stibogluconate is available in the United Kingdom as Pentostam, where it is manufactured by GlaxoSmithKline. It is available in the United States on a named-patient basis from the Centers for Disease Control and Prevention (CDC).

The dose of sodium stibogluconate is by slow intravenous infusion (at least five minutes with cardiac monitoring). The injection are stopped if there is coughing or central chest pain. The chemotherapeutic index was established by Leonard Goodwin during the Second World War when a treatment was urgently required for Allied troops during the invasion of Sicily.[3]

The duration of treatment is usually 10 to 21 days and depends on the species of Leishmania and the type of infection (cutaneous or visceral).

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.[4]

Pharmacokinetics

Although antimony itself is a cause of heavy metal poisoning, stibogluconate does not appear to accumulate in the body and is excreted by the kidneys.[5]

References

  1. Mukhopadhyay R, Dey S, Xu N, Gage D, Lightbody J, Ouellette M, Rosen BP (1996). "Trypanothione Overproduction and Resistance to Antimonials and Arsenicals in Leishmania" (pdf). PNAS. 93 (19): 10383–10387. doi:10.1073/pnas.93.19.10383. PMC 38393. PMID 8816809.
  2. "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.
  3. "Leonard Goodwin - Telegraph". The Daily Telegraph. 14 January 2009. Retrieved 2009-01-18.
  4. Frézard F, Demicheli C, Ribeiro PR (2009). "Pentavalent Antimonials: New Perspectives for Old Drugs" (pdf). Molecules. 14 (7): 2317–2336. doi:10.3390/molecules14072317. PMID 19633606.
  5. Rees PH, Keating MI, Kager PA, Hockmeyer WT (1980). "Renal clearance of pentavalent antimony (sodium stibogluconate)". Lancet. 2 (8188): 226&ndash, 9. PMID 6105394.