Sulfadoxine: Difference between revisions

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Sulfadoxine
Clinical data
AHFS/Drugs.com	International Drug Names
ATCvet code	Template:Infobox drug/formatATCvet; Template:Infobox drug/formatATCvet;
Identifiers
	IUPAC name 4-Amino-N-(5,6-dimethoxy-4-pyrimidinyl)benzenesulfonamide;
CAS Number	2447-57-6 ;
PubChem CID	17134;
DrugBank	DB01299 ;
ChemSpider	16218 ;
UNII	88463U4SM5;
KEGG	D00580 ;
ChEMBL	ChEMBL1539 ;
NIAID ChemDB	007816;
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
Formula	C12H14N4O4S
Molar mass	310.33 g/mol
3D model (JSmol)	Interactive image;
	SMILES COC1=C(N=CN=C1OC)NS(=O)(=O)C2=CC=C(C=C2)N;
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VisualWikitext

Latest revision as of 14:55, 13 April 2015

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

Overview

Sulfadoxine (also spelled sulphadoxine) is an ultra-long-lasting sulfonamide previously used in combination with pyrimethamine to treat or prevent malaria.^[1] Due to high levels of resistance, its use is no longer recommended routinely.^[2] It is also used, usually in combination with other drugs, to treat or prevent various infections in livestock.^[3]

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.^[4]

Mechanism of action

Sulfadoxine competitively inhibits dihydropteroate synthase, interfering with folate synthesis.

Synthesis

700px U.S. Patent 3,132,139 BE 618639 [5][6] — 700px U.S. Patent 3,132,139 BE 618639 ^[5]^[6]

References

↑ Medical Treatment - Sulphadoxine and Pyrimethamine.
↑ Matondo SI, Temba GS, Kavishe AA; et al. (2014). "High levels of sulphadoxine-pyrimethamine resistance Pfdhfr-Pfdhps quintuple mutations: a cross sectional survey of six regions in Tanzania". Malar J. 13: 152. doi:10.1186/1475-2875-13-152. PMC 3998221. PMID 24751352.
↑ http://en.scientificcommons.org/19483411.
↑ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.
↑ Template:Cite doi
↑ Template:Cite doi

Template:Nucleic acid inhibitors

Template:Antibiotic-stub

[autogenerated1-1] Medical Treatment - Sulphadoxine and Pyrimethamine.

[2] Matondo SI, Temba GS, Kavishe AA; et al. (2014). "High levels of sulphadoxine-pyrimethamine resistance Pfdhfr-Pfdhps quintuple mutations: a cross sectional survey of six regions in Tanzania". Malar J. 13: 152. doi:10.1186/1475-2875-13-152. PMC 3998221. PMID 24751352.

[3] ttp://en.scientificcommons.org/19483411.

[4] "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.

[5] Template:Cite doi

[6] Template:Cite doi

[1]

[2]

[3]

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[5]

[6]

@@ Line 1: / Line 1: @@
-{{Chembox new
+{{Drugbox
-|ImageFile=Sulfadoxine.png
+| Verifiedfields = changed
-|ImageSize=200px
+| verifiedrevid = 408901454
-|IUPACName=4-Amino-''N''-(5,6-dimethoxy-4-pyrimidinyl)benzenesulfonamide
+| IUPAC_name = 4-Amino-''N''-(5,6-dimethoxy-4-pyrimidinyl)benzenesulfonamide
-|OtherNames=Sulfadoxine
+| image = Sulfadoxine Wiki Str.png
-|Section1= {{Chembox Identifiers
-|  CASNo=
-|  PubChem=17134
+<!--Clinical data-->
-|  SMILES=COC1=C(N=CN=C1OC)NS(=O)(=O)C2=CC=C(C=C2)N
+| tradename =
-  }}
+| Drugs.com = {{drugs.com|international|sulfadoxine}}
-|Section2= {{Chembox Properties
+| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
-|  Formula=C<sub>12</sub>H<sub>14</sub>N<sub>4</sub>O<sub>4</sub>S
+| pregnancy_US = <!-- A / B            / C / D / X -->
-|  MolarMass=310.33 g/mol
+| pregnancy_category =
-|  Appearance=
+| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
-|  Density=
+| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
-|  MeltingPt=
+| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
-|  BoilingPt=
+| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
-|  Solubility=
+| legal_status =
-  }}
+| routes_of_administration =
-|Section3= {{Chembox Hazards
-|  MainHazards=
+<!--Pharmacokinetic data-->
-|  FlashPt=
+| bioavailability =
-|  Autoignition=
+| protein_bound =
-  }}
+| metabolism =
+| elimination_half-life =
+| excretion =
+<!--Identifiers-->
+| CASNo_Ref = {{cascite}}
+| CAS_number_Ref = {{cascite|correct|??}}
+| CAS_number = 2447-57-6
+| CAS_supplemental =
+| ATCvet = yes
+| ATC_prefix = J01
+| ATC_suffix = EQ13
+| ATC_supplemental =
+| PubChem = 17134
+| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
+| DrugBank = DB01299
+| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
+| ChemSpiderID = 16218
+| NIAID_ChemDB = 007816
+| UNII_Ref = {{fdacite|changed|FDA}}
+| UNII = 88463U4SM5
+| KEGG_Ref = {{keggcite|correct|kegg}}
+| KEGG = D00580
+| ChEMBL_Ref = {{ebicite|changed|EBI}}
+| ChEMBL = 1539
+<!--Chemical data-->
+| chemical_formula =
+| C=12 | H=14 | N=4 | O=4 | S=1
+| molecular_weight = 310.33 g/mol
+| smiles = COC1=C(N=CN=C1OC)NS(=O)(=O)C2=CC=C(C=C2)N
 }}
+__NOTOC__
+{{SI}}
+{{CMG}}
+== Overview ==
+'''Sulfadoxine''' (also spelled '''sulphadoxine''') is an ultra-long-lasting [[Sulfonamide (medicine)|sulfonamide]] previously used in [[Sulfadoxine/pyrimethamine|combination]] with [[pyrimethamine]] to treat or prevent [[malaria]].<ref name=autogenerated1>[http://www.malaria-ipca.com/sulphadoxine_pyrimethamine.html Medical Treatment - Sulphadoxine and Pyrimethamine<!-- Bot generated title -->].</ref> Due to high levels of resistance, its use is no longer recommended routinely.<ref>{{cite journal | author = Matondo SI, Temba GS, Kavishe AA, ''et al.'' | title = High levels of sulphadoxine-pyrimethamine resistance ''Pfdhfr-Pfdhps'' quintuple mutations: a cross sectional survey of six regions in Tanzania.
+| journal = Malar J | year = 2014 | volume = 13 | page = 152 | doi = 10.1186/1475-2875-13-152 | pmid = 24751352 | pmc=3998221}}</ref>
+It is also used, usually in combination with other drugs, to treat or prevent various infections in livestock.<ref>http://en.scientificcommons.org/19483411.</ref>
-'''Sulfadoxine''' (also spelled '''sulphadoxine''') is an ultra-long-lasting [[sulfonamide]] often used in combination with [[pyrimethamine]] to treat or prevent [[malaria]].<ref>[http://www.malaria-ipca.com/sulphadoxine_pyrimethamine.html Medical Treatment - Sulphadoxine and Pyrimethamine<!-- Bot generated title -->]</ref>
+<!-- Society and culture -->
-It is also used, usually in combination with other drugs, to treat or prevent various infections in livestock.<ref>http://en.scientificcommons.org/19483411</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>
-==Sulfadoxine/pyrimethamine combination==
+==Mechanism of action==
+Sulfadoxine competitively inhibits dihydropteroate synthase, interfering with folate synthesis.
-Both drugs are [[antifolate|antifolates]]; they inhibit the production of enzymes involved in the synthesis of [[folic acid]] within the parasites.  Either drug by itself is only moderately effective in treating malaria,  because the [[parasite]] ''[[Plasmodium falciparum]]'' may be able to use [[exogeny|exogenous]] folic acid, i.e. folic acid which is present in the parasite's environment, while in combination, the two substances have a [[synergy|synergistic]] effect which outbalances that ability.<ref>[http://www.ajtmh.org/cgi/content/abstract/33/3/325 Synergistic Antimalarial Activity of Pyrimethamine and Sulfadoxine against Plasmodium falciparum In Vitro - Chulay et al. 33 (3): 325 - American Journal of Tropical Medicine and Hygiene<!-- Bot generated title -->]</ref>
+==Synthesis==
+[[File:Sulfadoxine Syn.png|none|center|700px {{US patent|3132139}} {{Cite patent|BE|618639}} <ref>{{Cite doi|10.1007/BF01185885}}</ref><ref>{{Cite doi|10.1007/BF01185886}}</ref>]]
-The combination is considered to be more effective in treating malaria caused by ''Plasmodium falciparum'' than that caused by ''[[Plasmodium vivax]]'', for which [[chloroquine]] is considered more effective, though in the absence of a species-specific diagnosis the sulfadoxine-pyrimethamine combination may be indicated.<ref>[http://jama.ama-assn.org/cgi/content/abstract/297/20/2201 JAMA - Abstract: Sulfadoxine-Pyrimethamine, Chlorproguanil-Dapsone, or Chloroquine for the Treatment of Plasmodium vivax Malaria in Afghanistan and Pakistan: A Randomized Controlled Trial, May 23/30, 2007, Leslie et al. 297 (20): 2201<!-- Bot generated title -->]</ref> Due to side effects, however, it is no longer recommended as a routine preventative,<ref>[http://www.malaria-ipca.com/sulphadoxine_pyrimethamine.html Medical Treatment - Sulphadoxine and Pyrimethamine<!-- Bot generated title -->]</ref> but only to treat serious malaria infections or to prevent them in areas where other drugs may not work.<ref>[http://www.mayoclinic.com/health/drug-information/DR600357 Pyrimethamine and Sulfadoxine (Oral Route) - MayoClinic.com<!-- Bot generated title -->]</ref>
+==See also==
+* [[Sulfadoxine/pyrimethamine]]
 ==References==
 {{reflist|2}}
+{{Nucleic acid inhibitors}}
+[[Category:Drug]]
+[[Category:Anilines]]
+[[Category:Ethers]]
+[[Category:Pyrimidines]]
+[[Category:Sulfonamide antibiotics]]
+[[Category:Dihydropteroate synthetase inhibitors]]
 [[Category:Antimalarial agents]]
-[[Category:Pyrimidines]]
-[[Category:Sulfonamides]]
+{{antibiotic-stub}}

Sulfadoxine: Difference between revisions

Latest revision as of 14:55, 13 April 2015

Overview

Mechanism of action

Synthesis

See also

References

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