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Latest revision as of 15:33, 8 October 2024 edit undoJWBE (talk | contribs)Extended confirmed users10,127 edits removed Category:Anilines; added Category:4-Aminophenyl compounds using HotCat |
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{{short description|Chemical compound}} |
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{{Drugbox| Verifiedfields = changed |
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<!-- not likely{{Distinguish|sulfisoxazole}} --> |
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| verifiedrevid = 376144071 |
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{{Drugbox |
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|IUPAC_name = 4-amino-''N''-pyrimidin- 2-yl-benzenesulfonamide |
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| Watchedfields = changed |
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| image=Sulfadiazine-2D-skeletal.png |
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| verifiedrevid = 408892547 |
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| width=250 |
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| IUPAC_name = 4-amino-''N''-pyrimidin- 2-yl-benzenesulfonamide |
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| image2=Sulfadiazine-3D-vdW.png |
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| image = Sulfadiazine.svg |
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| width2=250 |
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| width = 250 |
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| CASNo_Ref = {{cascite}} |
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| image2 = Sulfadiazine-3D-vdW.png |
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| CAS_number=68-35-9 |
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| width2 = 250 |
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| ATC_prefix=J01 |
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<!--Clinical data--> |
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| ATC_suffix=EC02 |
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| tradename = |
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| ATC_supplemental={{ATCvet|J01|EQ10}} |
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| class = ] (])<ref name=AHFS2016/> |
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| PubChem=5215 |
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| Drugs.com = {{drugs.com|monograph|sulfadiazine}} |
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| DrugBank=APRD00190 |
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| MedlinePlus = a682130 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| pregnancy_US = C |
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|pregnancy_US_comment=<ref name="pregnancy">{{cite web|title=Sulfadiazine Use During Pregnancy {{!}} Drugs.com|url=https://www.drugs.com/pregnancy/sulfadiazine.html|website=www.drugs.com|access-date=28 June 2017|url-status=live|archive-url=https://web.archive.org/web/20161220222638/https://www.drugs.com/pregnancy/sulfadiazine.html|archive-date=20 December 2016}}</ref> |
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| legal_status = Rx only |
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| routes_of_administration = Topical cream, by mouth |
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<!--Pharmacokinetic data--> |
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| bioavailability = ? |
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| protein_bound = 38-48%<ref name=AHFS2016 /> |
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| metabolism = ] (])<ref name = AHFS2016 /> |
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| elimination_half-life = 7-17 hours <ref name = AHFS2016 /> |
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| excretion = Urine <ref name = AHFS2016 /> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 68-35-9 |
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| CAS_supplemental ={{CAS|547-32-0}} (sodium salt) |
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| ATC_prefix = J01 |
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| ATC_suffix = EC02 |
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| ATC_supplemental = {{ATCvet|J01|EQ10}} |
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| PubChem = 5215 |
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| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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| DrugBank = DB00359 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 5026 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = 0N7609K889 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D00587 |
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| KEGG = D00587 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 439 |
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<!--Chemical data--> |
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| C=10 | H=10 | N=4 | O=2 | S=1 |
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| C=10 | H=10 | N=4 | O=2 | S=1 |
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| melting_point = 252 |
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| molecular_weight = 250.278 g/mol |
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| melting_high = 256 |
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| bioavailability= ? |
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| metabolism = ? |
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| elimination_half-life= ? |
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| excretion = ? |
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| pregnancy_category = ? |
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| legal_status = Approved Drug |
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| routes_of_administration= Cream |
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}} |
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}} |
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'''Sulfadiazine''' is a ] ]. |
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<!-- Definition and medical uses --> |
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==Uses== |
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'''Sulfadiazine''' is an ].<ref name=AHFS2016>{{cite web|title=Sulfadiazine|url=https://www.drugs.com/monograph/sulfadiazine.html|publisher=The American Society of Health-System Pharmacists|access-date=8 December 2016|url-status=live|archive-url=https://web.archive.org/web/20161220223703/https://www.drugs.com/monograph/sulfadiazine.html|archive-date=20 December 2016}}</ref> Used together with ], a ] inhibitor, it is the treatment of choice for ].<ref name=WHO2008>{{cite book | title = WHO Model Formulary 2008 | year = 2009 | isbn = 9789241547659 | vauthors = ((World Health Organization)) | veditors = Stuart MC, Kouimtzi M, Hill SR | hdl = 10665/44053 | author-link = World Health Organization | publisher = World Health Organization |pages=126, 205 }}</ref> It is a second-line treatment for ], prophylaxis of ], ], ], and infections by '']''.<ref name=AHFS2016/> It is also used as adjunct therapy for chloroquine-resistant malaria and several forms of bacterial meningitis.<ref name=":0">{{Citation|title=Sulfadiazine|date=2012|url=http://www.ncbi.nlm.nih.gov/books/NBK548681/|work=LiverTox: Clinical and Research Information on Drug-Induced Liver Injury|place=Bethesda (MD)|publisher=National Institute of Diabetes and Digestive and Kidney Diseases|pmid=31643992|access-date=2021-12-27}}</ref> It is taken by mouth.<ref name=AHFS2016/> Sulfadiazine is available in multiple generic tablets of 500 mg. For urinary tract infections, the usual dose is 4 to 6 grams daily in 3 to 6 divided doses.<ref name=":0" /> |
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It eliminates ] that cause infections by stopping the production of ] inside the bacterial cell, and is commonly used to treat ]s (UTIs). |
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<!-- Side effects and mechanism --> |
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In combination, sulfadiazine and ], can be used to treat ], a disease caused by '']''. |
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Common side effects include nausea, diarrhea, headache, fever, rash, depression, and ].<ref name=AHFS2016/> It should not be used in people who have severe liver problems, kidney problems, or ].<ref name=WHO2008/> If used during ], it may increase the risk of ] in the baby.<ref name=AHFS2016/> While the company that makes it does not recommend use during ], use is believed to be safe if the baby is otherwise healthy.<ref name=pregnancy/> It is in the ] class of medications.<ref name=AHFS2016/> |
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<!-- Society and culture --> |
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Sulfadiazine was approved for medical use in the United States in 1941.<ref name=AHFS2016/><ref>{{cite web |title=Drugs@FDA: FDA Approved Drug Products |url=https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=reportsSearch.process&rptName=2&reportSelectMonth=8&reportSelectYear=1941&nav |website=www.accessdata.fda.gov |access-date=11 November 2018}}</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> Sulfadiazine is available as a ].<ref name=AHFS2016/> |
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==Medical uses== |
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It eliminates ] that cause infections by stopping the production of ] inside the bacterial cell, and is commonly used to treat ]s and burns. |
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In combination, sulfadiazine and pyrimethamine can be used to treat toxoplasmosis, the disease caused by '']''. |
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==Other uses== |
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Sulfadiazine is used in ] for ] and maintaining genetically manipulated cells.<ref name="Kobercová_2023 p. ">{{cite journal | vauthors = Kobercová E, Srba M, Fischer L | title = Sulfadiazine and phosphinothricin selection systems optimised for the transformation of tobacco BY-2 cells | journal = Plant Cell Reports | volume = 42 | issue = 3 | pages = 535–548 | date = March 2023 | pmid = 36609768 | doi = 10.1007/s00299-022-02975-7 | publisher = Springer Science and Business Media LLC | s2cid = 255501050 }}</ref> |
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==Mechanism of action== |
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Sulfadiazine works by inhibiting the enzyme ]. |
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==Side effects== |
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==Side effects== |
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Side effects reported for sulfadiazine include: ], ], ], and ]. |
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Side effects reported for sulfadiazine include ], ], ], gastrointestinal upset, rash and fever.<ref name=":0" /> |
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== Brand names == |
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== Brand names == |
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Lantrisul; Neotrizine; Sulfa-Triple #2; Sulfadiazine; Sulfaloid; Sulfonamides Duplex; Sulfose; Terfonyl; Triple Sulfa; Triple Sulfas; Triple Sulfoid |
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This drug is sold branded as Lantrisul, Neotrizine, Sulfa-Triple #2, Sulfadiazine, Sulfaloid, Sulfonamides Duplex, Sulfose, Terfonyl, Triple Sulfa, Triple Sulfas, and Triple Sulfoid. |
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==See also== |
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== See also == |
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* ] |
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* ] |
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== References == |
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{{Reflist}} |
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== External links == |
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== External links == |
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* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/sulfadiazine | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Sulfadiazine }} |
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* (patient information) |
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{{Sulfonamides and trimethoprim}} |
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{{Sulfonamides and trimethoprim}} |
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{{Antiprotozoal agent}} |
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{{Antiprotozoal agent}} |
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{{Portal bar|Medicine}} |
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{{antiinfective-drug-stub}} |
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