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Revision as of 16:11, 10 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank').← Previous edit		Latest revision as of 21:27, 10 March 2024 edit undoMaxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,043 edits ISBN formatted. Added the cs1 style template to denote Vancouver ("vanc") citation style, because references contain "vauthors" attribute to specify the list of authors. Added date. | Use this tool. Report bugs. | #UCB_Gadget
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			{{Short description|A loop diuretic}}
			{{cs1 config|name-list-style=vanc|display-authors=6}}
	{{Drugbox		{{Drugbox
	| verifiedrevid = 443669885		| verifiedrevid = 459985487
⚫	| IUPAC_name = 3-butylamino-4-phenoxy-5-sulfamoyl-benzoic acid
	| image = Bumetanide structure.svg		| image = Bumetanide structure.svg
	| width = 156		| width = 200
			| image2 = Bumetanide_ball-and-stick.png
			| width2 = 200
	<!--Clinical data-->		<!--Clinical data-->
	| tradename = Bumex		| tradename = Bumex, Burinex, others
	| Drugs.com = {{drugs.com|monograph|bumetanide}}		| Drugs.com = {{drugs.com|monograph|bumetanide}}
	| MedlinePlus = a684051		| MedlinePlus = a684051
			| DailyMedID = Bumetanide
	| pregnancy_AU = B3		| pregnancy_AU = B3
			| routes_of_administration = ], ], ]
	| pregnancy_US = C
		⚫	| ATC_prefix = C03
		⚫	| ATC_suffix = CA02
		⚫	| ATC_supplemental =
	| legal_AU = S4		| legal_AU = S4
	| legal_UK = POM		| legal_UK = POM
	| legal_US = Rx-only		| legal_US = Rx-only
	| routes_of_administration = oral
	<!--Pharmacokinetic data-->		<!--Pharmacokinetic data-->
	| bioavailability = almost complete (~80%)		| bioavailability = Almost complete (~80%)
	| protein_bound = 97%		| protein_bound = 97%
	| metabolism = hepatic		| metabolism = ]
	| elimination_half-life = ~0.8 hours		| elimination_half-life = ~0.8 hours
	| excretion = renal		| excretion = ]
	<!--Identifiers-->		<!--Identifiers-->
			| IUPHAR_ligand = 4837
	| CASNo_Ref = {{cascite|correct|CAS}}		| CAS_number_Ref = {{cascite|correct|??}}
	| CAS_number = 28395-03-1		| CAS_number = 28395-03-1
⚫	| ATC_prefix = C03
⚫	| ATC_suffix = CA02
⚫	| ATC_supplemental =
	| PubChem = 2471		| PubChem = 2471
	| DrugBank_Ref = {{drugbankcite|correct|drugbank}}		| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
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	<!--Chemical data-->		<!--Chemical data-->
		⚫	| IUPAC_name = 3-butylamino-4-phenoxy-5-sulfamoyl-benzoic acid
	| C=17 | H=20 | N=2 | O=5 | S=1		| C=17 | H=20 | N=2 | O=5 | S=1
	| molecular_weight = 364.417 g/mol
	| smiles = O=S(=O)(c2cc(cc(NCCCC)c2Oc1ccccc1)C(=O)O)N		| smiles = c1ccccc1Oc2c(NCCCC)cc(C(=O)O)cc2S(=O)(=O)N
	| InChI = 1/C17H20N2O5S/c1-2-3-9-19-14-10-12(17(20)21)11-15(25(18,22)23)16(14)24-13-7-5-4-6-8-13/h4-8,10-11,19H,2-3,9H2,1H3,(H,20,21)(H2,18,22,23)
	| InChIKey = MAEIEVLCKWDQJH-UHFFFAOYAE
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C17H20N2O5S/c1-2-3-9-19-14-10-12(17(20)21)11-15(25(18,22)23)16(14)24-13-7-5-4-6-8-13/h4-8,10-11,19H,2-3,9H2,1H3,(H,20,21)(H2,18,22,23)		| StdInChI = 1S/C17H20N2O5S/c1-2-3-9-19-14-10-12(17(20)21)11-15(25(18,22)23)16(14)24-13-7-5-4-6-8-13/h4-8,10-11,19H,2-3,9H2,1H3,(H,20,21)(H2,18,22,23)
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	| StdInChIKey = MAEIEVLCKWDQJH-UHFFFAOYSA-N		| StdInChIKey = MAEIEVLCKWDQJH-UHFFFAOYSA-N
	}}		}}
	<!-- FAIR USE of Bumetanide_Bumex .gif: see image description page at http://en.wikipedia.org/Image:Bumetanide_Bumex .gif for rationale -->
⚫	'''Bumetanide''' (trade names '''Bumex''' or '''Burinex''') is a ] of the sulfamyl category to treat ]. It is often used in people in whom high doses of ] are ineffective. It is marketed by ]. The main difference between the two substances is in ] and pharmacodynamic potency. Furosemide is incompletely absorbed in the intestine (60%), and there is substantial inter- and intraindividual differences in bioavailability (range 10-90%). Bumetanide is almost completely absorbed (80%), and the absorption is not altered when it is taken with food. It is said to be a more predictable diuretic, meaning that the predictable absorption is reflected in a more predictable effect.<ref name="Brunton, Laurence 2006">{{cite book |editor1-last=Brunton |editor1-first=Laurence |editor2-last=Lazo |editor2-first=John S. |editor3-last=Parker |editor3-first=Keith L. |year=2006 |title=Goodman & Gilman's The Pharmacological Basis of Therapeutics |location=New York |publisher=McGraw-Hill |isbn=0071422803 |edition=11th |pages=749–753 }}</ref>
			<!-- Definition and medical uses -->
	Bumetanide is 40 times more potent than furosemide (for patients with normal ]).<ref name="Brunton, Laurence 2006" />
			'''Bumetanide''', sold under the brand name '''Bumex''' among others, is a ] used to treat ] and ].<ref name=AHFS2019/> This includes swelling as a result of ], ], or ].<ref name=AHFS2019/> It may work for swelling when other medications have not.<ref name=AHFS2019/> For high blood pressure it is not a preferred treatment.<ref name=AHFS2019/> It is taken by mouth, or by ] or ].<ref name=AHFS2019>{{cite web |title=Bumetanide Monograph for Professionals |url=https://www.drugs.com/monograph/bumetanide.html |website=Drugs.com |publisher=American Society of Health-System Pharmacists |access-date=8 April 2019 |language=en}}</ref> Effects generally begin within an hour and last for about six hours.<ref name=AHFS2019/>
			<!-- Side effects and mechanism -->
⚫	In the brain, bumetanide blocks the ] cation-chloride co-transporter, and thus decreases internal chloride concentration in ]. In turn, this concentration change makes the action of ] more hyperpolarizing, which may be useful for treatment of ] ]s, that quite often are not responsive to traditional GABA-targeted treatment, such as ]. Bumetanide is therefore currently under evaluation as a prospective antiepileptic drug.<ref name="Kahle et al. 2006">{{cite journal |last=Kahle |first=K. T. |last2=Barnett |first2=S. M. |last3=Sassower |first3=K. C. |last4=Staley |first4=K. J. |title=Decreased Seizure Activity in a Human Neonate Treated With Bumetanide, an Inhibitor of the Na<sup>+</sup>–K<sup>+</sup>–2Cl<sup>−</sup> Cotransporter NKCC1 |journal=Journal of Child Neurology |volume=24 |issue=5 |pages=572–576 |doi=10.1177/0883073809333526 |year=2009 |pmid=19406757 }}</ref>
			Common side effects include dizziness, ], ], ], and ].<ref name=AHFS2019/> Other serious side effects may include ] and ].<ref name=AHFS2019/> Blood tests are recommended regularly for those on treatment.<ref name=AHFS2019/> Safety during ] and ] is unclear.<ref name=Preg2019>{{cite web |title=Bumetanide (Bumex) Use During Pregnancy |url=https://www.drugs.com/pregnancy/bumetanide.html |website=Drugs.com |access-date=8 April 2019 |language=en}}</ref> Bumetanide is a ] and works by decreasing the reabsorption of sodium by the kidneys.<ref name=BNF76>{{cite book|title=British national formulary : BNF 76|date=2018|publisher=Pharmaceutical Press|isbn=978-0-85711-338-2|pages=225–226|edition=76}}</ref><ref name=AHFS2019/>
			<!-- History and culture -->
	==Abuse==
			Bumetanide was patented in 1968 and came into medical use in 1972.<ref>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=978-3-527-60749-5 |page=458 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA458 |language=en}}</ref> It is on the ].<ref name="WHO22nd">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 22nd list (2021) | year = 2021 | hdl = 10665/345533 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2021.02 | hdl-access=free }}</ref> It is available as a ].<ref name=BNF76/> In 2020, it was the 270th most commonly prescribed medication in the United States, with more than 1{{nbsp}}million prescriptions.<ref>{{cite web | title = The Top 300 of 2020 | url = https://clincalc.com/DrugStats/Top300Drugs.aspx | website = ClinCalc | access-date = 7 October 2022}}</ref><ref>{{cite web | title = Bumetanide - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Bumetanide | access-date = 7 October 2022}}</ref>
	On October 24, 2008, ESPN reported a number of ] players were being suspended under the steroid policy as a result of taking bumetanide. The drug is often used for weight loss, but also to mask other drugs or steroids by helping to dilute the contents of the user's urine, yielding a lower concentration of filtered substances which may then go undetected.
			==Medical uses==
	Bumetanide was an undisclosed ] in the ] ] supplement ]. StarCaps was pulled off the market after the presence of the undisclosed ingredient was discovered by the ].
			It is used to treat ] and ].<ref name=AHFS2019/> This includes swelling as a result of ], ], or ].<ref name=AHFS2019/> For high blood pressure it is not a preferred treatment.<ref name=AHFS2019/> It is taken by mouth, or by ] or ].<ref name=AHFS2019/>
	==References==		==Side effects==
			Common side effects include dizziness, ], ], ], and ].<ref name=AHFS2019/> Other serious side effects may include ] and ].<ref name=AHFS2019/> A large observational study <ref>{{cite journal | vauthors = Strom BL, Schinnar R, Apter AJ, Margolis DJ, Lautenbach E, Hennessy S, Bilker WB, Pettitt D | title = Absence of cross-reactivity between sulfonamide antibiotics and sulfonamide nonantibiotics | journal = The New England Journal of Medicine | volume = 349 | issue = 17 | pages = 1628–1635 | date = October 2003 | pmid = 14573734 | doi = 10.1056/NEJMoa022963 | doi-access = free }}</ref> concluded that people with a sulfonamide antibiotic allergy may be allergic to sulfonamide non-antibiotics, such as bumetanide, but this is likely due to certain people being at an increased risk in general to developing allergic reactions rather than cross-reactivity between sulfonamide-containing drugs. In smaller studies, the lack of cross-reactivity between sulfonamide antibiotics and sulfonamide non-antibiotics has been demonstrated. <ref>{{cite journal | vauthors = Hemstreet BA, Page RL | title = Sulfonamide allergies and outcomes related to use of potentially cross-reactive drugs in hospitalized patients | journal = Pharmacotherapy | volume = 26 | issue = 4 | pages = 551–557 | date = April 2006 | pmid = 16553515 | doi = 10.1592/phco.26.4.551 | s2cid = 21612858 }}</ref><ref>{{cite journal | vauthors = Tornero P, De Barrio M, Baeza ML, Herrero T | title = Cross-reactivity among p-amino group compounds in sulfonamide fixed drug eruption: diagnostic value of patch testing | journal = Contact Dermatitis | volume = 51 | issue = 2 | pages = 57–62 | date = August 2004 | pmid = 15373844 | doi = 10.1111/j.0105-1873.2004.00274.x | s2cid = 10908796 }}</ref>
			Safety during ] and ] is unclear.<ref name=Preg2019/>
			== Pharmacology ==
			=== Pharmacodynamics ===
			Bumetanide is a loop diuretic and works by decreasing the reabsorption of sodium by the kidneys.
		⚫	The main difference between bumetanide and furosemide is in their ] and potency. About 60% of furosemide is absorbed in the intestine, and there are substantial inter- and intraindividual differences in bioavailability (range 10-90%). About 80% of bumetanide is absorbed, and its absorption does not change when it is taken with food. It is said to be a more predictable diuretic, meaning that the predictable absorption is reflected in a more predictable effect.<ref name="Brunton, Laurence 2006">{{cite book | veditors = Brunton L, Lazo JS, Parker KL |year=2006 |title=Goodman & Gilman's The Pharmacological Basis of Therapeutics |location=New York |publisher=McGraw-Hill |isbn=0-07-142280-3 |edition=11th |pages=749–753 }}</ref> Bumetanide is 40 times more potent than furosemide for people with normal ].<ref name="Brunton, Laurence 2006" />
			==Synthesis==
			Bumetanide is synthesized from ].<ref name="Ger. Pat. 19 64 503.5">{{cite patent | country = DE | number = 1964504 | title = Arzneimittelzubereitung mit einem Gehalt an 3-Butylamino-4-phenoxy-5-sulfamyl-benzoesaeure und deren Salzen | inventor = Feit PW | assign1 = Leo Pharma Products, Ltd. | gdate = 9 July 1970 }}</ref><ref name="Feit">{{cite journal | vauthors = Feit PW | title = Aminobenzoic acid diuretics. 2. 4-Substituted-3-amino-5-sulfamylbenzoic acid derivatives | journal = Journal of Medicinal Chemistry | volume = 14 | issue = 5 | pages = 432–9 | date = May 1971 | pmid = 5117690 | doi = 10.1021/jm00287a014 }}</ref><ref>{{cite patent | country = US | number = 3634583 |title=Pharmaceutical composition for the treatment of oedematous conditions and hypertension | inventor = Feit PW | assign1 = Leo Pharmaceutical Products Ltd AS | gdate = 11 January 1972 }}</ref><ref>{{cite patent | country = US | number = 4082851 | title = Sulphonamides, compositions containing the same and methods for using the same in the treatment of hypertension or odemeas | inventor = Feit PW, Nielsen OB, Bruun H, Bretting CA | assign1 = Leo Pharmaceutical Products Ltd AS | gdate = 4 April 1978 }}</ref> In the first stage of synthesis, it undergoes sulfonylchlorination by ], forming 4-chloro-3-chlorosulfonylbenzoic acid, which is further nitrated with nitric acid to 4-chloro-3-chlorosulfonyl-5-nitrobenzoic acid. Reacting this with ammonia gives 5-aminosulfonyl-4-chloro-3-nitrobenzoic acid, which when reacted with sodium phenolate is transformed into 5-amino-sulfonyl-3-nitro-5-phenoxybenzoic acid. Reduction of the nitro group in this product by hydrogen using a palladium on carbon catalyst gives 3-amino-5-aminosulfonyl-5-phenoxybenzoic acid. Finally, reacting this with butyl alcohol in the presence of ], followed by treatment with sodium hydroxide to hydrolyze the butyl ester, gives the desired bumetanide.
			:]
			{{Clear}}
			== Society and culture ==
			It 2008, ESPN reported that four ] players were being suspended under the steroid policy as a result of taking bumetanide.<ref>{{cite web|title=McAllister, Smith, Grant, Texans' Pittman among players testing positive|url=http://www.espn.com/nfl/news/story?id=3661845|website=ESPN.com|publisher=ESPN|access-date=June 6, 2017|date=October 26, 2008}}</ref>
			Bumetanide was an undisclosed ] in the ] ] supplement ], which was removed from the market after its presence was discovered by the United States ].<ref>{{cite web| author = Food and Drug Administration Office of Criminal Investigations | work = U.S. Department of Justice Press Release | title = Pills Sold Throughout the United States Contained an Undisclosed Prescription Drug Banned By the National Football League|url=https://www.fda.gov/iceci/criminalinvestigations/ucm391757.htm |publisher=United States Food and Drug Administration|access-date=June 6, 2017|date=March 26, 2014}}</ref>
			==Research==
		⚫	In the brain, bumetanide blocks the ] cation-chloride co-transporter, and thus decreases internal chloride concentration in ]. In turn, this concentration change makes the action of ] more hyperpolarizing, which may be useful for treatment of ] ]s, which quite often are not responsive to traditional GABA-targeted treatment, such as ]. Bumetanide is therefore under evaluation as a prospective antiepileptic drug.<ref>{{cite journal | vauthors = Löscher W, Puskarjov M, Kaila K | title = Cation-chloride cotransporters NKCC1 and KCC2 as potential targets for novel antiepileptic and antiepileptogenic treatments | journal = Neuropharmacology | volume = 69 | pages = 62–74 | date = June 2013 | pmid = 22705273 | doi = 10.1016/j.neuropharm.2012.05.045 | s2cid = 22267675 }}</ref>
			The drug has also been studied as a treatment for ].<ref>{{cite journal | vauthors = Sprengers JJ, van Andel DM, Zuithoff NP, Keijzer-Veen MG, Schulp AJ, Scheepers FE, Lilien MR, Oranje B, Bruining H | title = Bumetanide for Core Symptoms of Autism Spectrum Disorder (BAMBI): A Single Center, Double-Blinded, Participant-Randomized, Placebo-Controlled, Phase-2 Superiority Trial | journal = Journal of the American Academy of Child and Adolescent Psychiatry | date = July 2020 | volume = 60 | issue = 7 | pages = 865–876 | pmid = 32730977 | doi = 10.1016/j.jaac.2020.07.888 | quote = Recent trials have indicated positive effects of bumetanide in autism spectrum disorder (ASD). | doi-access = free }}</ref><ref>{{cite journal | vauthors = Zhang L, Huang CC, Dai Y, Luo Q, Ji Y, Wang K, Deng S, Yu J, Xu M, Du X, Tang Y, Shen C, Feng J, Sahakian BJ, Lin CP, Li F | title = Symptom improvement in children with autism spectrum disorder following bumetanide administration is associated with decreased GABA/glutamate ratios | journal = Translational Psychiatry | volume = 10 | issue = 1 | pages = 9 | date = January 2020 | pmid = 32066666 | pmc = 7026137 | doi = 10.1038/s41398-020-0692-2 | doi-access = free }}</ref>
			== References ==
	{{reflist}}		{{reflist}}
	==External links==		== External links ==
			* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/bumetanide | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Bumetanide }}
	* (manufacturer's website)
	* (patient information)
⚫	{{Symporter inhibitors}}
	{{Diuretics}}		{{Diuretics}}
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			* {{cite web | url = https://www.helsinki.fi/en/hilife-helsinki-institute-life-science/news/repurposed-drug-boosts-positive-effect-microglia-improve-cognitive-performance-following-brain-trauma | title = Repurposed drug boosts the positive effect of microglia to improve cognitive performance following brain trauma | date = 24 May 2023 }}
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