bretylium

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 456485013

| IUPAC_name = N-(2-bromobenzyl)-N,N-dimethylethanaminium

| image = Bretylium.svg

| image2 = Bretylium 3D BS.png

| tradename =

| MedlinePlus = a682861

| pregnancy_AU = C

| pregnancy_US = C

| legal_US = Rx-only

| routes_of_administration = IV, IM

| bioavailability = NA

| protein_bound = NA

| metabolism = None

| elimination_half-life = 7-8 hours

| excretion = Renal

| IUPHAR_ligand = 7130

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 59-41-6

| ATC_prefix = C01

| ATC_suffix = BD02

| ATC_supplemental =

| PubChem = 2431

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB01158

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 2337

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = RZR75EQ2KJ

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = C06855

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 3172

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1199080

| C=11 | H=17 | Br=1 | N=1| charge = +

| smiles = Brc1ccccc1C[N+](CC)(C)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C11H17BrN/c1-4-13(2,3)9-10-7-5-6-8-11(10)12/h5-8H,4,9H2,1-3H3/q+1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = AAQOQKQBGPPFNS-UHFFFAOYSA-N

}}

Bretylium (also bretylium tosylate) is an antiarrhythmic agent.{{cite journal | vauthors = Tiku PE, Nowell PT | title = Selective inhibition of K⁺-stimulation of Na,K-ATPase by bretylium | journal = British Journal of Pharmacology | volume = 104 | issue = 4 | pages = 895–900 | date = December 1991 | pmid = 1667290 | pmc = 1908819 | doi = 10.1111/j.1476-5381.1991.tb12523.x }} It blocks the release of noradrenaline from nerve terminals. In effect, it decreases output from the peripheral sympathetic nervous system. It also acts by blocking K⁺ channels and is considered a class III antiarrhythmic. The dose is 5–10 mg/kg and side effects are high blood pressure followed by low blood pressure and ventricular ectopy.

Originally introduced in 1959 for the treatment of hypertension.{{cite journal | vauthors = Harington M | title = The drug treatment of hypertension. The results of drug treatment | journal = Proceedings of the Royal Society of Medicine | volume = 55 | pages = 283–6 | date = April 1962 | issue = 4 | pmid = 13904707 | pmc = 1896727 }} Its use as an antiarrhythmic for ventricular fibrillation was discovered and patented by Marvin Bacaner in 1969 at the University of Minnesota.{{cite patent| url=http://www.google.com/patents/US3441649 |title= Suppression of cardiac ventricular fibrillation and cardiac arrhythmias with bretylium tosylate | country= US |number= 3441649 |status= |pubdate= |gdate= |fdate= |pridate= 1966-08-18 |inventor= Marvin B Bacaner |invent1= |invent2= |assign1= University of Minnesota|assign2= |class= }}

The American Heart Association removed bretylium from their 2000 ECC/ACC guidelines due to its unproven efficacy and ongoing supply problems. Many have cited these supply problems as an issue of raw materials needed in the production of Bretylium. By the release of the AHA 2005 ECC/ACC guidelines there is no mention of Bretylium and it is virtually unavailable throughout most of the world.{{cite book |last= Khan |first= M. Gabriel |date= December 14, 2005 |title= Encyclopedia of Heart Diseases |url= https://books.google.com/books?id=xco9aJ_Y9XIC&q=bretylium+raw+materials&pg=PA221 |publisher= Academic Press |page= 221 |isbn= 978-0-12-406061-6 |access-date=2015-07-01 }}{{EMedicine|article|770542|Hypothermia|treatment}}

On June 8, 2011 bretylium tosylate was announced as unavailable in the US after request of Hospira Inc. to withdraw its NDA from the market. Bretylium will remain on the FDA's discontinued drug list since its withdrawal was not the result of a safety or effectiveness concern.{{cite web| url= https://www.federalregister.gov/articles/2011/12/19/2011-32367/determination-that-bretylium-tosylate-injection-50-milligramsmilliliter-was-not-withdrawn-from-sale| via= federalregister.gov| date= December 19, 2011| title= Determination that Bretylium Tosylate Injection, 50 Milligrams/Milliliter, Was Not Withdrawn From Sale for Reasons of Safety or Effectiveness| publisher= Food and Drug Administration| pages= 78669–70 | access-date= February 22, 2018}} {{Federal Register|76|78669}} In mid 2019, it was reintroduced. {{CN|date=January 2024}}