Merbromin: Difference between revisions

{{Use dmy dates|date=June 2021}}

{{short description|Organomercuric antiseptic for external use on minor cuts}}

|Verifiedfields = changed

|Watchedfields = changed

|verifiedrevid = 444787469

|ImageFile = Mercurochrome.png

|ImageFile1 = Merbromin-3D-vdW.png

|ImageFile2 = Merbromin-Anti-Infective.jpg

|IUPACName = dibromohydroxymercurifluorescein

|Section1={{Chembox Identifiers

|CASNo_Ref = {{cascite|correct|??}}

|CASNo = 129-16-8

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

|ChemSpiderID = 10808965

|ChEMBL_Ref = {{ebicite|correct|EBI}}

|ChEMBL = 2097077

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

|ChEBI = 6763

|DrugBank = DB13392

|PubChem = 8505

|EINECS = 204-933-6

|KEGG_Ref = {{keggcite|correct|kegg}}

|KEGG = D00861

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

|UNII = M0T18YH28D

|InChI = 1/C20H9Br2O5.Hg.2Na.H2O/c21-13-5-11-17(7-15(13)23)27-18-8-16(24)14(22)6-12(18)19(11)9-3-1-2-4-10(9)20(25)26;;;;/h1-7,24H,(H,25,26);;;;1H2/q;3*+1;/p-3/rC20H10Br2HgO6.2Na/c21-12-5-10-15(7-14(12)24)29-19-11(6-13(22)18(25)17(19)23-28)16(10)8-3-1-2-4-9(8)20(26)27;;/h1-7,25,28H,(H,26,27);;/q;2*+1/p-2

|InChIKey = SQFDQLBYJKFDDO-ISOIBTJNAR

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

|StdInChI = 1S/C20H9Br2O5.Hg.2Na.H2O/c21-13-5-11-17(7-15(13)23)27-18-8-16(24)14(22)6-12(18)19(11)9-3-1-2-4-10(9)20(25)26;;;;/h1-7,24H,(H,25,26);;;;1H2/q;3*+1;/p-3

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

|StdInChIKey = SQFDQLBYJKFDDO-UHFFFAOYSA-K

|SMILES = [Na+].[Na+].[O-]C(=O)c4ccccc4C=1c3cc(Br)c([O-])c([Hg]O)c3O/C/2=C/C(=O)C(/Br)=C\C=1\2

|Section2={{Chembox Properties

|C=20 | H=8 | Br=2 | Hg=1 | Na=2 | O=6

|Appearance = dark red liquid

}}

|Section3={{Chembox Pharmacology

|ATCCode_prefix = D08

|ATCCode_suffix = AK04

}}

|Section4={{Chembox Hazards

|MainHazards = Toxic, dangerous for the environment

[[File:GHS-pictogram-pollu.svg|50px]] [[File:GHS-pictogram-silhouette.svg|50px]] [[File:GHS-pictogram-skull.svg|50px]] [[File:GHS-pictogram-exclam.svg|50px]]

|GHSPictograms = {{GHS06}}{{GHS08}}{{GHS09}}

|GHSSignalWord = Danger

|HPhrases = {{H-phrases|300|310|330|373|410}}

|PPhrases = {{P-phrases|260|264|273|280|284|301+310}}

}}

}}

'''Merbromin''' (marketed as '''Mercurochrome''', '''Merbromine''', '''Mercurocol''', '''Sodium mercurescein''', '''Asceptichrome''', '''Supercrome''', '''Brocasept''' and '''Cinfacromin''') is an [[organomercury|organomercuric]] [[sodium|disodium]] [[Salt (chemistry)|salt]] [[Chemical compound|compound]] used as a [[topical]] [[antiseptic]] for minor cuts and scrapes and as a biological [[dye]]. Readily available in most countries, it is no longer sold in Switzerland, Brazil, France, Iran, Germany, Denmark, or the United States, due to its [[Mercury (element)|mercury]] content.<ref name="us" /><ref name="de" />

Merbromin's best-known use is as a topical [[antiseptic]] to treat minor wounds, burns, and scratches.<ref>{{Cite web |title=Prospecto autorizado Mercromina Film ® |url=http://www.aemps.es/cima/especialidad.do?metodo=verFichaWordPdf&codigo=49319&formato=pdf&formulario=PROSPECTOS&file=prospecto.pdf |access-date=15 May 2013}}{{dead link|date=January 2018 |bot=InternetArchiveBot |fix-attempted=yes }}</ref> It is also used in the antisepsis of the [[umbilical cord]],<ref>{{Cite journal |last=Sellares Casas |first=E |display-authors=etal |title=Eficacia de una aplicación frente a 3 de merbromina en el tiempo de caída del cordón |journal=Acta Pediátrica Española |volume=60 |issue=9}}</ref> and the antisepsis of wounds with inhibited scar formation, such as neuropathic ulcers and diabetic foot sores.<ref>{{Cite journal |last=Gaitan Enríquez |first=J |date=September 1997 |title=Merbromina como tratamiento de elección en úlceras de pie diabético |journal=Clínica Rural |volume=497 |quote=Se ha estudiado en 72 pacientes la eficacia de la merbromina comparativamente con la clorhexidina como antisépticos usados en la curación de múltiples afecciones en el pie diabético. Con el uso de merbromina se consigue disminuir apreciablemente el tiempo de cicatrización de las heridas, y se ha observado también una ausencia de complicaciones en los casos estudiados.}}</ref> When applied on a wound, it stains the skin a distinctive [[carmine]] red, which can persist through repeated washings. Due to its persistence and to its [[antimicrobial|lethality to bacteria]], Merbromin is useful on infections of the fingernail or toenail.

In 1998, the U.S. Food and Drug Administration reclassified merbromin from "generally recognized as safe" to "untested," due to a lack of recent studies or updated supporting information.<ref>{{Cite journal |date=22 April 1998 |title=Status of Certain Additional Over-the-Counter Drug Category II and III Active Ingredients |url=https://www.federalregister.gov/documents/1998/04/22/98-10578/status-of-certain-additional-over-the-counter-drug-category-ii-and-iii-active-ingredients |journal=Federal Register |volume=63 |ref=21 CFR part 310, 63 FR 19799 |number=77}}</ref> Consequently, its use in the United States has been superseded by other agents (e.g., [[povidone iodine]], [[benzalkonium chloride]], [[chloroxylenol]]).

==Synthesis==

Merbromin is synthesized by combining dibromofluorescein with mercuric acetate and sodium hydroxide or, alternatively, through action of the mercuric acetate upon (or combining with) sodium dibromofluorescein.  Because of its [[Ion#Anions and cations|anionic]] character, it is chemically incompatible with acids, the majority of alkaloid salts and most local anesthetics.<ref>{{Cite book |url=https://archive.org/details/merckindexency00buda |title=The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals |date=1989 |publisher=Merck & Co |isbn=091191028X |editor-last=Budavary |editor-first=Susan |edition=11 |location=Rahway, New Jersey, USA. |url-access=registration}}</ref>

Merbromin is sold under the trade name Mercurochrome (in which the suffix "-chrome" denotes "color"<ref>{{Cite web |title=Mercurochrome |url=https://www.cnrtl.fr/definition/mercurochrome |access-date=11 April 2020 |website=Trésor de la Langue Française informatisé |publisher=Centre National de Ressources Textuelles et Lexicales |language=fr}}</ref>). The name is also commonly used for [[Over-the-counter drug|over-the-counter]] antiseptic [[Solution (chemistry)|solution]]s consisting of merbromin (typically at 2% concentration) dissolved in either [[ethanol|ethyl alcohol]] ([[tincture]]) or water ([[aqueous solution|aqueous]]).

Its antiseptic qualities were discovered in 1918 by [[Hugh H. Young]], a physician at [[Johns Hopkins Hospital]].<ref>{{Cite journal |last=Young |first=Hugh |date=November 15, 1919 |title=A New Germicide for Use in the Genito-Urinary Tract: Mercurochrome-220 |url=https://archive.org/details/pt02journalamericanm73ameruoft/page/1482/mode/2up |journal=Journal of the American Medical Association |volume=73 |issue=20 |pages=1483–1491 |doi=10.1001/jama.1919.02610460001001 |access-date=July 8, 2022}}</ref> The chemical soon became popular among parents and physicians for everyday antiseptic uses, in part because the dye component made it easy to see where the antiseptic had been applied.

On 19 October 1998, citing potential for [[mercury poisoning]], the [[Food and Drug Administration (United States)|US Food and Drug Administration]] (FDA) reclassified merbromin from "generally recognized as safe" to "untested," effectively halting its distribution within the United States.<ref name="us">{{Cite web |date=30 April 2009 |title=Quantitative and Qualitative Analysis of Mercury Compounds in the List |url=https://www.fda.gov/RegulatoryInformation/LawsEnforcedbyFDA/SignificantAmendmentstotheFDCAct/FDAMA/ucm100219.htm |website=Federal Food, Drug, and Cosmetic Act (FD&C Act) |publisher=[[U.S. Food and Drug Administration]]}}</ref> Sales were subsequently halted in Brazil (2001), Germany (2003),<ref name="de">{{Cite web |date=22 September 2003 |title=Merbromin im Spiegel der Expertenmeinungen |url=https://www.pharmazeutische-zeitung.de/index.php?id=pharm2_39_2003 |website=[idiomatically: Merbromin in Light of Expert Opinion]}}</ref> and France (2006).{{cn|date=June 2023}} It remains readily available in most other countries.{{citation needed|date=July 2012}}

Within the United States, products such as [[Humco]] Mercuroclear ("Aqueous solution of [[Benzalkonium chloride/lidocaine|benzalkonium chloride and lidocaine hydrochloride]]") play on the brand recognition history of Mercurochrome but substitute other ingredients with similar properties.<ref>{{Cite web |title=Mercuroclear MSDS |url=http://www.humco.com/_pdfs/data-sheets/1637-Mercuroclear.pdf |url-status=dead |archive-url=https://web.archive.org/web/20160303224725/http://www.humco.com/_pdfs/data-sheets/1637-Mercuroclear.pdf |archive-date=3 March 2016 |publisher=Humco}}</ref> In Canada, [[Jean Coutu Group]] markets a [[chlorhexidine]] solution under the name Mercurochrome.<ref>{{Cite web |title=Antiseptique solution de premiers soins sans mercure, 25 ml – Personnelle : Désinfectant |url=https://www.jeancoutu.com/magasiner/produit/mercurochrome-sm-25-ml/792661/ |url-status=dead |archive-url=https://web.archive.org/web/20190402043629/https://www.jeancoutu.com/magasiner/produit/mercurochrome-sm-25-ml/792661/ |archive-date=2 April 2019 |access-date=2 April 2019}}</ref>

* [[Nitromersol]], an organomercury antiseptic and antifungal agent

* [[Phenylmercuric nitrate|Phenyl mercuric nitrate]]

{{Reflist}}

{{Mercury compounds}}

[[Category:Bromoarenes]]

[[Category:Organic sodium salts]]

[[Category:Triarylmethane dyes]]