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Merbromin

From Wikipedia, the free encyclopedia

Organomercuric antiseptic for external use on minor cuts
Merbromin
Names
IUPAC name
dibromohydroxymercurifluorescein
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.004.486Edit this at Wikidata
EC Number
  • 204-933-6
KEGG
UNII
  • InChI=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 checkY
    Key: SQFDQLBYJKFDDO-UHFFFAOYSA-K checkY
  • 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
    Key: SQFDQLBYJKFDDO-ISOIBTJNAR
  • [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
Properties
C20H8Br2HgNa2O6
Molar mass750.658 g·mol−1
Appearancedark red liquid
Pharmacology
D08AK04 (WHO)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Toxic, dangerous for the environment

GHS labelling:
GHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
Danger
H300,H310,H330,H373,H410
P260,P264,P273,P280,P284,P301+P310
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Merbromin (marketed asMercurochrome,Merbromine,Mercurocol,Sodium mercurescein,Asceptichrome,Supercrome,Brocasept andCinfacromin) is anorganomercuricdisodiumsaltcompound used as atopicalantiseptic for minor cuts and scrapes and as a biologicaldye. Readily available in most countries, it is no longer sold in Switzerland, Brazil, France, Iran, Germany, Denmark, or the United States, due to itsmercury content.[1][2]

Uses

[edit]

Merbromin's best-known use is as a topicalantiseptic to treat minor wounds, burns, and scratches.[3] It is also used in the antisepsis of theumbilical cord,[4] and the antisepsis of wounds with inhibited scar formation, such as neuropathic ulcers and diabetic foot sores.[5] When applied on a wound, it stains the skin a distinctivecarmine red, which can persist through repeated washings. Due to its persistence and to itslethality 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.[6] Consequently, its use in the United States has been superseded by other agents (e.g.,povidone iodine,benzalkonium chloride,chloroxylenol).

Synthesis

[edit]

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 itsanionic character, it is chemically incompatible with acids, the majority of alkaloid salts and most local anesthetics.[7]

Mercurochrome

[edit]

Merbromin is sold under the trade name Mercurochrome (in which the suffix "-chrome" denotes "color"[8]). The name is also commonly used forover-the-counter antisepticsolutions consisting of merbromin (typically at 2% concentration) dissolved in eitherethyl alcohol (tincture) or water (aqueous).

Its antiseptic qualities were discovered in 1918 byHugh H. Young, a physician atJohns Hopkins Hospital.[9] 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 formercury poisoning, theUS Food and Drug Administration (FDA) reclassified merbromin from "generally recognized as safe" to "untested," effectively halting its distribution within the United States.[1] Sales were subsequently halted in Brazil (2001), Germany (2003),[2] and France (2006).[citation needed] It remains readily available in most other countries.[citation needed]

Within the United States, products such asHumco Mercuroclear ("Aqueous solution ofbenzalkonium chloride and lidocaine hydrochloride") play on the brand recognition history of Mercurochrome but substitute other ingredients with similar properties.[10] In Canada,Jean Coutu Group markets achlorhexidine solution under the name Mercurochrome.[11]

See also

[edit]

References

[edit]
  1. ^ab"Quantitative and Qualitative Analysis of Mercury Compounds in the List".Federal Food, Drug, and Cosmetic Act (FD&C Act).U.S. Food and Drug Administration. 30 April 2009.
  2. ^ab"Merbromin im Spiegel der Expertenmeinungen".[idiomatically: Merbromin in Light of Expert Opinion]. 22 September 2003.
  3. ^"Prospecto autorizado Mercromina Film ®"(PDF). Retrieved15 May 2013.[permanent dead link]
  4. ^Sellares Casas, E; et al. "Eficacia de una aplicación frente a 3 de merbromina en el tiempo de caída del cordón".Acta Pediátrica Española.60 (9).
  5. ^Gaitan Enríquez, J (September 1997). "Merbromina como tratamiento de elección en úlceras de pie diabético".Clínica Rural.497.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.
  6. ^"Status of Certain Additional Over-the-Counter Drug Category II and III Active Ingredients".Federal Register.63 (77). 22 April 1998.
  7. ^Budavary, Susan, ed. (1989).The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals (11 ed.). Rahway, New Jersey, USA.: Merck & Co.ISBN 091191028X.
  8. ^"Mercurochrome".Trésor de la Langue Française informatisé (in French). Centre National de Ressources Textuelles et Lexicales. Retrieved11 April 2020.
  9. ^Young, Hugh (15 November 1919)."A New Germicide for Use in the Genito-Urinary Tract: Mercurochrome-220".Journal of the American Medical Association.73 (20):1483–1491.doi:10.1001/jama.1919.02610460001001. Retrieved8 July 2022.
  10. ^"Mercuroclear MSDS"(PDF). Humco. Archived fromthe original(PDF) on 3 March 2016.
  11. ^"Antiseptique solution de premiers soins sans mercure, 25 ml – Personnelle : Désinfectant". Archived fromthe original on 2 April 2019. Retrieved2 April 2019.
Mercury(I)
Mercury(II)
Organomercury
compounds
Mercury(IV)
Amalgams
Mercury cations
Acridine derivatives
Biguanides andamidines
Phenol and derivatives
Nitrofuran derivatives
Iodine products
Quinoline derivatives
Quaternary ammonium compounds
Mercurial products
Silver compounds
Alcohols
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