Merbromin

Merbromin
Names
IUPAC name
dibromohydroxymercurifluorescein
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.004.486
Edit this at Wikidata
EC Number
  • 204-933-6
KEGG
PubChem CID
UNII
InChI
  • 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
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
Properties
Chemical formula
 C20H8Br2HgNa2O6
Molar mass 750.658 g·mol−1
Appearance dark red liquid
Pharmacology
D08AK04 (WHO)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic, dangerous for the environment

GHS labelling:
Pictograms
Signal word
 Danger
Hazard statements
 H300, H310, H330, H373, H410
Precautionary statements
 P260, P264, P273, P280, P284, P301+P310
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Merbromin (marketed as Mercurochrome, Merbromine, Mercurocol, Sodium mercurescein, Asceptichrome, Supercrome, Brocasept and Cinfacromin) is an organomercuric disodium salt 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, or the United States due to its mercury content.[1][2][3]

Uses

Merbromin's best-known use is as a topical antiseptic to treat minor wounds, burns, and scratches.[4] It is also used in the antisepsis of the umbilical cord[5] and the antisepsis of wounds with inhibited scar formation, such as neuropathic ulcers and diabetic foot sores.[6] 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 lethality to bacteria as an antiseptic, Merbromin is useful on infections of the fingernail or toenail.

The U.S. Food and Drug Administration in 1998 classified merbromin as not generally recognized as safe due to a lack of recent studies and updated supporting information.[7] In the United States, its use has thus been superseded by other agents (e.g., povidone iodine, benzalkonium chloride, chloroxylenol).

Merbromin is also used as a biological dye to mark tissue margins and as a metal dye in industrial dye penetrant inspection to detect metal fractures.

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 anionic character, it is chemically incompatible with acids (meaning that it can create dangerous exothermic or toxic gas reactions), the majority of alkaloid salts and most local anesthetics.[8]

Mercurochrome

Merbromin is sold under the trade name Mercurochrome (where the suffix "- chrome" denotes "color"[9]). The name is also commonly used for over-the-counter antiseptic solutions consisting of merbromin (typically at 2% concentration) dissolved in either ethyl alcohol (tincture) or water (aqueous).

Its antiseptic qualities were discovered in 1918 by Hugh H. Young, a physician at Johns Hopkins Hospital.[10] The chemical soon became popular among parents and physicians for everyday antiseptic uses.

On 19 October 1998, citing potential for mercury poisoning, the 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).[3] It is readily available in most other countries.

Within the United States, products such as Humco Mercuroclear ("Aqueous solution of benzalkonium chloride and lidocaine hydrochloride") play on the brand recognition history of Mercurochrome but substitute other ingredients with similar properties.[11] In Canada, Jean Coutu Group markets a chlorhexidine solution under the name Mercurochrome.[12]

See also

References

  1. 1 2 "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. 1 2 "Merbromin im Spiegel der Expertenmeinungen". [idiomatically: Merbromin in Light of Expert Opinion]. 22 September 2003.
  3. 1 2 fr:Merbromine
  4. ↑ "Prospecto autorizado Mercromina Film ®" (PDF). Retrieved 15 May 2013.
  5. ↑ 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).
  6. ↑ 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.
  7. ↑ "Status of Certain Additional Over-the-Counter Drug Category II and III Active Ingredients".{{cite web}}: CS1 maint: url-status (link)
  8. ↑ Budavary, Susan, ed. (1989). The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals (11 ed.). Rahway, New Jersey, USA.: Merck & Co. ISBN 091191028X.
  9. ↑ "Mercurochrome". Trésor de la Langue Française informatisé (in French). Centre National de Ressources Textuelles et Lexicales. Retrieved 11 April 2020.
  10. ↑ Wilner, I. (2006). The Man Time Forgot: A Tale of Genius, Betrayal, and the Creation of Time Magazine. Harper Collins. p. 230. ISBN 0-06-050549-4.
  11. ↑ "Mercuroclear MSDS" (PDF). Humco. Archived from the original (PDF) on 3 March 2016.
  12. ↑ "Antiseptique solution de premiers soins sans mercure, 25 ml – Personnelle : Désinfectant".
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