Merbromin

Last updated

Merbromin
Mercurochrome.png
Merbromin-3D-vdW.png
Merbromin-Anti-Infective.jpg
Names
IUPAC name
dibromohydroxymercurifluorescein
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.004.486 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 204-933-6
KEGG
PubChem CID
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 Yes check.svgY
    Key: SQFDQLBYJKFDDO-UHFFFAOYSA-K Yes check.svgY
  • 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 mass 750.658 g·mol−1
Appearancedark red liquid
Pharmacology
D08AK04 ( WHO )
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Toxic, dangerous for the environment

GHS-pictogram-pollu.svg GHS-pictogram-silhouette.svg GHS-pictogram-skull.svg GHS-pictogram-exclam.svg

GHS labelling:
GHS-pictogram-skull.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Danger
H300, H310, H330, H373, H410
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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, Denmark, or the United States, due to its mercury content. [1] [2]

Contents

Uses

Merbromin's best-known use is as a topical antiseptic to treat minor wounds, burns, and scratches. [3] It is also used in the antisepsis of the umbilical 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 distinctive carmine red, which can persist through repeated washings. Due to its persistence and to its 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. [6] 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 anionic character, it is chemically incompatible with acids, the majority of alkaloid salts and most local anesthetics. [7]

Mercurochrome

Merbromin is sold under the trade name Mercurochrome (in which the suffix "-chrome" denotes "color" [8] ). 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. [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 for mercury poisoning, the US 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 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. [10] In Canada, Jean Coutu Group markets a chlorhexidine solution under the name Mercurochrome. [11]

See also

Related Research Articles

A bactericide or bacteriocide, sometimes abbreviated Bcidal, is a substance which kills bacteria. Bactericides are disinfectants, antiseptics, or antibiotics. However, material surfaces can also have bactericidal properties based solely on their physical surface structure, as for example biomaterials like insect wings.

<span class="mw-page-title-main">Phenol</span> Organic compound (C6H5OH)

Phenol is an aromatic organic compound with the molecular formula C6H5OH. It is a white crystalline solid that is volatile. The molecule consists of a phenyl group bonded to a hydroxy group. Mildly acidic, it requires careful handling because it can cause chemical burns.

An antiseptic is an antimicrobial substance or compound that is applied to living tissue to reduce the possibility of sepsis, infection or putrefaction. Antiseptics are generally distinguished from antibiotics by the latter's ability to safely destroy bacteria within the body, and from disinfectants, which destroy microorganisms found on non-living objects.

<span class="mw-page-title-main">Sodium hypochlorite</span> Chemical compound (known in solution as bleach)

Sodium hypochlorite is an alkaline inorganic chemical compound with the formula NaOCl. It is commonly known in a dilute aqueous solution as bleach or chlorine bleach. It is the sodium salt of hypochlorous acid, consisting of sodium cations and hypochlorite anions.

<span class="mw-page-title-main">Mercury(II) chloride</span> Chemical compound known as corrosive sublimate

Mercury(II) chloride (or mercury bichloride, mercury dichloride), historically also known as sulema or corrosive sublimate, is the inorganic chemical compound of mercury and chlorine with the formula HgCl2, used as a laboratory reagent. It is a white crystalline solid and a molecular compound that is very toxic to humans. Once used as a treatment for syphilis, it is no longer used for medicinal purposes because of mercury toxicity and the availability of superior treatments.

<span class="mw-page-title-main">Benzalkonium chloride</span> Surfactant and antiseptic agent

Benzalkonium chloride, also known as alkyldimethylbenzylammonium chloride (ADBAC) and by the trade name Zephiran, is a type of cationic surfactant. It is an organic salt classified as a quaternary ammonium compound. ADBACs have three main categories of use: as a biocide, a cationic surfactant, and a phase transfer agent. ADBACs are a mixture of alkylbenzyldimethylammonium chlorides, in which the alkyl group has various even-numbered alkyl chain lengths.

ATC code D08Antiseptics and disinfectants is a therapeutic subgroup of the Anatomical Therapeutic Chemical Classification System, a system of alphanumeric codes developed by the World Health Organization (WHO) for the classification of drugs and other medical products. Subgroup D08 is part of the anatomical group D Dermatologicals.

Merthiolate refers to:

<span class="mw-page-title-main">Povidone-iodine</span> Antiseptic solution

Povidone-iodine (PVP-I), also known as iodopovidone, is an antiseptic used for skin disinfection before and after surgery. It may be used both to disinfect the hands of healthcare providers and the skin of the person they are caring for. It may also be used for minor wounds. It may be applied to the skin as a liquid, an ointment or a powder.

<span class="mw-page-title-main">Tin(II) chloride</span> Chemical compound

Tin(II) chloride, also known as stannous chloride, is a white crystalline solid with the formula SnCl2. It forms a stable dihydrate, but aqueous solutions tend to undergo hydrolysis, particularly if hot. SnCl2 is widely used as a reducing agent (in acid solution), and in electrolytic baths for tin-plating. Tin(II) chloride should not be confused with the other chloride of tin; tin(IV) chloride or stannic chloride (SnCl4).

<span class="mw-page-title-main">Sodium erythorbate</span> Chemical compound

Sodium erythorbate (C6H7NaO6) is a food additive used predominantly in meats, poultry, and soft drinks. Chemically, it is the sodium salt of erythorbic acid. When used in processed meat such as hot dogs and beef sticks, it increases the rate at which nitrite reduces to nitric oxide, thus facilitating a faster cure and retaining the pink coloring. As an antioxidant structurally related to vitamin C, it helps improve flavor stability and prevents the formation of carcinogenic nitrosamines. When used as a food additive, its E number is E316. The use of erythorbic acid and sodium erythorbate as a food preservative has increased greatly since the U.S. Food and Drug Administration banned the use of sulfites as preservatives in foods intended to be eaten fresh (such as ingredients for fresh salads) and as food processors have responded to the fact that some people are allergic to sulfites. It can also be found in bologna, and is occasionally used in beverages, baked goods, and potato salad. Sodium erythorbate is produced from sugars derived from different sources, such as beets, sugarcane, and corn. Sodium erythorbate is usually produced via a fermentation process from D-glucose by Pseudomonas fluorescens bacteria. Most syntheses proceed through the 2-keto-D-gluconic acid intermediate. An urban myth claims that sodium erythorbate is made from ground earthworms; however, there is no truth to the myth. It is thought that the origin of the legend comes from the similarity of the chemical name to the words earthworm and bait.

<span class="mw-page-title-main">Hand sanitizer</span> Alternative to hand washing

Hand sanitizer is a liquid, gel, or foam used to kill viruses, bacteria, and other microorganisms on the hands. It can also come in the form of a cream, spray, or wipe. While hand washing with soap and water is generally preferred, hand sanitizer is a convenient alternative in settings where soap and water are unavailable. However, it is less effective against certain pathogens like norovirus and Clostridioides difficile and cannot physically remove harmful chemicals. Improper use, such as wiping off sanitizer before it dries, can also reduce its effectiveness, and some sanitizers with low alcohol concentrations are less effective. Additionally, frequent use of hand sanitizer may disrupt the skin's microbiome and cause dermatitis.

<span class="mw-page-title-main">Organomercury chemistry</span> Group of chemical compounds containing mercury

Organomercury chemistry refers to the study of organometallic compounds that contain mercury. Typically the Hg–C bond is stable toward air and moisture but sensitive to light. Important organomercury compounds are the methylmercury(II) cation, CH3Hg+; ethylmercury(II) cation, C2H5Hg+; dimethylmercury, (CH3)2Hg, diethylmercury and merbromin ("Mercurochrome"). Thiomersal is used as a preservative for vaccines and intravenous drugs.

<span class="mw-page-title-main">Benzethonium chloride</span> Chemical compound

Benzethonium chloride, also known as hyamine is a synthetic quaternary ammonium salt. This compound is an odorless white solid, soluble in water. It has surfactant, antiseptic, and anti-infective properties and it is used as a topical antimicrobial agent in first aid antiseptics. It is also found in cosmetics and toiletries such as soap, mouthwashes, anti-itch ointments, and antibacterial moist towelettes. Benzethonium chloride is also used in the food industry as a hard surface disinfectant.

<span class="mw-page-title-main">Mercuric amidochloride</span> Chemical compound

Mercuric amidochloride is an inorganic compound with the formula Hg(NH2)Cl.

<span class="mw-page-title-main">Acetic acid</span> Colorless and faint organic acid found in vinegar

Acetic acid, systematically named ethanoic acid, is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH. Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water. It has been used, as a component of vinegar, throughout history from at least the third century BC.

<span class="mw-page-title-main">Hydrochloric acid</span> Aqueous solution of hydrogen chloride

Hydrochloric acid, also known as muriatic acid or spirits of salt, is an aqueous solution of hydrogen chloride (HCl). It is a colorless solution with a distinctive pungent smell. It is classified as a strong acid. It is a component of the gastric acid in the digestive systems of most animal species, including humans. Hydrochloric acid is an important laboratory reagent and industrial chemical.

<span class="mw-page-title-main">Antoine Germain Labarraque</span> French chemist and pharmacist

Antoine Germain Labarraque was a French chemist and pharmacist, notable for formulating and finding important uses for "Eau de Labarraque" or "Labarraque's solution", a solution of sodium hypochlorite widely used as a disinfectant and deodoriser.

Aluminium triacetate, formally named aluminium acetate, is a chemical compound with composition Al(CH
3CO
2)
3. Under standard conditions it appears as a white, water-soluble solid that decomposes on heating at around 200 °C. The triacetate hydrolyses to a mixture of basic hydroxide / acetate salts, and multiple species co-exist in chemical equilibrium, particularly in aqueous solutions of the acetate ion; the name aluminium acetate is commonly used for this mixed system.

<span class="mw-page-title-main">Phenylmercuric nitrate</span> Organomercury compound with powerful antiseptic and antifungal effects

Phenylmercuric nitrate is an organomercury compound with powerful antiseptic and antifungal effects. It was once commonly used as a topical solution for disinfecting wounds, but as with all organomercury compounds it is highly toxic, especially to the kidneys, and is no longer used in this application. However it is still used in low concentrations as a preservative in eye drops for ophthalmic use, making it one of the few organomercury derivatives remaining in current medical use.

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. ↑ "Prospecto autorizado Mercromina Film ®" (PDF). Retrieved 15 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. Retrieved 11 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 . Retrieved 8 July 2022.
  10. ↑ "Mercuroclear MSDS" (PDF). Humco. Archived from the original (PDF) on 3 March 2016.
  11. ↑ "Antiseptique solution de premiers soins sans mercure, 25 ml – Personnelle : Désinfectant". Archived from the original on 2 April 2019. Retrieved 2 April 2019.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.