Sulfacetamide

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Sulfacetamide
Sulfacetamide.svg
Sulfacetamide molecule ball.png
Clinical data
Trade names Bleph-10
AHFS/Drugs.com Monograph
MedlinePlus a601114
ATC code
Pharmacokinetic data
Elimination half-life 7 to 12.8 hours
Identifiers
  • N-[(4-aminophenyl)sulfonyl]acetamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.005.128 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C8H10N2O3S
Molar mass 214.24 g·mol−1
3D model (JSmol)
Melting point 182 to 184 °C (360 to 363 °F)
  • O=S(=O)(c1ccc(N)cc1)NC(=O)C
  • InChI=1S/C8H10N2O3S/c1-6(11)10-14(12,13)8-4-2-7(9)3-5-8/h2-5H,9H2,1H3,(H,10,11) Yes check.svgY
  • Key:SKIVFJLNDNKQPD-UHFFFAOYSA-N Yes check.svgY
   (verify)
Pure Sulfacetamide sodium salt is a white or slightly yellow crystalline powder Sulfacetamide substance photo.jpg
Pure Sulfacetamide sodium salt is a white or slightly yellow crystalline powder

Sulfacetamide is a sulfonamide antibiotic commonly used in the treatment of bacterial infections, particularly those affecting the eyes and skin. It functions by inhibiting the synthesis of folic acid in bacteria, which is essential for their growth and reproduction, thereby exerting a bacteriostatic effect. Available in various forms, including eye drops, topical solutions, and creams, sulfacetamide is often prescribed for conditions such as conjunctivitis, seborrheic dermatitis, and acne vulgaris. Its efficacy, coupled with a relatively low risk of side effects, makes it a widely utilized agent in both ophthalmic and dermatologic care.

Contents

Medical uses

Sulfacetamide is a sulfonamide antibiotic, that is used as a cream to treat skin infections and as eye drops to treat eye infections. On the skin it is used to treat acne and seborrheic dermatitis. [1] In cream form it is used to treat bacterial infections on the skin. It can also be used orally to treat urinary tract infections. [2] It kills the bacteria by restricting the production of folic acid, which is essential for bacterial growth. [3] It mainly inhibits the multiplication of bacteria as it acts in a competitive inhibitor.

Sulfacetamide 10% topical lotion, sold under the brand name Klaron or Ovace, is approved for the treatment of acne and seborrheic dermatitis. [4] When combined with sulfur, it is sold under the brand names Plexion, Clenia, Prascion, and Avar, which contain 10% sulfacetamide and 5% sulfur. [5] [6] [7] [8]

Available forms

Sulfacetamide as a medicine is available as solution, eye drops, lotion, and powder. [9] It can also be found in the form of the sodium salt, sulfacetamide sodium. [10]

It is available in fixed-dose combinations with prednisolone. [11] [12]

Side effects

The most common side effects are irritation, stinging or burning of the skin. Other side effects include nausea, vomiting, dizziness, tiredness and headache. [2] There are however also severe side effects including severe allergic reactions, like (nettle) rash, itch, tightness in chest, difficult breathing and swelling in either the face, mouth, lips or tongue. Other severe side effects include bloody or severe diarrhea, fever, joint pain, red, blistered or swollen skin and stomach pain. [3] In the eye, it can cause conjunctivitis. There are also life-threatening conditions which can be produced by the antibiotic, like Stevens Johnson syndrome and Erythema multiforme. [13] Higher exposure can also cause unconsciousness. [2] One case showed that sulfacetamide eyedrops can very rarely cause life-threatening skin condition toxic epidermal necrolysis (TEN). [14] These are however not all side effects. For more information the health care provider can be contacted.

Sulfacetamide should not be used by individuals who have a sensitivity to sulfur or sulfa.

Toxicity

The acute oral toxicity (LD50) in a mouse is 16.5 g/kg. [2] [15] As this falls within Toxicity Category IV of the toxicity category rating for oral administration, it is practically non-toxic and also not an irritant when taken in orally. However, it is very hazardous in case of skin contact (irritant), ingestion and inhalation.

Research proved that it is more toxic in the presence of light than in the dark. Sulfacetamide is slightly irritant when UV-A light is present. In the presence of light sulfacetamide gets sensitized and degraded which might cause irritation which will lead to toxicity when it is used continuously. In the dark only slight irritation has been shown. Therefore it should be stored in the dark. [16]

There are no known carcinogenic and mutagenic effects. It has a moderate toxicity according to the Chemwatch hazard ratings. [17]

Pharmacology

Mechanisms of action

Sulfacetamide is a sulfonamide antibiotic. [1] Sulfonamides are synthetic bacteriostatic antibiotics, that are active against gram-positive and gram-negative bacteria. It blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase. It is a competitive inhibitor of bacterial para-aminobenzoic acid (PABA). PABA is required for bacterial synthesis of folic acid and it is an essential component for bacterial growth. [2] The multiplication of bacteria is therefore inhibited by the action of sulfacetamide.

Sulfonamides are generally effective against most gram-positive and many gram-negative organisms. [18] Specifically enteric bacteria and other eubacteria are affected by the antibiotic as it kills the bacteria by restricting the production of folic acid, which is essential for their growth. [13] However strains of bacteria can be resistant to the antibiotic. If a bacterium is resistant to a sulfonamide, it is resistant to all the forms. Furthermore, sulfacetamide is toxic to soil organisms. [17]

Pharmacokinetics

Sulfacetamide is absorbed orally. The oral absorption of sulfacetamide is found to be 100% [13] and the plasma protein binding is 80–85%. In the liver it is metabolized to inactive metabolites. [19] Plasma half-life is 7 – 12.8 hours. [18]

Sulfonamides are usually metabolized by several oxidative pathways, acetylation, and conjugation with sulfate or glucuronic acid. [20] However, there are some differences in biotransformation between certain species. Acetylation, which reduces the solubility of sulfonamides, is for example poor developed in dogs. The acetylated, hydroxylated, and conjugated forms have little antibacterial activity. Furthermore, the hydroxylated and conjugated forms are less likely to precipitate in urine. The hydrolysis takes place by the action of amidases. [21]

It is excreted primarily in the urine. [19] Secretory routes of less significance are bile, feces, milk and sweat. [20] Glomerular filtration, active tubular secretion, and tubular reabsorption are the main processes involved.

Chemistry

Structure and chemical properties

These are organic compounds containing an benzenesulfonamide moiety with an amine group attached to the benzene ring. [2] The molecular formula is C8H10N2O3S. Its scientific name is N-(4-aminophenyl)sulfonylacetamide. At room temperature, it appears as a white powder. [18]

Degradation reactions and stability

Sulfacetamide is stable under normal temperatures and pressures. No dangerous reactions occur under known conditions of normal use. [22] It is an important bacteriostatic agent that is commonly used in human and veterinary medicine. Therefore it can accumulate in the environment (mostly surface water). [23]

It has a long lifetime in the environment so different degradation reactions are researched:

The photocatalytic degradation of sulfacetamide in water solutions during illumination of UV radiation with TiO2 was examined. It was found that sulfacetamide is resistant to biodegradation and that it is toxic to the green alga Chlorella vulgaris . It undergoes photocatalytic degradation and the toxicity of the intermediate products is significantly lower than the initial toxicity. The intermediates can be mineralized in contrast to sulfacetamide. [24]

Sulfonamide → organic intermediate products (degradation) (in presence of OH−). [24]

Oxidation of sulfacetamide by diperiodatocuperate(III) Sul2.png
Oxidation of sulfacetamide by diperiodatocuperate(III)

At higher temperatures sulfacetamide solutions degrade to its hydrolysed product, sulphanilamide with a first-order rate constant. [25]

Also oxidation of sulfacetamide by diperiodatocuperate(III) in an aqueous alkaline medium can occur. Copper(III) is used, as it is involved in many biological electron transfer reactions. [23]

The sulphanilamide can oxidise to a blue product with a first order reaction and it can form azo dye with a second order reaction. [26]

Synthesis

Sulfacetamide is synthesized either by direct alkylation of acetamide with 4-aminobenzenesulfonyl chloride, or by reacting 4-aminobenzenesulfonamide with acetic anhydride and subsequent selective, reductive deacylation of the resultant acetamide using a system of zinc-sodium hydroxide. [27] [28]

Research

Sulfacetamide has been investigated for use in the treatment of pityriasis versicolor [29] and rosacea. [30] It also has anti-inflammatory properties when used to treat blepharitis or conjunctivitis (in eye-drop solution). It is believed to work by limiting the presence of folic acid which bacteria need to survive. It has been suggested that sulfacetamide may also serve as a treatment for mild forms of hidradenitis suppurativa.[ citation needed ] Sulfacetamide has antibacterial activity and is used to control acne. Products containing sulfacetamide and sulfur (a keratolytic) are commonly promoted for the treatment of acne rosacea (rosacea with papules, pustules, or both). There are several prescription topical products containing sulfacetamide, such as foams, shampoos, cream and washes.

Some research indicates that sulfacetamide derivatives may act as antifungals by an CYP51A1-independent mechanism. [31]

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">Acne</span> Skin condition characterized by pimples

Acne also known as acne vulgaris, is a long-term skin condition that occurs when dead skin cells and oil from the skin clog hair follicles. Typical features of the condition include blackheads or whiteheads, pimples, oily skin, and possible scarring. It primarily affects skin with a relatively high number of oil glands, including the face, upper part of the chest, and back. The resulting appearance can lead to lack of confidence, anxiety, reduced self-esteem, and, in extreme cases, depression or thoughts of suicide.

<span class="mw-page-title-main">Ertapenem</span> Antibiotic medication

Ertapenem, sold under the brand name Invanz, is a carbapenem antibiotic medication used for the treatment of infections of the abdomen, the lungs, the upper part of the female reproductive system, and the diabetic foot.

<span class="mw-page-title-main">Broad-spectrum antibiotic</span> Treatment for a wide range of bacteria

A broad-spectrum antibiotic is an antibiotic that acts on the two major bacterial groups, Gram-positive and Gram-negative, or any antibiotic that acts against a wide range of disease-causing bacteria. These medications are used when a bacterial infection is suspected but the group of bacteria is unknown or when infection with multiple groups of bacteria is suspected. This is in contrast to a narrow-spectrum antibiotic, which is effective against only a specific group of bacteria. Although powerful, broad-spectrum antibiotics pose specific risks, particularly the disruption of native, normal bacteria and the development of antimicrobial resistance. An example of a commonly used broad-spectrum antibiotic is ampicillin.

<i>Cutibacterium acnes</i> Species of bacterium

Cutibacterium acnes is the relatively slow-growing, typically aerotolerant anaerobic, gram-positive bacterium (rod) linked to the skin condition of acne; it can also cause chronic blepharitis and endophthalmitis, the latter particularly following intraocular surgery. Its genome has been sequenced and a study has shown several genes can generate enzymes for degrading skin and proteins that may be immunogenic.

<span class="mw-page-title-main">Prednisolone</span> Corticosteroid medication

Prednisolone is a corticosteroid, a steroid hormone used to treat certain types of allergies, inflammatory conditions, autoimmune disorders, and cancers. Some of these conditions include adrenocortical insufficiency, high blood calcium, rheumatoid arthritis, dermatitis, eye inflammation, asthma, and multiple sclerosis. It can be taken by mouth, injected into a vein, used topically as a skin cream, or as eye drops. It differs from the similarly named prednisone in having a hydroxyl at the 11th carbon instead of a ketone.

<span class="mw-page-title-main">Clindamycin</span> Antibiotic

Clindamycin is a lincosamide antibiotic medication used for the treatment of a number of bacterial infections, including osteomyelitis (bone) or joint infections, pelvic inflammatory disease, strep throat, pneumonia, acute otitis media, and endocarditis. It can also be used to treat acne, and some cases of methicillin-resistant Staphylococcus aureus (MRSA). In combination with quinine, it can be used to treat malaria. It is available by mouth, by injection into a vein, and as a cream or a gel to be applied to the skin or in the vagina.

<span class="mw-page-title-main">Blepharitis</span> Inflammation of the eyelid

Blepharitis, sometimes known as granulated eyelids, is one of the most common ocular conditions characterized by inflammation, scaling, reddening, and crusting of the eyelid. This condition may also cause swelling, burning, itching, or a grainy sensation when introducing foreign objects or substances to the eye. Although blepharitis by itself is not sight-threatening, it can lead to permanent alterations of the eyelid margin. The primary cause is bacteria and inflammation from congested meibomian oil glands at the base of each eyelash. Other conditions may give rise to blepharitis, whether they be infectious or noninfectious, including, but not limited to, bacterial infections or allergies.

<span class="mw-page-title-main">Rosacea</span> Skin condition, usually on the face

Rosacea is a long-term skin condition that typically affects the face. It results in redness, pimples, swelling, and small and superficial dilated blood vessels. Often, the nose, cheeks, forehead, and chin are most involved. A red, enlarged nose may occur in severe disease, a condition known as rhinophyma.

<span class="mw-page-title-main">Topical medication</span> Medication applied to body surfaces

A topical medication is a medication that is applied to a particular place on or in the body. Most often topical medication means application to body surfaces such as the skin or mucous membranes to treat ailments via a large range of classes including creams, foams, gels, lotions, and ointments. Many topical medications are epicutaneous, meaning that they are applied directly to the skin. Topical medications may also be inhalational, such as asthma medications, or applied to the surface of tissues other than the skin, such as eye drops applied to the conjunctiva, or ear drops placed in the ear, or medications applied to the surface of a tooth. The word topical derives from Greek τοπικόςtopikos, "of a place".

<span class="mw-page-title-main">Fusidic acid</span> Antibiotic

Fusidic acid, sold under the brand name Fucidin among others, is a steroid antibiotic that is often used topically in creams or ointments and eyedrops but may also be given systemically as tablets or injections. As of October 2008, the global problem of advancing antimicrobial resistance has led to a renewed interest in its use.

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

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<span class="mw-page-title-main">Azelaic acid</span> Organic chemical compound

Azelaic acid (AzA) is an organic compound with the formula HOOC(CH2)7COOH. This saturated dicarboxylic acid exists as a white powder. It is found in wheat, rye, and barley. It is a precursor to diverse industrial products including polymers and plasticizers, as well as being a component of a number of hair and skin conditioners. AzA inhibits tyrosinase.

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

Oxacillin is a narrow-spectrum beta-lactam antibiotic of the penicillin class developed by Beecham.

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

Sulfanilamide is a sulfonamide antibacterial drug. Chemically, it is an organic compound consisting of an aniline derivatized with a sulfonamide group. Powdered sulfanilamide was used by the Allies in World War II to reduce infection rates and contributed to a dramatic reduction in mortality rates compared to previous wars. Sulfanilamide is rarely if ever used systemically due to toxicity and because more effective sulfonamides are available for this purpose. Modern antibiotics have supplanted sulfanilamide on the battlefield; however, sulfanilamide remains in use today in the form of topical preparations, primarily for treatment of vaginal yeast infections such as vulvovaginitis caused by Candida albicans.

<span class="mw-page-title-main">Skin flora</span> Microbiota that reside on the skin

Skin flora, also called skin microbiota, refers to microbiota that reside on the skin, typically human skin.

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

Sulfadimethoxine is a long-lasting sulfonamide antimicrobial medication used in veterinary medicine. It is used to treat many infections, including respiratory, urinary tract, enteric, and soft tissue infections and can be given as a standalone or combined with ormetoprim to broaden the target range. Like all sulfamides, sulfadimethoxine inhibits bacterial synthesis of folic acid by acting as a competitive inhibitor against PABA. It is the most common drug prescribed to dogs who have coccidiosis.

The drug combination sulfacetamide/sulfur is a topical acne medication manufactured by Medicis under the trade name Plexion and also available under other trade names such as Clenia, Prascion, and Avar. It combines sodium sulfacetamide, a sulfonamide antibiotic, and sulfur, a keratolytic agent. It is available in four formulations: as a cleansing cloth, cleanser, topical suspension, and as a facial mask. The sulfacetamide inhibits the growth of the bacterium Cutibacterium acnes that is associated with acne, while sulfur facilitates the removal of dead skin cells to prevent clogged pores.

<span class="mw-page-title-main">Pimple</span> Type of comedo

A pimple or zit is a kind of comedo that results from excess sebum and dead skin cells getting trapped in the pores of the skin. In its aggravated state, it may evolve into a pustule or papule. Pimples can be treated by acne medications, antibiotics, and anti-inflammatories prescribed by a physician, or various over the counter remedies purchased at a pharmacy.

<span class="mw-page-title-main">Sulfur in pharmacy</span> Molecule used for pharmaceutical treatment of skin conditions

Sulfur is used in pharmaceutical skin preparations for the treatment of acne and other conditions. It acts as a keratolytic agent and also kills bacteria, fungi, scabies mites and other parasites.

References

  1. 1 2 "Sulfacetamide ≥98.0% | Sigma-Aldrich". www.sigmaaldrich.com. Retrieved 2016-03-09.
  2. 1 2 3 4 5 6 "Sulfacetamide". DrugBank. 2013-09-16.
  3. 1 2 "Sulfacetamide cream: Indications, Side Effects, Warnings - Drugs.com". www.drugs.com. Retrieved 2016-03-09.
  4. ↑ "Klaron medical facts". Drugs.com.
  5. ↑ "Avar cream: Indications, Side Effects, Warnings". Drugs.com.
  6. ↑ "Plexion medical facts". Drugs.com.
  7. ↑ "| Drug Information | Pharmacy". Walgreens. Archived from the original on 2013-05-16. Retrieved 2013-01-31.
  8. ↑ "Clenia Cream - FDA prescribing information, side effects and uses".
  9. ↑ "Sulfacetamide (sulfacetamide sodium) drug & pharmaceuticals. Sulfacetamide available forms, doses, prices". www.medicatione.com. Retrieved 2016-03-09.
  10. ↑ "Bleph-10- sulfacetamide sodium solution/ drops". DailyMed. 16 July 2014. Retrieved 10 June 2020.
  11. ↑ "Blephamide- sulfacetamide sodium and prednisolone acetate ointment". DailyMed. 29 June 2018. Retrieved 10 June 2020.
  12. ↑ "Blephamide- sulfacetamide sodium and prednisolone acetate suspension/ drops". DailyMed. 10 November 2016. Retrieved 10 June 2020.
  13. 1 2 3 "Sulphacetamide". www.druginfosys.com. Retrieved 2016-03-09.
  14. ↑ Byrom L, Zappala T, Muir J (May 2013). "Toxic epidermal necrolysis caused by over the counter eyedrops". The Australasian Journal of Dermatology. 54 (2): 144–6. doi:10.1111/j.1440-0960.2012.00936.x. PMID   22897159. S2CID   37140124.
  15. ↑ "Material Safety Data Sheet Sulfacetamide MSDS". ScienceLab.com. 2013. Archived from the original on 2016-04-04. Retrieved 2016-03-09.
  16. ↑ Sahu RK, Singh B, Saraf SA, Kaithwas G, Kishor K (June 2014). "Photochemical toxicity of drugs intended for ocular use". Arhiv Za Higijenu Rada I Toksikologiju. 65 (2): 157–67. doi: 10.2478/10004-1254-65-2014-2461 . PMID   24846953.
  17. 1 2 "Sulfacetamide" (PDF). CHEMWATCH. 2011.
  18. 1 2 3 "sulfacetamide | C8H10N2O3S". PubChem. U.S. National Library of Medicine. Retrieved 2016-03-09.
  19. 1 2 "SULFACETAMIDE SODIUM". www.robholland.com. Retrieved 2016-03-09.
  20. 1 2 "Sulfonamides and Sulfonamide Combinations: Antibacterial Agents: Merck Veterinary Manual". www.merckvetmanual.com. Retrieved 2016-03-09.
  21. ↑ HSU, W.H. (2008). Handbook Of Veterinary Pharmacology. Ames, Iowa: John Wiley & Sons.
  22. ↑ Bausch and Lomb. (2015). Sulfacetamide Sodium 10% and Prednisolone Sodium Phosphate 0.25% Ophthalmic Solution.
  23. 1 2 Naik PN, Kulkarni SD, Chimatadar SA, Nandibewoor ST (November 2008). "Mechanistic study of oxidation of sulfacetamide by diperiodatocuparate(III) in aqueous alkaline medium" (PDF). Indian Journal of Chemistry. 47A (11): 1666–1670.
  24. 1 2 Baran W, Sochacka J, Wardas W (November 2006). "Toxicity and biodegradability of sulfonamides and products of their photocatalytic degradation in aqueous solutions". Chemosphere. 65 (8): 1295–9. Bibcode:2006Chmsp..65.1295B. doi:10.1016/j.chemosphere.2006.04.040. PMID   16750553.
  25. ↑ Ahmad T (July 1983). "Stability of Suiphacetamide [sic] Eye drops at Higher Temperature". Journal of Pakistan Medical Association. Archived from the original on 2016-03-09. Retrieved 2016-03-09.
  26. ↑ Ahmad T (August 1982). "Degradation studies on sulphacetamide eye-drops. Part 2: Spectrophotometric evaluation of decomposition products of UV-irradiated solutions of sulphacetamide". Die Pharmazie. 37 (8): 559–61. PMID   7146062.
  27. ↑ U.S. patent 2,411,495
  28. ↑ Crossley ML, Northey EH, Hultquist ME (1939). "Sulfanilamide Derivatives. IV. N1,N4-Diacylsulfanilamides and N1-Acylsulfanilamides". Journal of the American Chemical Society. 61 (10): 2950–2955. doi:10.1021/ja01265a107.
  29. ↑ Hull CA, Johnson SM (June 2004). "A double-blind comparative study of sodium sulfacetamide lotion 10% versus selenium sulfide lotion 2.5% in the treatment of pityriasis (tinea) versicolor". Cutis. 73 (6): 425–9. PMID   15224788.
  30. ↑ Del Rosso JQ (January 2004). "Evaluating the role of topical therapies in the management of rosacea: focus on combination sodium sulfacetamide and sulfur formulations". Cutis. 73 (1 Suppl): 29–33. PMID   14959943.
  31. ↑ Mastrolorenzo A, Supuran CT (2000). "Antifungal Activity of Ag(I) and Zn(II) Complexes of Sulfacetamide Derivatives". Metal-Based Drugs. 7 (1): 49–54. doi: 10.1155/MBD.2000.49 . PMC   2365193 . PMID   18475922.
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