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| Clinical data | |
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| Trade names | Bleph-10 |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a601114 |
| ATC code | |
| Pharmacokinetic data | |
| Elimination half-life | 7 to 12.8 hours |
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| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.005.128 |
| 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) |
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Sulfacetamide is a sulfonamide antibiotic.
Sulfacetamide 10% topical lotion, sold under the brand name Klaron or Ovace, is approved for the treatment of acne and seborrheic dermatitis. [1] When combined with sulfur, it is sold under the brand names Plexion, Clenia, Prascion, and Avar, which contain 10% sulfacetamide and 5% sulfur. [2] [3] [4] [5]
Sulfacetamide has been investigated for use in the treatment of pityriasis versicolor [6] and rosacea. [7] 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. [8]
These are organic compounds containing an benzenesulfonamide moiety with an amine group attached to the benzene ring. [9] The molecular formula is C8H10N2O3S. Its scientific name is N-(4-aminophenyl)sulfonylacetamide. At room temperature, it appears as a white powder. [10]
Sulfacetamide is stable under normal temperatures and pressures. No dangerous reactions occur under known conditions of normal use. [11] 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). [12]
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. [13]
Sulfonamide → organic intermediate products (degradation) (in presence of OH−). [13]
At higher temperatures sulfacetamide solutions degrade to its hydrolysed product, sulphanilamide with a first-order rate constant. [14]
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. [12]
The sulphanilamide can oxidise to a blue product with a first order reaction and it can form azo dye with a second order reaction. [15]
Sulfacetamide as a medicine is available as solution, eye drops, lotion, and powder. [16] It can also be found in the form of the sodium salt, sulfacetamide sodium. [17]
It is available in fixed-dose combinations with prednisolone. [18] [19]
Sulfacetamide is a sulfonamide antibiotic. [20] 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. [9] The multiplication of bacteria is therefore inhibited by the action of sulfacetamide.
Sulfacetamide is absorbed orally. The oral absorption of sulfacetamide is found to be 100% [21] and the plasma protein binding is 80–85%. In the liver it is metabolized to inactive metabolites. [22] Plasma half-life is 7 – 12.8 hours. [10]
Sulfonamides are usually metabolized by several oxidative pathways, acetylation, and conjugation with sulfate or glucuronic acid. [23] 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. [24]
It is excreted primarily in the urine. [22] Secretory routes of less significance are bile, feces, milk and sweat. [23] Glomerular filtration, active tubular secretion, and tubular reabsorption are the main processes involved.
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. [20] In cream form it is used to treat bacterial infections on the skin. It can also be used orally to treat urinary tract infections. [9] It kills the bacteria by restricting the production of folic acid, which is essential for bacterial growth. [25] It mainly inhibits the multiplication of bacteria as it acts in a competitive inhibitor.
The most common side effects are irritation, stinging or burning of the skin. Other side effects include nausea, vomiting, dizziness, tiredness and headache. [9] 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. [25] 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. [21] Higher exposure can also cause unconsciousness. [9] One case showed that sulfacetamide eyedrops can very rarely cause life-threatening skin condition toxic epidermal necrolysis (TEN). [26] 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.
The acute oral toxicity (LD50) in a mouse is 16.5 g/kg. [9] [27] 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. [28]
There are no known carcinogenic and mutagenic effects. It has a moderate toxicity according to the Chemwatch hazard ratings. [29]
| Incident | Measures taken |
|---|---|
| Swallowing | Do not induce vomiting. If it does occur prevent aspiration by keeping the airway open. This can be done by leaning the patient forward or by placing him on the left side. Observe the patient. Do not give liquid when the patient is being sleepy or when his awareness is reduced. |
| Eye contact | Hold eyelids apart and flush the eye continuously with running water. Flush at least for 15 minutes and make sure that the entire eye is being cleaned. Immediately transport to a hospital or doctor. |
| Skin contact | Remove all contaminated clothing immediately. Flush hair and skin with running water and preferably in combination with non-abrasive soap. Cover the irritated skin with an emollient. When irritated seek medical attention. |
| Inhalation | Remove from contaminated area. Lay patient down and keep him warm. Let the patient rest in a well-ventilated area. Make sure nothing blocks the airway. Apply artificial respiration if the patient does not breath. Perform CPR when necessary. |
Sulfonamides are generally effective against most gram-positive and many gram-negative organisms. [10] 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. [21] 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. [29]
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. [30] [31]
Clarithromycin, sold under the brand name Biaxin among others, is an antibiotic used to treat various bacterial infections. This includes strep throat, pneumonia, skin infections, H. pylori infection, and Lyme disease, among others. Clarithromycin can be taken by mouth as a pill or liquid.
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.
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.
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.
Clindamycin is an 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.
Doxycycline is a broad-spectrum antibiotic of the tetracycline class used in the treatment of infections caused by bacteria and certain parasites. It is used to treat bacterial pneumonia, acne, chlamydia infections, Lyme disease, cholera, typhus, and syphilis. It is also used to prevent malaria. Doxycycline may be taken by mouth or by injection into a vein.
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.
Benzoyl peroxide is a chemical compound (specifically, an organic peroxide) with structural formula (C6H5−C(=O)O−)2, often abbreviated as (BzO)2. In terms of its structure, the molecule can be described as two benzoyl (C6H5−C(=O)−, Bz) groups connected by a peroxide (−O−O−). It is a white granular solid with a faint odour of benzaldehyde, poorly soluble in water but soluble in acetone, ethanol, and many other organic solvents. Benzoyl peroxide is an oxidizer, which is principally used as in the production of polymers.
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".
Fusidic acid, sold under the brand names Fucidin among others, is an 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.
Sulfamethoxazole is an antibiotic. It is used for bacterial infections such as urinary tract infections, bronchitis, and prostatitis and is effective against both gram negative and positive bacteria such as Listeria monocytogenes and E. coli.
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.
Oxacillin is a narrow-spectrum beta-lactam antibiotic of the penicillin class developed by Beecham.
Lotion is a low-viscosity topical preparation intended for application to the skin. By contrast, creams and gels have higher viscosity, typically due to lower water content. Lotions are applied to external skin with bare hands, a brush, a clean cloth, or cotton wool.
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 mainly vulvovaginitis which is caused by Candida albicans.
Skin flora, also called skin microbiota, refers to microbiota that reside on the skin, typically human skin.
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.
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.
Infantile acne is a form of acneiform eruption that occurs in infants from 6 weeks to 1 year of age. Typical symptoms include inflammatory and noninflammatory lesions, papules and pustules most commonly present on the face. No cause of infantile acne has been established but it may be caused by increased sebaceous gland secretions due to elevated androgens, genetics and the fetal adrenal gland causing increased sebum production. Infantile acne can resolve by itself by age 1 or 2. However, treatment options include topical benzyl peroxide, topical retinoids and topical antibiotics in most cases.
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.
