Sulfacetamide
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| Systematic (IUPAC) name | |
|---|---|
|
N-[(4-aminophenyl)sulfonyl]acetamide | |
| Clinical data | |
| Trade names | Bleph-10 |
| AHFS/Drugs.com | monograph |
| MedlinePlus | a601114 |
| Pharmacokinetic data | |
| Biological half-life | 7 to 12.8 hours |
| Identifiers | |
| CAS Number |
144-80-9  |
| ATC code | D10AF06 S01AB04, QJ01EQ21 |
| PubChem | CID 5320 |
| DrugBank |
DB00634 |
| ChemSpider |
5129 |
| UNII |
4965G3J0F5 |
| KEGG |
D05947 |
| ChEMBL |
CHEMBL455 |
| Chemical data | |
| Formula | C8H10N2O3S |
| Molar mass | 214.243 g/mol |
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Sulfacetamide is a sulfonamide antibiotic.
Uses
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. 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]
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.
Adverse effects
The most common side effects of sulfacetamide/sulfur combination products are local irritation and contact dermatitis. Sulfacetamide should not be used by individuals who have a sensitivity to sulfur or sulfa.
References
- ↑ Klaron medical facts from Drugs.com
- ↑ Avar Cream Facts and Comparisons at Drugs.com
- ↑ Plexion medical facts from Drugs.com
- ↑ http://www.walgreens.com/marketing/library/finddrug/druginfo1.html;jsessionid=PbrFt7xeQx07A7CTF6HcFA**.p_dotcom34?particularDrug=Prascion&id=645494
- ↑ Clenia Cream Official FDA information, side effects and uses
- ↑ Hull CA, Johnson SM (June 2004). "A double-blind comparative study of Sulfacetamide lotion 10% versus selenium sulfide lotion 2.5% in the treatment of pityriasis (tinea) versicolor". Cutis 73 (6): 425–9. PMID 15224788.
- ↑ Del Rosso JQ (January 2004). "Evaluating the role of topical therapies in the management of rosacea: focus on combination Sulfacetamide and sulfur formulations". Cutis 73 (1 Suppl): 29–33. PMID 14959943.
- ↑ Mastrolorenzo A, Supuran CT (2000). "Antifungal Activity of Ag(I) and Zn(II) Complexes of Sulfacetamide Derivatives". Met Based Drugs 7 (1): 49–54. doi:10.1155/MBD.2000.49. PMC 2365193. PMID 18475922.
- ↑ Crossley, M. L.; Northey, E. H.; Hultquist, M. E. (1939). "Sulfanilamide Derivatives. IV. N1,N4-Diacylsulfanilamides and N1-Acylsulfanilamides". Journal of the American Chemical Society 61 (10): 2950. doi:10.1021/ja01265a107.
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