Sulfacetamide

Sulfacetamide

File:Sulfacetamide.svg
File:Sulfacetamid molecule.png
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 Y
ATC code	D10AF06 (WHO) S01AB04, QJ01EQ21 (WHO)
PubChem	CID: 5320
DrugBank	DB00634 Y
ChemSpider	5129 Y
UNII	4965G3J0F5 Y
KEGG	D05947 Y
ChEMBL	CHEMBL455 Y
Chemical data
Formula	C8H10N2O3S
Molecular mass	214.243 g/mol
SMILES O=S(=O)(c1ccc(N)cc1)NC(=O)C
InChI 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) Y Key:SKIVFJLNDNKQPD-UHFFFAOYSA-N Y
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File:Sulfacetamide substance photo.jpg

Pure Sulfacetamide sodium salt is a white or slightly yellow crystalline powder

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. When combined with sulfur, it is sold under the brand names Plexion, Clenia, Prascion, and Avar, which contain 10% sulfacetamide and 5% sulfur.

Sulfacetamide has been investigated for use in the treatment of pityriasis versicolor and rosacea. 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.

Synthesis

File:Sulfacetamide synthesis.svg

Sulfacetamide synthesis: U.S. Patent 2,411,495

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.