Chemical Properties
white crystalline powder
Originator
Sulamyd,Schering,US,1941
Uses
Sulfacetamide is an antibiotic used for the treatment of skin infections and urinary tract infections. Sulfacetamide is also used to treat acne and seborrheic dermatitis. Sulfacetamide was investigated for potential anti-inflammatory properties
Definition
ChEBI: A sulfonamide that is sulfanilamide acylated on the sulfonamide nitrogen.
Manufacturing Process
17.2 grams of 4-aminobenzene-sulfonamide are heated to boiling with 75 cc
of acetic anhydride for 1 hour and thereupon the diacetyl product caused to
separate by stirring into ice water. After recrystallization from alcohol the 4-
acetylaminobenzene-sulfonacetyl-amide forms colorless prisms of melting
point 253°C with decomposition. The product is easily soluble in alkalies and
forms neutral salts. The acetylation can also take place with acetyl chloride.
Instead of the 4-aminobenzene-sulfonamide also 4-acetylaminobenzenesulfonamide
can be employed. The action of 4-acetyla
By heating the diacetyl compound with sodium hydroxide solution partial
saponification of the acetyl groups takes place. 25.6 grams of diacetyl
compound are heated to boiling for some hours with 100 cc of 2N sodium
hydroxide solution. The precipitate produced by acidification of the solution
with acetic acid is filtered off and treated with dilute sodium carbonate
solution. The 4-aminobenzene-sulfonacetylamide passes into solution while
the simultaneously formed 4-acetylaminobenzene-sulfonamide remains
undissolved. It is filtered with suction and the filtrate again acidified with
acetic acid. The 4-aminobenzene-sulfon-acetamide separates out and is
recrystallized from water. It forms colorless lustrous rhombic crystals of MP
181°C.
Therapeutic Function
Antimicrobial
General Description
Sulfacetamide’s plasmahalf-life is 7 hours. This compound is a white crystallinepowder, soluble in water (1:62.5 at 37°C) and in alcohol. It is very soluble in hot water, and its water solution is acidic.It has a pKa of 5.4.
General Description
White powder.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
N-((4-Aminophenyl)sulfonyl)acetamide is an amide. Organic amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generate mixed oxides of nitrogen (NOx)
Fire Hazard
Flash point data for N-((4-Aminophenyl)sulfonyl)acetamide are not available. N-((4-Aminophenyl)sulfonyl)acetamide is probably combustible.
Pharmaceutical Applications
N-acetylsulfanilamide. It is very soluble in water and was
formerly used in urinary tract infection. It is available in
some countries in ophthalmic preparations and as a component
(with sulfathiazole and sulfabenzamide) of a triple
sulfonamide cream for the topical treatment of bacterial
vaginosis.
Sulfacetamide is one of the least active sulfonamides. It
is well absorbed when given orally and is excreted in the
urine with a half-life of around 9 h. About 70% is excreted
unchanged, the remainder being present as the acetyl metabolite.
Adverse reactions are those common to the group.
Stevens–Johnson syndrome has been reported several times
after topical use in conjunctivitis.
Biochem/physiol Actions
Sulfacetamide is a sulfonamide antibiotic that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase. Sulfacetamide is a competitive inhibitor of bacterial para-aminobenzoic acid (PABA), which is required for bacterial synthesis of folic acid. It is active against Gram positive bacteria, Gram negative bacteria and Chlamydia. Mode of resistance is via the alteration of dihydropteroate synthase or alternative pathway for folic acid synthesis.
Safety Profile
Mildly toxic by ingestion and intravenous routes. An experimental teratogen. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and SOx.
Synthesis
Sulfacetamide, N1
-acetylsulfanilamide (33.1.44), 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 resulting acetamide 33.1.45 using a system of zinc¨Csodium hydroxide.
Purification Methods
Crystallise the amide from aqueous EtOH. [Beilstein 14 IV 2662.]
References
[1] Patent: CN105884712, 2016, A. Location in patent: Paragraph 0163; 0164; 0165
[2] Journal of the American Chemical Society, 1939, vol. 61, p. 2950,2953
[3] J. Chim. chem. Soc., 1942, vol. 9, p. 61,63
