Sulfacetamide Chemical Properties

Melting point:

182-184 °C

Density 

1.3844 (rough estimate)

refractive index 

1.5690 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

ethanol: soluble50mg/mL

pka

pKa 1.76±0.04(H2O t = 25 I = 0.15 (KCl) Ar atmosphere)(Approximate);5.22±0.01(H2O t = 25 I = 0.15 (KCl) Ar atmosphere)(Approximate)

form 

powder

color 

white to off-white

Water Solubility 

<0.01 g/100 mL at 16 ºC

Merck 

14,8899

BRN 

981718

Stability:

Stable. Incompatible with strong oxidizing agents, strong bases, strong reducing agents, strong acids.

InChIKey

SKIVFJLNDNKQPD-UHFFFAOYSA-N

CAS DataBase Reference

144-80-9(CAS DataBase Reference)

NIST Chemistry Reference

N-(p-Aminobenzenesulfonyl)acetamide(144-80-9)

EPA Substance Registry System

Sulfacetamide (144-80-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

22-24/25-36-26

WGK Germany 

2

RTECS 

AC8450000

TSCA 

Yes

HS Code 

29350090

Toxicity

LD50 orally in dogs: 8000 mg/kg (Fisher)

MSDS

• Language:English Provider:N-((4-Aminophenyl)sulfonyl)acetamide
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Sulfacetamide Usage And Synthesis

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.]

Sulfacetamide(144-80-9)Related Product Information

• Sulfacetamide sodium
• Sulfabenzamide
• Sulfacetamide sodium
• Sulfamethoxazole
• Sulfamic acid monosodium salt
• Sulfadimethoxine sodium salt
• Sulfachloropyridazine sodium
• Sulfanilamide
• sulfadicramide
• SULFISOXAZOLE ACETYL (200 MG)
• sulfaproxyline
• N,N'-DIACETYLSULFANILAMIDE
• PHTHALYLSULFACETAMIDE
• Sulfacetamide
• Stearylsulfamide
• IRGAFEN
• ((4-((((Hydroxyamino)oxoacetyl)amino)sulfonyl)phenyl)amino)oxoacetic a cid ethyl ester
• ((4-((((Methylamino)oxoacetyl)amino)sulfonyl)phenyl)amino)oxoacetic ac id ethyl ester