Superiority:
PRODUCT DETAILS
Sulfacetamide Basic information |
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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) |
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) |
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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 |
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 investigate d 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. |
Chemical 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–sodium hydroxide.
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Purification Methods |
Crystallise the amide from aqueous EtOH. [Beilstein 14 IV 2662.] |
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Sulfacetamide Preparation Products And Raw materials |
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Leader Biochemical Group is a large leader incorporated industry manufacturers and suppliers of advanced refined raw materials From the year of 1996 when our factory was put into production to year of 2020, our group has successively invested in more than 52 factories with shares and subordinates.We focus on manufacture Pharm & chemicals, functional active ingredients, nutritional Ingredients, health care products, cosmetics, pharmaceutical and refined feed, oil, natural plant ingredients industries to provide top quality of GMP standards products.All the invested factories' product lines cover API and intermediates, vitamins, amino acids, plant extracts, daily chemical products, cosmetics raw materials, nutrition and health care products, food additives, feed additives, essential oil products, fine chemical products and agricultural chemical raw materials And flavors and fragrances. Especially in the field of vitamins, amino acids, pharmaceutical raw materials and cosmetic raw materials, we have more than 20 years of production and sales experience. All products meet the requirements of high international export standards and have been recognized by customers all over the world. Our manufacture basement & R&D center located in National Aerospace Economic & Technical Development Zone Xi`an Shaanxi China. Now not only relying on self-cultivation and development as well as maintains good cooperative relations with many famous research institutes and universities in China. Now, we have closely cooperation with Shanghai Institute of Organic Chemistry of Chinese Academy of Science, Beijing Institute of Material Medical of Chinese Academy of Medical Science, China Pharmaceutical University, Zhejiang University. Closely cooperation with them not only integrating Science and technology resources, but also increasing the R&D speed and improving our R&D power. Offering Powerful Tech supporting Platform for group development. Keep serve the manufacture and the market as the R&D central task, focus on the technical research. Now there are 3 technology R & D platforms including biological extract, microorganism fermentation and chemical synthesis, and can independently research and develop kinds of difficult APIs and pharmaceutical intermediates. With the strong support of China State Institute of Pharmaceutical Industry (hereinafter short for CSIPI), earlier known as Shanghai Institute of Pharmaceutical Industry (SIPI), we have unique advantages in the R & D and industrialization of high-grade, precision and advanced products. Now our Group technical force is abundant, existing staff more that 1000 people, senior professional and technical staff accounted for more than 50% of the total number of employees, including 15 PhD research and development personnel, 5 master′ S degree in technical and management personnel 9 people. We have advanced equipment like fermentation equipment and technology also extraction, isolation, purification, synthesis with rich production experience and strict quality control system, According to the GMP required, quickly transforming the R&D results to industrial production in time, it is our advantages and our products are exported to North and South America, Europe, Middle East, Africa, and other five continents and scale the forefront in the nation, won good international reputation. We believe only good quality can bring good cooperation, quality is our key spirit during our production, we are warmly welcome clients and partner from all over the world contact us for everlasting cooperation, Leader will be your strong, sincere and reliable partner in China.
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