127-56-0

Basic information

• Product Name: Sulfacetamide sodium
• Synonyms: SODIUM SULFACETAMIDE;SULPHACETAMIDE;SULFACETAMIDE SODIUM USP;N-(4-Aminophenylsulfonyl)acetamide sodium salt;N-Sulfanilylacetamide monosodium salt;Sulfacetamide sodium;N-Acetyl-4-aminobenzenesulfonamide Sodium Salt;N-Acetylsulfanilamide Sodium Salt
• CAS NO: 127-56-0
• Molecular Formula: C₈H₉N₂O₃S*Na
• Molecular Weight: 236.22
• EINECS: 204-848-4
• Product Categories: Antibiotics for Research and Experimental Use;Biochemistry;Sulfonamides (Antibiotics for Research and Experimental Use);Used to treat conjunctivitis, sand holes and other eye infections;API
• Mol File: 127-56-0.mol
• Article Data: 0

Chemical Properties

• Melting Point: 257 °C
• Boiling Point: 450.8 °C at 760 mmHg
• Flash Point: 226.4 °C
• Appearance: White crystalline powder
• Vapor Pressure: 6.51E-09mmHg at 25°C
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Water Solubility: Soluble in water
• Merck: 14,8899
• CAS DataBase Reference: Sulfacetamide sodium(CAS DataBase Reference)
• NIST Chemistry Reference: Sulfacetamide sodium(127-56-0)
• EPA Substance Registry System: Sulfacetamide sodium(127-56-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: 3249
• WGK Germany: 3
• RTECS: AC8480000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 127-56-0(Hazardous Substances Data)

Usage

Description

Sulfacetamide is a sulfonamide antibiotic that is bacteriostatic against Gram-positive and Gram-negative bacteria. It inhibits dihydropteroate synthase (IC50 = 9.6 μM), blocking the synthesis of dihydrofolic acid, and also inhibits bacterial 4-aminobenzoic acid , which is required for the synthesis of folic acid.

Uses

Different sources of media describe the Uses of 127-56-0 differently. You can refer to the following data:
1. Sulfacetamide Sodium Salt is an antibiotic that blocks synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase. It can be used in biological study to explore topical application of benzoyl peroxide, antibiotics, sulfur and sodium sulfacetamide, azelaic acid for treatment of acne vulgaris in humans.
2. Sulfacetamide Sodium is an anti-biotic

Definition

ChEBI: An organic sodium salt that is the monosodium salt of sulfacetamide.

Brand name

Bleph (Allergan); Cetamide (Alcon); Klaron (Sanofi Aventis); Ocusulf (MIZA); Sodium Sulamyd (Schering); Sulf (Novartis); Sulfacel (Optopics); Sulfair (Pharmafair); Sulten (Bausch & Lomb).

InChI:InChI=1/C8H10N2O3S.Na.H2O/c1-6(11)10-14(12,13)8-4-2-7(9)3-5-8;;/h2-5H,9H2,1H3,(H,10,11);;1H2/q;+1;/p-1

Synthetic route

cetylpyridinium chloride (123-03-5) + sodium 4-aminobenzenesulfonylacetamide (127-56-0) → hexadecylpyridinium sulfacetamide (934544-27-1)

Conditions	Yield
In water for 0.5h; Heating / reflux;	99.22%

4-(4-fluorophenyl)-4-oxo-2-hydroxy-2-butenoic acid methyl ester (41167-60-6) + sodium 4-aminobenzenesulfonylacetamide (127-56-0) → 2-hydroxy-4-oxo-4-(4-fluorophenyl)-2-butenoic acid N-(4-(acetylaminosulfonyl)phenyl)amide (900325-79-3)

Conditions	Yield
With acetic acid Reflux;	95%

chloroformic acid ethyl ester (541-41-3) + sodium 4-aminobenzenesulfonylacetamide (127-56-0) → C11H14N2O5S (81865-29-4)

Conditions	Yield
Ambient temperature;	91.5%

sodium 4-aminobenzenesulfonylacetamide (127-56-0) + chloroacetic acid ethyl ester (105-39-5) → N-Sulfanilyl-N-carbethoxymethylacetamine (81865-32-9)

Conditions	Yield
In ethanol for 4h; Ambient temperature;	89.7%

2-(4-fluorophenyl)-3-(4-fluorophenyl)-5-phenyl-2H-tetrazolium chloride + sodium 4-aminobenzenesulfonylacetamide (127-56-0) → C19H13F2N4(1+)*C8H9N2O3S(1-)

Conditions	Yield
In methanol; water at 20℃; for 2h;	88%

sodium 4-aminobenzenesulfonylacetamide (127-56-0) + N,N-didecyl-N,N-dimethylammonium bromide (2390-68-3) → didecyldimethylammonium sulfacetamide (934544-26-0)

Conditions	Yield
In water for 0.5h;	87.74%

sodium 4-aminobenzenesulfonylacetamide (127-56-0) + methyl chloroacetate (96-34-4) → [Acetyl-(4-amino-benzenesulfonyl)-amino]-acetic acid methyl ester (81865-31-8)

Conditions	Yield
Ambient temperature;	87.5%

sodium 4-aminobenzenesulfonylacetamide (127-56-0) + methyl chloroformate (79-22-1) → C10H12N2O5S (81865-28-3)

Conditions	Yield
Ambient temperature;	85.8%

sodium 4-aminobenzenesulfonylacetamide (127-56-0) + 4,6-dichloro-5-methoxypyrimidine (5018-38-2) → 4-(p-aminobenzenesulfonamido)-5-methoxy-6-chloropyrimidine (5018-23-5)

Conditions	Yield
In N,N-dimethyl-formamide at 88 - 90℃; for 3h;	85.3%

C11H8Cl2O4 (934063-39-5) + sodium 4-aminobenzenesulfonylacetamide (127-56-0) → 2-hydroxy-4-(2,4-dichlorophenyl)-4-oxo-2-butenoic acid N-(4-acetylaminosulfonylphenyl)amide (1610537-08-0)

Conditions	Yield
With acetic acid Reflux;	83%

triphenyltetrazolium chloride (298-96-4) + sodium 4-aminobenzenesulfonylacetamide (127-56-0) → C19H15N4(1+)*C8H9N2O3S(1-)

Conditions	Yield
In methanol; water at 20℃; for 2h;	83%

sodium 4-aminobenzenesulfonylacetamide (127-56-0) + 2-hydroxy-4-(3-methoxyphenyl)-4-oxo-but-2-enoic acid methyl ester → 2-hydroxy-4-(3-methoxyphenyl)-4-oxo-2-butenoic acid N-(4-acetylaminosulfonylphenyl)amide (900310-00-1)

Conditions	Yield
With acetic acid Reflux;	81%

sodium 4-aminobenzenesulfonylacetamide (127-56-0) + chloroacetic acid (79-11-8) → [Acetyl-(4-amino-benzenesulfonyl)-amino]-acetic acid (81865-30-7)

Conditions	Yield
	80.3%

4-(4-chlorophenyl)-2-hydroxy-4-oxo-but-2-enoic acid methyl ester (41167-59-3) + sodium 4-aminobenzenesulfonylacetamide (127-56-0) → 2-hydroxy-4-oxo-4-(4-chlorophenyl)-2-butenoic acid N-(4-acetylaminosulfonylphenyl)amide (1610537-06-8)

Conditions	Yield
With acetic acid Reflux;	79%

2-hydroxy-4-oxo-4-phenyl-but-2-enoic acid methyl ester (41167-58-2) + sodium 4-aminobenzenesulfonylacetamide (127-56-0) → 2-hydroxy-4-oxo-4-phenyl-2-butenoic acid N-(4-acetylaminosulfonylphenyl)amide (1610537-07-9)

Conditions	Yield
With acetic acid Reflux;	76%

6,8-dibromo-2-phenyl-3,1-benzoxazin-4-one (67090-34-0) + sodium 4-aminobenzenesulfonylacetamide (127-56-0) → C22H14Br2N3O4S(1-)*Na(1+)

Conditions	Yield
at 150℃; for 2h;	75%

Indole-3-carboxaldehyde (487-89-8) + sodium 4-aminobenzenesulfonylacetamide (127-56-0) → C17H14N3O3S(1-)*Na(1+)

Conditions	Yield
In ethanol for 1h; Reflux;	72%

sodium 4-aminobenzenesulfonylacetamide (127-56-0) + ranitidine hydrochloride (66357-59-3, 71130-06-8) → ranitidinium sulfacetamide

Conditions	Yield
In water at 40℃; for 24h;	50%

sodium 4-aminobenzenesulfonylacetamide (127-56-0) → N,N'-bis(acetyl)azoxybenzene-p,p'-disulphonamide

Conditions	Yield
With dipotassium peroxodisulfate In water at 34.9℃; Kinetics; Mechanism; Thermodynamic data; ΔG(excit.), ΔH(excit.), ΔS(excit.); other temperatures, salt effect (K2SO4), pH and dielectric constant dependence, inhibition by diphenyl picryl hydrazyl;

sodium 4-aminobenzenesulfonylacetamide (127-56-0) → p-nitrobenzenesulfonamide (6325-93-5)

Conditions	Yield
With Cu(2+)*2HO(1-)*H3IO6(1-)*K(1+) In water at 29.84℃; Kinetics; Mechanism; Temperature;

formaldehyd (50-00-0) + ganciclovir (82410-32-0) + sodium 4-aminobenzenesulfonylacetamide (127-56-0) → C18H22N7O7S(1-)*Na(1+)

Conditions	Yield
In ethanol at 0℃; Mannich Aminomethylation; Reflux;

water (7732-18-5) + sodium 4-aminobenzenesulfonylacetamide (127-56-0) + silver nitrate → [Ag(sulfacetamide sodium)(NO3)(H2O)]·3H2O

Conditions	Yield
In methanol at 60℃; for 2h;

water (7732-18-5) + sodium 4-aminobenzenesulfonylacetamide (127-56-0) + cadmium(II) chloride (10108-64-2) → [Cd(sulfacetamide sodium)(Cl)2]·10H2O

Conditions	Yield
In methanol at 60℃; for 2h;

copper(II) chloride pentahydrate + sodium 4-aminobenzenesulfonylacetamide (127-56-0) → [Cu(sulfacetamide sodium)2(Cl)2]

Conditions	Yield
In methanol; water at 60℃; for 2h;

tetraphenylphosphonium bromide (2751-90-8) + sodium 4-aminobenzenesulfonylacetamide (127-56-0) → C24H20P(1+)*C8H9N2O3S(1-)

Conditions	Yield
In dichloromethane; water at 20℃; for 24h;	3 g

4-bromo-phenol (106-41-2) + sodium 4-aminobenzenesulfonylacetamide (127-56-0) + triphenylphosphine (603-35-0) → C8H9N2O3S(1-)*C24H20OP(1+)

Conditions	Yield
Stage #1: 4-bromo-phenol; triphenylphosphine In ethylene glycol at 180℃; for 5h; Stage #2: sodium 4-aminobenzenesulfonylacetamide In dichloromethane; water at 20℃; for 24h;	4 g

ruthenium trichloride + sodium 4-aminobenzenesulfonylacetamide (127-56-0) → [Ru(SD2)2(Cl)2(H2O)2]Cl·2H2O

Conditions	Yield
In methanol at 60℃; Reflux;

8-hydroxy-7-iodo-quinoline-5-sulfonic acid (547-91-1) + sodium 4-aminobenzenesulfonylacetamide (127-56-0) → C17H12IN4O7S2(1-)*Na(1+)

Conditions	Yield
Stage #1: sodium 4-aminobenzenesulfonylacetamide With hydrogenchloride; sodium nitrite In water at 15℃; Stage #2: 8-hydroxy-7-iodo-quinoline-5-sulfonic acid With ammonium hydroxide In water for 0.166667h; Reagent/catalyst; Time;

C18H19N2(1+)*Cl(1-) + sodium 4-aminobenzenesulfonylacetamide (127-56-0) → C18H19N2(1+)*C8H9N2O3S(1-)

Conditions	Yield
In dichloromethane; water at 20℃; for 24h;	3 g

sodium 4-aminobenzenesulfonylacetamide (127-56-0) → sulphaacetamide (144-80-9)

Conditions	Yield
With hydrogenchloride In water pH=2 - 3;

Downstream Products

• 81865-32-9 N-Sulfanilyl-N-carbethoxymethylacetamine 
• 934544-27-1 hexadecylpyridinium sulfacetamide 
• 6325-93-5 p-nitrobenzenesulfonamide 
• 5018-23-5 4-(p-aminobenzenesulfonamido)-5-methoxy-6-chloropyrimidine 
• 144-80-9 sulphaacetamide 
• 81865-29-4 C₁₁H₁₄N₂O₅S 
• 1610537-08-0 2-hydroxy-4-(2,4-dichlorophenyl)-4-oxo-2-butenoic acid N-(4-acetylaminosulfonylphenyl)amide 
• 900310-00-1 2-hydroxy-4-(3-methoxyphenyl)-4-oxo-2-butenoic acid N-(4-acetylaminosulfonylphenyl)amide 
• 900325-79-3 2-hydroxy-4-oxo-4-(4-fluorophenyl)-2-butenoic acid N-(4-(acetylaminosulfonyl)phenyl)amide 
• 1610537-07-9 2-hydroxy-4-oxo-4-phenyl-2-butenoic acid N-(4-acetylaminosulfonylphenyl)amide 
• 1610537-06-8 2-hydroxy-4-oxo-4-(4-chlorophenyl)-2-butenoic acid N-(4-acetylaminosulfonylphenyl)amide 

Related news

Pharmaceutical AnalysisAssay of Sulfacetamide sodium (cas 127-56-0) Ophthalmic Solutions by High‐pressure Liquid Chromatography09/27/2019

A high‐pressure liquid chromatographic method, using an adsorption column and sulfabenzamide as the internal standard, is proposed for the determination of sulfacetamide sodium and its principal hydrolysis product, sulfanilamide, in eye drops. It affords an average recovery of 100.9% of added s...detailed

Research paperBioadhesive Sulfacetamide sodium (cas 127-56-0) microspheres: Evaluation of their effectiveness in the treatment of bacterial keratitis caused by Staphylococcus aureus and Pseudomonas aeruginosa in a rabbit model09/26/2019

The aim of this study was to prepare bioadhesive sulfacetamide sodium (SA) microspheres to increase their residence time on the ocular surface and to enhance their treatment efficacy on ocular keratitis. Microspheres were fabricated by spray drying method using mixture of polymers such as pectin...detailed

Evaluation of limiting molar conductance, Walden product, association constant and thermodynamic properties of Sulfacetamide sodium (cas 127-56-0) in water + EtOH mixtures09/10/2019

The ion solvation behavior of sulfacetamide sodium in water and various volume fractions of ethanol (EtOH) in water in the range of 283 to 313 K, using electrical conductivity principle have been studied. The conductance data were analyzed according to Kraus–Bray and Shedlovsky models of conduc...detailed