N-(4-aminobenzenesulfonyl)acetamide

• ChemBase ID: 516
• Molecular Formular: C8H10N2O3S
• Molecular Mass: 214.2416
• Monoisotopic Mass: 214.04121319
• SMILES: S(=O)(=O)(NC(=O)C)c1ccc(N)cc1
• Canonical SMILES: CC(=O)NS(=O)(=O)c1ccc(cc1)N
• 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)
• InChIKey: SKIVFJLNDNKQPD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(4-aminobenzenesulfonyl)acetamide
• IUPAC Traditional name: N-(4-aminobenzenesulfonyl)acetamide; sulfacetamide
• Brand Name: Acetocid; Acetosulfamin; Acetosulfamine; Ak-Sulf; Albamine; Albucid; Alesten; Bleph-10; Bleph-10 Liquifilm; Cetamide; Formosulfacetamide; Gyne-Sulf; I-Sulfacet; Isopto Cetamide; Isopto-Cetamide; Klaron; N'-Acetylsulfanilamide; N-Acetylsulfanilamide; N-Acetylsulfanilamine; N-Sulfanilylacetamide; N-Sulphanilylacetamide; Oclucid; Ocusulf-10; Op-Sulfa 30; Ophthacet; Ophthel-S; P-Aminobenzenesulfonacetamide; P-Aminobenzenesulfonoacetamide; Region; Sebizon; Sodium Sulamyd; Sodium Sulfacetamide; Steramide; Steri-Units Sulfacetamide; Sulamyd; Sulf-10; Sulf-15; Sulfacel-15; Sulfacet; Sulfacetamide Sodium; Sulfacetamide Sodium Anhydrous; Sulfacetamide Sodium Usp; Sulfacetimide; Sulfacyl; Sulfair; Sulfair 10; Sulfair 15; Sulfair Forte; Sulfair-15; Sulfamide; Sulfanilacetamide; Sulfanilazetamid; Sulfex; Sulphacetamide; Sulphacetamide Sodium; Sulphasil; Sulten-10; Sultrin; Trysul; Urosulfon; Urosulfone
• Synonyms: Sulfacetamide; N-(4-Aminophenylsulfonyl)acetamide; Sulfacetamide; N-(4-Aminobenzenesulfonyl)acetamide; N1-Acetylsulfanilamide; N-Sulfanilylacetamide; N-((4-aminophenyl)sulfonyl)acetamide; N-Acetyl-4-aminobenzenesulfonamide; N-(4-氨基苯磺酰)乙酰胺; N1-乙酰磺胺; 磺乙酰胺; 磺胺醋酰

Database IDs

• CAS Number: 144-80-9
• EC Number: 205-640-6
• MDL Number: MFCD00066501
• Beilstein Number: 981718
• Merck Index: 148899
• PubChem SID: 160963979; 24870432; 46504544; 24899803
• PubChem CID: 5320

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.2999835
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.0395306
• LogD (pH = 7.4): -1.2013199
• Log P: -0.26104107
• Molar Refractivity: 52.4822 cm^3
• Polarizability: 20.56703 Å^3
• Polar Surface Area: 89.26 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.15
• LOG S: -1.71
• Solubility (Water): 4.21e+00 g/l

PROPERTIES

Physical Property

• Solubility: 1.25E+004 mg/L
• Melting Point: 182-184 °C; 182-184°C
• Hydrophobicity(logP): -0.6

Safety Information

• Storage Warning: IRRITANT
• RTECS: AC8450000
• German water hazard class: 2
• Risk Statements: 68
• Safety Statements: 36/37
• TSCA Listed: false; 是
• GHS Pictograms: GHS08
• GHS Hazard statements: H341
• GHS Precautionary statements: P281-P201-P202-P308+P313-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0%; ≥98.0% (NT); 98%
• Grade: VETRANAL™, analytical standard
• Ignition Residue: ≤0.4%
• Empirical Formula (Hill Notation): C8H10N2O3S

DETAILS

DrugBank - DB00634

• Drug Groups: approved
• Description: An anti-infective agent that is used topically to treat skin infections and orally for urinary tract infections. [PubChem]
• Indication: For the treatment of bacterial vaginitis, keratitis, acute conjunctivitis, and blepharitis.
• Pharmacology: Sulfacetamide is a sulfonamide antibiotic. The sulfonamides are synthetic bacteriostatic antibiotics with a wide spectrum against most gram-positive and many gram-negative organisms. However, many strains of an individual species may be resistant. Sulfonamides inhibit multiplication of bacteria by acting as competitive inhibitors of p-aminobenzoic acid in the folic acid metabolism cycle. Bacterial sensitivity is the same for the various sulfonamides, and resistance to one sulfonamide indicates resistance to all. Most sulfonamides are readily absorbed orally. However, parenteral administration is difficult, since the soluble sulfonamide salts are highly alkaline and irritating to the tissues. The sulfonamides are widely distributed throughout all tissues. High levels are achieved in pleural, peritoneal, synovial, and ocular fluids. Although these drugs are no longer used to treat meningitis, CSF levels are high in meningeal infections. Their antibacterial action is inhibited by pus.
• Toxicity: Oral LD₅₀ Mouse : 16500 mg/kg. Side effects include moderate to severe erythema (redness) and moderate edema (raised kin), nausea, vomiting, headache, dizziness, and tiredness. Higher exposure causes unconsciousness.
• Affected Organisms: Enteric bacteria and other eubacteria
• Half Life: 7-12.8 hours
• References: Hull CA, Johnson SM: A double-blind comparative study of sodium sulfacetamide lotion 10% versus selenium sulfide lotion 2.5% in the treatment of pityriasis (tinea) versicolor. Cutis. 2004 Jun;73(6):425-9. [Pubmed] ; Del Rosso JQ: Evaluating the role of topical therapies in the management of rosacea: focus on combination sodium sulfacetamide and sulfur formulations. Cutis. 2004 Jan;73(1 Suppl):29-33. [Pubmed] ; Roth HW, Leimbeck R, Sonnenschein B, Anger CB, Weber S: [The effective antibacterial spectrum of sulfacetamide] Klin Monatsbl Augenheilkd. 1992 Mar;200(3):182-6. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Sigma Aldrich - S8627

Application
Sulfacetamide is an antibiotic that is used to treat skin infections and urinary tract infections1. Sulfacetamide is used to study the treatment of acne and seborrheic dermatitis2. It is used to study neonatal chlamydial conjunctivitis and meningococcal 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 acid1. 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.

Sigma Aldrich - 46770

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

REFERENCES

• Hull CA, Johnson SM: A double-blind comparative study of sodium sulfacetamide lotion 10% versus selenium sulfide lotion 2.5% in the treatment of pityriasis (tinea) versicolor. Cutis. 2004 Jun;73(6):425-9. Pubmed
• Del Rosso JQ: Evaluating the role of topical therapies in the management of rosacea: focus on combination sodium sulfacetamide and sulfur formulations. Cutis. 2004 Jan;73(1 Suppl):29-33. Pubmed
• Roth HW, Leimbeck R, Sonnenschein B, Anger CB, Weber S: [The effective antibacterial spectrum of sulfacetamide] Klin Monatsbl Augenheilkd. 1992 Mar;200(3):182-6. Pubmed