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144-80-9 molecular structure
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N-(4-aminobenzenesulfonyl)acetamide

ChemBase ID: 516
Molecular Formular: C8H10N2O3S
Molecular Mass: 214.2416
Monoisotopic Mass: 214.04121319
SMILES and InChIs

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

Cite this record

CBID:516 http://www.chembase.cn/molecule-516.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.2999835  H Acceptors
H Donor LogD (pH = 5.5) -1.0395306 
LogD (pH = 7.4) -1.2013199  Log P -0.26104107 
Molar Refractivity 52.4822 cm3 Polarizability 20.56703 Å3
Polar Surface Area 89.26 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 0.15  LOG S -1.71 
Solubility (Water) 4.21e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
1.25E+004 mg/L expand Show data source
Melting Point
182-184 °C expand Show data source
182-184°C expand Show data source
Hydrophobicity(logP)
-0.6 expand Show data source
Storage Warning
IRRITANT expand Show data source
RTECS
AC8450000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
Risk Statements
68 expand Show data source
Safety Statements
36/37 expand Show data source
TSCA Listed
false expand Show data source
expand Show data source
GHS Pictograms
GHS08 expand Show data source
GHS Hazard statements
H341 expand Show data source
GHS Precautionary statements
P281-P201-P202-P308+P313-P405-P501A expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Purity
≥98.0% expand Show data source
≥98.0% (NT) expand Show data source
98% expand Show data source
Grade
VETRANAL™, analytical standard expand Show data source
Ignition Residue
≤0.4% expand Show data source
Empirical Formula (Hill Notation)
C8H10N2O3S expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich
DrugBank - DB00634 external link
Item Information
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 external link
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 external link
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
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