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Showing drug card for Sulfacetamide (DB00634)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-02-19 16:03:43
Primary Accession Number DB00634
Secondary Accession Number
  • APRD00452
Name Sulfacetamide
Drug Type
  • Approved
  • Small Molecule
Description An anti-infective agent that is used topically to treat skin infections and orally for urinary tract infections. [PubChem]
Synonyms Not Available
Brand Names
  1. Acetocid
  2. Acetosulfamin
  3. Acetosulfamine
  4. Ak-Sulf
  5. Albamine
  6. Albucid
  7. Alesten
  8. Bleph-10
  9. Bleph-10 Liquifilm
  10. Cetamide
  11. Formosulfacetamide
  12. Gyne-Sulf
  13. I-Sulfacet
  14. Isopto Cetamide
  15. Isopto-Cetamide
  16. Klaron
  17. N'-Acetylsulfanilamide
  18. N-Acetylsulfanilamide
  19. N-Acetylsulfanilamine
  20. N-Sulfanilylacetamide
  21. N-Sulphanilylacetamide
  22. Oclucid
  23. Ocusulf-10
  24. Op-Sulfa 30
  25. Ophthacet
  26. Ophthel-S
  27. P-Aminobenzenesulfonacetamide
  28. P-Aminobenzenesulfonoacetamide
  29. Region
  30. Sebizon
  31. Sodium Sulamyd
  32. Sodium Sulfacetamide
  33. Steramide
  34. Steri-Units Sulfacetamide
  35. Sulamyd
  36. Sulf-10
  37. Sulf-15
  38. Sulfacel-15
  39. Sulfacet
  40. Sulfacetamide Sodium
  41. Sulfacetamide Sodium Anhydrous
  42. Sulfacetamide Sodium Usp
  43. Sulfacetimide
  44. Sulfacyl
  45. Sulfair
  46. Sulfair 10
  47. Sulfair 15
  48. Sulfair Forte
  49. Sulfair-15
  50. Sulfamide
  51. Sulfanilacetamide
  52. Sulfanilazetamid
  53. Sulfex
  54. Sulphacetamide
  55. Sulphacetamide Sodium
  56. Sulphasil
  57. Sulten-10
  58. Sultrin
  59. Trysul
  60. Urosulfon
  61. Urosulfone
Brand Mixtures
  1. Ak Cide Oph Soln (Prednisolone Acetate + Sulfacetamide Sodium)
  2. Blephamide Oph Ont (Prednisolone Acetate + Sulfacetamide Sodium)
  3. Blephamide Opht Suspension (Prednisolone Acetate + Sulfacetamide Sodium)
  4. Cocci Bol O Tab Jr (Calcium Carbonate + Charcoal Activated + Cobalt Gluconate + Copper Sulfate + Ferrous Gluconate + Sodium Arsanilate + Sulfabenzamide Sodium + Sulfacetamide Sodium + Sulfaquinoxaline + Tannic Acid)
  5. Cocci Bol-O-Tab (Calcium Carbonate + Charcoal Activated + Cobalt Gluconate + Copper Sulfate + Ferrous Gluconate + Sodium Arsanilate + Sulfabenzamide Sodium + Sulfacetamide Sodium + Sulfaquinoxaline + Tannic Acid)
  6. Dioptimyd Ointment (Prednisolone Acetate + Sulfacetamide Sodium)
  7. Dioptimyd Suspension (Prednisolone Acetate + Sulfacetamide Sodium)
  8. Medicocci-Jr (Arsenic (Sodium Arsanilate) + Calcium Carbonate + Charcoal Activated + Cobalt Gluconate + Copper Sulfate + Ferrous Gluconate + Sulfabenzamide Sodium + Sulfacetamide Sodium + Sulfaquinoxaline + Tannic Acid)
  9. Medicocci-Sr (Arsenic (Sodium Arsanilate) + Calcium Carbonate + Charcoal Activated + Cobalt Gluconate + Copper Sulfate + Ferrous Gluconate + Sulfabenzamide Sodium + Sulfacetamide Sodium + Sulfaquinoxaline + Tannic Acid)
  10. Metimyd Oph Sus (Prednisolone Acetate + Sulfacetamide Sodium)
  11. Neo Atropec 25 Tab (Aluminum Hydroxide + Atropine Methylnitrate + Kaolin + Neomycin Sulfate + Pectin + Sulfacetamide + Sulfaguanidine)
  12. Neo Atropec C Tab (Aluminum Hydroxide + Atropine Methylnitrate + Kaolin + Neomycin Sulfate + Pectin + Sulfacetamide + Sulfaguanidine)
  13. Neo Atropec Tab (Aluminum Hydroxide + Atropine Methylnitrate + Kaolin + Neomycin Sulfate + Pectin + Sulfacetamide + Sulfaguanidine)
  14. Sulfacet R Lotion (Sulfacetamide Sodium + Sulfur (Sulfur))
  15. Sulfacet-R Lotion (Sulfacetamide Sodium + Sulfur)
  16. Sultrin Triple Sulfa Crm (Sulfacetamide + Sulfanilylbenzamide + Sulfathiazole + Urea)
  17. Vasocidin Ophthalmic Solution (Prednisolone Sodium Phosphate + Sulfacetamide Sodium)
  18. Vasosulf Oph Soln (Phenylephrine Hydrochloride + Sulfacetamide Sodium)
Chemical IUPAC Name N-(4-aminophenyl)sulfonylacetamide
Chemical Formula C8H10N2O3S
Chemical Structure Structure
CAS Registry Number 144-80-9
InChI Identifier InChI=1/C8H10N2O3S/c1-6(11)10-14(12,13)8-4-2-7(9)3-5-8/h2-5H,9H2,1H3,(H,10,11)/f/h10H
InChI Key SKIVFJLNDNKQPD-KZFATGLACW
KEGG Drug Not Available
KEGG Compound Not Available
PubChem Compound 5320 Link Image
PubChem Substance 152109 Link Image
ChEBI ID Not Available
PharmGKB ID PA451536 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 00838934 Link Image
RxList Link http://www.rxlist.com/cgi/generic3/plexion.htm Link Image
PDRhealth Link http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/ava1674.shtml Link Image
Wikipedia Link http://en.wikipedia.org/wiki/Sulfacetamide Link Image
FDA Label
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 214.2420
Monoisotopic Molecular Weight 214.0412
State Solid
Melting Point 183 oC
Experimental Water Solubility 1.25E+004 mg/L Source: PhysProp
Predicted Water Solubility 4.21e+00 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity -0.6 Source: PhysProp
Predicted LogP 0.15 Calculated using ALOGPS
Experimental LogS -1.23 [ADME Research, USCD]
Predicted LogS -1.71 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID 1K0G Link Image
Experimental PDB File Show
Experimental PDB Structure
Isomeric SMILES CC(=O)NS(=O)(=O)C1=CC=C(N)C=C1
Canonical SMILES CC(=O)NS(=O)(=O)C1=CC=C(N)C=C1
Drug Category
  • Anti-Bacterial Agents
  • Anti-Infective Agents, Local
  • Anti-Infective Agents, Urinary
  • Sulfonamides
ATC Codes
AHFS Codes
  • 52:04.04
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.
Mechanism of Action Sulfacetamide is a competitive inhibitor of bacterial para-aminobenzoic acid (PABA), an essential component for bacterial growth (according to the Woods-Fildes theory). The inhibited reaction is necessary in these organisms for the synthesis of folic acid.
Absorption Not Available
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.
Protein Binding Not Available
Biotransformation Not Available
Half Life 7-12.8 hours
Dosage Forms
Form Route
Liquid Ophthalmic
Ointment Ophthalmic
Solution / drops Ophthalmic
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. 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 Link Image]
  2. 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 Link Image]
  3. 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 Link Image]
  4. Drugs.com Link Image
  5. Wikipedia Link Image
  6. RxList Link Image
  7. PDRhealth Link Image
Organisms Affected
  • Enteric bacteria and other eubacteria
Targets
  1. Para-aminobenzoate synthase component 1
Drug Target 1 [top]
Target 1 ID 658
Target 1 Name Para-aminobenzoate synthase component 1
Target 1 Synonyms
  1. ADC synthase
  2. EC 6.3.5.8
  3. Para- aminobenzoate synthase component I
Target 1 Gene Name pabB
Target 1 Protein Sequence >Para-aminobenzoate synthase component 1 
MKTLSPAVITLLWRQDAAEFYFSRLSHLPWAMLLHSGYADHPYSRFDIVVAEPICTLTTF
GKETVVSESEKRTTTTDDPLQVLQQVLDRADIRPTHNEDLPFQGGALGLFGYDLGRRFES
LPEIAEQDIVLPDMAVGIYDWALIVDHQRHTVSLLSHNDVNARRAWLESQQFSPQEDFTL
TSDWQSNMTREQYGEKFRQVQEYLHSGDCYQVNLAQRFHATYSGDEWQAFLQLNQANRAP
FSAFLRLEQGAILSLSPERFILCDNSEIQTRPIKGTLPRLPDPQEDSKQAVKLANSAKDR
AENLMIVDLMRNDIGRVAVAGSVKVPELFVVEPFPAVHHLVSTITAQLPEQLHASDLLRA
AFPGGSITGAPKVRAMEIIDELEPQRRNAWCGSIGYLSFCGNMDTSITIRTLTAINGQIF
CSAGGGIVADSQEEAEYQETFDKVNRILKQLEK
Target 1 Number of Residues 460
Target 1 Molecular Weight 50970
Target 1 Theoretical pI 4.88
Target 1 GO Classification
Function
catalytic activity
lyase activity
carbon-carbon lyase activity
oxo-acid-lyase activity
Process
cellular metabolism
aromatic compound metabolism
folic acid and derivative metabolism
folic acid and derivative biosynthesis
physiological process
metabolism
biosynthesis
Component
Not Available
Target 1 General Function Amino acid transport and metabolism
Target 1 Specific Function Catalyzes the biosynthesis of 4-amino-4-deoxychorismate (ADC) from chorismate and glutamine
Target 1 Pathways
Name SMPDB Link KEGG Link
Folate biosynthesis map00790 Link Image
Target 1 Reactions
  • chorismate + L-glutamine = 4-amino-4-deoxychorismate + L-glutamate
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Essential
Target 1 GenBank ID Protein 147058 Link Image
Target 1 UniProtKB/Swiss-Prot ID P05041 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name PABB_ECOLI Link Image
Target 1 PDB ID 1K0G Link Image
Target 1 PDB File Show
Target 1 3D Structure
Target 1 Cellular Location Not Available
Target 1 Gene Sequence >1362 bp 
ATGAAGACGTTATCTCCCGCTGTGATTACTTTACTCTGGCGTCAGGACGCCGCTGAATTT
TATTTCTCCCGCTTAAGCCACCTGCCGTGGGCGATGCTTTTACACTCCGGCTATGCCGAT
CATCCGTATAGCCGCTTTGATATTGTGGTCGCCGAGCCGATTTGCACTTTAACCACTTTC
GGTAAAGAAACCGTTGTTAGTGAAAGCGAAAAACGCACAACGACCACTGATGACCCGCTA
CAGGTGCTCCAGCAGGTGCTGGATCGCGCAGACATTCGCCCAACGCATAACGAAGATTTG
CCATTTCAGGGCGGCGCACTGGGGTTGTTTGGCTACGATCTGGGCCGCCGTTTTGAGTCA
CTGCCAGAAATTGCGGAACAAGATATCGTTCTGCCGGATATGGCAGTGGGTATCTACGAT
TGGGCGCTCATTGTCGACCACCAGCGTCATACAGTTTCTTTGCTGAGTCATAATGATGTC
AATGCCCGTCGGGCCTGGCTGGAAAGCCAGCAATTCTCGCCGCAGGAAGATTTCACGCTC
ACTTCCGACTGGCAATCCAATATGACCCGCGAGCAGTACGGCGAAAAATTTCGCCAGGTA
CAGGAATATCTGCACAGCGGTGATTGCTATCAGGTGAATCTCGCCCAACGTTTTCATGCG
ACCTATTCTGGCGATGAATGGCAGGCATTCCTTCAGCTTAATCAGGCCAACCGCGCGCCA
TTTAGCGCTTTTTTACGTCTTGAACAGGGTGCAATTTTAAGCCTTTCGCCAGAGCGGTTT
ATTCTTTGTGATAATAGTGAAATCCAGACCCGCCCGATTAAAGGCACGCTACCACGCCTG
CCCGATCCTCAGGAAGATAGCAAACAAGCAGTAAAACTGGCGAACTCAGCGAAAGATCGT
GCCGAAAATCTGATGATTGTCGATTTAATGCGTAATGATATCGGTCGTGTTGCCGTAGCA
GGTTCGGTAAAAGTACCAGAGCTGTTCGTGGTGGAACCCTTCCCTGCCGTGCATCATCTG
GTCAGCACCATAACGGCGCAACTACCAGAACAGTTACACGCCAGCGATCTGCTGCGCGCA
GCTTTTCCTGGTGGCTCAATAACCGGGGCTCCGAAAGTACGGGCTATGGAAATTATCGAC
GAACTGGAACCGCAGCGACGCAATGCCTGGTGCGGCAGCATTGGCTATTTGAGCTTTTGC
GGCAACATGGATACCAGTATTACTATCCGCACGCTGACTGCCATTAACGGACAAATTTTC
TGCTCTGCGGGCGGTGGAATTGTCGCCGATAGCCAGGAAGAAGCGGAATATCAGGAAACT
TTTGATAAAGTTAATCGTATCCTGAAGCAACTGGAGAAGTAA
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus Not Available
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Ye QZ, Liu J, Walsh CT: p-Aminobenzoate synthesis in Escherichia coli: purification and characterization of PabB as aminodeoxychorismate synthase and enzyme X as aminodeoxychorismate lyase. Proc Natl Acad Sci U S A. 1990 Dec;87(23):9391-5. [PubMed Link Image]
  2. Goncharoff P, Nichols BP: Nucleotide sequence of Escherichia coli pabB indicates a common evolutionary origin of p-aminobenzoate synthetase and anthranilate synthetase. J Bacteriol. 1984 Jul;159(1):57-62. [PubMed Link Image]
  3. Viswanathan VK, Green JM, Nichols BP: Kinetic characterization of 4-amino 4-deoxychorismate synthase from Escherichia coli. J Bacteriol. 1995 Oct;177(20):5918-23. [PubMed Link Image]
  4. Guttman DS, Dykhuizen DE: Detecting selective sweeps in naturally occurring Escherichia coli. Genetics. 1994 Dec;138(4):993-1003. [PubMed Link Image]
  5. Itoh T, Aiba H, Baba T, Hayashi K, Inada T, Isono K, Kasai H, Kimura S, Kitakawa M, Kitagawa M, Makino K, Miki T, Mizobuchi K, Mori H, Mori T, Motomura K, Nakade S, Nakamura Y, Nashimoto H, Nishio Y, Oshima T, Saito N, Sampei G, Seki Y, Horiuchi T, et al.: A 460-kb DNA sequence of the Escherichia coli K-12 genome corresponding to the 40.1-50.0 min region on the linkage map. DNA Res. 1996 Dec 31;3(6):379-92. [PubMed Link Image]
  6. Blattner FR, Plunkett G 3rd, Bloch CA, Perna NT, Burland V, Riley M, Collado-Vides J, Glasner JD, Rode CK, Mayhew GF, Gregor J, Davis NW, Kirkpatrick HA, Goeden MA, Rose DJ, Mau B, Shao Y: The complete genome sequence of Escherichia coli K-12. Science. 1997 Sep 5;277(5331):1453-74. [PubMed Link Image]
Target 1 Drug References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.