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Showing drug card for Sulfanilamide (DB00259)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-02-19 16:03:41
Primary Accession Number DB00259
Secondary Accession Number
  • APRD00438
Name Sulfanilamide
Drug Type
  • Approved
  • Small Molecule
Description Sulfanilamide is a molecule containing the sulfonamide functional group attached to an aniline. [Wikipedia]
Synonyms
  1. P-Aminobenzenesulfamide
  2. P-Aminobenzenesulfonamide
  3. P-Aminobenzenesulfonylamide
  4. P-Aminobenzensulfonamide
  5. P-Aminophenylsulfonamide
  6. P-Anilinesulfonamide
  7. P-Sulfamidoaniline
  8. P-Sulfamoylaniline
  9. PABS
  10. Sulfanilimidic Acid
  11. Sulfonylamide
  12. Sulphanilamide
  13. Sulphonamide
Brand Names
  1. AVC
  2. Albexan
  3. Albosal
  4. Ambeside
  5. Antistrept
  6. Astreptine
  7. Astrocid
  8. Bacteramid
  9. Bactesid
  10. Collomide
  11. Colsulanyde
  12. Copticide
  13. Deseptyl
  14. Desseptyl
  15. Dipron
  16. Ergaseptine
  17. Erysipan
  18. Estreptocida
  19. Exoseptoplix
  20. Fourneau 1162
  21. Gerison
  22. Gombardol
  23. HSDB 223
  24. Infepan
  25. Lusil
  26. Lysococcine
  27. Neococcyl
  28. Orgaseptine
  29. Prontalbin
  30. Prontosil Album
  31. Prontosil I
  32. Prontosil White
  33. Prontylin
  34. Pronzin Album
  35. Proseptal
  36. Proseptine
  37. Proseptol
  38. Pysococcine
  39. Rubiazol A
  40. Sanamid
  41. Septamide Album
  42. Septanilam
  43. Septinal
  44. Septolix
  45. Septoplex
  46. Septoplix
  47. Stopton Album
  48. Stramid
  49. Strepamide
  50. Strepsan
  51. Streptagol
  52. Streptamid
  53. Streptamin
  54. Streptasol
  55. Streptocid
  56. Streptocid Album
  57. Streptocide
  58. Streptocide White
  59. Streptocidum
  60. Streptoclase
  61. Streptocom
  62. Streptol
  63. Strepton
  64. Streptopan
  65. Streptosil
  66. Streptozol
  67. Streptozone
  68. Streptrocide
  69. Sulfamidyl
  70. Sulfamine
  71. Sulfana
  72. Sulfanalone
  73. Sulfanidyl
  74. Sulfanil
  75. Sulfanilamide Vaginal Cream
  76. Sulfocidin
  77. Sulfocidine
  78. Sulfonamide
  79. Sulfonamide P
  80. Sulphanilamide Extra Pure
  81. Sulphanilamide Gr
  82. Therapol
  83. Tolder
  84. White Streptocide
Brand Mixtures
  1. After Calf Bolus (Sulfanilamide + Sulfathiazole + Urea)
  2. Pinkamin (Methyl Salicylate + O-Phenylphenol + Sodium Thiosulfate + Sulfanilamide + Sulfur + Zinc Oxide)
  3. Proud Flesh Dust (Boric Acid + Copper Sulfate + Sulfanilamide + Sulfathiazole + Tannic Acid)
  4. Scour Bolus Plus (Calcium Carbonate + Magnesium Oxide + Menadione (Menadione Sodium Bisulfite) + Neomycin (Neomycin Sulfate) + Potassium Acetate + Sodium Acetate + Sodium Chloride + Streptomycin (Streptomycin Sulfate) + Sulfamerazine + Sulfamethazine + Sulfanilamide + Sulfathiazole + Vitamin a + Vitamin D)
  5. Sulectim Plus Scour Boluses (Calcium Carbonate + Magnesium Oxide + Menadione Sodium Bisulfite + Neomycin (Neomycin Sulfate) + Potassium Acetate + Sodium Acetate + Sodium Chloride + Streptomycin (Streptomycin Sulfate) + Sulfamerazine + Sulfamethazine + Sulfanilamide + Sulfathiazole Sodium + Vitamin a + Vitamin D)
  6. Sulfa Urea Crm (Sulfanilamide + Sulfathiazole + Urea)
  7. Sulfa-Urea-Bolus (Sulfanilamide + Sulfathiazole + Urea)
  8. Triple Sulfa Bolus (Sulfamethazine + Sulfanilamide + Sulfathiazole)
  9. Triple Sulfa Bolus 240gr (Sulfamethazine + Sulfanilamide + Sulfathiazole)
Chemical IUPAC Name 4-aminobenzenesulfonamide
Chemical Formula C6H8N2O2S
Chemical Structure Structure
CAS Registry Number 63-74-1
InChI Identifier InChI=1/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10)/f/h8H2
InChI Key FDDDEECHVMSUSB-FSHFIPFOCT
KEGG Drug Not Available
KEGG Compound C07458 Link Image
PubChem Compound 5333 Link Image
PubChem Substance 9661 Link Image
ChEBI ID 9333 Link Image
PharmGKB ID PA451545 Link Image
HET ID SAN Link Image
GenBank ID Not Available
Drug ID Number [DIN] 02236620 Link Image
RxList Link Not Available
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Sulfanilamide Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS)
Synthesis Reference Gelmo, J.Prakt. Chem 77, 369
Average Molecular Weight 172.2050
Monoisotopic Molecular Weight 172.0306
State Solid
Melting Point 165.5 oC
Experimental Water Solubility 7500 mg/L Source: PhysProp
Predicted Water Solubility 1.04e+01 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity -0.8 Source: PhysProp
Predicted LogP -0.15 Calculated using ALOGPS
Experimental LogS -1.36 [ADME Research, USCD]
Predicted LogS -1.22 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point 10.6
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 Not Available
Isomeric SMILES NC1=CC=C(C=C1)S(N)(=O)=O
Canonical SMILES NC1=CC=C(C=C1)S(N)(=O)=O
Drug Category
  • Anti-Bacterial Agents
  • Homeopathic Agents
  • Sulfonamides
ATC Codes
AHFS Codes
  • 92:02.00*
Indication For the treatment of vulvovaginitis caused by Candida albicans.
Pharmacology Sulfanilamide 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 Sulfanilamide is a competitive inhibitor of bacterial para-aminobenzoic acid (PABA), a substrate of the enzyme dihydropteroate synthetase. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.
Absorption Sulfonamides are absorbed through the vaginal mucosa. There are no pharmacokinetic data available describing how much of an intravaginal dose reaches the systemic circulation.
Toxicity Oral, mouse LD50 = 3700 mg/kg; Intravenous, mouse LD50 = 621 mg/kg; Oral, rabbit LD50 = 1300 mg/kg. Side effects include itching, burning, skin rash, redness, swelling, or other sign of irritation not present before use of this medicine and long-term use of sulfonamides may cause cancer of the thyroid gland.
Protein Binding Not Available
Biotransformation Not Available
Half Life Not Available
Dosage Forms
Form Route
Liquid Oral
Patient Information Show Link Image
Contraindications Not Available
Interactions Show Link Image
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. Drugs.com Link Image
  2. Wikipedia Link Image
Organisms Affected
  • Candida albicans and other yeasts
Targets
  1. Para-aminobenzoate synthase
Drug Target 1 [top]
Target 1 ID 255
Target 1 Name Para-aminobenzoate synthase
Target 1 Synonyms
  1. EC 6.3.5.8
  2. P-aminobenzoic acid synthase
  3. PABA synthase
Target 1 Gene Name ABZ1
Target 1 Protein Sequence >Para-aminobenzoate synthase 
MLSDTIDTKQQQQQLHVLFIDSYDSFTYNVVRLIEQQTDISPGVNAVHVTTVHSDTFQSM
DQLLPLLPLFDAIVVGPGPGNPNNGAQDMGIISELFENANGKLDEVPILGICLGFQAMCL
AQGADVSELNTIKHGQVYEMHLNDAARACGLFSGYPDTFKSTRYHSLHVNAEGIDTLLPL
CTTEDENGILLMSAQTKNKPWFGVQYHPESCCSELGGLLVSNFLKLSFINNVKTGRWEKK
KLNGEFSDILSRLDRTIDRDPIYKVKEKYPKGEDTTYVKQFEVSEDPKLTFEICNIIREE
KFVMSSSVISENTGEWSIIALPNSASQVFTHYGAMKKTTVHYWQDSEISYTLLKKCLDGQ
DSDLPGSLEVIHEDKSQFWITLGKFMENKIIDNHREIPFIGGLVGILGYEIGQYIACGRC
NDDENSLVPDAKLVFINNSIVINHKQGKLYCISLDNTFPVALEQSLRDSFVRKKNIKQSL
SWPKYLPEEIDFIITMPDKLDYAKAFKKCQDYMHKGDSYEMCLTTQTKVVPSAVIEPWRI
FQTLVQRNPAPFSSFFEFKDIIPRQDETPPVLCFLSTSPERFLKWDADTCELRPIKGTVK
KGPQMNLAKATRILKTPKEFGENLMILDLIRNDLYELVPDVRVEEFMSVQEYATVYQLVS
VVKAHGLTSASKKTRYSGIDVLKHSLPPGSMTGAPKKITVQLLQDKIESKLNKHVNGGAR
GVYSGVTGYWSVNSNGDWSVNIRCMYSYNGGTSWQLGAGGAITVLSTLDGELEEMYNKLE
SNLQIFM
Target 1 Number of Residues 800
Target 1 Molecular Weight 88545
Target 1 Theoretical pI 5.55
Target 1 GO Classification
Function
anthranilate synthase activity
catalytic activity
lyase activity
carbon-carbon lyase activity
oxo-acid-lyase activity
Process
cellular metabolism
amino acid and derivative metabolism
amino acid metabolism
glutamine family amino acid metabolism
glutamine metabolism
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 295637 Link Image
Target 1 UniProtKB/Swiss-Prot ID P37254 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name PABS_YEAST Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Cytoplasm
Target 1 Gene Sequence >2364 bp 
ATGCTGTCCGATACAATTGACACAAAGCAACAACAGCAACAGCTTCATGTCCTGTTCATA
GACTCTTATGATTCATTCACCTACAATGTAGTGAGACTAATTGAACAACAAACTGATATC
TCACCGGGAGTCAACGCCGTGCACGTGACGACGGTACATAGTGATACGTTCCAATCTATG
GATCAGCTATTGCCACTTTTGCCGCTTTTTGATGCTATCGTTGTTGGCCCAGGACCTGGG
AATCCCAACAATGGTGCACAAGATATGGGTATAATATCTGAGCTTTTCGAGAATGCCAAT
GGAAAGTTAGATGAAGTTCCAATATTGGGTATATGTCTTGGGTTCCAAGCAATGTGCTTG
GCTCAAGGTGCTGATGTCAGTGAGCTAAATACTATCAAGCATGGGCAAGTGTATGAAATG
CATTTAAACGATGCAGCCAGAGCTTGTGGCCTTTTTTCTGGTTATCCCGATACGTTCAAA
TCTACGAGGTACCATTCATTGCATGTCAATGCCGAAGGCATTGACACCCTTTTGCCCTTA
TGCACAACCGAAGATGAGAACGGTATTCTTTTGATGAGTGCTCAAACGAAAAATAAGCCA
TGGTTTGGCGTACAGTACCACCCGGAGTCATGTTGTTCAGAATTGGGGGGGCTGTTAGTC
AGTAACTTTCTCAAGTTGAGTTTCATAAATAACGTGAAGACAGGAAGGTGGGAAAAGAAG
AAACTTAATGGAGAGTTTTCCGATATCCTATCTCGATTGGATAGGACTATTGATAGAGAC
CCCATATACAAGGTAAAAGAGAAATATCCGAAGGGCGAGGACACAACTTACGTTAAGCAG
TTCGAGGTCTCTGAAGACCCGAAATTGACATTTGAAATTTGCAACATCATACGAGAAGAA
AAATTTGTCATGTCATCTTCTGTGATTAGTGAAAATACGGGTGAATGGTCTATCATTGCT
TTACCAAACTCCGCATCCCAGGTATTCACTCATTATGGAGCTATGAAAAAGACTACAGTT
CATTATTGGCAAGATAGTGAAATTAGTTACACCTTGTTGAAAAAGTGTCTAGATGGTCAA
GATTCGGATTTGCCTGGCTCCCTTGAGGTAATACATGAAGATAAATCCCAATTTTGGATC
ACTTTGGGTAAATTTATGGAGAATAAAATAATCGATAACCACAGAGAAATACCTTTTATT
GGAGGTCTTGTTGGCATTTTAGGTTATGAAATAGGTCAGTACATTGCATGCGGCCGTTGC
AATGATGATGAGAATTCCCTTGTTCCCGACGCCAAACTAGTTTTTATCAACAATAGTATA
GTCATTAATCACAAGCAAGGGAAGCTTTATTGTATTTCTCTGGATAATACATTTCCAGTG
GCATTAGAACAATCATTAAGGGACAGTTTTGTTAGAAAGAAGAATATTAAGCAATCCCTG
TCCTGGCCCAAGTATCTTCCAGAGGAGATAGACTTCATTATAACTATGCCCGATAAACTT
GACTACGCTAAGGCGTTTAAGAAATGTCAGGATTATATGCATAAGGGTGATTCTTATGAA
ATGTGTCTCACAACGCAAACCAAAGTTGTACCATCTGCGGTGATAGAACCCTGGAGGATT
TTCCAGACCTTGGTACAAAGAAACCCGGCTCCATTTTCAAGTTTTTTTGAGTTTAAAGAC
ATTATTCCCCGCCAAGATGAAACGCCTCCAGTTTTGTGCTTCTTAAGTACTTCTCCAGAA
AGGTTTTTGAAGTGGGATGCAGACACATGCGAGCTACGTCCCATCAAGGGAACTGTGAAA
AAAGGACCGCAAATGAACTTGGCAAAAGCCACACGAATCCTGAAGACACCAAAAGAATTT
GGTGAGAACTTAATGATTTTGGACTTAATCAGAAATGACCTTTACGAGTTGGTTCCTGAC
GTTCGGGTGGAGGAGTTCATGTCCGTGCAAGAATATGCCACCGTTTACCAACTCGTTAGC
GTCGTAAAGGCACATGGATTGACCTCTGCCAGTAAGAAGACGAGATATTCAGGCATTGAT
GTCCTTAAACACTCGCTTCCTCCGGGATCTATGACGGGAGCCCCCAAGAAGATTACTGTG
CAATTATTGCAGGACAAGATAGAAAGCAAGCTAAACAAACATGTCAATGGTGGAGCACGT
GGTGTTTACAGCGGTGTCACGGGATATTGGTCTGTGAATTCCAACGGAGATTGGTCTGTT
AACATTAGATGTATGTATTCCTACAACGGCGGAACCAGCTGGCAACTCGGTGCAGGGGGG
GCCATAACAGTCTTAAGCACACTAGATGGCGAACTAGAGGAAATGTACAACAAGTTGGAG
AGCAACTTACAAATTTTCATGTAG
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. Huh WK, Falvo JV, Gerke LC, Carroll AS, Howson RW, Weissman JS, O'Shea EK: Global analysis of protein localization in budding yeast. Nature. 2003 Oct 16;425(6959):686-91. [PubMed Link Image]
  2. Ghaemmaghami S, Huh WK, Bower K, Howson RW, Belle A, Dephoure N, O'Shea EK, Weissman JS: Global analysis of protein expression in yeast. Nature. 2003 Oct 16;425(6959):737-41. [PubMed Link Image]
  3. Edman JC, Goldstein AL, Erbe JG: Para-aminobenzoate synthase gene of Saccharomyces cerevisiae encodes a bifunctional enzyme. Yeast. 1993 Jun;9(6):669-75. [PubMed Link Image]
  4. Shen WC, Stanford DR, Hopper AK: Los1p, involved in yeast pre-tRNA splicing, positively regulates members of the SOL gene family. Genetics. 1996 Jun;143(2):699-712. [PubMed Link Image]
  5. Philippsen P, Kleine K, Pohlmann R, Dusterhoft A, Hamberg K, Hegemann JH, Obermaier B, Urrestarazu LA, Aert R, Albermann K, Altmann R, Andre B, Baladron V, Ballesta JP, Becam AM, Beinhauer J, Boskovic J, Buitrago MJ, Bussereau F, Coster F, Crouzet M, D'Angelo M, Dal Pero F, De Antoni A, Hani J, et al.: The nucleotide sequence of Saccharomyces cerevisiae chromosome XIV and its evolutionary implications. Nature. 1997 May 29;387(6632 Suppl):93-8. [PubMed Link Image]
Target 1 Drug References
  1. Chang Z, Sun Y, He J, Vining LC: p-Aminobenzoic acid and chloramphenicol biosynthesis in Streptomyces venezuelae: gene sets for a key enzyme, 4-amino-4-deoxychorismate synthase. Microbiology. 2001 Aug;147(Pt 8):2113-26. [PubMed Link Image]
  2. 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]
  3. 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.