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Identification
Name Sulfanilamide
Accession Number DB00259 (APRD00438)
Type small molecule
Groups approved
Description

Sulfanilamide is a molecule containing the sulfonamide functional group attached to an aniline. [Wikipedia]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • P-Aminobenzenesulfamide
  • P-Aminobenzenesulfonamide
  • P-Aminobenzenesulfonylamide
  • P-Aminobenzensulfonamide
  • P-Aminophenylsulfonamide
  • P-Anilinesulfonamide
  • P-Sulfamidoaniline
  • P-Sulfamoylaniline
  • PABS
  • Sulfanilimidic Acid
  • Sulfonylamide
  • Sulphanilamide
  • Sulphonamide
Brand names
  • Albexan
  • Albosal
  • Ambeside
  • Antistrept
  • Astreptine
  • Astrocid
  • AVC
  • Bacteramid
  • Bactesid
  • Collomide
  • Colsulanyde
  • Copticide
  • Deseptyl
  • Desseptyl
  • Dipron
  • Ergaseptine
  • Erysipan
  • Estreptocida
  • Exoseptoplix
  • Fourneau 1162
  • Gerison
  • Gombardol
  • HSDB 223
  • Infepan
  • Lusil
  • Lysococcine
  • Neococcyl
  • Orgaseptine
  • Prontalbin
  • Prontosil Album
  • Prontosil I
  • Prontosil White
  • Prontylin
  • Pronzin Album
  • Proseptal
  • Proseptine
  • Proseptol
  • Pysococcine
  • Rubiazol A
  • Sanamid
  • Septamide Album
  • Septanilam
  • Septinal
  • Septolix
  • Septoplex
  • Septoplix
  • Stopton Album
  • Stramid
  • Strepamide
  • Strepsan
  • Streptagol
  • Streptamid
  • Streptamin
  • Streptasol
  • Streptocid
  • Streptocid Album
  • Streptocide
  • Streptocide White
  • Streptocidum
  • Streptoclase
  • Streptocom
  • Streptol
  • Strepton
  • Streptopan
  • Streptosil
  • Streptozol
  • Streptozone
  • Streptrocide
  • Sulfamidyl
  • Sulfamine
  • Sulfana
  • Sulfanalone
  • Sulfanidyl
  • Sulfanil
  • Sulfanilamide Vaginal Cream
  • Sulfocidin
  • Sulfocidine
  • Sulfonamide
  • Sulfonamide P
  • Sulphanilamide Extra Pure
  • Sulphanilamide Gr
  • Therapol
  • Tolder
  • White Streptocide
Brand name mixtures
  • After Calf Bolus (Sulfanilamide + Sulfathiazole + Urea)
  • Pinkamin (Methyl Salicylate + O-Phenylphenol + Sodium Thiosulfate + Sulfanilamide + Sulfur + Zinc Oxide)
  • Proud Flesh Dust (Boric Acid + Copper Sulfate + Sulfanilamide + Sulfathiazole + Tannic Acid)
  • 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)
  • 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)
  • Sulfa Urea Crm (Sulfanilamide + Sulfathiazole + Urea)
  • Sulfa-Urea-Bolus (Sulfanilamide + Sulfathiazole + Urea)
  • Triple Sulfa Bolus (Sulfamethazine + Sulfanilamide + Sulfathiazole)
  • Triple Sulfa Bolus 240gr (Sulfamethazine + Sulfanilamide + Sulfathiazole)
Categories
  • Anti-Bacterial Agents
  • Homeopathic Agents
  • Sulfonamides
CAS number 63-74-1
Weight Average: 172.205
Monoisotopic: 172.030648200
Chemical Formula C6H8N2O2S
InChI Key InChIKey=FDDDEECHVMSUSB-UHFFFAOYSA-N
InChI
InChI=1S/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10)
Plain Text
IUPAC Name
4-aminobenzene-1-sulfonamide
SMILES
NC1=CC=C(C=C1)S(N)(=O)=O
Plain Text
Mass Spec show (9 KB)
Taxonomy
Kingdom Organic
Classes
  • Benzenesulfonamides
  • Sulfanilamides
Substructures
  • Sulfonyls
  • Aliphatic and Aryl Amines
  • Benzene and Derivatives
  • Benzenesulfonamides
  • Aromatic compounds
  • Sulfanilamides
  • Sulfonamides
  • Anilines
Pharmacology
Indication For the treatment of vulvovaginitis caused by Candida albicans.
Pharmacodynamics 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 enzyme dihydropteroate synthetase. This enzyme normally uses para-aminobenzoic acid (PABA) for synthesizing the necessary folic acid. The inhibited reaction is normally necessary in these organisms for the synthesis of folic acid. Without it, bacteria cannot replicate.
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.
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Route of elimination Not Available
Half life Not Available
Clearance Not Available
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.
Affected organisms
  • Candida albicans and other yeasts
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Azur pharma international ltd
  • Teva pharmaceuticals usa inc
Packagers
Dosage forms
Form Route Strength
Liquid Oral
Prices
Unit description Cost Unit
AVC Vaginal 15% Cream 120 gm Tube 110.97 USD tube
Avc 15% cream 0.33 USD g
Sodium sulfanilamide powder 0.22 USD g
Patents Not Available
Properties
State solid
Melting point 165.5 oC
Experimental Properties
Property Value Source
water solubility 7500 mg/L PhysProp
logP -0.8 PhysProp
logS -1.36 [ADME Research, USCD] PhysProp
pKa 10.6 Various sources
Predicted Properties
Property Value Source
water solubility 1.04e+01 g/l ALOGPS
logP -0.16 ALOGPS
logP -0.25 ChemAxon Molconvert
logS -1.22 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 3 ChemAxon Molconvert
hydrogen donor count 2 ChemAxon Molconvert
polar surface area 86.18 ChemAxon Molconvert
rotatable bond count 1 ChemAxon Molconvert
refractivity 42.92 ChemAxon Molconvert
polarizability 16.25 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. Nzila A: Inhibitors of de novo folate enzymes in Plasmodium falciparum. Drug Discov Today. 2006 Oct;11(19-20):939-44. Epub 2006 Sep 7. Pubmed
External Links
Resource Link
KEGG Compound C07458 Link_out
PubChem Compound 5333 Link_out
PubChem Substance 46508306 Link_out
ChemSpider 5142 Link_out
BindingDB 10857 Link_out
ChEBI 9333 Link_out
ChEMBL 9333 Link_out
Therapeutic Targets Database DNC001391 Link_out
PharmGKB PA451545 Link_out
HET SAN Link_out
Drug Product Database 2236620 Link_out
Drugs.com http://www.drugs.com/cdi/sulfanilamide.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Sulfanilamide Link_out
ATC Codes
  • J01EB06
  • D06BA05
AHFS Codes
  • 92:02.00*
PDB Entries Not Available
FDA label Not Available
MSDS show (74.9 KB)
Interactions
Drug Interactions
Drug Interaction
Food Interactions Not Available
Targets

1. Dihydropteroate synthase

Pharmacological action: yes
Actions: inhibitor

DHPS catalyzes the formation of the immediate precursor of folic acid. It is implicated in resistance to sulfonamide

Organism class: bacterial
UniProt ID: P0AC13 Link_out
Gene: folP
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Djapa LY, Zelikson R, Delahodde A, Bolotin-Fukuhara M, Mazabraud A: Plasmodium vivax dihydrofolate reductase as a target of sulpha drugs. FEMS Microbiol Lett. 2006 Mar;256(1):105-11. Pubmed
  2. Nzila A: Inhibitors of de novo folate enzymes in Plasmodium falciparum. Drug Discov Today. 2006 Oct;11(19-20):939-44. Epub 2006 Sep 7. Pubmed
  3. Prabhu V, Lui H, King J: Arabidopsis dihydropteroate synthase: general properties and inhibition by reaction product and sulfonamides. Phytochemistry. 1997 May;45(1):23-7. Pubmed
Enzymes

1. Cytochrome P450 2C19

Actions: inhibitor

Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine

UniProt ID: P33261 Link_out
Gene: CYP2C19 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 2C9

Actions: inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S- warfarin, diclofenac, phenytoin, tolbutamide and losartan

UniProt ID: P11712 Link_out
Gene: CYP2C9
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 2D6

Actions: inhibitor

Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants

UniProt ID: P10635 Link_out
Gene: CYP2D6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

4. Cytochrome P450 2E1

Actions: inhibitor

Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms

UniProt ID: P05181 Link_out
Gene: CYP2E1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

5. Cytochrome P450 3A4

Actions: inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide

UniProt ID: P08684 Link_out
Gene: CYP3A4
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on September 03, 2011 17:04

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.