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Sulfanilamide
Identification
- Name
- Sulfanilamide
- Accession Number
- DB00259
- Description
Sulfanilamide is a molecule containing the sulfonamide functional group attached to an aniline.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Sulfanilamide (DB00259)
- Weight
- Average: 172.205
Monoisotopic: 172.0306482 - Chemical Formula
- C6H8N2O2S
- Synonyms
- 4-aminobenzene sulfonic acid amide
- 4-azanylbenzenesulfonamide
- p-aminobenzenesulfamide
- p-aminobenzenesulfonamide
- para-aminobenzenesulfonamide
- Prontosil album
- SA
- Streptocide
- Sulfamine
- Sulfanilamida
- Sulfanilamide
- Sulfanilamidum
- Sulphanilamide
- External IDs
- 1162 F
- F 1162
- F-1162
- NSC-7618
Pharmacology
- Indication
For the treatment of vulvovaginitis caused by Candida albicans.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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.
Target Actions Organism ADihydropteroate synthase inhibitorEscherichia coli (strain K12) - 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
- Not Available
- Route of elimination
- Not Available
- Half-life
- Not Available
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- 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
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataBenzylpenicillin Sulfanilamide may decrease the excretion rate of Benzylpenicillin which could result in a higher serum level. Dapsone The risk or severity of methemoglobinemia can be increased when Dapsone is combined with Sulfanilamide. Entrectinib The metabolism of Entrectinib can be decreased when combined with Sulfanilamide. Haloperidol The serum concentration of Haloperidol can be increased when it is combined with Sulfanilamide. Levamlodipine The serum concentration of Levamlodipine can be increased when it is combined with Sulfanilamide. Magnesium The serum concentration of Magnesium can be decreased when it is combined with Sulfanilamide. Prilocaine The risk or severity of methemoglobinemia can be increased when Sulfanilamide is combined with Prilocaine. Tramadol The metabolism of Tramadol can be decreased when combined with Sulfanilamide. Vibrio cholerae CVD 103-HgR strain live antigen The therapeutic efficacy of Vibrio cholerae CVD 103-HgR strain live antigen can be decreased when used in combination with Sulfanilamide. Voxelotor The serum concentration of Voxelotor can be increased when it is combined with Sulfanilamide. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- No interactions found.
Products
- International/Other Brands
- Streptocid
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataAvc Cream 15 g/100g Vaginal MEDA Pharmaceuticals 2014-12-01 2019-09-30 US 
Avc Cream - 15% Cream Vaginal Hoechst Marion Roussel 1995-12-31 2000-07-28 Canada 
AVC Vaginal Cream 15 g/100g Vaginal Physicians Total Care, Inc. 1965-06-05 2012-06-30 US AVC Vaginal Cream 15 g/100g Vaginal Jazz Pharmaceuticals Commercial Corp. 1965-06-05 2016-12-31 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
Categories
- ATC Codes
- G01AE10 — Combinations of sulfonamides
- G01AE — Sulfonamides
- G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
- G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- J01EB — Short-acting sulfonamides
- J01E — SULFONAMIDES AND TRIMETHOPRIM
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- Drug Categories
- Amides
- Amines
- Aniline Compounds
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 inhibitors (strength unknown)
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2E1 Inhibitors
- Cytochrome P-450 CYP2E1 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Dermatologicals
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Methemoglobinemia Associated Agents
- Short-Acting Sulfonamides
- Sulfanilamides
- Sulfonamide Antibacterial
- Sulfonamides
- SULFONAMIDES AND TRIMETHOPRIM
- Sulfones
- Sulfur Compounds
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzenesulfonamides
- Direct Parent
- Aminobenzenesulfonamides
- Alternative Parents
- Benzenesulfonyl compounds / Aniline and substituted anilines / Organosulfonamides / Aminosulfonyl compounds / Primary amines / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
- Substituents
- Amine / Aminobenzenesulfonamide / Aminosulfonyl compound / Aniline or substituted anilines / Aromatic homomonocyclic compound / Benzenesulfonyl group / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide / Organic oxygen compound
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- substituted aniline, sulfonamide, sulfonamide antibiotic (CHEBI:45373)
Chemical Identifiers
- UNII
- 21240MF57M
- CAS number
- 63-74-1
- InChI Key
- 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)
- IUPAC Name
- 4-aminobenzene-1-sulfonamide
- SMILES
- NC1=CC=C(C=C1)S(N)(=O)=O
References
- Synthesis Reference
Donald R. Randell, Emyr Phillips, "Anthraquinone sulphonamide compounds and preparation." U.S. Patent US4276224, issued May, 1937.
US4276224- General References
- 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:16997145]
- External Links
- Human Metabolome Database
- HMDB0014404
- KEGG Drug
- D08543
- KEGG Compound
- C07458
- PubChem Compound
- 5333
- PubChem Substance
- 46508306
- ChemSpider
- 5142
- BindingDB
- 10857
- 10184
- ChEBI
- 45373
- ChEMBL
- CHEMBL21
- ZINC
- ZINC000000002101
- Therapeutic Targets Database
- DNC001391
- PharmGKB
- PA451545
- PDBe Ligand
- SAN
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Sulfanilamide
- PDB Entries
- 1aj0 / 4coq / 4f92 / 4f93 / 6rl9
- MSDS
- Download (74.9 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Azur pharma international ltd
- Teva pharmaceuticals usa inc
- Packagers
- Mallinckrodt Inc.
- Pharmedix
- Pharmelle LLC
- Physicians Total Care Inc.
- Sanofi-Aventis Inc.
- Dosage Forms
Form Route Strength Cream Vaginal Cream Vaginal 15 g/100g - Prices
Unit description Cost Unit AVC Vaginal 15% Cream 120 gm Tube 110.97USD tube Avc 15% cream 0.33USD g Sodium sulfanilamide powder 0.22USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 165.5 °C PhysProp water solubility 7500 mg/L (at 25 °C) MERCK INDEX (1976) logP -0.62 HANSCH,C ET AL. (1995) logS -1.36 ADME Research, USCD pKa 10.6 (at 20 °C) SERJEANT,EP & DEMPSEY,B (1979) - Predicted Properties
Property Value Source Water Solubility 10.4 mg/mL ALOGPS logP -0.16 ALOGPS logP -0.25 ChemAxon logS -1.2 ALOGPS pKa (Strongest Acidic) 10.99 ChemAxon pKa (Strongest Basic) 2.27 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 86.18 Å2 ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 42.92 m3·mol-1 ChemAxon Polarizability 16.25 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9893 Blood Brain Barrier + 0.9795 Caco-2 permeable + 0.5881 P-glycoprotein substrate Non-substrate 0.9243 P-glycoprotein inhibitor I Non-inhibitor 0.969 P-glycoprotein inhibitor II Non-inhibitor 0.9313 Renal organic cation transporter Non-inhibitor 0.9254 CYP450 2C9 substrate Non-substrate 0.8093 CYP450 2D6 substrate Non-substrate 0.9117 CYP450 3A4 substrate Non-substrate 0.7625 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9418 CYP450 2D6 inhibitor Non-inhibitor 0.9478 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8891 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8059 Ames test Non AMES toxic 0.9253 Carcinogenicity Non-carcinogens 0.8711 Biodegradation Not ready biodegradable 0.9867 Rat acute toxicity 1.6762 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9432 hERG inhibition (predictor II) Non-inhibitor 0.9451
Spectra
- Mass Spec (NIST)
- Download (9 KB)
- Spectra
Targets
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Metal ion binding
- Specific Function
- Catalyzes the condensation of para-aminobenzoate (pABA) with 6-hydroxymethyl-7,8-dihydropterin diphosphate (DHPt-PP) to form 7,8-dihydropteroate (H2Pte), the immediate precursor of folate derivatives.
- Gene Name
- folP
- Uniprot ID
- P0AC13
- Uniprot Name
- Dihydropteroate synthase
- Molecular Weight
- 30614.855 Da
References
- 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:16487326]
- 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:16997145]
- 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:9127492]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- Current data regarding this enzyme inhibition are limited to one in vitro study.
- General Function
- Steroid hydroxylase activity
- Specific Function
- 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 im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- van den Bongard HJ, Sparidans RW, Critchley DJ, Beijnen JH, Schellens JH: Pharmacokinetic drug-drug interaction of the novel anticancer agent E7070 and acenocoumarol. Invest New Drugs. 2004 Apr;22(2):151-8. [PubMed:14739663]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- 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...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- van den Bongard HJ, Sparidans RW, Critchley DJ, Beijnen JH, Schellens JH: Pharmacokinetic drug-drug interaction of the novel anticancer agent E7070 and acenocoumarol. Invest New Drugs. 2004 Apr;22(2):151-8. [PubMed:14739663]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- 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 ...
- Gene Name
- CYP2E1
- Uniprot ID
- P05181
- Uniprot Name
- Cytochrome P450 2E1
- Molecular Weight
- 56848.42 Da
References
- van den Bongard HJ, Sparidans RW, Critchley DJ, Beijnen JH, Schellens JH: Pharmacokinetic drug-drug interaction of the novel anticancer agent E7070 and acenocoumarol. Invest New Drugs. 2004 Apr;22(2):151-8. [PubMed:14739663]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- 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 react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- van den Bongard HJ, Sparidans RW, Critchley DJ, Beijnen JH, Schellens JH: Pharmacokinetic drug-drug interaction of the novel anticancer agent E7070 and acenocoumarol. Invest New Drugs. 2004 Apr;22(2):151-8. [PubMed:14739663]
Drug created on June 13, 2005 07:24 / Updated on September 03, 2020 19:02
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