Sulfanilamide

Identification

Summary

Sulfanilamide is a sulfonamide anti-infective used to treat vulvovaginal candidiasis caused by Candida albicans.

Generic Name
Sulfanilamide
DrugBank Accession Number
DB00259
Background

Sulfanilamide is a molecule containing the sulfonamide functional group attached to an aniline.

Type
Small Molecule
Groups
Approved
Structure
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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofVulvovaginal candidiasis••••••••••••
Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
ADihydropteroate synthase
inhibitor
Escherichia 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
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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.

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.
DrugInteraction
AmbroxolThe risk or severity of methemoglobinemia can be increased when Sulfanilamide is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Sulfanilamide is combined with Articaine.
BelzutifanThe serum concentration of Belzutifan can be increased when it is combined with Sulfanilamide.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Sulfanilamide is combined with Benzocaine.
Benzyl alcoholThe risk or severity of methemoglobinemia can be increased when Sulfanilamide is combined with Benzyl alcohol.
Food Interactions
No interactions found.

Products

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International/Other Brands
Streptocid
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AvcCream15 g/100gVaginalMEDA Pharmaceuticals2014-12-012019-09-30US flag
Avc Cream - 15%Cream15 %VaginalHoechst Marion Roussel1995-12-312000-07-28Canada flag
AVC VaginalCream15 g/100gVaginalPhysicians Total Care, Inc.1965-06-052012-06-30US flag
AVC VaginalCream15 g/100gVaginalJazz Pharmaceuticals Commercial Corp.1965-06-052016-12-31US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
บุษบาSulfanilamide (99.3 G/100G) + Tannic acid (0.41 G/100G)PowderTopicalบริษัท ไบร์วู๊ดฟาร์มาซูติคอล จำกัด1986-12-292019-10-21Thailand flag
บุษบา ไบร์วู๊ดSulfanilamide (99.3 G/100G) + Tannic acid (0.41 G/100G)PowderTopicalบริษัท ไบร์วู๊ดฟาร์มาซูติคอล จำกัด1997-08-262019-10-21Thailand flag
ยาผง เอ็มบีซีSulfanilamide (25 G/100G) + Octasulfur (16.5 G/100G) + Zinc oxide (25 G/100G)PowderTopicalห้างหุ้นส่วนจำกัด ห้างขายยา กรุงเทพฯฟามาซี1984-08-15Not applicableThailand flag
ยาผงพิเศษ ตราร่มชูชีพSulfanilamide (99.3 G/100G) + Tannic acid (0.41 G/100G)PowderTopicalบริษัท สมจิตต์โอสถ จำกัด1986-04-24Not applicableThailand flag
ยาผงอารายาSulfanilamide (99.3 G/100G) + Tannic acid (0.41 G/100G)PowderTopicalบริษัท ฮีโร่มัยซิน ฟาร์ม่า จำกัด จำกัด2004-02-112020-08-23Thailand flag

Categories

ATC Codes
G01AE10 — Combinations of sulfonamidesJ01EB06 — SulfanilamideD06BA05 — Sulfanilamide
Drug Categories
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)
Affected organisms
  • Candida albicans and other yeasts

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
  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. [Article]
Human Metabolome Database
HMDB0014404
KEGG Drug
D08543
KEGG Compound
C07458
PubChem Compound
5333
PubChem Substance
46508306
ChemSpider
5142
BindingDB
10857
RxNav
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 / 8bcb
MSDS
Download (74.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
FormRouteStrength
CreamVaginal15 %
CreamVaginal15 g/100g
PowderTopical
Prices
Unit descriptionCostUnit
AVC Vaginal 15% Cream 120 gm Tube110.97USD tube
Avc 15% cream0.33USD g
Sodium sulfanilamide powder0.22USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)165.5 °CPhysProp
water solubility7500 mg/L (at 25 °C)MERCK INDEX (1976)
logP-0.62HANSCH,C ET AL. (1995)
logS-1.36ADME Research, USCD
pKa10.6 (at 20 °C)SERJEANT,EP & DEMPSEY,B (1979)
Predicted Properties
PropertyValueSource
Water Solubility10.4 mg/mLALOGPS
logP-0.16ALOGPS
logP-0.25Chemaxon
logS-1.2ALOGPS
pKa (Strongest Acidic)10.99Chemaxon
pKa (Strongest Basic)2.27Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area86.18 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity42.92 m3·mol-1Chemaxon
Polarizability16.25 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9893
Blood Brain Barrier+0.9795
Caco-2 permeable+0.5881
P-glycoprotein substrateNon-substrate0.9243
P-glycoprotein inhibitor INon-inhibitor0.969
P-glycoprotein inhibitor IINon-inhibitor0.9313
Renal organic cation transporterNon-inhibitor0.9254
CYP450 2C9 substrateNon-substrate0.8093
CYP450 2D6 substrateNon-substrate0.9117
CYP450 3A4 substrateNon-substrate0.7625
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9418
CYP450 2D6 inhibitorNon-inhibitor0.9478
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8891
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8059
Ames testNon AMES toxic0.9253
CarcinogenicityNon-carcinogens0.8711
BiodegradationNot ready biodegradable0.9867
Rat acute toxicity1.6762 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9432
hERG inhibition (predictor II)Non-inhibitor0.9451
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (9 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-05c6-9500000000-b4fc349159a78c29204b
GC-MS Spectrum - EI-BGC-MSsplash10-0avl-9800000000-517ec40f53253fdb0135
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-05fr-0900000000-50278150b601ad9e8f07
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-05fr-0900000000-43cb75637a921937a7a5
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0uk9-5900000000-50aaf376888d903aa161
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0h93-9400000000-cf00412f8d6022da5a4e
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-02h9-9100000000-d798abed368c30f832c4
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00lr-9000000000-5cd62daf8fa463f7b17c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0900000000-f30f6f3b6a87d68a8a30
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0900000000-626fa06fc0a89418269b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9500000000-5f2e3512b98c3142d94d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0900000000-b82a77e499ce01ce1709
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9100000000-43378dee54753319c785
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-9000000000-a41486066327aaede8c4
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-136.1672422
predicted
DarkChem Lite v0.1.0
[M-H]-136.1060422
predicted
DarkChem Lite v0.1.0
[M-H]-136.3338422
predicted
DarkChem Lite v0.1.0
[M-H]-136.1634422
predicted
DarkChem Lite v0.1.0
[M-H]-130.60469
predicted
DeepCCS 1.0 (2019)
[M+H]+137.2475422
predicted
DarkChem Lite v0.1.0
[M+H]+137.2683422
predicted
DarkChem Lite v0.1.0
[M+H]+137.2426422
predicted
DarkChem Lite v0.1.0
[M+H]+137.5036422
predicted
DarkChem Lite v0.1.0
[M+H]+134.43202
predicted
DeepCCS 1.0 (2019)
[M+Na]+136.4445422
predicted
DarkChem Lite v0.1.0
[M+Na]+136.6324422
predicted
DarkChem Lite v0.1.0
[M+Na]+136.4993422
predicted
DarkChem Lite v0.1.0
[M+Na]+136.5104422
predicted
DarkChem Lite v0.1.0
[M+Na]+143.76819
predicted
DeepCCS 1.0 (2019)

Targets

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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
  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. [Article]
  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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at January 02, 2024 23:43