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
Synonyms
  • 4-Aminobenzene sulfonic acid amide
  • 4-Azanylbenzenesulfonamide
  • P-Aminobenzenesulfamide
  • P-Aminobenzenesulfonamide
  • Para-aminobenzenesulfonamide
  • Prontosil album
  • SA
  • Streptocide
  • Sulfamine
  • Sulfanilamide
  • Sulphanilamide
External IDs
NSC-7618
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AvcCream15 g/100gVaginalMeda Pharmaceuticals Ltd2014-12-01Not applicableUs
Avc Cream - 15%Cream15 %VaginalHoechst Marion Roussel1995-12-312000-07-28Canada
AVC VaginalCream15 g/100gVaginalJazz Pharmaceuticals Commercial Corp.1965-06-05Not applicableUs
International/Other Brands
Streptocid
Categories
UNII
21240MF57M
CAS number
63-74-1
Weight
Average: 172.205
Monoisotopic: 172.0306482
Chemical Formula
C6H8N2O2S
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

Pharmacology

Indication

For the treatment of vulvovaginitis caused by Candida albicans.

Structured Indications
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
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
DrugInteractionDrug group
AtorvastatinThe risk or severity of adverse effects can be increased when Sulfanilamide is combined with Atorvastatin.Approved
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Sulfanilamide.Investigational
BromocriptineThe risk or severity of adverse effects can be increased when Bromocriptine is combined with Sulfanilamide.Approved, Investigational
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Sulfanilamide.Approved
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Sulfanilamide.Withdrawn
CilostazolThe serum concentration of Cilostazol can be increased when it is combined with Sulfanilamide.Approved
DexketoprofenThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with Sulfanilamide.Approved, Investigational
DihydroergocornineThe risk or severity of adverse effects can be increased when Dihydroergocornine is combined with Sulfanilamide.Approved
DihydroergocristineThe risk or severity of adverse effects can be increased when Dihydroergocristine is combined with Sulfanilamide.Experimental
DihydroergocryptineThe risk or severity of adverse effects can be increased when Dihydroergocryptine is combined with Sulfanilamide.Experimental
DihydroergotamineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Sulfanilamide.Approved
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Sulfanilamide.Approved
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Sulfanilamide.Approved
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Sulfanilamide.Approved
FluvastatinThe serum concentration of Fluvastatin can be increased when it is combined with Sulfanilamide.Approved
LisurideThe risk or severity of adverse effects can be increased when Lisuride is combined with Sulfanilamide.Approved, Investigational
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Sulfanilamide.Approved, Investigational
Lysergic Acid DiethylamideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Sulfanilamide.Illicit, Investigational, Withdrawn
MecamylamineThe risk or severity of adverse effects can be increased when Sulfanilamide is combined with Mecamylamine.Approved
MetergolineThe risk or severity of adverse effects can be increased when Metergoline is combined with Sulfanilamide.Experimental
MethylergometrineThe risk or severity of adverse effects can be increased when Methylergometrine is combined with Sulfanilamide.Approved
MethysergideThe risk or severity of adverse effects can be increased when Methysergide is combined with Sulfanilamide.Approved
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Sulfanilamide.Approved, Investigational
MevastatinThe serum concentration of Mevastatin can be increased when it is combined with Sulfanilamide.Experimental
NicergolineThe risk or severity of adverse effects can be increased when Nicergoline is combined with Sulfanilamide.Approved, Investigational
PergolideThe risk or severity of adverse effects can be increased when Pergolide is combined with Sulfanilamide.Approved, Investigational, Vet Approved, Withdrawn
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Sulfanilamide.Approved
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Sulfanilamide.Approved
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Sulfanilamide.Approved
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Sulfanilamide.Approved
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Sulfanilamide.Approved
TergurideThe risk or severity of adverse effects can be increased when Terguride is combined with Sulfanilamide.Experimental
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Sulfanilamide.Approved, Withdrawn
UbidecarenoneThe serum concentration of Ubidecarenone can be increased when it is combined with Sulfanilamide.Approved, Experimental
Food Interactions
Not Available

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. [PubMed:16997145]
External Links
Human Metabolome Database
HMDB14404
KEGG Compound
C07458
PubChem Compound
5333
PubChem Substance
46508306
ChemSpider
5142
BindingDB
10857
ChEBI
45373
ChEMBL
CHEMBL21
Therapeutic Targets Database
DNC001391
PharmGKB
PA451545
HET
SAN
Drugs.com
Drugs.com Drug Page
Wikipedia
Sulfanilamide
ATC Codes
J01EB06 — SulfanilamideD06BA05 — SulfanilamideG01AE10 — Combinations of sulfonamides
PDB Entries
1aj0 / 4coq / 4f92 / 4f93
MSDS
Download (74.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingBasic ScienceHealthy Volunteers1
4CompletedTreatmentHysterectomy / Postoperative pain1

Pharmacoeconomics

Manufacturers
  • Azur pharma international ltd
  • Teva pharmaceuticals usa inc
Packagers
Dosage forms
FormRouteStrength
CreamVaginal15 %
CreamVaginal15 g/100g
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-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0avl-9800000000-517ec40f53253fdb0135
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
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

Taxonomy

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
Aminobenzenesulfonamide / Benzenesulfonyl group / Aniline or substituted anilines / Organosulfonic acid amide / Organic sulfonic acid or derivatives / Organosulfonic acid or derivatives / Sulfonyl / Aminosulfonyl compound / Organic oxygen compound / Organic nitrogen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
substituted aniline, sulfonamide, sulfonamide antibiotic (CHEBI:45373)

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
  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:16487326]
  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:16997145]
  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:9127492]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
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
  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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid 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 oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
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
  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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
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
  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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
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
  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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Drug created on June 13, 2005 07:24 / Updated on November 07, 2017 01:35