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	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.

Drug	Interaction
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Benzylpenicillin	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.
Estetrol	The therapeutic efficacy of Estetrol can be decreased when used in combination 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.

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Food Interactions

No interactions found.

Products

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International/Other Brands

Streptocid

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Avc	Cream	15 g/100g	Vaginal	MEDA Pharmaceuticals	2014-12-01	2019-09-30
Avc Cream - 15%	Cream	15 %	Vaginal	Hoechst Marion Roussel	1995-12-31	2000-07-28
AVC Vaginal	Cream	15 g/100g	Vaginal	Jazz Pharmaceuticals Commercial Corp.	1965-06-05	2016-12-31
AVC Vaginal	Cream	15 g/100g	Vaginal	Physicians Total Care, Inc.	1965-06-05	2012-06-30

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
บุษบา	Sulfanilamide (99.3 G/100G) + Tannic acid (0.41 G/100G)	Powder	Topical	บริษัท ไบร์วู๊ดฟาร์มาซูติคอล จำกัด	1986-12-29	2019-10-21
บุษบา ไบร์วู๊ด	Sulfanilamide (99.3 G/100G) + Tannic acid (0.41 G/100G)	Powder	Topical	บริษัท ไบร์วู๊ดฟาร์มาซูติคอล จำกัด	1997-08-26	2019-10-21
ยาผง เอ็มบีซี	Sulfanilamide (25 G/100G) + Octasulfur (16.5 G/100G) + Zinc oxide (25 G/100G)	Powder	Topical	ห้างหุ้นส่วนจำกัด ห้างขายยา กรุงเทพฯฟามาซี	1984-08-15	Not applicable
ยาผงพิเศษ ตราร่มชูชีพ	Sulfanilamide (99.3 G/100G) + Tannic acid (0.41 G/100G)	Powder	Topical	บริษัท สมจิตต์โอสถ จำกัด	1986-04-24	Not applicable
ยาผงอารายา	Sulfanilamide (99.3 G/100G) + Tannic acid (0.41 G/100G)	Powder	Topical	บริษัท ฮีโร่มัยซิน ฟาร์ม่า จำกัด จำกัด	2004-02-11	2020-08-23

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. [Article]

External Links

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

MSDS

Download (74.9 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count

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	15 %
Cream	Vaginal	15 g/100g
Powder	Topical

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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Download (9 KB)

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
GC-MS Spectrum - EI-B	GC-MS	splash10-0avl-9800000000-517ec40f53253fdb0135
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-05fr-0900000000-50278150b601ad9e8f07
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-05fr-0900000000-43cb75637a921937a7a5
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-0uk9-5900000000-50aaf376888d903aa161
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-0h93-9400000000-cf00412f8d6022da5a4e
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-02h9-9100000000-d798abed368c30f832c4
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-00lr-9000000000-5cd62daf8fa463f7b17c

Targets

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Details1. Dihydropteroate synthase

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. [Article]
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]
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 on June 13, 2005 13:24 / Updated on June 12, 2021 10:51

Sulfanilamide

Identification

Structure for Sulfanilamide (DB00259)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Targets

References