Identification

Name
Sulfacetamide
Accession Number
DB00634  (APRD00452)
Type
Small Molecule
Groups
Approved
Description

An anti-infective agent that is used topically to treat skin infections and orally for urinary tract infections. [PubChem]

Structure
Thumb
Synonyms
  • Acetosulfamine
  • N-((P-Aminophenyl)sulfonyl)acetamide
  • N-(P-Aminobenzenesulfonyl)acetamide
  • N-[(P-Aminophenyl)sulfonyl]acetamide
  • N-Acetyl-4-aminobenzenesulfonamide
  • N-Acetylsulfanilamide
  • N-Sulfanilylacetamide
  • N-Sulphanilylacetamide
  • N'-acetylsulfanilamide
  • N(1)-Acetyl-4-aminophenylsulfonamide
  • N(1)-Acetylsulfanilamide
  • P-Aminobenzenesulfonacetamide
  • P-Aminobenzenesulfonoacetamide
  • Sulfacetamid
  • Sulfacetamida
  • Sulfacétamide
  • Sulfacetamidum
  • Sulfanilazetamid
  • Sulphacetamide
  • Sulphacetamidum
External IDs
NSC-63871
Product Ingredients
IngredientUNIICASInChI Key
Sulfacetamide sodium4NRT660KJQ6209-17-2IHCDKJZZFOUARO-UHFFFAOYSA-M
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Balsulph Oph Liq 10.0%Solution / drops100 mgOphthalmicBausch & Lomb Inc1989-12-311996-09-09Canada
Balsulph Oph Ont 10.0%Ointment10 %OphthalmicBausch & Lomb Inc1989-12-311997-09-12Canada
Bleph 10 DpsSolution / drops10 %OphthalmicAllergan1964-12-312011-08-04Canada
Bleph-10Solution / drops100 mg/mLOphthalmicAllergan1971-06-01Not applicableUs
Cetamide Ont 10%Ointment10 %OphthalmicAlcon, Inc.1972-12-312009-04-24Canada
KlaronLotion10 mg/mLTopicalPhysicians Total Care, Inc.2005-09-01Not applicableUs
KlaronLotion100 mg/mLTopicalValeant Pharmaceuticals North America1996-12-23Not applicableUs
Odan-sulfacetamideSolution10 %OphthalmicOdan Laboratories Ltd1985-12-31Not applicableCanada
Ophtho-sulf Liq 10%Liquid10 %OphthalmicAltimed Pharma Inc.1986-12-311997-08-14Canada
PMS-sulfacetamide Sod Oph Soln 30%Solution / drops300 mgOphthalmicPharmascience Inc1991-12-312016-10-28Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
SulfacetamideSolution / drops100 mg/mLOphthalmicPacific Pharma2015-02-06Not applicableUs
Sulfacetamide SodiumSolution / drops100 mg/mLOphthalmicBauch & Lomb Incorporated1994-12-28Not applicableUs
Sulfacetamide SodiumSolution / drops100 mg/mLOphthalmicAkorn2014-09-11Not applicableUs
Sulfacetamide SodiumLotion100 mg/mLTopicalPerrigo New York Inc.2012-10-17Not applicableUs
Sulfacetamide SodiumSuspension100 mg/mLTopicalE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.2006-11-17Not applicableUs
Sulfacetamide SodiumSolution100 mg/mLOphthalmicA S Medication Solutions2003-03-252017-06-20Us
Sulfacetamide SodiumSuspension100 mg/mLTopicalTaro Pharmaceuticals U.S.A., Inc.2009-05-20Not applicableUs
Sulfacetamide SodiumSolution / drops100 mg/mLOphthalmicStat Rx USA1988-10-18Not applicableUs
Sulfacetamide SodiumSolution / drops100 mg/mLOphthalmicCentral Texas Community Health Centers1994-12-28Not applicableUs
Sulfacetamide SodiumSolution / drops100 mg/mLOphthalmicA S Medication Solutions1994-12-28Not applicableUs
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Exact-Rx Sodium Sulfacetamide Wash 10%Liquid100 mg/mLTopicalExact Rx, Inc.2011-08-01Not applicableUs
Exact-Rx Sodium Sulfacetamide Wash 10%Liquid100 mg/mLTopicalExact Rx, Inc.2011-08-01Not applicableUs
OvaceLiquid100 mg/mLTopicalMission Pharmacal2011-09-15Not applicableUs
Ovace PlusLiquid100 mg/mLTopicalMission Pharmacal2011-09-07Not applicableUs
OVACE PlusShampoo100 mg/mLTopicalMission Pharmacal2011-09-15Not applicableUs
Ovace PlusAerosol, foam98 mg/gTopicalMission Pharmacal2010-07-15Not applicableUs
OVACE PlusLiquid100 mg/mLTopicalMission Pharmacal2011-09-15Not applicableUs
Ovace PlusLotion98 mg/gTopicalMission Pharmacal2011-09-15Not applicableUs
OvacePlus PlusCream100 mg/gTopicalMission Pharmacal2011-09-15Not applicableUs
Perrigo Seb PrevCream100 mg/gTopicalPerrigo New York Inc.2008-08-072017-01-18Us
International/Other Brands
Acetopt (Sigma Pharma) / Albucid (Allergan) / Anginamide (Medgenix) / Antebor (Kela) / Apisulfa (Amman) / Blef-10 (Allergan) / Bleph (Allergan) / Cetamide (Alcon) / Cetazin (Sigmapharm) / Oftasul (Dr. Collado) / Optal (Olan-Kemed) / Ovace / Riacetamid (Riyadh Pharma) / Sulfacil (Farmak) / Sulphacalyre (Wallace) / Unisulf (Roster)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AvarSulfacetamide sodium (100 mg/g) + Sulfur (50 mg/g)EmulsionTopicalMission Pharmacal2011-09-15Not applicableUs
AvarSulfacetamide sodium (95 mg/g) + Sulfur (50 mg/g)Aerosol, foamTopicalMission Pharmacal2010-07-15Not applicableUs
Avar Cleansing PadsSulfacetamide sodium (95 mg/g) + Sulfur (50 mg/g)ClothTopicalMission Pharmacal2011-09-15Not applicableUs
Avar LsSulfacetamide sodium (100 mg/g) + Sulfur (20 mg/g)EmulsionTopicalMission Pharmacal2011-09-15Not applicableUs
Avar LSSulfacetamide sodium (100 mg/g) + Sulfur (20 mg/g)Aerosol, foamTopicalMission Pharmacal2010-07-15Not applicableUs
Avar LS Cleansing PadsSulfacetamide sodium (100 mg/g) + Sulfur (20 mg/g)ClothTopicalMission Pharmacal2011-09-15Not applicableUs
Avar-eSulfacetamide sodium (100 mg/g) + Sulfur (50 mg/g)CreamTopicalMission Pharmacal2011-09-15Not applicableUs
Avar-e GreenSulfacetamide sodium (100 mg/g) + Sulfur (50 mg/g)CreamTopicalMission Pharmacal2011-09-15Not applicableUs
Avar-e LSSulfacetamide sodium (100 mg/g) + Sulfur (20 mg/g)CreamTopicalMission Pharmacal2011-09-15Not applicableUs
BlephamideSulfacetamide sodium (100 mg/g) + Prednisolone acetate (2 mg/g)OintmentOphthalmicAllergan1987-01-01Not applicableUs
Categories
UNII
4965G3J0F5
CAS number
144-80-9
Weight
Average: 214.242
Monoisotopic: 214.041212886
Chemical Formula
C8H10N2O3S
InChI Key
SKIVFJLNDNKQPD-UHFFFAOYSA-N
InChI
InChI=1S/C8H10N2O3S/c1-6(11)10-14(12,13)8-4-2-7(9)3-5-8/h2-5H,9H2,1H3,(H,10,11)
IUPAC Name
N-(4-aminobenzenesulfonyl)acetamide
SMILES
CC(=O)NS(=O)(=O)C1=CC=C(N)C=C1

Pharmacology

Indication

For the treatment of bacterial vaginitis, keratitis, acute conjunctivitis, and blepharitis.

Structured Indications
Pharmacodynamics

Sulfacetamide 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

Sulfacetamide is a competitive inhibitor of bacterial para-aminobenzoic acid (PABA), an essential component for bacterial growth (according to the Woods-Fildes theory). The inhibited reaction is necessary in these organisms for the synthesis of folic acid.

TargetActionsOrganism
ADihydropteroate synthase
inhibitor
Escherichia coli (strain K12)
ADihydropteroate synthase type-1
inhibitor
Escherichia coli
AFolic acid synthesis protein FOL1
inhibitor
Baker's yeast
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life

7-12.8 hours

Clearance
Not Available
Toxicity

Oral LD50 Mouse : 16500 mg/kg. Side effects include moderate to severe erythema (redness) and moderate edema (raised kin), nausea, vomiting, headache, dizziness, and tiredness. Higher exposure causes unconsciousness.

Affected organisms
  • Enteric bacteria and other eubacteria
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Sulfacetamide.Investigational
DexketoprofenThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with Sulfacetamide.Approved, Investigational
MecamylamineThe risk or severity of adverse effects can be increased when Sulfacetamide is combined with Mecamylamine.Approved
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Sulfacetamide.Approved
Food Interactions
Not Available

References

General References
  1. Hull CA, Johnson SM: A double-blind comparative study of sodium sulfacetamide lotion 10% versus selenium sulfide lotion 2.5% in the treatment of pityriasis (tinea) versicolor. Cutis. 2004 Jun;73(6):425-9. [PubMed:15224788]
  2. Del Rosso JQ: Evaluating the role of topical therapies in the management of rosacea: focus on combination sodium sulfacetamide and sulfur formulations. Cutis. 2004 Jan;73(1 Suppl):29-33. [PubMed:14959943]
  3. Roth HW, Leimbeck R, Sonnenschein B, Anger CB, Weber S: [The effective antibacterial spectrum of sulfacetamide]. Klin Monbl Augenheilkd. 1992 Mar;200(3):182-6. [PubMed:1578876]
External Links
Human Metabolome Database
HMDB14772
KEGG Drug
D05947
PubChem Compound
5320
PubChem Substance
46504544
ChemSpider
5129
BindingDB
50316126
ChEBI
63845
ChEMBL
CHEMBL455
Therapeutic Targets Database
DAP001191
PharmGKB
PA451536
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Sulfacetamide
ATC Codes
S01AB04 — SulfacetamideD10AF06 — SulfacetamideG01AE10 — Combinations of sulfonamides
AHFS Codes
  • 52:04.04 — Antibacterials
FDA label
Download (455 KB)
MSDS
Download (72.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentOsteomyelitis1
4CompletedTreatmentMeibomian Gland Dysfunction (MGD)1

Pharmacoeconomics

Manufacturers
  • Sanofi aventis us llc
  • Altana inc
  • Perrigo co tennessee inc
  • Taro pharmaceuticals usa inc
  • Allergan pharmaceutical
  • Alcon laboratories inc
  • Schering corp sub schering plough corp
  • Pharmafair inc
  • Allergan
  • Miza pharmaceuticals usa inc
  • Akorn inc
  • Sola barnes hind
  • Novartis pharmaceuticals corp
  • Optopics laboratories corp
  • Alcon inc
  • Alcon universal ltd
  • Bausch and lomb pharmaceuticals inc
  • Bausch and lomb inc
Packagers
Dosage forms
FormRouteStrength
Aerosol, foamTopical
Solution / dropsOphthalmic100 mg
Solution / dropsOphthalmic10 %
OintmentOphthalmic
Suspension / dropsOphthalmic
Solution / dropsOphthalmic
LiquidTopical
OintmentOphthalmic10 %
OintmentOphthalmic; Topical
LotionTopical10 mg/mL
SuspensionOphthalmic
SolutionOphthalmic10 %
Aerosol, foamTopical98 mg/g
LotionTopical98 mg/g
CreamTopical100 mg/g
GelTopical100 mg/g
SoapTopical
LiquidTopical100 mg/.95mL
Solution / dropsOphthalmic300 mg
GelTopical100 mg/mL
LiquidTopical100 mg/mL
ShampooTopical100 mg/mL
SolutionTopical100 mg/g
SwabTopical100 mg/mL
SwabTopical
ClothTopical
RinseTopical
SolutionTopical
CreamTopical
EmulsionTopical
GelTopical
SuspensionTopical
LotionTopical100 mg/mL
OintmentOphthalmic100 mg/g
SolutionOphthalmic100 mg/mL
Solution / dropsOphthalmic100 mg/mL
Solution / dropsOphthalmic300 mg/mL
SuspensionTopical100 mg/mL
SolutionOphthalmic
LotionTopical
LiquidOphthalmic10 %
CreamVaginal
Kit
LiquidOphthalmic
Prices
Unit descriptionCostUnit
Klaron 10% Lotion 118ml Bottle155.38USD bottle
Sulfacetamide-Sulfur Wash 10-4% Emulsion 473ml Bottle138.03USD bottle
Sulfacetamide Sodium-Sulfur 10-5% Lotion 25 gm Bottle70.99USD bottle
Sulfacetamide Sodium-Sulfur 10-5% Suspension 30 gm Tube70.57USD tube
Sulfacetamide Sodium-Sulfur 10-5% Lotion 30 gm Tube63.38USD tube
Sulfacetamide Sod-Sulfur Wash 10-5% Emulsion 170.1 gm Tube55.94USD tube
Bleph-10 10% Solution 5ml Bottle22.7USD bottle
Sulfacetamide Sodium 10% Solution 15ml Bottle12.99USD bottle
Bleph-10 10% eye drops3.89USD ml
Sulfacetamide powder1.55USD g
Klaron 10% lotion1.29USD ml
Sulfacetamide sod cryst powder0.98USD g
Sodium sulfacetamide 10% lot0.94USD ml
Sulfacetamide sod 10% top susp0.8USD ml
Ovace wash 10% liquid0.44USD ml
Re 10 wash0.42USD ml
Sulfacetamide 10% eye drops0.34USD ml
Sulfacetamide 10% ophth sol0.34USD ml
Sulfamide 10% eye drops0.22USD ml
Sodium sulfacetamide powder0.1USD 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)183 °CPhysProp
water solubility1.25E+004 mg/L (at 37 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-0.96HANSCH,C ET AL. (1995)
logS-1.23ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility4.21 mg/mLALOGPS
logP0.15ALOGPS
logP-0.26ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)4.3ChemAxon
pKa (Strongest Basic)2.14ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area89.26 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity52.48 m3·mol-1ChemAxon
Polarizability20.49 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9912
Blood Brain Barrier+0.9881
Caco-2 permeable-0.5396
P-glycoprotein substrateNon-substrate0.8806
P-glycoprotein inhibitor INon-inhibitor0.9743
P-glycoprotein inhibitor IINon-inhibitor0.9449
Renal organic cation transporterNon-inhibitor0.9484
CYP450 2C9 substrateNon-substrate0.6975
CYP450 2D6 substrateNon-substrate0.9058
CYP450 3A4 substrateNon-substrate0.7775
CYP450 1A2 substrateNon-inhibitor0.9609
CYP450 2C9 inhibitorNon-inhibitor0.9595
CYP450 2D6 inhibitorNon-inhibitor0.9312
CYP450 2C19 inhibitorNon-inhibitor0.9546
CYP450 3A4 inhibitorNon-inhibitor0.9552
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8371
Ames testNon AMES toxic0.9279
CarcinogenicityNon-carcinogens0.8623
BiodegradationNot ready biodegradable0.9686
Rat acute toxicity1.7849 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9919
hERG inhibition (predictor II)Non-inhibitor0.9775
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (9.68 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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

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 / Organosulfonic acids and derivatives / Aminosulfonyl compounds / Acetamides / Amino acids and derivatives / Primary amines / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Aminobenzenesulfonamide / Benzenesulfonyl group / Aniline or substituted anilines / Organic sulfonic acid or derivatives / Organosulfonic acid or derivatives / Sulfonyl / Acetamide / Aminosulfonyl compound / Amino acid or derivatives / Carboxylic acid derivative
show 12 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
substituted aniline, sulfonamide (CHEBI:63845)

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. Hevener KE, Zhao W, Ball DM, Babaoglu K, Qi J, White SW, Lee RE: Validation of molecular docking programs for virtual screening against dihydropteroate synthase. J Chem Inf Model. 2009 Feb;49(2):444-60. doi: 10.1021/ci800293n. [PubMed:19434845]
  2. BROWN GM: The biosynthesis of folic acid. II. Inhibition by sulfonamides. J Biol Chem. 1962 Feb;237:536-40. [PubMed:13873645]
  3. Patel OG, Mberu EK, Nzila AM, Macreadie IG: Sulfa drugs strike more than once. Trends Parasitol. 2004 Jan;20(1):1-3. [PubMed:14700578]
Kind
Protein
Organism
Escherichia coli
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 derivativ...
Gene Name
sulI
Uniprot ID
P0C002
Uniprot Name
Dihydropteroate synthase type-1
Molecular Weight
30125.83 Da
References
  1. Patel OG, Mberu EK, Nzila AM, Macreadie IG: Sulfa drugs strike more than once. Trends Parasitol. 2004 Jan;20(1):1-3. [PubMed:14700578]
Kind
Protein
Organism
Baker's yeast
Pharmacological action
Yes
Actions
Inhibitor
General Function
Metal ion binding
Specific Function
Catalyzes three sequential steps of tetrahydrofolate biosynthesis.
Gene Name
FOL1
Uniprot ID
P53848
Uniprot Name
Folic acid synthesis protein FOL1
Molecular Weight
93119.085 Da
References
  1. Patel OG, Mberu EK, Nzila AM, Macreadie IG: Sulfa drugs strike more than once. Trends Parasitol. 2004 Jan;20(1):1-3. [PubMed:14700578]

Drug created on June 13, 2005 07:24 / Updated on November 19, 2017 20:34