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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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Brand names
  • Acetocid
  • Acetosulfamin
  • Acetosulfamine
  • Ak-Sulf
  • Albamine
  • Albucid
  • Alesten
  • Bleph-10
  • Bleph-10 Liquifilm
  • Cetamide
  • Formosulfacetamide
  • Gyne-Sulf
  • I-Sulfacet
  • Isopto Cetamide
  • Isopto-Cetamide
  • Klaron
  • N-Acetylsulfanilamide
  • N-Acetylsulfanilamine
  • N-Sulfanilylacetamide
  • N-Sulphanilylacetamide
  • N'-Acetylsulfanilamide
  • Oclucid
  • Ocusulf-10
  • Op-Sulfa 30
  • Ophthacet
  • Ophthel-S
  • P-Aminobenzenesulfonacetamide
  • P-Aminobenzenesulfonoacetamide
  • Region
  • Sebizon
  • Sodium Sulamyd
  • Sodium Sulfacetamide
  • Steramide
  • Steri-Units Sulfacetamide
  • Sulamyd
  • Sulf-10
  • Sulf-15
  • Sulfacel-15
  • Sulfacet
  • Sulfacetamide Sodium
  • Sulfacetamide Sodium Anhydrous
  • Sulfacetamide Sodium Usp
  • Sulfacetimide
  • Sulfacyl
  • Sulfair
  • Sulfair 10
  • Sulfair 15
  • Sulfair Forte
  • Sulfair-15
  • Sulfamide
  • Sulfanilacetamide
  • Sulfanilazetamid
  • Sulfex
  • Sulphacetamide
  • Sulphacetamide Sodium
  • Sulphasil
  • Sulten-10
  • Sultrin
  • Trysul
  • Urosulfon
  • Urosulfone
Brand name mixtures
  • Ak Cide Oph Soln (Prednisolone Acetate + Sulfacetamide Sodium)
  • Blephamide Oph Ont (Prednisolone Acetate + Sulfacetamide Sodium)
  • Blephamide Opht Suspension (Prednisolone Acetate + Sulfacetamide Sodium)
  • Cocci Bol O Tab Jr (Calcium Carbonate + Charcoal Activated + Cobalt Gluconate + Copper Sulfate + Ferrous Gluconate + Sodium Arsanilate + Sulfabenzamide Sodium + Sulfacetamide Sodium + Sulfaquinoxaline + Tannic Acid)
  • Cocci Bol-O-Tab (Calcium Carbonate + Charcoal Activated + Cobalt Gluconate + Copper Sulfate + Ferrous Gluconate + Sodium Arsanilate + Sulfabenzamide Sodium + Sulfacetamide Sodium + Sulfaquinoxaline + Tannic Acid)
  • Dioptimyd Ointment (Prednisolone Acetate + Sulfacetamide Sodium)
  • Dioptimyd Suspension (Prednisolone Acetate + Sulfacetamide Sodium)
  • Medicocci-Jr (Arsenic (Sodium Arsanilate) + Calcium Carbonate + Charcoal Activated + Cobalt Gluconate + Copper Sulfate + Ferrous Gluconate + Sulfabenzamide Sodium + Sulfacetamide Sodium + Sulfaquinoxaline + Tannic Acid)
  • Medicocci-Sr (Arsenic (Sodium Arsanilate) + Calcium Carbonate + Charcoal Activated + Cobalt Gluconate + Copper Sulfate + Ferrous Gluconate + Sulfabenzamide Sodium + Sulfacetamide Sodium + Sulfaquinoxaline + Tannic Acid)
  • Metimyd Oph Sus (Prednisolone Acetate + Sulfacetamide Sodium)
  • Neo Atropec 25 Tab (Aluminum Hydroxide + Atropine Methylnitrate + Kaolin + Neomycin Sulfate + Pectin + Sulfacetamide + Sulfaguanidine)
  • Neo Atropec C Tab (Aluminum Hydroxide + Atropine Methylnitrate + Kaolin + Neomycin Sulfate + Pectin + Sulfacetamide + Sulfaguanidine)
  • Neo Atropec Tab (Aluminum Hydroxide + Atropine Methylnitrate + Kaolin + Neomycin Sulfate + Pectin + Sulfacetamide + Sulfaguanidine)
  • Sulfacet R Lotion (Sulfacetamide Sodium + Sulfur (Sulfur))
  • Sulfacet-R Lotion (Sulfacetamide Sodium + Sulfur)
  • Sultrin Triple Sulfa Crm (Sulfacetamide + Sulfanilylbenzamide + Sulfathiazole + Urea)
  • Vasocidin Ophthalmic Solution (Prednisolone Sodium Phosphate + Sulfacetamide Sodium)
  • Vasosulf Oph Soln (Phenylephrine Hydrochloride + Sulfacetamide Sodium)
Categories
  • Anti-Bacterial Agents
  • Anti-Infective Agents, Local
  • Sulfonamides
  • Anti-Infective Agents, Urinary
CAS number 144-80-9
Weight Average: 214.242
Monoisotopic: 214.041212886
Chemical Formula C8H10N2O3S
InChI Key InChIKey=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)
Plain Text
IUPAC Name
N-[(4-aminobenzene)sulfonyl]acetamide
SMILES
CC(=O)NS(=O)(=O)C1=CC=C(N)C=C1
Plain Text
Mass Spec show (9.7 KB)
Taxonomy
Kingdom Organic
Classes
  • Benzenesulfonamides
  • Sulfanilamides
Substructures
  • Amino Ketones
  • Sulfonyls
  • Aliphatic and Aryl Amines
  • Benzene and Derivatives
  • Benzenesulfonamides
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Sulfanilamides
  • Sulfonamides
  • Anilines
Pharmacology
Indication For the treatment of bacterial vaginitis, keratitis, acute conjunctivitis, and blepharitis.
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.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism
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
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
Form Route Strength
Liquid Ophthalmic
Ointment Ophthalmic
Solution / drops Ophthalmic
Prices
Unit description Cost Unit
Klaron 10% Lotion 118ml Bottle 155.38 USD bottle
Sulfacetamide-Sulfur Wash 10-4% Emulsion 473ml Bottle 138.03 USD bottle
Sulfacetamide Sodium-Sulfur 10-5% Lotion 25 gm Bottle 70.99 USD bottle
Sulfacetamide Sodium-Sulfur 10-5% Suspension 30 gm Tube 70.57 USD tube
Sulfacetamide Sodium-Sulfur 10-5% Lotion 30 gm Tube 63.38 USD tube
Sulfacetamide Sod-Sulfur Wash 10-5% Emulsion 170.1 gm Tube 55.94 USD tube
Bleph-10 10% Solution 5ml Bottle 22.7 USD bottle
Sulfacetamide Sodium 10% Solution 15ml Bottle 12.99 USD bottle
Bleph-10 10% eye drops 3.89 USD ml
Sulfacetamide powder 1.55 USD g
Klaron 10% lotion 1.29 USD ml
Sulfacetamide sod cryst powder 0.98 USD g
Sodium sulfacetamide 10% lot 0.94 USD ml
Sulfacetamide sod 10% top susp 0.8 USD ml
Ovace wash 10% liquid 0.44 USD ml
Re 10 wash 0.42 USD ml
Sulfacetamide 10% eye drops 0.34 USD ml
Sulfacetamide 10% ophth sol 0.34 USD ml
Sulfamide 10% eye drops 0.22 USD ml
Sodium sulfacetamide powder 0.1 USD g
Patents Not Available
Properties
State solid
Melting point 183 oC
Experimental Properties
Property Value Source
water solubility 1.25E+004 mg/L PhysProp
logP -0.6 PhysProp
logS -1.23 [ADME Research, USCD] PhysProp
Predicted Properties
Property Value Source
water solubility 4.21e+00 g/l ALOGPS
logP 0.15 ALOGPS
logP -0.26 ChemAxon Molconvert
logS -1.71 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 4 ChemAxon Molconvert
hydrogen donor count 2 ChemAxon Molconvert
polar surface area 89.26 ChemAxon Molconvert
rotatable bond count 1 ChemAxon Molconvert
refractivity 52.48 ChemAxon Molconvert
polarizability 20.49 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  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
  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
  3. Roth HW, Leimbeck R, Sonnenschein B, Anger CB, Weber S: [The effective antibacterial spectrum of sulfacetamide] Klin Monatsbl Augenheilkd. 1992 Mar;200(3):182-6. Pubmed
External Links
Resource Link
PubChem Compound 5320 Link_out
PubChem Substance 46504544 Link_out
ChemSpider 5129 Link_out
Therapeutic Targets Database DAP001191 Link_out
PharmGKB PA451536 Link_out
Drug Product Database 838934 Link_out
RxList http://www.rxlist.com/cgi/generic3/plexion.htm Link_out
Drugs.com http://www.drugs.com/cdi/sulfacetamide-drops.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/ava1674.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Sulfacetamide Link_out
ATC Codes
  • S01AB04
AHFS Codes
  • 52:04.04
PDB Entries
FDA label show (455.1 KB)
MSDS show (72.7 KB)
Interactions
Drug Interactions
Drug Interaction
Food Interactions Not Available
Targets

1. Dihydropteroate synthase

Pharmacological action: yes
Actions: inhibitor

DHPS catalyzes the formation of the immediate precursor of folic acid. It is implicated in resistance to sulfonamide

Organism class: bacterial
UniProt ID: P0AC13 Link_out
Gene: folP
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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 Jan 27. Pubmed
  2. BROWN GM: The biosynthesis of folic acid. II. Inhibition by sulfonamides. J Biol Chem. 1962 Feb;237:536-40. Pubmed
  3. Patel OG, Mberu EK, Nzila AM, Macreadie IG: Sulfa drugs strike more than once. Trends Parasitol. 2004 Jan;20(1):1-3. Pubmed

2. Dihydropteroate synthase

Pharmacological action: yes
Actions: inhibitor
UniProt ID: P0C002 Link_out
Gene: sulI
SNPs: SNPJam Report Link_out

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

3. Folic acid synthesis protein FOL1

Pharmacological action: yes
Actions: inhibitor
UniProt ID: P53848 Link_out
Gene: FOL1
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 13, 2005 07:24 / Updated on November 10, 2010 13:41

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.