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Identification
NameSulfacytine
Accession NumberDB01298
Typesmall molecule
Groupsapproved
Description

Sulfacytine is a short-acting sulfonamide. 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.

Sulfacytine is a competitive inhibitor of the enzyme dihydropteroate synthetase. It inhibits bacterial synthesis of of dihydrofolic acid by preventing the condensation of the pteridine with para-aminobenzoic acid (PABA), a substrate of the enzyme dihydropteroate synthetase. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.

Structure
Thumb
Synonyms
SynonymLanguageCode
1-ethyl N4-sulfanilylcytosinNot AvailableNot Available
1-ethyl-N-sulfanilylcytosineNot AvailableNot Available
N-sulfanilyl-l-ethylcytosineNot AvailableNot Available
RenoquidNot AvailableNot Available
SulfacitinaSpanishINN
SulfacitinumLatinINN
SaltsNot Available
Brand names
NameCompany
RenoquidNot Available
Brand mixturesNot Available
Categories
CAS number17784-12-2
WeightAverage: 294.33
Monoisotopic: 294.078661024
Chemical FormulaC12H14N4O3S
InChI KeySIBQAECNSSQUOD-UHFFFAOYSA-N
InChI
InChI=1S/C12H14N4O3S/c1-2-16-8-7-11(14-12(16)17)15-20(18,19)10-5-3-9(13)4-6-10/h3-8H,2,13H2,1H3,(H,14,15,17)
IUPAC Name
4-amino-N-(1-ethyl-2-oxo-1,2-dihydropyrimidin-4-yl)benzene-1-sulfonamide
SMILES
CCN1C=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC1=O
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassBenzenesulfonamides
Direct parentAminobenzenesulfonamides
Alternative parentsSulfonylanilines; Aminopyrimidines and Derivatives; Pyrimidones; Hydropyrimidines; Primary Aromatic Amines; Sulfonamides; Sulfonyls; Polyamines
Substituentsaminopyrimidine; pyrimidone; aniline; pyrimidine; primary aromatic amine; hydropyrimidine; sulfonic acid derivative; sulfonamide; sulfonyl; polyamine; amine; primary amine; organonitrogen compound
Classification descriptionThis compound belongs to the aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.
Pharmacology
IndicationUsed orally in the treatment of acute urinary tract infections.
PharmacodynamicsSulfacytine is a short-acting sulfonamide. 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 actionSulfacytine is a competitive inhibitor of the enzyme dihydropteroate synthetase. It inhibits bacterial synthesis of of dihydrofolic acid by preventing the condensation of the pteridine with para-aminobenzoic acid (PABA), a substrate of the enzyme dihydropteroate synthetase. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.
AbsorptionWell absorbed following oral administration.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Bacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9934
Blood Brain Barrier + 0.899
Caco-2 permeable - 0.6162
P-glycoprotein substrate Non-substrate 0.7261
P-glycoprotein inhibitor I Non-inhibitor 0.8802
P-glycoprotein inhibitor II Non-inhibitor 0.8838
Renal organic cation transporter Non-inhibitor 0.8709
CYP450 2C9 substrate Non-substrate 0.5727
CYP450 2D6 substrate Non-substrate 0.8572
CYP450 3A4 substrate Non-substrate 0.7104
CYP450 1A2 substrate Non-inhibitor 0.8277
CYP450 2C9 substrate Non-inhibitor 0.6327
CYP450 2D6 substrate Non-inhibitor 0.8413
CYP450 2C19 substrate Non-inhibitor 0.7461
CYP450 3A4 substrate Non-inhibitor 0.6874
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7815
Ames test Non AMES toxic 0.7561
Carcinogenicity Non-carcinogens 0.7885
Biodegradation Not ready biodegradable 0.9959
Rat acute toxicity 1.9655 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9493
hERG inhibition (predictor II) Non-inhibitor 0.771
Pharmacoeconomics
Manufacturers
  • Glenwood inc
PackagersNot Available
Dosage forms
FormRouteStrength
TabletOral
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point166.5 °CPhysProp
water solubility1750 mg/L (at 37 °C)MERCK INDEX (1996); pH 5
Predicted Properties
PropertyValueSource
water solubility4.68e-01 g/lALOGPS
logP0.51ALOGPS
logP0.055ChemAxon
logS-2.8ALOGPS
pKa (strongest acidic)10.55ChemAxon
pKa (strongest basic)2.17ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count2ChemAxon
polar surface area104.86ChemAxon
rotatable bond count3ChemAxon
refractivity75.49ChemAxon
polarizability29.43ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
PubChem Compound5322
PubChem Substance46505483
ChemSpider5131
Therapeutic Targets DatabaseDAP001201
PharmGKBPA164754808
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
ChlorpropamideSulfonamide/sulfonylurea: possible hypoglycemia
MethotrexateThe sulfamide increases the toxicity of methotrexate
Food InteractionsNot Available

Targets

1. Dihydropteroate synthase

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Dihydropteroate synthase P0AC13 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Hughes J, Roberts LC, Coppridge AJ: Sulfacytine: a new sulfonamide. Double-blind comparison with sulfisoxazole in acute uncomplicated urinary tract infections. J Urol. 1975 Dec;114(6):912-4. Pubmed

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Drug created on June 30, 2007 08:20 / Updated on September 16, 2013 17:14