Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Sulfacytine
- DrugBank Accession Number
- DB01298
- Background
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.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Sulfacytine (DB01298)
- Weight
- Average: 294.33
Monoisotopic: 294.078661024 - Chemical Formula
- C12H14N4O3S
- Synonyms
- 1-ethyl N4-sulfanilylcytosin
- 1-ethyl-N-sulfanilylcytosine
- Sulfacitina
- Sulfacitine
- Sulfacitinum
- Sulfacytine
- External IDs
- CI 636
- CI-636
- NSC-356717
Pharmacology
- Indication
Used orally in the treatment of acute urinary tract infections.
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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. Their antibacterial action is inhibited by pus.
- Mechanism of action
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.
Target Actions Organism ADihydropteroate synthase inhibitorEscherichia coli (strain K12) - Absorption
Well absorbed following oral administration.
- 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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Not Available
- 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 Integrate drug-drug
interactions in your softwareAcarbose The therapeutic efficacy of Acarbose can be increased when used in combination with Sulfacytine. Acetohexamide The therapeutic efficacy of Acetohexamide can be increased when used in combination with Sulfacytine. Albiglutide The therapeutic efficacy of Albiglutide can be increased when used in combination with Sulfacytine. Alogliptin The therapeutic efficacy of Alogliptin can be increased when used in combination with Sulfacytine. Benzylpenicillin Sulfacytine may decrease the excretion rate of Benzylpenicillin which could result in a higher serum level. - Food Interactions
- Not Available
Products
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- Renoquid
Categories
- ATC Codes
- G01AE10 — Combinations of sulfonamides
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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 / Pyrimidones / Organosulfonamides / Imidolactams / Hydropyrimidines / Heteroaromatic compounds / Aminosulfonyl compounds / Azacyclic compounds / Primary amines show 4 more
- Substituents
- Amine / Aminobenzenesulfonamide / Aminosulfonyl compound / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Azacycle / Benzenesulfonyl group / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine show 16 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Bacteria
Chemical Identifiers
- UNII
- T795873AJP
- CAS number
- 17784-12-2
- InChI Key
- SIBQAECNSSQUOD-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
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015412
- PubChem Compound
- 5322
- PubChem Substance
- 46505483
- ChemSpider
- 5131
- 78902
- ChEBI
- 135230
- ChEMBL
- CHEMBL1201056
- ZINC
- ZINC000000002092
- Therapeutic Targets Database
- DAP001201
- PharmGKB
- PA164754808
- Wikipedia
- Sulfacytine
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 166.5 °C PhysProp water solubility 1750 mg/L (at 37 °C) MERCK INDEX (1996); pH 5 - Predicted Properties
Property Value Source Water Solubility 0.468 mg/mL ALOGPS logP 0.51 ALOGPS logP 0.055 Chemaxon logS -2.8 ALOGPS pKa (Strongest Acidic) 10.55 Chemaxon pKa (Strongest Basic) 2.17 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 104.86 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 75.49 m3·mol-1 Chemaxon Polarizability 29.39 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - 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 inhibitor Non-inhibitor 0.6327 CYP450 2D6 inhibitor Non-inhibitor 0.8413 CYP450 2C19 inhibitor Non-inhibitor 0.7461 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0699-5970000000-fcf781e9c8d92fac41fe Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-052b-0890000000-4dd720fa5ed6640da8d2 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0090000000-50f0a930dcb71e30498d Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0k97-0950000000-bc82cb451dc9216b827e Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-2890000000-bde8f06dc7c126a133a4 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0007-5900000000-204afd3bad0c0fbeb933 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-9540000000-a46bda97de659addb65e Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 182.4142548 predictedDarkChem Lite v0.1.0 [M-H]- 183.1411548 predictedDarkChem Lite v0.1.0 [M-H]- 165.47166 predictedDeepCCS 1.0 (2019) [M+H]+ 183.3133548 predictedDarkChem Lite v0.1.0 [M+H]+ 183.7886548 predictedDarkChem Lite v0.1.0 [M+H]+ 167.82967 predictedDeepCCS 1.0 (2019) [M+Na]+ 182.6776548 predictedDarkChem Lite v0.1.0 [M+Na]+ 182.7566548 predictedDarkChem Lite v0.1.0 [M+Na]+ 173.92287 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General 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.
- Specific Function
- dihydropteroate synthase activity
- Gene Name
- folP
- Uniprot ID
- P0AC13
- Uniprot Name
- Dihydropteroate synthase
- Molecular Weight
- 30614.855 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at June 30, 2007 14:20 / Updated at February 21, 2021 18:51