Sulfacytine

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
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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Pharmacodynamics

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.

TargetActionsOrganism
ADihydropteroate synthase
inhibitor
Escherichia 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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Toxicity

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.
DrugInteraction
AcarboseThe therapeutic efficacy of Acarbose can be increased when used in combination with Sulfacytine.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be increased when used in combination with Sulfacytine.
AlbiglutideThe therapeutic efficacy of Albiglutide can be increased when used in combination with Sulfacytine.
AlogliptinThe therapeutic efficacy of Alogliptin can be increased when used in combination with Sulfacytine.
BenzylpenicillinSulfacytine may decrease the excretion rate of Benzylpenicillin which could result in a higher serum level.
Food Interactions
Not Available

Products

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International/Other Brands
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
Human Metabolome Database
HMDB0015412
PubChem Compound
5322
PubChem Substance
46505483
ChemSpider
5131
RxNav
78902
ChEBI
135230
ChEMBL
CHEMBL1201056
ZINC
ZINC000000002092
Therapeutic Targets Database
DAP001201
PharmGKB
PA164754808
Wikipedia
Sulfacytine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)166.5 °CPhysProp
water solubility1750 mg/L (at 37 °C)MERCK INDEX (1996); pH 5
Predicted Properties
PropertyValueSource
Water Solubility0.468 mg/mLALOGPS
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 Area104.86 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity75.49 m3·mol-1Chemaxon
Polarizability29.39 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9934
Blood Brain Barrier+0.899
Caco-2 permeable-0.6162
P-glycoprotein substrateNon-substrate0.7261
P-glycoprotein inhibitor INon-inhibitor0.8802
P-glycoprotein inhibitor IINon-inhibitor0.8838
Renal organic cation transporterNon-inhibitor0.8709
CYP450 2C9 substrateNon-substrate0.5727
CYP450 2D6 substrateNon-substrate0.8572
CYP450 3A4 substrateNon-substrate0.7104
CYP450 1A2 substrateNon-inhibitor0.8277
CYP450 2C9 inhibitorNon-inhibitor0.6327
CYP450 2D6 inhibitorNon-inhibitor0.8413
CYP450 2C19 inhibitorNon-inhibitor0.7461
CYP450 3A4 inhibitorNon-inhibitor0.6874
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7815
Ames testNon AMES toxic0.7561
CarcinogenicityNon-carcinogens0.7885
BiodegradationNot ready biodegradable0.9959
Rat acute toxicity1.9655 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9493
hERG inhibition (predictor II)Non-inhibitor0.771
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0699-5970000000-fcf781e9c8d92fac41fe
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-052b-0890000000-4dd720fa5ed6640da8d2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-50f0a930dcb71e30498d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0k97-0950000000-bc82cb451dc9216b827e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-2890000000-bde8f06dc7c126a133a4
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0007-5900000000-204afd3bad0c0fbeb933
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9540000000-a46bda97de659addb65e
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-182.4142548
predicted
DarkChem Lite v0.1.0
[M-H]-183.1411548
predicted
DarkChem Lite v0.1.0
[M-H]-165.47166
predicted
DeepCCS 1.0 (2019)
[M+H]+183.3133548
predicted
DarkChem Lite v0.1.0
[M+H]+183.7886548
predicted
DarkChem Lite v0.1.0
[M+H]+167.82967
predicted
DeepCCS 1.0 (2019)
[M+Na]+182.6776548
predicted
DarkChem Lite v0.1.0
[M+Na]+182.7566548
predicted
DarkChem Lite v0.1.0
[M+Na]+173.92287
predicted
DeepCCS 1.0 (2019)

Targets

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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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  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. [Article]
  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. [Article]

Drug created at June 30, 2007 14:20 / Updated at February 21, 2021 18:51