ChemFOnt: Showing chemical card for Sulfacytine (CFc000009686)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:54 UTC

Chemfont ID

CFc000009686

Molecule Identification

Common Name

Sulfacytine

Definition

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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Renoquid	Kegg
Sulphacytine	Generator
1-Ethyl N4-sulfanilylcytosin	HMDB
1-Ethyl-N-sulfanilylcytosine	HMDB
N-Sulfanilyl-L-ethylcytosine	HMDB
N(1)-(1-Ethyl-1,2-dihydro-2-oxo-4-pyrimidinyl)sulfanilamide	HMDB

Chemical Formula

C₁₂H₁₄N₄O₃S

Average Molecular Weight

294.33

Monoisotopic Molecular Weight

294.078661024

IUPAC Name

4-amino-N-(1-ethyl-2-oxo-1,2-dihydropyrimidin-4-yl)benzene-1-sulfonamide

Traditional Name

sulfacytine

CAS Registry Number

17784-12-2

SMILES

CCN1C=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC1=O

InChI Identifier

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)

InChI Key

SIBQAECNSSQUOD-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Substituents

Aminobenzenesulfonamide
Benzenesulfonyl group
Aniline or substituted anilines
Pyrimidone
Hydropyrimidine
Pyrimidine
Organosulfonic acid amide
Imidolactam
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Aminosulfonyl compound
Heteroaromatic compound
Organoheterocyclic compound
Azacycle
Hydrocarbon derivative
Organic nitrogen compound
Amine
Organic oxide
Organopnictogen compound
Primary amine
Organosulfur compound
Organooxygen compound
Organic oxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Source

Exogenous

Exogenous (HMDB: HMDB0015412)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.47 g/L	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	29.43 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0015412

DrugBank ID

DB01298

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5131

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sulfacytine

METLIN ID

Not Available

PubChem Compound

5322

PDB ID

Not Available

ChEBI ID

775007

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Sulfacytine (CFc000009686)

MOL for CFc000009686 (Sulfacytine)

3D MOL for CFc000009686 (Sulfacytine)

3D SDF for CFc000009686 (Sulfacytine)

3D-SDF for CFc000009686 (Sulfacytine)

PDB for CFc000009686 (Sulfacytine)

3D PDB for CFc000009686 (Sulfacytine)

SMILES for CFc000009686 (Sulfacytine)

INCHI for CFc000009686 (Sulfacytine)

Structure for CFc000009686 (Sulfacytine)

3D Structure for CFc000009686 (Sulfacytine)