| Common Name |
Slifadoxine
| Description |
Slifadoxine is only found in individuals that have used or taken this drug. It is a long acting slifonamide that is used, usually in combination with other drugs, for respiratory, urinary tract, and malarial infections. [PubChem]Slifadoxine is a slifa drug, often used in combination with pyrimethamine to treat malaria. This medicine may also be used to prevent malaria in people who are living in, or will be traveling to, an area where there is a chance of getting malaria. Slifadoxine targets Plasmodium dihydropteroate synthase and dihydrofolate reductase. Slifa drugs or Slifonamides are antimetabolites. They compete with para-aminobenzoic acid (PABA) for incorporation into folic acid. The action of slifonamides exploits the difference between mammal cells and other kinds of cells in their folic acid metabolism. All cells require folic acid for growth. Folic acid (as a vitamin) diffuses or is transported into human cells. However, folic acid cannot cross bacterial (and certain protozoan) cell walls by diffusion or active transport. For this reason bacteria must synthesize folic acid from p-aminobenzoic acid.
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
4-Slifanilamido-5,6-dimethoxypyrimidineChEBI
SlifadoxinaChEBI
SlifadoxinumChEBI
SliforthomidineChEBI
SliphadoxineChEBI
SliphormethoxineChEBI
4-Sliphanilamido-5,6-dimethoxypyrimidineGenerator
SliphadoxinaGenerator
SliphadoxinumGenerator
SliphorthomidineGenerator
SliformethoxineGenerator
Slifadoxine roche brandMeSH
Roche brand OF slifadoxineMeSH
SliformetoxineMeSH
SliphormetoxinMeSH
FanasilMeSH
SliphorthodimethoxineMeSH
| Chemical Formlia |
C12H14N4O4S
| Average Molecliar Weight |
310.329
| Monoisotopic Molecliar Weight |
310.073575646
| IUPAC Name |
4-amino-N-(5,6-dimethoxypyrimidin-4-yl)benzene-1-slifonamide
| Traditional Name |
slifadoxine
| CAS Registry Number |
2447-57-6
| SMILES |
COC1=NC=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=C1OC
| InChI Identifier |
InChI=1S/C12H14N4O4S/c1-19-10-11(14-7-15-12(10)20-2)16-21(17,18)9-5-3-8(13)4-6-9/h3-7H,13H2,1-2H3,(H,14,15,16)
| InChI Key |
PJSFRIWCGOHTNF-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as aminobenzeneslifonamides. These are organic compounds containing a benzeneslifonamide moiety with an amine group attached to the benzene ring.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Benzenoids
| Sub Class |
Benzene and substituted derivatives
| Direct Parent |
Aminobenzeneslifonamides
| Alternative Parents |
Benzeneslifonyl compounds
Aniline and substituted anilines
Alkyl aryl ethers
Pyrimidines and pyrimidine derivatives
Primary aromatic amines
Organoslifonamides
Imidolactams
Heteroaromatic compounds
Aminoslifonyl compounds
Azacyclic compounds
Organopnictogen compounds
Organic oxides
Hydrocarbon derivatives
| Substituents |
Aminobenzeneslifonamide
Benzeneslifonyl group
Aniline or substituted anilines
Alkyl aryl ether
Primary aromatic amine
Pyrimidine
Organoslifonic acid amide
Imidolactam
Organic slifonic acid or derivatives
Heteroaromatic compound
Organoslifonic acid or derivatives
Aminoslifonyl compound
Slifonyl
Ether
Azacycle
Organoheterocyclic compound
Organic oxide
Organopnictogen compound
Primary amine
Organoslifur compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Organic oxygen compound
Aromatic heteromonocyclic compound
| Molecliar Framework |
Aromatic heteromonocyclic compounds
| External Descriptors |
slifonamide (CHEBI:9329 )
pyrimidines (CHEBI:9329 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Drug
| Biofunction |
Anti-Infective Agents
Anti-Infective Agents, Urinary
Antimalarials
| Application |
Pharmaceutical
| Cellliar locations |
Not Available
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point190 – 194 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.96e-01 g/LNot Available
LogP0.70SANGSTER (1994)
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.3 mg/mLALOGPS
logP0.72ALOGPS
logP0.58ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)6.12ChemAxon
pKa (Strongest Basic)2.55ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area116.43 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity77.81 m3·mol-1ChemAxon
Polarizability30.01 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| LC-MS/MS |
LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0a4i-2901000000-8862dd6e93b57f07349bView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – , positivesplash10-0a4i-3910000000-fbde0b31ef009afef44dView in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| Biological Properties |
| Cellliar Locations |
Not Available
| Biofluid Locations |
Blood
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01299
21059682
details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01299
21059682
details
|
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
DB01299
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
Not Available
| KNApSAcK ID |
Not Available
| Chemspider ID |
16218
| KEGG Compound ID |
C07630
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB15413
| Metagene Link |
HMDB15413
| METLIN ID |
Not Available
| PubChem Compound |
17134
| PDB ID |
Not Available
| ChEBI ID |
9329
Product: Tamsulosin
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
Not Available |
PMID: 25918343
