Record Information
Version1.0
Creation date2010-04-08 22:09:14 UTC
Update date2018-05-28 23:28:45 UTC
Primary IDFDB010662
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSulfadiazine
DescriptionAntibacterial agent. It is used in some countries for control of bacterial disease in farmed fish. Not approved for aquacultural use in the USA Sulfadiazine is a sulfonamide antibiotic.; Sulfadiazine is a sulfonamide antibiotic. 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.
CAS Number68-35-9
Structure
Thumb
Synonyms
SynonymSource
2-SulfanilamidopyrimidineChEBI
2-SulfanilylaminopyrimidineChEBI
4-Amino-N-2-pyrimidinylbenzenesulfonamideChEBI
N(1)-2-PyrimidinylsulfanilamideChEBI
N(1)-2-PyrimidylsulfanilamideChEBI
SulfadiazinChEBI
SulfadiazinaChEBI
SulfadiazinumChEBI
SulfapyrimidineChEBI
SulphadiazineChEBI
2-SulphanilamidopyrimidineGenerator
2-SulphanilylaminopyrimidineGenerator
4-Amino-N-2-pyrimidinylbenzenesulphonamideGenerator
N(1)-2-PyrimidinylsulphanilamideGenerator
N(1)-2-PyrimidylsulphanilamideGenerator
SulphadiazinGenerator
SulphadiazinaGenerator
SulphadiazinumGenerator
SulphapyrimidineGenerator
SDAHMDB
SulfadiazeneHMDB
SulfanilamidopyrimidineHMDB
SulfapirimidinHMDB
SulfapyrimidinHMDB
SulfazinHMDB
Zinc sulfadiazineHMDB
Sulfadiazine, zincHMDB
SulfazineHMDB
zinabiospider
2-(4-Aminobenzenesulfonamido)pyrimidinedb_source
2-Sulfanilamido-pyrimidinebiospider
2-Sulfanilamidopyridinebiospider
2-Sulfanilamidopyrimidinbiospider
2-Sulfapyrimidinebiospider
4-Amino-N-(2-pyrimidinyl)benzenesulfonamidebiospider
4-amino-N-(pyrimidin-2-yl)benzenesulfonamidebiospider
4-Amino-N-2-pyrimidinyl- benzenesulfonamidebiospider
4-Amino-N-2-pyrimidinyl-benzenesulfonamidebiospider
4-Amino-N-2-pyrimidinylbenzenesulfonamide, 9CIdb_source
4-amino-N-2-PyrimidinylbenzenesulphonamideGenerator
4-amino-N-pyrimidin-2-ylbenzenesulfonamidebiospider
Adiazinbiospider
Adiazinedb_source
Benzenesulfonamide, 4-amino-N-2-pyrimidinyl-biospider
Coco-Diazinedb_source
Cocodiazinebiospider
Codiazinebiospider
Cremodiazinedb_source
Cremotresbiospider
CRL-8131 & Sulfadiazinebiospider
Debenaldb_source
Deltazinabiospider
Di-azo-mulbiospider
Diazinbiospider
Diazolonebiospider
Diazovitbiospider
Eskadiazinedb_source
Honey diazinebiospider
Lipo-diazinebiospider
Lipo-levazinebiospider
Liquadiazinebiospider
Metha-meridiazinebiospider
Microsulfonbiospider
Mixture of sulfadiazine, sulfamerazine, and sulfamethazinebiospider
N'-(2-Pyrimidinyl)sulfanilamide, 8CIdb_source
N(1)-2-pyrimidinylsulfanilamidebiospider
N(1)-2-pyrimidylsulfanilamidebiospider
N(sup 1)-2-Pyrimidinylsulfanilamidebiospider
N(sup1)-2-Pyrimidinylsulfanilamidebiospider
N(sup1)-2-Pyrimidylsulfanilamidebiospider
N1-(Pyrimidin-2-yl)sulfanilamidebiospider
N1-2-Pyrimidinylsulfanilamidebiospider
N1-2-Pyrimidylsulfanilamidebiospider
Neazinebiospider
Neotrizinebiospider
Palatrizebiospider
Pecta-diazine, suspensionbiospider
Piridisirbiospider
Pirimalbiospider
Pyrimalbiospider
Pyrimidine, 2-sulfanilamido-biospider
Quadettsbiospider
Quadramoidbiospider
rBPI21 & Sulfabiospider
Sanodiazinebiospider
Sodium sulfadiazinebiospider
Solfadiazinabiospider
Solfadiazina [dcit]biospider
Spofadrizinebiospider
Sterazinebiospider
Sulfacombinbiospider
Sulfadiazine (jan/usp/inn)biospider
Sulfadiazine (TN)biospider
Sulfadiazine [usan:inn:jan]biospider
Sulfanilamide, N(sup 1)-2-pyrimidinyl-biospider
Sulfanilamide, N1-2-pyrimidinyl-biospider
Sulfanilamide, N1-2-pyrimidinyl- (8CI)biospider
Sulfanilamide, N1-2(1H)-pyrimidinylidene-biospider
Sulfapyrimidin (german)biospider
Sulfatrylbiospider
Sulfazin (Russian pharmaceutical)db_source
Sulfazin (russian)biospider
Sulfolexbiospider
Sulfonamide duplexbiospider
Sulfonamides duplexbiospider
Sulfonsolbiospider
Sulfosebiospider
Sulphadiazine ebiospider
Sulphadiazine, BANdb_source
Terfonylbiospider
Theradiazinedb_source
Thi-di-merbiospider
Tri-sulfamethbiospider
Trifonamidebiospider
Triple sulfasbiospider
Trisembiospider
Trisulfapyrimidine, oral suspensionbiospider
Truozinebiospider
Predicted Properties
PropertyValueSource
Water Solubility0.6 g/LALOGPS
logP0.25ALOGPS
logP0.39ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)6.99ChemAxon
pKa (Strongest Basic)2.01ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area97.97 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity64.2 m³·mol⁻¹ChemAxon
Polarizability24.39 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H10N4O2S
IUPAC name4-amino-N-(pyrimidin-2-yl)benzene-1-sulfonamide
InChI IdentifierInChI=1S/C10H10N4O2S/c11-8-2-4-9(5-3-8)17(15,16)14-10-12-6-1-7-13-10/h1-7H,11H2,(H,12,13,14)
InChI KeySEEPANYCNGTZFQ-UHFFFAOYSA-N
Isomeric SMILESNC1=CC=C(C=C1)S(=O)(=O)NC1=NC=CC=N1
Average Molecular Weight250.277
Monoisotopic Molecular Weight250.052446274
Classification
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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentAminobenzenesulfonamides
Alternative Parents
Substituents
  • Aminobenzenesulfonamide
  • Benzenesulfonyl group
  • Aniline or substituted anilines
  • Pyrimidine
  • Organosulfonic acid amide
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • Sulfonyl
  • Azacycle
  • Organoheterocyclic compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Organosulfur compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
OntologyShould have ontology for this compound
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 47.99%; H 4.03%; N 22.39%; O 12.79%; S 12.81%DFC
Melting PointMp 255-256° dec.DFC
Boiling PointNot Available
Experimental Water Solubility0.077 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-0.09HANSCH,C ET AL. (1995)
Experimental pKapKa2 6.25 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f8a-9340000000-39ac1159346610a1332bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0090000000-1bc83eabade65dc8953aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0910000000-bd163c77861c5a8afa49View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0900000000-260a572b5c7f3c070c26View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-052r-0900000000-580f983ba25c4cb3eb30View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-1900000000-8dc8c152ec6044f1c2e9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0090000000-23afa7ea3ef67a93a2e6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0pb9-3960000000-355dcad6c59ae9c75fb7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-4900000000-337c5e4fc08cc648b85dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4l-8900000000-63cd0dba3c4894d64ae1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4l-9500000000-64c8a8332030e3f700a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-05mo-9300000000-746250effd08ec8bf51bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0090000000-e8005ac37727f1c540d8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0pb9-2960000000-ff127258fb7c09ae3665View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-4900000000-4fa5b350b17254bc9a1aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4l-8900000000-4a998ad7772889643c1fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4l-9500000000-7e0d8190b4e7f7ced956View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-05mo-9300000000-9cca42d677a6ef782a2cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-1900000000-4b5c2f7e29a6399f475cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0190000000-67ad2e08ca1d769ef136View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pb9-5690000000-6430cecd9bf7a43ae649View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00o0-9010000000-57f00ddb968c873de4edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-9a91c28ea8399756ca2bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1940000000-4e16dfc23fbb7da4f648View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-d2a79b1ca177af6ee656View in MoNA
ChemSpider ID5026
ChEMBL IDCHEMBL439
KEGG Compound IDC07658
Pubchem Compound ID5215
Pubchem Substance IDNot Available
ChEBI ID9328
Phenol-Explorer IDNot Available
DrugBank IDDB00359
HMDB IDHMDB14503
CRC / DFC (Dictionary of Food Compounds) IDFLV92-D:FLV92-D
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDSulfadiazine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference