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68-35-9 molecular structure
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4-amino-N-(pyrimidin-2-yl)benzene-1-sulfonamide

ChemBase ID: 243
Molecular Formular: C10H10N4O2S
Molecular Mass: 250.277
Monoisotopic Mass: 250.05244658
SMILES and InChIs

SMILES:
S(=O)(=O)(Nc1ncccn1)c1ccc(N)cc1
Canonical SMILES:
Nc1ccc(cc1)S(=O)(=O)Nc1ncccn1
InChI:
InChI=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)
InChIKey:
SEEPANYCNGTZFQ-UHFFFAOYSA-N

Cite this record

CBID:243 http://www.chembase.cn/molecule-243.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
4-amino-N-(pyrimidin-2-yl)benzene-1-sulfonamide
IUPAC Traditional name
4-amino-N-(pyrimidin-2-yl)benzene-1-sulfonamide
sulfadiazine
Brand Name
Adiazin
Adiazine
Coco-Diazine
Cocodiazine
Codiazine
Cremodiazine
Cremotres
Debenal
Deltazina
Diazin
Diazolone
Diazovit
Diazyl
Eskadiazine
Honey Diazine
Lantrisul
Lipo-Diazine
Lipo-Levazine
Liquadiazine
Metha-Meridiazine
Microsulfon
Neazine
Neotrizine
Palatrize
Pecta-Diazine
Piridisir
Pirimal
Pyrimal
Quadetts
Quadramoid
Sanodiazine
Spofadrizine
Sterazine
Sulfacombin
Sulfaloid
Sulfatryl
Sulfazine
Sulfolex
Sulfonamides Duplex
Sulfonsol
Sulfose
Terfonyl
Theradiazine
Tri-Sulfameth
Trifonamide
Triple Sulfa
Triple Sulfas
Triple Sulfoid
Trisem
Truozine
Sulfa-Triple #2
Synonyms
Sulfadiazine
4-Amino-N-(2-pyrimidinyl)benzenesulfonamide
N1-(Pyrimidin-2-yl)sulfanilamide
4-amino-N-(pyrimidin-2-yl)benzenesulfonamide
Adiazin
Adiazine
Debenal
Liquadiazine
4-Amino-N-2-pyrimidinyl-benzenesulfonamide
N1-(Pyrimidin-2-yl)sulfanilamide
Lantrisul
Neotrizine
Sulfadiazine
Sulfaloid
Sulfonamides Duplex
Sulfose
Terfonyl
Triple Sulfa
Triple Sulfas
Triple Sulfoid
Sulfadiazin
Sulfadiazene
Sulfanilamidopyrimidine
Sulfapirimidin
Sulfapyrimidine
Sulfapyrimidin
Sulphadiazine
SDA
Sulfadiazine
4-Amino-N-pyrimidin-2-ylbenzenesulfonamide
N(1)-(2-Pyrimidinyl)sulfanilamide
-Amino-N-2-pyrimidinylbenzenesulfonamide
2-(4-Aminobenzenesulfonamido)pyrimidine
2-Sulfanilylaminopyrimidine
Microsulfon
Sulfazine
Sulfolex
Theradiazine
N-2-嘧啶基-4-氨基苯磺酰胺
N1-(嘧啶-2-基)磺胺
磺胺嘧啶
CAS Number
68-35-9
116-44-9
EC Number
200-685-8
MDL Number
MFCD00006065
Beilstein Number
6733588
Merck Index
148903
PubChem SID
24899802
160963706
46506164
24861734
PubChem CID
5215

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 6.9899154  H Acceptors
H Donor LogD (pH = 5.5) 0.3748896 
LogD (pH = 7.4) -0.053857565  Log P 0.3872608 
Molar Refractivity 64.2009 cm3 Polarizability 24.589895 Å3
Polar Surface Area 97.97 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 0.25  LOG S -2.62 
Solubility (Water) 6.01e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
0.077 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] expand Show data source
DMSO expand Show data source
Methanol expand Show data source
Apperance
White Solid expand Show data source
Melting Point
253 °C (dec.)(lit.) expand Show data source
253-256°C expand Show data source
260-262°C expand Show data source
Hydrophobicity(logP)
-0.2 expand Show data source
Storage Condition
-20°C expand Show data source
Refrigerator expand Show data source
Room Temperature (15-30°C) expand Show data source
Storage Warning
IRRITANT expand Show data source
RTECS
WP1925000 expand Show data source
European Hazard Symbols
X expand Show data source
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22-36/37/38-42/43 expand Show data source
Safety Statements
22-24-26-37-45 expand Show data source
26-36 expand Show data source
TSCA Listed
false expand Show data source
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H302-H315-H317-H319-H334-H335 expand Show data source
H334-H315-H319-H317-H302-H335 expand Show data source
GHS Precautionary statements
P261-P280-P305 + P351 + P338-P342 + P311 expand Show data source
P285-P305+P351+P338-P302+P352-P321-P405-P501A expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand Show data source
Mechanism of Action
Folate antagonist expand Show data source
Folate synthesis inhibitor expand Show data source
Restrict folate synthesis through competitive antagonism of PABA expand Show data source
Purity
≥99.0% expand Show data source
99% expand Show data source
Grade
VETRANAL™, analytical standard expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Suitability
suitable for 1694 per US EPA expand Show data source
Application(s)
Antibacterial agent expand Show data source
Used in some countries for control of bacterial disease in farmed fish expand Show data source
Empirical Formula (Hill Notation)
C10H10N4O2S expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00359 external link
Item Information
Drug Groups approved
Description One of the short-acting sulfonamides used in combination with pyrimethamine to treat toxoplasmosis in patients with acquired immunodeficiency syndrome and in newborns with congenital infections. [PubChem]
Indication For the treatment of rheumatic fever and meningococcal meningitis
Pharmacology 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.
Toxicity Oral LD50 in mouse is 1500 mg/kg.
Affected Organisms
Enteric bacteria and other eubacteria
Elimination Sulfadiazine is excreted largely in the urine.
External Links
Wikipedia
Drugs.com
Selleck Chemicals - S1770 external link
Research Area: Infection
Biological Activity:
Sulfadiazine is a sulfonamide antibiotic. It eliminates bacteria that cause infections by stopping the production of folic acid inside the bacterial cell, and is commonly used to treat urinary tract infections (UTIs). In combination, sulfadiazine and pyrimethamine, can be used to treat toxoplasmosis, a disease caused by Toxoplasma gondii. [1]
Sigma Aldrich - S8626 external link
包装
25, 50, 100, 250, 500 g in poly bottle
Application
Sulfadiazine is a short-acting sulfonamide that is commonly used with pyrimethamine to treat toxoplasmosis in patients with acquired immunodeficiency syndrome. It is also used to treat newborns with congenital infections1. Sulfadiazine has been used to control acute infections when studying murine models of reactivated toxoplasmosis2.
Biochem/physiol Actions
Sulfadiazine is a sulfonamide antibiotic that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase. Sulfadiazine is a competitive inhibitor of bacterial para-aminobenzoic acid (PABA), which is required for bacterial synthesis of folic acid1. It is active against Gram positive bacteria, Gram negative bacteria and Chlamydia. Mode of resistance is via the alteration of dihydropteroate synthase or alternative pathway for folic acid synthesis.
Sigma Aldrich - 35033 external link
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • •  http://en.wikipedia.org/wiki/Sulfadiazine
  • • Bohni, et al.: Chemotherapy, 14, 195 (1969)
  • • Carr, et al.: Antimicrob. Agents Chemother., 4, 585 (1969)
  • • Stober, H., et al.: Anal. Profiles Drug Subs., 11, 523 (1969)
  • • Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 392A, (nmr)
  • • Roblin, R.O., J.A.C.S., 1940, 62, 2002, (synth)
  • • Bass, A.D., Drill's Pharmacol. Med., 4th edn., McGraw-Hill, New York, 1971, 1657, (rev, pharmacol)
  • • Chang, C.J. et al., J. Med. Chem., 1975, 18, 505, (pmr)
  • • Kracmar, J. et al., Pharmazie, 1975, 30; 447, (uv)
  • • Przybylski, M. et al., Adv. Mass Spectrom. Biochem. Med., Proc. Int. Symp. Mass Spectrom. Biochem. Med. 2nd, 3rd, 1976, 1, 309, (ms)
  • • Stober, H. et al., Anal. Profiles Drug Subst., 1982, 11, 523; 1984, 13, 553, (rev, synth, pharmacol, anal)
  • • Cai, E., CA, 1982, 96, 57702, (synth)
  • • Sigel, C.W., Handb. Exp. Pharmacol., 1983, 64, 163, (rev, metab)
  • • Joshi, V.V. et al., Indian J. Phys., A, 1983, 57, 79, (cryst struct)
  • • Bult, A., Pharm. Weekbl., Sci. Ed., 1983, 5, 77, (cmr, tautom)
  • • Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 1477
  • • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 201; 206
  • • Kokila, M.K. et al., Acta Cryst. C, 1995, 51, 333, (cryst struct)
  • • Gehring, T.A. et al., J. Agric. Food Chem., 1996, 44, 3164-3169, (anal)
  • • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, MRM250; SNI425; PPP500
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