4-amino-N-(pyrimidin-2-yl)benzene-1-sulfonamide

• ChemBase ID: 243
• Molecular Formular: C10H10N4O2S
• Molecular Mass: 250.277
• Monoisotopic Mass: 250.05244658
• 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

NAMES AND DATABASE IDS

Names

• 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; N^1-(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

Database IDs

• CAS Number: 68-35-9; 116-44-9
• EC Number: 200-685-8
• MDL Number: MFCD00006065
• Beilstein Number: 6733588
• Merck Index: 148903
• PubChem SID: 46506164; 24899802; 160963706; 24861734
• PubChem CID: 5215

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.9899154
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.3748896
• LogD (pH = 7.4): -0.053857565
• Log P: 0.3872608
• Molar Refractivity: 64.2009 cm^3
• Polarizability: 24.589895 Å^3
• Polar Surface Area: 97.97 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.25
• LOG S: -2.62
• Solubility (Water): 6.01e-01 g/l

PROPERTIES

Physical Property

• Solubility: 0.077 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; DMSO; Methanol
• Apperance: White Solid
• Melting Point: 253 °C (dec.)(lit.); 253-256°C; 260-262°C
• Hydrophobicity(logP): -0.2

Safety Information

• Storage Condition: -20°C; Refrigerator; Room Temperature (15-30°C)
• Storage Warning: IRRITANT
• RTECS: WP1925000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38-42/43
• Safety Statements: 22-24-26-37-45; 26-36
• TSCA Listed: false; 是
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H315-H317-H319-H334-H335; H334-H315-H319-H317-H302-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338-P342 + P311; P285-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Pharmacology Properties

• Mechanism of Action: Folate antagonist; Folate synthesis inhibitor; Restrict folate synthesis through competitive antagonism of PABA

Product Information

• Purity: ≥99.0%; 99%
• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Suitability: suitable for 1694 per US EPA
• Application(s): Antibacterial agent; Used in some countries for control of bacterial disease in farmed fish
• Empirical Formula (Hill Notation): C10H10N4O2S

DETAILS

MP Biomedicals - 02102983

Crystalline

DrugBank - DB00359

• 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

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

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

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - S699054

Antibacterial.

REFERENCES

• 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