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

• ChemBase编号: 243
• 分子式: C10H10N4O2S
• 平均质量: 250.277
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 4-amino-N-(pyrimidin-2-yl)benzene-1-sulfonamide
• IUPAC传统名: 4-amino-N-(pyrimidin-2-yl)benzene-1-sulfonamide; sulfadiazine
• 商标名: 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
• 别名: N-2-嘧啶基-4-氨基苯磺酰胺; N1-(嘧啶-2-基)磺胺; 磺胺嘧啶; 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

登记号

• CAS号: 68-35-9; 116-44-9
• EC号: 200-685-8
• MDL号: MFCD00006065
• Beilstein号: 6733588
• 默克索引号: 148903
• PubChem SID: 46506164; 24899802; 160963706; 24861734
• PubChem CID: 5215

理论计算性质

JChem

• Acid pKa: 6.9899154
• 质子受体: 5
• 质子供体: 2
• LogD (pH = 5.5): 0.3748896
• LogD (pH = 7.4): -0.053857565
• Log P: 0.3872608
• 摩尔折射率: 64.2009 cm^3
• 极化性: 24.589895 Å^3
• 极化表面积: 97.97 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.25
• LOG S: -2.62
• 溶解度: 6.01e-01 g/l

分子性质

理化性质

• 溶解度: 0.077 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; DMSO; Methanol
• 外观: White Solid
• 熔点: 253 °C (dec.)(lit.); 253-256°C; 260-262°C
• 疏水性(logP): -0.2

安全信息

• 保存条件: -20°C; Refrigerator; Room Temperature (15-30°C)
• 保存注意事项: IRRITANT
• RTECS编号: WP1925000
• 欧盟危险性物质标志: X; 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22-36/37/38-42/43
• 安全公开号: 22-24-26-37-45; 26-36
• TSCA收录: false; 是
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Danger
• GHS危险声明: H302-H315-H317-H319-H334-H335; H334-H315-H319-H317-H302-H335
• GHS警示性声明: P261-P280-P305 + P351 + P338-P342 + P311; P285-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

药理学性质

• 生物活性机理: Folate antagonist; Folate synthesis inhibitor; Restrict folate synthesis through competitive antagonism of PABA

产品相关信息

• 纯度: ≥99.0%; 99%
• 级别: VETRANAL™, analytical standard
• 成盐信息: Free Base
• 适用性: suitable for 1694 per US EPA
• 应用领域: Antibacterial agent; Used in some countries for control of bacterial disease in farmed fish
• Empirical Formula (Hill Notation): C10H10N4O2S

详细说明

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

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

Toronto Research Chemicals - S699054

Antibacterial.

参考文献

• http://en.wikipedia.org/wiki/Sulfadiazine
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• 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)
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• 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