4-(4-aminobenzenesulfonyl)aniline

• ChemBase编号: 135
• 分子式: C12H12N2O2S
• 平均质量: 248.30088
• 单一同位素质量: 248.06194863
• SMILES: S(=O)(=O)(c1ccc(N)cc1)c1ccc(N)cc1
• Canonical SMILES: Nc1ccc(cc1)S(=O)(=O)c1ccc(cc1)N
• InChI: InChI=1S/C12H12N2O2S/c13-9-1-5-11(6-2-9)17(15,16)12-7-3-10(14)4-8-12/h1-8H,13-14H2
• InChIKey: MQJKPEGWNLWLTK-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 4-(4-aminobenzenesulfonyl)aniline
• IUPAC传统名: dapsone; 4-(4-aminobenzenesulfonyl)aniline
• 商标名: Araldite Ht; Avlosulfon; Avlosulfone; Avlosulphone; Croysulfone; Croysulphone; Dimitone; Diphone; Dubronax; Dumitone; Eporal; ICI; Normet; Novophone; Recolip; Sulfadione; Sulfanona-Mae; Sulfon-Mere; Sulfona; Sulfona-Mae; Sulfone Ucb; Sulphon-Mere; Sumicure S; Tarimyl; Udolac; Aczone
• 别名: 4,4'-二氨基二苯砜; 4,4′-磺酰基二苯胺; 双(4-氨基苯基)砜; 氨苯砜; 4-氨基苯砜; 4,4'-二氨基二苯砜; 4-氨基苯砜; 氨苯砜; bis(4-AMINOPHENYL)SULFONE; 4,4′-Diaminodiphenyl sulfone; 4,4′-Sulfonyldianiline; Bis(4-aminophenyl) sulfone; 4-Aminophenyl sulfone; 4-[(4-Aminophenyl)sulfonyl]aniline; 4,4'-Diaminodiphenyl sulfone; DADPS, DDS, Avlosulfon, Croysulfone, Diphenasone, Disulone, Dumitone, Eporal, Novophone, Sulfona-Mae, Sulphadione, 4,4’-Sulfonylbisbenzeneamine; 1,1'-Sulfonylbis[4-aminobenzene]; 4,4'-Diaminodiphenyl Sulfone; NSC 6091; 4-Aminophenyl sulfone; Dapson; P, P'-Sulfonyldianiline; P-Aminophenyl Sulfone; P,P-Sulphonyldianiline; P,P-Sulphonylbisbenzenamine; P,P-Sulphonylbisbenzamine; P,P-Sulfonylbisbenzenamine; P,P-Sulfonylbisbenzamine; P,P-Diaminodiphenyl Sulphone; P,P'-Diaminodiphenyl Sulfone; N, N'-Diphenyl Sulfondiamide; Metabolite C; Sulfonyldianiline; Sulphadione; Sulphonyldianiline; Diphenasone; Diaphenylsulphone; Diaphenylsulphon; Diaphenylsulfone; Diaphenylsulfon; Diaminodiphenyl Sulfone; Diaminodifenilsulfona; Dds, Pharmaceutical; Dds, Diaphenylsulfone; DDS; Dapsonum; Dapson; DADPS; Acedapsone; Diamino-diphenyl sulphone; DSS; dapsone; Dapsone

登记号

• CAS号: 80-08-0
• EC号: 201-248-4
• MDL号: MFCD00007887
• Beilstein号: 788055
• 默克索引号: 142822
• PubChem SID: 24869870; 24859802; 46505300; 160963598; 24891242
• PubChem CID: 2955
• CHEBI ID: 4325
• ATC码: D10AX05; J04BA02
• CHEMBL: 1043
• Chemspider ID: 2849
• DrugBank ID: DB00250
• KEGG ID: D00592
• 美国药典/FDA物质标识码: 8W5C518302
• 维基百科标题: Dapsone
• Medline Plus: a682128

理论计算性质

JChem

• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 1.2698921
• LogD (pH = 7.4): 1.2702243
• Log P: 1.2702285
• 摩尔折射率: 68.991 cm^3
• 极化性: 26.662663 Å^3
• 极化表面积: 86.18 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: 1.19
• LOG S: -2.94
• 溶解度: 2.84e-01 g/l

分子性质

理化性质

• 溶解度: 380 mg/L; Acetone; DMSO; Ethanol; Methanol
• 外观: Off -White Solid
• 熔点: 172-174°C; 175°C; 175-177 °C(lit.); 175-178°C; 175-179 °C
• 疏水性(logP): 0.4

安全信息

• 保存条件: -20°C Freezer
• 保存注意事项: IRRITANT
• RTECS编号: BY8925000
• 欧盟危险性物质标志: X; 有害性(Harmful) (Xn)
• 德国WGK号: 1
• 危险公开号: 22; R:22
• 安全公开号: 22; S:22
• TSCA收录: false; 是
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• GHS警示性声明: P261
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

药理学性质

• 给药途径: Oral
• 生物利用度: 70 to 80%
• 排泄: Renal
• 半衰期: 20 to 30 hours
• 代谢: Hepatic (mostly CYP2E1-mediated)
• 蛋白结合率: 70 to 90%
• 法定药品分级: ?-only (U.S.), POM (UK)
• 妊娠期药物分类: B2 (Australia); C (US)

产品相关信息

• 纯度: ≥97.0% (NT); 97%; 98%
• 级别: purum; VETRANAL™, analytical standard
• 线性分子式: (H2NC6H4)2SO2

详细说明

MP Biomedicals - 05212644

MP Biomedicals Rare Chemical collection

DrugBank - DB00250

• Drug Groups: approved; investigational
• Description: A sulfone active against a wide range of bacteria but mainly employed for its actions against mycobacterium leprae. Its mechanism of action is probably similar to that of the sulfonamides which involves inhibition of folic acid synthesis in susceptible organisms. It is also used with pyrimethamine in the treatment of malaria. (From Martindale, The Extra Pharmacopoeia, 30th ed, p157-8)
• Indication: For the treatment and management of leprosy and dermatitis herpetiformis.
• Pharmacology: Dapsone is a sulfone with anti-inflammatory immunosuppressive properties as well as antibacterial and antibiotic properties. Dapsone is the principal drug in a multidrug regimen recommended by the World Health Organization for the treatment of leprosy. As an anti-infective agent, it is also used for treating malaria and, recently, for Pneumocystic carinii pneumonia in AIDS patients. Dapsone is absorbed rapidly and nearly completely from the gastrointestinal tract. Dapsone is distributed throughout total body water and is present in all tissues. However, it tends to be retained in skin and muscle and especially in the liver and kidney: traces of the drug are present in these organs up to 3 weeks after therapy cessation.
• Toxicity: Overdosage might be expected to produce nasal congestion, syncope, or hallucinations. Measures to support blood pressure should be taken if necessary.
• Affected Organisms: Mycobacteria
• Biotransformation: Hepatic, mostly CYP2E1-mediated.
• Absorption: Bioavailability is 70 to 80% following oral administration.
• Half Life: 28 hours (range 10-50 hours)
• Protein Binding: 70 to 90%
• Elimination: Renal
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - A74807

包装
100, 500 g in poly bottle

Sigma Aldrich - 46158

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

Toronto Research Chemicals - D193250

An antibacterial used in the treatment of dermatitis herpetiformis.

参考文献

• Francis, J., et al.: Br. J. Pharmacol., 5, 565 (1950)
• Uetrecht, J., et al.: Clin. Dermatol., 7, 111 (1950)
• Reszka, K., et al.: Chem. Res. Toxicol., 22, 1137 (1950)
• Santos, J., et al.: Bioorg. Med. Chem., 17, 3795 (1950)
• Varma, M., et al.: J. Med. Chem