4-(dipropylsulfamoyl)benzoic acid

• ChemBase编号: 904
• 分子式: C13H19NO4S
• 平均质量: 285.35926
• 单一同位素质量: 285.10347909
• SMILES: S(=O)(=O)(N(CCC)CCC)c1ccc(cc1)C(=O)O
• Canonical SMILES: CCCN(S(=O)(=O)c1ccc(cc1)C(=O)O)CCC
• InChI: InChI=1S/C13H19NO4S/c1-3-9-14(10-4-2)19(17,18)12-7-5-11(6-8-12)13(15)16/h5-8H,3-4,9-10H2,1-2H3,(H,15,16)
• InChIKey: DBABZHXKTCFAPX-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 4-(dipropylsulfamoyl)benzoic acid
• IUPAC传统名: probenecid
• 商标名: Apurina; Benecid; Benemid; Benuryl; Col-Probenecid; Colbenemid; Polycillin-PRB; Probalan; Probampacin; Probecid; Proben; Proben-C; Probenemid; Probexin; Prolongine; Synergid R; Tubophan; Uricosid
• 别名: 丙磺舒; p-(Dipropylsulfamoyl)benzoic acid; Probenecid; 4-(Di-n-propylaminosulfonyl)benzoic acid; 4-(Di-n-propylsulfamoyl)benzoic acid; probenicid; Probenecid Acid; Probenecid; 4-[(dipropylamino)sulphonyl]benzoic acid; Probalan; Probenecid (Benemid); p-[Dipropylsulfamoyl]benzoic acid; 4-[(dipropylamino)sulfonyl]benzoic acid; 4[(Dipropylamino)sulfonyl]benzoic Acid; Apurina; Benecid; Benemid; Benuryl; Probecid; NSC 18786; 4-(dipropylsulfamoyl)benzoic acid

登记号

• CAS号: 57-66-9
• EC号: 200-344-3
• MDL号: MFCD00038402
• 默克索引号: 147754
• PubChem SID: 24898976; 160964367; 46506554
• PubChem CID: 4911

理论计算性质

JChem

• Acid pKa: 3.5343497
• 质子受体: 4
• 质子供体: 1
• LogD (pH = 5.5): 0.48424464
• LogD (pH = 7.4): -0.9219675
• Log P: 2.4428723
• 摩尔折射率: 73.8107 cm^3
• 极化性: 29.016191 Å^3
• 极化表面积: 74.68 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.52
• LOG S: -2.83
• 溶解度: 4.25e-01 g/l

分子性质

理化性质

• 溶解度: 27.1 mg/L; DMSO; Methanol
• 外观: White to Off-White Solid
• 熔点: 194-196; 196-198°C; 198 - 200°C; 198-199°C
• 疏水性(logP): 2.3; 3.371

安全信息

• 保存条件: -20°C Freezer; Room Temperature (15-30°C)
• RTECS编号: DG9400000
• 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; 22-36/37/38; R:22
• 安全公开号: 26-36/37; S:36/37/39
• TSCA收录: 是
• GHS危险品标识: GHS06; GHS07
• GHS警示词: Warning
• GHS危险声明: H301-H315-H319-H335; H302
• GHS警示性声明: P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

药理学性质

• 作用靶点: Others

产品相关信息

• 纯度: ≥98% (NaOH, titration); 95%; 97%; 98%
• 成盐信息: Free Base

详细说明

MP Biomedicals - 02156370

Crystalline

DrugBank - DB01032

• Drug Groups: approved
• Description: The prototypical uricosuric agent. It inhibits the renal excretion of organic anions and reduces tubular reabsorption of urate. Probenecid has also been used to treat patients with renal impairment, and, because it reduces the renal tubular excretion of other drugs, has been used as an adjunct to antibacterial therapy. [PubChem]
• Indication: For the reduction of serum uric acid concentrations in chronic gouty arthritis and tophaceous gout in patients with frequent disabling gout attacks. Has also been effectively used to promote uric acid excretion in hyperuricemia secondary to the administration of thiazide and related diuretics.
• Pharmacology: Probenecid is a uricosuric and renal tubular blocking agent and is used in combination with colchicine to treat chronic gouty arthritis when complicated by frequent, recurrent acute attacks of gout. It inhibits the reabsorption of urate at the proximal convoluted tubule, thus increasing the urinary excretion of uric acid and decreasing serum urate levels. Effective uricosuria reduces the miscible urate pool, retards urate deposition, and promotes resorption of urate deposits. At the proximal and distal tubles, probenecid competitively inhibits the secretion of many weak organic acids including penicillins, most cephalosporins, and some other β-lactam antibiotics. This results in an increase in the plasma concentrations of acidic drugs eliminated principally by renal secretion, but only a slight increase if the drug is eliminated mainly by filtration. Thus, the drug can be used for therapeutic advantages to increase concentrations of certain β-lactam antibiotics in the treatment of gonorrhea, neurosyphilis, or pelvic inflammatory disease (PID).
• Affected Organisms: Humans and other mammals
• Half Life: 6-12 hours
• Protein Binding: 75-95%
• Elimination: Excreted principally in the urine as monoacyl glucuronide and unchanged drug. Alkalinization of urine increases renal probenecid excretion.
• References: Butler D: Wartime tactic doubles power of scarce bird-flu drug. Nature. 2005 Nov 3;438(7064):6. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - P8761

Application
Useful as an inhibitor of the organic anion transporter, MRP.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. P8761.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - P755000

Uricosuric.

参考文献

• Butler D: Wartime tactic doubles power of scarce bird-flu drug. Nature. 2005 Nov 3;438(7064):6. Pubmed
• McKinney, S.E., et al.: J. Pharmacol. Exp. Ther., 102, 208 (1951)
• Israili, Z.H., et al.: J. Med. Chem., 15, 709 (1951)
• Al-Badr, A.A., et al.: Anal. Profiles Drug Subs., 10, 639 (1951)
• Cunningham, R.F., et al.: Clin. Pharmacokinet., 6, 135 (1951)