4-(dipropylsulfamoyl)benzoic acid

• ChemBase ID: 904
• Molecular Formular: C13H19NO4S
• Molecular Mass: 285.35926
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(dipropylsulfamoyl)benzoic acid
• IUPAC Traditional name: probenecid
• Brand Name: Apurina; Benecid; Benemid; Benuryl; Col-Probenecid; Colbenemid; Polycillin-PRB; Probalan; Probampacin; Probecid; Proben; Proben-C; Probenemid; Probexin; Prolongine; Synergid R; Tubophan; Uricosid
• Synonyms: 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; 丙磺舒

Database IDs

• CAS Number: 57-66-9
• EC Number: 200-344-3
• MDL Number: MFCD00038402
• Merck Index: 147754
• PubChem SID: 24898976; 160964367; 46506554
• PubChem CID: 4911

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.5343497
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.48424464
• LogD (pH = 7.4): -0.9219675
• Log P: 2.4428723
• Molar Refractivity: 73.8107 cm^3
• Polarizability: 29.016191 Å^3
• Polar Surface Area: 74.68 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.52
• LOG S: -2.83
• Solubility (Water): 4.25e-01 g/l

PROPERTIES

Physical Property

• Solubility: 27.1 mg/L; DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 194-196; 196-198°C; 198 - 200°C; 198-199°C
• Hydrophobicity(logP): 2.3; 3.371

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C)
• RTECS: DG9400000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; 22-36/37/38; R:22
• Safety Statements: 26-36/37; S:36/37/39
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H301-H315-H319-H335; H302
• GHS Precautionary statements: P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Target: Others

Product Information

• Purity: ≥98% (NaOH, titration); 95%; 97%; 98%
• Salt Data: Free Base

DETAILS

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.

REFERENCES

• 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)