4-((Dipropylamino)sulfonyl)-benzoesäure
4-(N,N-Dipropylsulfamoyl)benzoic acid · PROBENICID · Binghuangshu · 4-(Dipropylsulfamoyl)benzoic acid · 4-((dipropylamino)sulfonyl)-benzoicaci · 4-[(dipropylamino)sulphonyl]benzoic acid · Benemid · benacen
Identifikatoren & physikalische Daten
| CAS No. | 57-66-9 |
|---|---|
| Summenformel | C13H19NO4S |
| Durchschnittliche Molmasse | 285,36 g/mol |
| Monoisotopische Masse | 285,10347909 g/mol |
| SMILES | CCCN(CCC)S(=O)(=O)c1ccc(C(=O)O)cc1 |
| InChIKey | DBABZHXKTCFAPX-UHFFFAOYSA-N |
| PubChem CID | 4911 |
| ChEMBL | CHEMBL897 |
| ChEBI | CHEBI:8426 |
| EC No. | 200-344-3 |
| DTXSID | DTXSID9021188 |
| Lokaler Name | 4-((Dipropylamino)sulfonyl)-benzoesäure |
Chemische & physikalische Eigenschaften
| XLogP | 3,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 83,1 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 5 |
| Frei drehbare Bindungen | 7 |
| Schwere Atome | 19 |
| Formalladung | 0 |
| Komplexität | 374 |
| Arzneimittel | PharmaceuticalsPharmaceuticals -> Listed in ZINC15 |
| SpringerMaterials Properties | Crystal structure |
| LogP (Verteilungskoeffizient) | 2.33.21 |
| Geruch | PRACTICALLY ODORLESS |
| Geschmack | SLIGHTLY BITTERPLEASANT AFTERTASTE |
| Color/Form | CRYSTALS FROM DIL ALCOHOLWHITE OR NEARLY WHITE, FINE, CRYSTALLINE POWDER |
| Löslichkeit | less than 1 mg/mL at 68 °F (NTP, 1992)FREELY SOL IN WATER /SODIUM SALT/SOL IN DIL ALKALI, ALCOHOL, CHLOROFORM & ACETONEPRACTICALLY INSOL IN WATER & DIL ACIDS4.25e-01 g/L>42.8 [ug/mL] (The mean of the results at pH 7.4)DMSO (Slightly), Methanol (Slightly)<0.1 g/100 mL at 20 ºC |
| Human Drugs | Breast FeedingLactationAntigout AgentsGout SuppressantsSulfonamidesUricosuric AgentsFDA approved drugs -> Active ingredientPharmaceuticals |
| Decomposition | When heated to decomposition it emits very toxic fumes of oxides of sulfur and oxides of nitrogen. |
| Schmelzpunkt | 381 to 385 °F (NTP, 1992)194-196 °C195 °C194-196°C |
| Physical Description | Probenecid appears as odorless white or almost white crystalline powder. Slightly bitter tastepleasant aftertaste. (NTP, 1992)Solid |
| Stability/Shelf Life | Probenecid tablets should be stored in well closed containers at a temperature less than 40 °C, preferably between 15-30 °C. Commercially available preparations containing probenecid and colchicine should be protected from light. Following the date of manufacture, commercially available probenecid tablets have an expiration date of 3-5 yr depending on the packaging. |
| Siedepunkt | 438.0±47.0 °C(Predicted) |
| Dichte | 1.2483 (rough estimate) |
| Brechungsindex | 1.6800 (estimate) |
| Lagerbedingungen | Store at RT |
| Aggregatzustand | Solid |
| pKa (Säurekonstante) | 5.8(at 25℃) |
| Farbe | White to Off-White |
| Merck | 14,7754 |
| Stabilität | Stable, but may be light sensitive. Incompatible with strong oxidizing agents. |
| 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 |
| SMILES | CCCN(CCC)S(=O)(=O)c1ccc(cc1)C(O)=O |
| CAS Datenbank | 57-66-9(CAS DataBase Reference) |
| NIST chemische Informationen | P-(dipropylsulfamoyl) benzoic acid(57-66-9) |
| EPA chemische Informationen | Probenecid (57-66-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 81 reports by companies from 5 notifications to the ECHA C&L Inventory. |
|---|---|
| Weitere Sicherheitsinformationen | IMAP assessments - Benzoic acid, 4-[(dipropylamino)sulfonyl]-: Environment tier I assessment |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992) |
| Gesundheitsgefahren | SYMPTOMS: Symptoms of exposure to this chemical include nausea, vomiting, headache, sore gums, flushing, dizziness, urinary frequency and anemia. On rare occasions an anaphylactic reaction or a hypersensitivity reaction with fever, dermatitis and pruritis has occurred, and there have been reports of hepatic necrosis, the nephrotic syndrome and aplastic anemia. Exposure may precipitate an acute attack of gout, and renal colic or renal calculi with or without hematuria may occur. It may also cause gastrointestinal upset. Other symptoms include urticaria, nephrosis, coma and status epilepticus. In massive overdosage, stimulation of the central nervous system with convulsions and death from respiratory failure may occur. Exposure may also cause increased plasma concentrations of methotrexate, costovertebral pain, precipitation of acute gouty arthritis, anorexia, leukopenia, alopecia and hemolytic anemia (which could be related to genetic deficiency of glucose-6-phosphate dehydrogenase in red blood cells). It may also cause skin rashes. It may occasionally cause drug fever. Jaundice, asthma and eosinophilia have preceded a massive hepatic necrosis. |
| FDA-Anforderungen | Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended21 U.S.C. 321-392).The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl probenecid, approved on the basis of safety and effectiveness by FDA under sections 505 and 507 of the Federal Food, Drug, and Cosmetic Act. |
Anwendungen & Verwendung
Beschreibung
Probenecid is insoluble in water and acidic solutions but is soluble in alkaline solutions buffered to pH 7.4. Probenecid initially was synthesized as a result of studies in the 1940s on sulfonamides that indicated the sulfonamides decreased the renal clearance of penicillin, extending the half-life of penicillin as supplies diminished. Probenecid thus was initially used—and is still indicated—for that purpose. Probenecid promotes the excretion of uric acid by inhibiting the urate anion exchange transporter (URAT 1), decreasing the reabsorption of uric acid in the proximal tubules. The overall effect is to decrease plasma uric acid concentrations, thereby decreasing the rate and extent of urate crystal deposition in joints and synovial fluids. Within the series of N-dialkylsulfamyl benzoates from which probenecid is derived, renal clearance of these compounds is decreased as the length of the N-alkyl substituents is increased. Uricosuric activity increases with increasing size of the alkyl group in the series methyl, ethyl, and propyl.
Verwenden
It is a uricosuric drug, that is, it increases uric acid excretion in the urine. It is primarily used in treating gout and hyperuricemia. Probenecid was developed as an alternative to caronamide to competitively inhibit renal excretion of some drugs, thereby increasing their plasma concentration and prolonging their effects.