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CAS NO.57-66-9
1(10-100)Kilogram1(100-500)Kilogram2(500-1000)Kilogram
1. Certificate Of Analysis (COA)
2. Material Safety Data Sheet (MSDS)
3. Route of synthesis (ROS)
4. Method of Aanlysis (MOA)
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| Probenecid Basic information |
| Anti-gout drug Indications Adverse reactions Chemical Properties Application Production methods |
| Product Name: | Probenecid |
| Synonyms: | 4-((dipropylamino)sulfonyl)-benzoicaci;4-(Dipropylsulfamoyl)benzoic acid;4-(dipropylsulfamoyl)benzoicacid;4-[(dipropylamino)sulfonyl]-benzoicaci;Apurina;benacen;Benemid;benemide |
| CAS: | 57-66-9 |
| MF: | C13H19NO4S |
| MW: | 285.36 |
| EINECS: | 200-344-3 |
| Product Categories: | Miscellaneous;API;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;API's;Vanilloid/TRPV channel;chemical additive;pharmaceutical intermediate;PROBENEMID;pharmaceutical chemicals;Pharmaceutical raw materials |
| Mol File: | 57-66-9.mol |
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| Probenecid Chemical Properties |
| mp | 194-196°C |
| storage temp. | Store at RT |
| Water Solubility | <0.1 g/100 mL at 20 ºC |
| Merck | 14,7754 |
| Stability: | Stable, but may be light sensitive. Incompatible with strong oxidizing agents. |
| CAS DataBase Reference | 57-66-9(CAS DataBase Reference) |
| NIST Chemistry Reference | P-(dipropylsulfamoyl) benzoic acid(57-66-9) |
| EPA Substance Registry System | Benzoic acid, 4-[(dipropylamino)sulfonyl]- (57-66-9) |
| Safety Information |
| Hazard Codes | Xn |
| Risk Statements | 22-40 |
| Safety Statements | 36/37 |
| RIDADR | 3249 |
| WGK Germany | 3 |
| RTECS | DG9400000 |
| Hazardous Substances Data | 57-66-9(Hazardous Substances Data) |
| MSDS Information |
| Provider | Language |
|---|---|
| 4-[(Dipropylamino)sulfonyl]benzoic acid | English |
| SigmaAldrich | English |
| ALFA | English |
| Probenecid Usage And Synthesis |
| Anti-gout drug | Probenecid is a chemically synthetic sulfa anti-gout drug, also known as oxybenzone sulfonamides, which has dual role of both promoting the excretion of uric acid excretion and inhibiting the excretion of penicillin. Clinically it is used for treating chronic gout and suppressing excretion of penicillin-type drugs in order to increase their clinical plasma concentration as an adjuvant drug of penicillin therapy. Its mechanism of action is inhibiting the re-absorption of renal tubular on uric acid, thus increasing uric acid excretion and further lowering plasma uric acid concentration for reducing the deposition of urate in tissues and prevent the crystallization of urate. This product can also promote the dissolution of the pre-formed urate, thereby reducing its damage on the joint. In addition, the product can also competitively inhibit the secretion of a weak organic acid (such as penicillin, cephalosporins) in the renal tubules, which can increase blood concentrations of these antibiotics and prolong their duration of action. This product is easy for oral administration with a plasma protein binding rate of 85% to 90%. Adults take 1 g orally each time with the plasma concentration reaches peak after 2 ~ 4 hour and with a half-life of being 6 to 12 hours. Probenecid is rapidly metabolized in the liver with the major metabolite being probenecid acetyl glucuronic acid. The main metabolite is excreted through the urine. This product has no anti-inflammatory and analgesic effect, and thus being invalid for treating acute gout. Acute toxicity test results: orally: LD50 of rats being 1600mg/kg. After the oral administration, the major adverse reactions are gastrointestinal reactions with others adverse reactions including dizziness, headache, facial flushing, urinary frequency, gingival swelling and pain, skin rash; there are also occasional allergic reactions. It is not suitable for being applied to patients of acute gout and with history of uric acid crystal deposition in kidney and ureter. Patients of peptic ulcer or blood abnormalities and pregnant women should take with caution. Patients of renal dysfunction are not allowed for using it. |
| Indications |
1. For treating hyperuricemia with chronic gouty arthritis and tophi, take 2 times per day for adults with the dose of each time being 25 mg, increase the dose to 2 times per day after 1 week with 500 mg each time. Upon the administration, maintain the daily intake of water being at 2500mL to prevent the formation of kidney stones, simultaneously take alkaline urine drug if necessary. But make sure that: 1, the filtration rate of glomerular should be greater than 50 ~ 60mL/min; 2, no kidney stones or history of kidney stones; 3, non-acidic urine; 4, patients of non-taking salicylates; 5, have regular tests of blood and urine pH value, liver and kidney function as well as the uric acid levels in blood and urine; 6, adjust the dose according to the clinical and uric acid level and maintain for a long time with the minimum effective amount. 2. As an adjunct drug for antibiotic treatment; it can be combined together with different antibiotics such as penicillin, ampicillin, oxacillin, amoxicillin ortho chlorine, and nafcillin; Probenecid can be used for inhibiting the discharge of these antibiotics, increase their blood concentration and can maintain for a relative long time. The above information is edited by the Chemicalbook of Dai Xiongfeng. |
| Adverse reactions |
1. Gastrointestinal reactions: main reactions are that a small number of patients have loss of appetite, nausea, vomiting, and abdominal discomfort. 2. Central nervous system reactions and allergic reactions: occasional headache, facial flushing, fever and some allergic reactions such as itchy skin, dermatitis. 3. Other serious toxicities: for very few patients, they have got bleeding, neutropenia, aplastic anemia, nephrotic syndrome, and liver necrosis. Probenecid belongs to sulfa drugs, so patients with hypersensitivity to sulfa drugs are not allowed for using. Pregnant women, patients of peptic ulcer, liver and kidney dysfunction should use with caution. In addition, patients should drink lots of water for the medication should drink lots of water and add appropriate amount of sodium carbonate for preventing urinary stones. During the medication, people should pay attention to checking the blood. |
| Chemical Properties | White crystalline powder. Its melting point is 194-196 °C. It is soluble in acetone, and slightly soluble in ethanol or chloroform, but almost insoluble in water. It is also soluble in dilute sodium hydroxide solution, but almost insoluble in dilute acid. It is odorless with a slightly bitter taste. |
| Application |
It is a kind of anti-gout drug. The product is organic acid, strongly fat-soluble, self-discharge from tubular secretion, very easily to be absorbed back. Therefore, in the presence of probenecid, the transfer of some organic acids in the tubular body will be inhibited, reducing the excretion of other organic acids. Thereby, it is used to treat chronic gout with being safe and effective. It has no effects on acute gout pain and inflammation and can’t be applied to acute gout. It is used for the treatment of gout, rheumatoid arthritis and other chronic diseases. |
| Production methods | Toluene sulfonamide is oxidized by sodium dichromate to generate carboxylic benzenesulfonamide; then use bromopropane for alkylation, the resulting sodium probenecid is further acidified by acetate to obtain probenecid. |
| Chemical Properties | White to Off-White Solid |
| Usage | pharmaceutical intermediate |
| Usage | 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 administra |
| Usage | Uricosuric |
| General Description | Odorless white or almost white crystalline powder. Slightly bitter taste; pleasant aftertaste. |
| Air & Water Reactions | Insoluble in water. |
| Reactivity Profile | Probenecid may be light sensitive . |
| Fire Hazard | Flash point data for Probenecid are not available. Probenecid is probably combustible. |
| Probenecid Preparation Products And Raw materials |
| Raw materials | Sodium dichromate dihydrate-->Sodium bromide-->1-Bromopropane-->p-Toluenesulfonamide |