Probenecid
Übersicht
Beschreibung
It was developed as an alternative to caronamide to inhibit the renal excretion of certain drugs, thereby increasing their plasma concentration and prolonging their effects . Probenecid is also used to enhance the efficacy of some antibiotics and protect the kidneys when administered with certain antiviral drugs .
Wirkmechanismus
Target of Action
Probenecid primarily targets the Organic Anion Transporters (OAT) . These transporters are located in the basolateral membrane of cells in the proximal tubule of the kidneys . They play a crucial role in the renal excretion of organic anions and the tubular reabsorption of urate .
Mode of Action
This compound acts by competitively inhibiting the reabsorption of uric acid through the OAT at the proximal tubules . This leads to preferential reabsorption of this compound back into plasma and excretion of uric acid in urine . By reducing the renal tubular excretion of other drugs, this compound has also been used as an adjunct to antibacterial therapy .
Biochemical Pathways
This compound affects the biochemical pathways involved in the excretion of uric acid and other drugs. It inhibits the renal secretion of organic anions and reduces tubular reabsorption of urate . This leads to increased urinary excretion of uric acid and decreased serum urate levels . This compound also inhibits pannexin 1, which is involved in the activation of inflammasomes and subsequent release of interleukin-1β causing inflammation .
Pharmacokinetics
This compound is extensively metabolized by glucuronide conjugation and by oxidation of the alkyl side chains . The half-life of this compound in plasma is dose-dependent and ranges from 4 to 12 hours . In the kidneys, this compound is filtered at the glomerulus, secreted in the proximal tubule, and reabsorbed in the distal tubule . The addition of this compound to oral β-lactams increases total AUC, Cmax, and serum t½ .
Result of Action
The primary result of this compound’s action is the reduction of serum uric acid concentrations in chronic gouty arthritis and tophaceous gout in patients with frequent disabling gout attacks . It has also been effectively used to promote uric acid excretion in hyperuricemia secondary to the administration of thiazide and related diuretics . When combined with certain antibiotics, this compound can increase their concentration and prolong their effects .
Action Environment
Environmental factors can influence the action, efficacy, and stability of this compound. For instance, this compound’s influence on penicillin clearance became mainly academic in the post-war era as the capability to produce more diverse, cheaper, and safer β-lactam antibiotics rapidly expanded .
Wissenschaftliche Forschungsanwendungen
Probenecid has a wide range of scientific research applications:
Chemistry: Used as a reagent in organic synthesis and as a model compound for studying sulfonamide chemistry.
Biology: Employed in studies involving organic anion transporters and cellular uptake mechanisms.
Medicine: Utilized to enhance the efficacy of antibiotics and antiviral drugs by inhibiting their renal excretion.
Industry: Applied in the formulation of pharmaceuticals and as an adjuvant in drug delivery systems.
Biochemische Analyse
Biochemical Properties
Probenecid is a prototypical uricosuric agent that inhibits the renal excretion of organic anions and reduces tubular reabsorption of urate . It interacts with organic anion transporters (OAT) in the basolateral membrane of cells in the proximal tubule . This results in reduced clearance and increased plasma levels of drugs normally secreted by this mechanism .
Cellular Effects
This compound has been shown to affect ATP release, leading to the suggestion that ATP release involves an organic anion transporter . In a study examining the effects of this compound on a transgenic mouse model of Huntington’s disease, this compound administration improved the duration of survival by 35% and significantly ameliorated motor activity .
Molecular Mechanism
This compound competitively inhibits the reabsorption of uric acid through the organic anion transporter (OAT) at the proximal tubules . This leads to preferential reabsorption of this compound back into plasma and excretion of uric acid in urine, thus reducing blood uric acid levels and reducing its deposition in various tissues .
Temporal Effects in Laboratory Settings
This compound has been shown to increase total AUC, Cmax, and serum t½ in pharmacokinetic analyses . This suggests that the effects of this compound may change over time in laboratory settings, potentially due to changes in the drug’s stability, degradation, and long-term effects on cellular function.
Dosage Effects in Animal Models
In animal models, the effects of this compound have been shown to vary with different dosages . For example, in a study examining the effects of this compound on a transgenic mouse model of Huntington’s disease, this compound administration improved the duration of survival by 35% .
Metabolic Pathways
This compound is extensively metabolised by glucuronide conjugation and by oxidation of the alkyl side chains . Oxidation of the aromatic ring does not occur . This suggests that this compound is involved in metabolic pathways that involve glucuronide conjugation and alkyl side chain oxidation.
Transport and Distribution
This compound inhibits both the Organic Anion Transporters (OAT) in the basolateral membrane of cells in the proximal tubule . This results in reduced clearance and increased plasma levels of drugs normally secreted by this mechanism .
Subcellular Localization
Given its role in inhibiting organic anion transporters in the basolateral membrane of cells in the proximal tubule , it is likely that this compound localizes to the cell membrane where these transporters are located.
Vorbereitungsmethoden
Synthetic Routes and Reaction Conditions: Probenecid can be synthesized through several methods. One common synthetic route involves the reaction of 4-aminobenzoic acid with dipropylamine and sulfuryl chloride to form 4-(dipropylsulfamoyl)benzoic acid. The reaction typically occurs under controlled temperature and pH conditions to ensure high yield and purity.
Industrial Production Methods: In industrial settings, this compound is produced through a similar synthetic route but on a larger scale. The process involves the use of large reactors and precise control of reaction parameters to maintain consistency and quality. The final product is purified through crystallization and filtration techniques to obtain pharmaceutical-grade this compound.
Analyse Chemischer Reaktionen
Types of Reactions: Probenecid undergoes various chemical reactions, including:
Oxidation: this compound can be oxidized to form sulfoxides and sulfones under specific conditions.
Reduction: Reduction reactions can convert this compound into its corresponding amine derivatives.
Substitution: this compound can undergo nucleophilic substitution reactions, particularly at the sulfonamide group.
Common Reagents and Conditions:
Oxidation: Common oxidizing agents include hydrogen peroxide and potassium permanganate.
Reduction: Reducing agents such as lithium aluminum hydride and sodium borohydride are used.
Substitution: Nucleophiles like amines and alcohols can react with this compound under basic conditions.
Major Products:
Oxidation: Sulfoxides and sulfones.
Reduction: Amine derivatives.
Substitution: Various substituted benzoic acid derivatives.
Vergleich Mit ähnlichen Verbindungen
Allopurinol: Used to reduce uric acid production by inhibiting xanthine oxidase.
Febuxostat: Another xanthine oxidase inhibitor used to lower uric acid levels.
Sulfinpyrazone: A uricosuric agent similar to probenecid but with different pharmacokinetic properties.
Comparison:
This compound vs. Allopurinol: this compound increases uric acid excretion, while allopurinol reduces its production.
This compound vs. Febuxostat: Both are used to manage hyperuricemia, but febuxostat is more potent and has a different mechanism of action.
This compound vs. Sulfinpyrazone: Both are uricosuric agents, but this compound has a longer half-life and is more commonly used in clinical practice.
This compound’s unique ability to inhibit renal excretion of various drugs makes it a valuable tool in both clinical and research settings, distinguishing it from other similar compounds.
Eigenschaften
IUPAC Name |
4-(dipropylsulfamoyl)benzoic acid |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
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) |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
DBABZHXKTCFAPX-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CCCN(CCC)S(=O)(=O)C1=CC=C(C=C1)C(=O)O |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C13H19NO4S |
Source
|
| Record name | PROBENECID | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20951 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID9021188 |
Source
|
| Record name | Probenecid | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID9021188 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
285.36 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Probenecid appears as odorless white or almost white crystalline powder. Slightly bitter taste; pleasant aftertaste. (NTP, 1992), Solid |
Source
|
| Record name | PROBENECID | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20951 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| Record name | Probenecid | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015166 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Solubility |
>42.8 [ug/mL] (The mean of the results at pH 7.4), less than 1 mg/mL at 68 °F (NTP, 1992), FREELY SOL IN WATER /SODIUM SALT/, SOL IN DIL ALKALI, ALCOHOL, CHLOROFORM & ACETONE; PRACTICALLY INSOL IN WATER & DIL ACIDS, 4.25e-01 g/L |
Source
|
| Record name | SID855953 | |
| Source | Burnham Center for Chemical Genomics | |
| URL | https://pubchem.ncbi.nlm.nih.gov/bioassay/1996#section=Data-Table | |
| Description | Aqueous solubility in buffer at pH 7.4 | |
| Record name | PROBENECID | |
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| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| Record name | Probenecid | |
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| Record name | Probenecid | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015166 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
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Mechanism of Action |
Probenecid inhibits the tubular reabsorption of urate, thus increasing the urinary excretion of uric acid and decreasing serum urate levels. Probenecid may also reduce plasma binding of urate and inhibit renal secretion of uric acid at subtherapeutic concentrations. The mechanism by which probenecid inhibits renal tubular transport is not known, but the drug may inhibit transport enzymes that require a source of high energy phosphate bonds and/or nonspecifically interfere with substrate access to protein receptor sites on the kidney tubules., IN HIGHER DOSES THAN ARE REQUIRED FOR URICOSURIC EFFECT, PROBENECID ALSO INHIBITS TRANSPORT OF ORG ACIDS AT OTHER SITES, IE, TRANSPORT SYSTEM THAT REMOVES ORG ACIDS FROM CEREBROSPINAL FLUID., IT INHIBITS TUBULAR REABSORPTION OF URATE, THUS INCR URINARY EXCRETION OF URIC ACID & DECR SERUM URIC ACID LEVELS., Probenecid is a renal tubular blocking agent. The drug competitively inhibits active reabsorption of uric acid at the proximal convoluted tubule, thus promoting urinary excretion of uric acid and reducing serum urate concentrations. Probenecid may reduce plasma protein binding of urate and, in subtherapeutic doses, may inhibit renal secretion of uric acid. In healthy individuals, probenecid has no effect on the glomerular filtration rate or on the tubular reabsorption of normal urinary constituents such as glucose, arginine, urea, sodium, potassium, chloride, or phosphate., At the proximal and distal tubules, probenecid competitively inhibits the secretion of many weak organic acids including penicillins, most cephalosporins, and some other beta-lactam antibiotics. In general, the net effect of probenecid on the plasma concentration of weak acids depends on the ratio of the amount of organic acid secreted by the kidneys to that amount filtered at the glomeruli. Thus, probenecid substantially increases plasma concentrations of acidic drugs eliminated principally by renal secretion, but increases plasma concentrations only slightly if the drug is eliminated mainly by filtration. Plasma concentrations of penicillins are often more than doubled by probenecid; the concentration of penicillin in the CSF is also increased. Probenecid also substantially increases plasma concentrations of most cephalosporins and some other beta-lactam antibiotics. In addition, half-lives of the penicillins and cephalosporins are prolonged and their volumes of distribution may be reduced by probenecid. ... The cellular mechanism(s) responsible for the inhibition of renal tubular transport by probenecid is not known. The drug may inhibit transport enzymes that require a source of high energy phosphate bonds and/or nonspecifically interfere with substrate access to protein receptor sites on the kidney tubules., CSF concentrations of 5-hydroxyindoleacetic acid, homovanillic acid, cyclic adenosine monophosphate, and 4-hydroxy-3-methoxyphenylglycol are elevated following administration of probenecid. It has been proposed that probenecid blocks the active transport of these organic acids from the CSF into blood. Probenecid-induced elevations of homovanillic acid (a dopamine metabolite) in the CSF of patients with parkinsonian syndrome and of 5-hydroxyindoleacetic acid(a metabolite of serotonin) in the CSF of mentally depressed patients are substantially lower than those in healthy patients. |
Source
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| Record name | Probenecid | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01032 | |
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Color/Form |
CRYSTALS FROM DIL ALCOHOL, WHITE OR NEARLY WHITE, FINE, CRYSTALLINE POWDER | |
CAS No. |
57-66-9 |
Source
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| Record name | PROBENECID | |
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| Record name | Probenecid | |
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| Record name | Benzoic acid, 4-[(dipropylamino)sulfonyl]- | |
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| Record name | Probenecid | |
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| URL | http://www.hmdb.ca/metabolites/HMDB0015166 | |
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Melting Point |
381 to 385 °F (NTP, 1992), 194-196 °C, 195 °C |
Source
|
| Record name | PROBENECID | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20951 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| Record name | Probenecid | |
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| Record name | Probenecid | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015166 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
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Retrosynthesis Analysis
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| Precursor scoring | Relevance Heuristic |
|---|---|
| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
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![[(11Z,13E)-6-[4-(dimethylamino)-3,5-dihydroxy-6-methyloxan-2-yl]oxy-10-[5-(dimethylamino)-6-methyloxan-2-yl]oxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-4-yl] propanoate](/img/structure/B1678178.png)
