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QuickView for Probenecid (compound)
PubChem
| Name: | Probenecid |
|---|---|
| PubChem Compound ID: | 4911 |
| 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. |
| Molecular formula: | C13H19NO4S |
| Molecular weight: | 285.36 g/mol |
| Synonyms: |
Robenecid; Prestwick_809; Uricosid; KBio3_001727; Apurina; D00475; Polycillin-BRB; Spectrum3_000554; Spectrum4_000486; SPBio_002504.
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Robenecid; Prestwick_809; Uricosid; KBio3_001727; Apurina; D00475; Polycillin-BRB; Spectrum3_000554; Spectrum4_000486; SPBio_002504; Spectrum2_001294; C07372; Probenecide [INN-French]; ColBenemid; Probenid; Synergid R; KBio2_006450; Ethamide; Proben; Probenecid acid; Benuryl; EINECS 200-344-3; Benemid (TN); MLS000028496; NCGC00023829-03; Probenecida [INN-Spanish]; Benemide; DivK1c_000056; 57-66-9; NCGC00016251-01; NCI-C56097; DRG-0053; HSDB 3387; Benzoic acid, 4-((dipropylamino)sulfonyl)-; Polycillin-PRB; CCRIS 3643; CAS-57-66-9; 4-((Dipropylamino)sulfonyl)benzoic acid; NINDS_000056; Prestwick1_000542; BRN 2815775; Probenecid (JP15/USP); Probecid; p-(Dipropylsulfamoyl)benzoic acid; KBio2_003882; KBio1_000056; Benecid; Probampacin; Benzoic acid, p- (dipropylsulfamoyl)-; component of ColBenemid; Spectrum_000834; KBioGR_000971; Prestwick0_000542; Benemid; Probenecid [BAN:INN:JAN]; Probenecid; Probenecidum [INN-Latin]; SMR000058280; Benzoic acid, p-(dipropylsulfamoyl)-; 4-(Dipropylsulfamoyl)benzoic acid; 4-(N,N-Dipropylsulfamoyl)benzoesaeure; NSC 18786; Probenemid; 4-11-00-00691 (Beilstein Handbook Reference); AI3-50078; Probalan; Col-Probenecid; 4-(Di-n-propylsulfamoyl)benzoesaeure; Probexin; Prolongine; NSC18786; KBio2_001314; Tubophan; p-(Dipropylsulfamyl)benzoic acid; Benzoic acid, 4-[(dipropylamino)sulfonyl]-; SPBio_001327; KBioSS_001314; Benzoic acid, 4-[ (dipropylamino)sulfonyl]-
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DrugBank
Identification
| Name: | Probenecid |
|---|---|
| Name (isomeric): | DB01032 |
| Drug Type: | small molecule |
| 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. |
| Synonyms: |
probenicid; Probenecid Acid
|
| Brand: | Tubophan, Apurina, Benemid, Col-Probenecid, Uricosid, Synergid R, Polycillin-PRB, Probenemid, Prolongine, Probalan, Probampacin, Benuryl, Probecid, Proben, Proben-C, Colbenemid, Benecid, Probexin |
| Category: | Adjuvants, Pharmaceutic, Uricosuric Agents |
| CAS number: | 57-66-9 |
Pharmacology
| 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 ...
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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).
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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, bu...
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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.
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| Protein binding: | 75-95% |
| Route of elimination: | Excreted principally in the urine as monoacyl glucuronide and unchanged drug. Alkalinization of urine increases renal probenecid excretion. |
| Half Life: | 6-12 hours |
| Affected organisms: | Humans and other mammals |
Interactions
| Food interaction: |
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| Drug interaction: |
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Targets
| UniProt ID: | Q4U2R8 | |||||
|---|---|---|---|---|---|---|
| Gene: | SLC22A6 | |||||
| Actions: | inhibitor | |||||
| References: |
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Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds
| UniProt ID: | Q9NSA0 | ||||
|---|---|---|---|---|---|
| Gene: | SLC22A11 | ||||
| Actions: | inhibitor | ||||
| References: |
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Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone- 3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA)
| UniProt ID: | Q8TCC7 | ||||||
|---|---|---|---|---|---|---|---|
| Gene: | SLC22A8 | ||||||
| Actions: | inhibitor | ||||||
| References: |
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Structural component of the gap junctions
| UniProt ID: | Q96RD7 | |||||
|---|---|---|---|---|---|---|
| Gene: | PANX1 | |||||
| Actions: | antagonist | |||||
| References: |
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Enzymes
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S- warfarin, diclofenac, phenytoin, tolbutamide and losartan
| UniProt ID: | P11712 | ||
|---|---|---|---|
| Gene: | CYP2C9 | ||
| Actions: | inhibitor | ||
| References: |
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Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine
| UniProt ID: | P33261 | ||
|---|---|---|---|
| Gene: | CYP2C19 | ||
| Actions: | inhibitor | ||
| References: |
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Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti- cancer drug paclitaxel (taxol)
| UniProt ID: | P10632 | |
|---|---|---|
| Gene: | CYP2C8 | |
| Actions: | inducer | |
| References: |
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Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide
| UniProt ID: | P08684 | |
|---|---|---|
| Gene: | CYP3A4 | |
| Actions: | inducer | |
| References: |
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Transporters
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, cisplatin and oxaliplatin. Cisplatin may develop a nephrotoxic action. Transport of creatinine is inhibited by fluoroquinolones such as DX-619 and LVFX. This transporter is a major determinant of the anticancer activity of oxaliplatin and may contribute to antitumor specificity
| UniProt ID: | O15244 | |
|---|---|---|
| Gene: | SLC22A2 | |
| Actions: | inhibitor | |
| References: |
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Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
| UniProt ID: | O15245 | |
|---|---|---|
| Gene: | SLC22A1 | |
| Actions: | inhibitor | |
| References: |
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May act as an inducible transporter in the biliary and intestinal excretion of organic anions
| UniProt ID: | O15438 | |||
|---|---|---|---|---|
| Gene: | ABCC3 | |||
| Actions: | inhibitor | |||
| References: |
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May be an organic anion pump relevant to cellular detoxification
| UniProt ID: | O15439 | |||
|---|---|---|---|---|
| Gene: | ABCC4 | |||
| Actions: | inhibitor | |||
| References: |
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Acts as a multispecific organic anion pump which can transport nucleotide analogs
| UniProt ID: | O15440 | |
|---|---|---|
| Gene: | ABCC5 | |
| Actions: | inhibitor | |
| References: |
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Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate. MCT2 is a high affinity pyruvate transporter
| UniProt ID: | O60669 | |
|---|---|---|
| Gene: | SLC16A7 | |
| Actions: | inhibitor | |
| References: |
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Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also Relative uptake activity ratio of carnitine to TEA is 11.3
| UniProt ID: | O76082 | |
|---|---|---|
| Gene: | SLC22A5 | |
| Actions: | inhibitor | |
| References: |
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May participate directly in the active transport of drugs into subcellular organelles or influence drug distribution indirectly. Transports glutathione conjugates as leukotriene-c4 (LTC4) and N-ethylmaleimide S-glutathione (NEM-GS)
| UniProt ID: | O95255 | |
|---|---|---|
| Gene: | ABCC6 | |
| Actions: | inhibitor | |
| References: |
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Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
| UniProt ID: | P08183 | |||
|---|---|---|---|---|
| Gene: | ABCB1 | |||
| Actions: | inhibitor | |||
| References: |
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May participate directly in the active transport of drugs into subcellular organelles or influence drug distribution indirectly. Confers resistance to anticancer drugs. Transports LTC4. May protect milk against xenobiotics
| UniProt ID: | P33527 | |||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Gene: | ABCC1 | |||||||||
| Actions: | inhibitor | |||||||||
| References: |
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Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity)
| UniProt ID: | P46721 | ||
|---|---|---|---|
| Gene: | SLCO1A2 | ||
| Actions: | inhibitor | ||
| References: |
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Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate
| UniProt ID: | P53985 | |
|---|---|---|
| Gene: | SLC16A1 | |
| Actions: | inhibitor | |
| References: |
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The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presence of sodium
| UniProt ID: | Q14973 | |
|---|---|---|
| Gene: | SLC10A1 | |
| Actions: | inhibitor | |
| References: |
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| UniProt ID: | Q4U2R8 | |||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Gene: | SLC22A6 | |||||||||||||||
| Actions: | inhibitor | |||||||||||||||
| References: |
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| UniProt ID: | Q63ZE4 | |
|---|---|---|
| Gene: | SLC22A10 | |
| Actions: | inhibitor | |
| References: |
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Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone- 3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA)
| UniProt ID: | Q8TCC7 | ||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Gene: | SLC22A8 | ||||||||||||
| Actions: | inhibitor | ||||||||||||
| References: |
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Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter
| UniProt ID: | Q92887 | |||||||
|---|---|---|---|---|---|---|---|---|
| Gene: | ABCC2 | |||||||
| Actions: | substrate, inhibitor | |||||||
| References: |
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Participates in physiological processes involving bile acids, conjugated steroids and cyclic nucleotides. Enhances the cellular extrusion of cAMP and cGMP. Stimulates the ATP-dependent uptake of a range of physiological and synthetic lipophilic anions, including the glutathione S-conjugates leukotriene C4 and dinitrophenyl S-glutathione, steroid sulfates such as dehydroepiandrosterone 3-sulfate (DHEAS) and estrone 3-sulfate, glucuronides such as estradiol 17-beta-D-glucuronide (E(2)17betaG), the monoanionic bile acids glycocholate and taurocholate, and methotrexate. Probably functions to secrete earwax
| UniProt ID: | Q96J66 | |
|---|---|---|
| Gene: | ABCC11 | |
| Actions: | inhibitor | |
| References: |
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Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds
| UniProt ID: | Q9NSA0 | ||||
|---|---|---|---|---|---|
| Gene: | SLC22A11 | ||||
| Actions: | inhibitor | ||||
| References: |
|
Mediates the Na(+)-independent high affinity transport of organic anions such as the thyroid hormones thyroxine (T4) and rT3. Other potential substrates, such as triiodothyronine (T3), 17-beta-glucuronosyl estradiol, estrone-3-sulfate and sulfobromophthalein (BSP) are transported with much lower efficiency
| UniProt ID: | Q9NYB5 | |
|---|---|---|
| Gene: | SLCO1C1 | |
| Actions: | inhibitor | |
| References: |
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Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha- ketoglutarate
| UniProt ID: | Q9Y694 | ||
|---|---|---|---|
| Gene: | SLC22A7 | ||
| Actions: | inhibitor | ||
| References: |
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Carriers
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood
| UniProt ID: | P02768 | |||
|---|---|---|---|---|
| Gene: | ALB | |||
| References: |
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