Probenecid | CAS#57-66-9

MedKoo Cat#: 318570 | Name: Probenecid

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Probenecid is an inhibitor of MRP1. This compound blocks the active site of MRP1 and prevents cellular efflux of other active compounds, enhancing their effectiveness by allowing them to remain in the cytoplasm. Probenecid is an inhibitor of Pannexin-1. 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.

Chemical Structure

Probenecid

CAS#57-66-9

Theoretical Analysis

MedKoo Cat#: 318570

Name: Probenecid

CAS#: 57-66-9

Chemical Formula: C13H19NO4S

Exact Mass: 285.1039

Molecular Weight: 285.36

Elemental Analysis: C, 54.72; H, 6.71; N, 4.91; O, 22.43; S, 11.24

Price and Availability

Size	Price	Availability
2g	USD 350.00	2 Weeks
5g	USD 550.00	2 Weeks
10g	USD 950.00	2 Weeks

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Synonym

Probenecid; Benemid; Benecid; Benuryl; Probecid; Probenecid Major Brand; Probenecid Martec Brand; Probenecid Parmed Brand; Probenecid Weimer; Probenecid Zenith Brand; Valdecasas Brand of Probenecid;

IUPAC/Chemical Name

4-(dipropylsulfamoyl)benzoic acid

InChi Key

DBABZHXKTCFAPX-UHFFFAOYSA-N

InChi Code

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)

SMILES Code

CCCN(CCC)S(=O)(=O)C1=CC=C(C=C1)C(=O)O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Probenecid is a potent and selective agonist of transient receptor potential vanilloid 2 (TRPV2) channels. Probenecid also inhibits pannexin 1 channels.

In vitro activity:

Probenecid specifically inhibits the cellular response mediated by the bitter taste receptor hTAS2R16 and provide molecular and pharmacological evidence for direct interaction with this GPCR using a non-competitive (allosteric) mechanism. Through a comprehensive analysis of hTAS2R16 point mutants, this study defines amino acid residues involved in the probenecid interaction that result in decreased sensitivity to probenecid while maintaining normal responses to salicin. Probenecid inhibits hTAS2R16, hTAS2R38, and hTAS2R43, but does not inhibit the bitter receptor hTAS2R31 or non-TAS2R GPCRs. Reference: PLoS One. 2011;6(5):e20123. https://pubmed.ncbi.nlm.nih.gov/21629661/

In vivo activity:

This study shows probenecid potently blocks SARS-CoV-2 replication in mammalian cells and virus replication in a hamster model. Furthermore, this study demonstrates that plasma concentrations up to 50-fold higher than the protein binding adjusted IC90 value are achievable for 24 h following a single oral dose. These data support the potential clinical utility of probenecid to control SARS-CoV-2 infection in humans. Reference: Sci Rep. 2021 Sep 10;11(1):18085. https://pubmed.ncbi.nlm.nih.gov/34508172/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	105.13
	DMSO	53.9	188.83
	DMSO:PBS (pH 7.2) (1:5)	0.2	0.53
	Ethanol	19.2	67.21

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 285.36 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Greene TA, Alarcon S, Thomas A, Berdougo E, Doranz BJ, Breslin PA, Rucker JB. Probenecid inhibits the human bitter taste receptor TAS2R16 and suppresses bitter perception of salicin. PLoS One. 2011;6(5):e20123. doi: 10.1371/journal.pone.0020123. Epub 2011 May 24. PMID: 21629661; PMCID: PMC3101243. 2. Silverman W, Locovei S, Dahl G. Probenecid, a gout remedy, inhibits pannexin 1 channels. Am J Physiol Cell Physiol. 2008 Sep;295(3):C761-7. doi: 10.1152/ajpcell.00227.2008. Epub 2008 Jul 2. PMID: 18596212; PMCID: PMC2544448. 3. Arkhipov SN, Potter DL, Sultanova RF, Ilatovskaya DV, Harris PC, Pavlov TS. Probenecid slows disease progression in a murine model of autosomal dominant polycystic kidney disease. Physiol Rep. 2023 Apr;11(7):e15652. doi: 10.14814/phy2.15652. PMID: 37024297; PMCID: PMC10079433. 4. Murray J, Hogan RJ, Martin DE, Blahunka K, Sancilio FD, Balyan R, Lovern M, Still R, Tripp RA. Probenecid inhibits SARS-CoV-2 replication in vivo and in vitro. Sci Rep. 2021 Sep 10;11(1):18085. doi: 10.1038/s41598-021-97658-w. PMID: 34508172; PMCID: PMC8433326.

In vitro protocol:

In vivo protocol:

1. Arkhipov SN, Potter DL, Sultanova RF, Ilatovskaya DV, Harris PC, Pavlov TS. Probenecid slows disease progression in a murine model of autosomal dominant polycystic kidney disease. Physiol Rep. 2023 Apr;11(7):e15652. doi: 10.14814/phy2.15652. PMID: 37024297; PMCID: PMC10079433. 2. Murray J, Hogan RJ, Martin DE, Blahunka K, Sancilio FD, Balyan R, Lovern M, Still R, Tripp RA. Probenecid inhibits SARS-CoV-2 replication in vivo and in vitro. Sci Rep. 2021 Sep 10;11(1):18085. doi: 10.1038/s41598-021-97658-w. PMID: 34508172; PMCID: PMC8433326.

1: Campos-Arroyo D, Maldonado V, Bahena I, Quintanar V, Patiño N, Carlos Martinez-Lazcano J, Melendez-Zajgla J. Probenecid Sensitizes Neuroblastoma Cancer Stem Cells to Cisplatin. Cancer Invest. 2016 Mar 15;34(3):155-66. doi: 10.3109/07357907.2016.1139717. Epub 2016 Mar 10. PubMed PMID: 26963048. 2: Du L, Empey PE, Ji J, Chao H, Kochanek PM, Bayır H, Clark RS. Probenecid and N-Acetylcysteine Prevent Loss of Intracellular Glutathione and Inhibit Neuronal Death after Mechanical Stretch Injury In Vitro. J Neurotrauma. 2016 Mar 22. [Epub ahead of print] PubMed PMID: 26830358. 3: Mendonza A, Hanna I, Meyers D, Koo P, Neelakantham S, Zhu B, Majumdar T, Rebello S, Sunkara G, Chen J. Assessment of pharmacokinetic drug-drug interaction between pradigastat and atazanavir or probenecid. J Clin Pharmacol. 2016 Mar;56(3):355-64. doi: 10.1002/jcph.595. Epub 2015 Nov 2. PubMed PMID: 26189431. 4: Hainz N, Wolf S, Tschernig T, Meier C. Probenecid Application Prevents Clinical Symptoms and Inflammation in Experimental Autoimmune Encephalomyelitis. Inflammation. 2016 Feb;39(1):123-8. doi: 10.1007/s10753-015-0230-1. PubMed PMID: 26276126. 5: Janakiraman U, Manivasagam T, Thenmozhi AJ, Essa MM, Barathidasan R, SaravanaBabu C, Guillemin GJ, Khan MA. Influences of Chronic Mild Stress Exposure on Motor, Non-Motor Impairments and Neurochemical Variables in Specific Brain Areas of MPTP/Probenecid Induced Neurotoxicity in Mice. PLoS One. 2016 Jan 14;11(1):e0146671. doi: 10.1371/journal.pone.0146671. eCollection 2016. PubMed PMID: 26765842; PubMed Central PMCID: PMC4713092. 6: Heng Y, Zhang QS, Mu Z, Hu JF, Yuan YH, Chen NH. Ginsenoside Rg1 attenuates motor impairment and neuroinflammation in the MPTP-probenecid-induced parkinsonism mouse model by targeting α-synuclein abnormalities in the substantia nigra. Toxicol Lett. 2016 Jan 22;243:7-21. doi: 10.1016/j.toxlet.2015.12.005. Epub 2015 Dec 23. PubMed PMID: 26723869. 7: Ahmed MU, Bennett DJ, Hsieh TC, Doonan BB, Ahmed S, Wu JM. Repositioning of drugs using open-access data portal DTome: A test case with probenecid (Review). Int J Mol Med. 2016 Jan;37(1):3-10. doi: 10.3892/ijmm.2015.2411. Epub 2015 Nov 13. PubMed PMID: 26572802. 8: Zhang YF, Dai XJ, Yang Y, Chen XY, Wang T, Tang YB, Tsai CY, Chang LW, Chang YT, Zhong DF. Effects of probenecid and cimetidine on the pharmacokinetics of nemonoxacin in healthy Chinese volunteers. Drug Des Devel Ther. 2016 Jan 20;10:357-70. doi: 10.2147/DDDT.S95934. eCollection 2016. PubMed PMID: 26855561; PubMed Central PMCID: PMC4725632. 9: Qian Y, Sherbini A, Matin B, Zhao Y, Castellot J, Greenblatt DJ. Inhibition of 2-methoxyestradiol glucuronidation by probenecid. J Pharm Pharmacol. 2015 Nov;67(11):1585-92. doi: 10.1111/jphp.12462. Epub 2015 Aug 14. PubMed PMID: 26272356. 10: Sung YH. Effects of treadmill exercise on hippocampal neurogenesis in an MPTP /probenecid-induced Parkinson's disease mouse model. J Phys Ther Sci. 2015 Oct;27(10):3203-6. doi: 10.1589/jpts.27.3203. Epub 2015 Oct 30. PubMed PMID: 26644675; PubMed Central PMCID: PMC4668166. 11: Mollica A, Costante R, Akdemir A, Carradori S, Stefanucci A, Macedonio G, Ceruso M, Supuran CT. Exploring new Probenecid-based carbonic anhydrase inhibitors: Synthesis, biological evaluation and docking studies. Bioorg Med Chem. 2015 Sep 1;23(17):5311-8. doi: 10.1016/j.bmc.2015.07.066. Epub 2015 Aug 1. PubMed PMID: 26264840. 12: Wei R, Wang J, Xu Y, Yin B, He F, Du Y, Peng G, Luo B. Probenecid protects against cerebral ischemia/reperfusion injury by inhibiting lysosomal and inflammatory damage in rats. Neuroscience. 2015 Aug 20;301:168-77. doi: 10.1016/j.neuroscience.2015.05.070. Epub 2015 Jun 3. PubMed PMID: 26047730. 13: Carradori S, Mollica A, Ceruso M, D'Ascenzio M, De Monte C, Chimenti P, Sabia R, Akdemir A, Supuran CT. New amide derivatives of Probenecid as selective inhibitors of carbonic anhydrase IX and XII: biological evaluation and molecular modelling studies. Bioorg Med Chem. 2015 Jul 1;23(13):2975-81. doi: 10.1016/j.bmc.2015.05.013. Epub 2015 May 14. PubMed PMID: 26007302. 14: Tanizaki R, Nishijima T, Aoki T, Teruya K, Kikuchi Y, Oka S, Gatanaga H. High-dose oral amoxicillin plus probenecid is highly effective for syphilis in patients with HIV infection. Clin Infect Dis. 2015 Jul 15;61(2):177-83. doi: 10.1093/cid/civ270. Epub 2015 Mar 31. PubMed PMID: 25829004. 15: Nauha E, Bernstein J. "Predicting" Polymorphs of Pharmaceuticals Using Hydrogen Bond Propensities: Probenecid and Its Two Single-Crystal-to-Single-Crystal Phase Transitions. J Pharm Sci. 2015 Jun;104(6):2056-61. doi: 10.1002/jps.24449. Epub 2015 Apr 22. PubMed PMID: 25904460. 16: Qi Y, Hainz N, Tschernig T, Meier C, Volmer DA. Differential distribution of probenecid as detected by on-tissue mass spectrometry. Cell Tissue Res. 2015 May;360(2):427-9. doi: 10.1007/s00441-015-2153-4. Epub 2015 Mar 12. PubMed PMID: 25759072. 17: Bao XQ, Wu LY, Wang XL, Sun H, Zhang D. Squamosamide derivative FLZ protected tyrosine hydroxylase function in a chronic MPTP/probenecid mouse model of Parkinson's disease. Naunyn Schmiedebergs Arch Pharmacol. 2015 May;388(5):549-56. doi: 10.1007/s00210-015-1094-5. Epub 2015 Feb 13. PubMed PMID: 25678053. 18: Donovan MD, O'Brien FE, Boylan GB, Cryan JF, Griffin BT. The effect of organic anion transporter 3 inhibitor probenecid on bumetanide levels in the brain: an integrated in vivo microdialysis study in the rat. J Pharm Pharmacol. 2015 Apr;67(4):501-10. doi: 10.1111/jphp.12341. Epub 2014 Dec 10. PubMed PMID: 25490899. 19: Devineni D, Vaccaro N, Murphy J, Curtin C, Mamidi RN, Weiner S, Wang SS, Ariyawansa J, Stieltjes H, Wajs E, Di Prospero NA, Rothenberg P. Effects of rifampin, cyclosporine A, and probenecid on the pharmacokinetic profile of canagliflozin, a sodium glucose co-transporter 2 inhibitor, in healthy participants. Int J Clin Pharmacol Ther. 2015 Feb;53(2):115-28. doi: 10.5414/CP202158. PubMed PMID: 25407255; PubMed Central PMCID: PMC4558628. 20: Töllner K, Brandt C, Römermann K, Löscher W. The organic anion transport inhibitor probenecid increases brain concentrations of the NKCC1 inhibitor bumetanide. Eur J Pharmacol. 2015 Jan 5;746:167-73. doi: 10.1016/j.ejphar.2014.11.019. Epub 2014 Nov 20. PubMed PMID: 25449033.