An inhibitor of OATs and MRP1 and an agonist of TRPV2
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Labeled Version(s)
26787Probenecid-d14
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Probenecid

Item No. 14981

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-[(dipropylamino)sulfonyl]-benzoic acid
CAS Number
57-66-9
Synonyms
  • NSC 18786
Molecular Formula
C13H19NO4S
Formula Weight
285.4
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:5): 0.15 mg/mlEthanol: 10 mg/ml
λmax
224, 249 nm
SMILES
O=C(O)C1=CC=C(S(N(CCC)CCC)(=O)=O)C=C1
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)
InChi Key
DBABZHXKTCFAPX-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 g

    $36

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    10 g

    $53

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    25 g

    $95

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    100 g

    $336

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    Product Description

    Probenecid is a benzoic acid derivative that inhibits organic anion transporters (OATs) and the ATP-binding cassette transporter (ABCC1) multidrug resistance protein 1 (MRP1) and activates the transient receptor potential (TRP) channel TRPV2.1,2,3,4,5,6 It inhibits OAT1, OAT3, and OAT6 (Kis = 6.3, 9.0, and 8.4 µM, respectively), as well as OAT2 (IC50 = 0.67 µM), and is selective for OATs over organic cation transporter 1 (OCT1) and OCT2 (IC50s = 1,600 and 1,700 µM, respectively).1,2,3,4 Probenecid (7 mM) decreases Fas antibody-induced glutathione (GSH) efflux and staurosporine-induced efflux of the MRP1 substrate calcein in Jurkat cells and decreases apoptotic progression.6 It is an agonist of TRPV2 (EC50 = 31.9 µM).5 It induces nociceptive behavior in mouse models of carrageenan- or complete Freund’s adjuvant-induced inflammatory pain when administered at a dose of 20 mM in drinking water in combination with doses of carrageenan or CFA that do not provoke pain responses alone.5 Formulations containing probenecid have been used in the treatment of gouty arthritis.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kaler, G., Truong, D.M., Khandelwal, A., et al. Structural variation governs substrate specificity for organic anion transporter (OAT) homologs. Potential remote sensing by OAT family members. The Journal of Biological Chemisty 282(33), 23841-23853 (2007).

    2. Takeda, M., Narikawa, S., Hosoyamada, M., et al. Characterization of organic anion transport inhibitors using cells stably expressing human organic anion transporters. Eur. J. Pharmacol. 419(2-3), 113-120 (2001).

    3. Khamdang, S., Takeda, M., Shimoda, M., et al. Interactions of human- and rat-organic anion transporters with pravastatin and cimetidine. J. Pharmacol. Sci. 94(2), 197-202 (2004).

    4. Arndt, P., Volk, C., Gorboulev, V., et al. Interaction of cations, anions, and weak base quinine with rat renal cation transporter rOCT2 compared with rOCT1. Am. J. Physiol. Renal Physiol. 281(3), F454-F468 (2001).

    5. Bang, S., Kim, K.Y., Yoo, S., et al. Transient receptor potential V2 expressed in sensory neurons is activated by probenecid. Neurosci. Lett. 425(2), 120-125 (2007).

    6. Hammonnd, C.L., Marchan, R., Krance, S.M., et al. Glutathione export during apoptosis requires functional multidrug resistance-associated proteins. The Journal of Biological Chemisty 282(19), 14337-14347 (2007).