An internal standard for the quantification of probenecid
Related Products
Unlabeled Version(s)
14981Probenecid 26294Probenecid
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Probenecid-d14

Item No. 26787

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-[[di(propyl-1,1,2,2,3,3,3-d7)amino]sulfonyl]-benzoic acid
CAS Number
1189657-87-1
Molecular Formula
C13H5D14NO4S
Formula Weight
299.4
Purity
≥99% deuterated forms (d1-d14)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 10 mg/ml
SMILES
O=C(O)C1=CC=C(S(N(C([2H])([2H])C([2H])([2H])C([2H])([2H])[2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])[2H])(=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)/i1D3,2D3,3D2,4D2,9D2,10D2
InChi Key
DBABZHXKTCFAPX-YTSTUSJFSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    5 mg

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    Product Description

    Probenecid-d14 is intended for use as an internal standard for the quantification of probenecid (Item No. 14981) by GC- or LC-MS. Probenecid is a benzoic acid derivative that inhibits organic anion transporters (OATs) but activates the transient receptor potential (TRP) channel TRPV2. It inhibits OAT1, OAT3, and OAT6 with Ki values of 6.3, 9.0, and 8.4 µM, respectively, as well as OAT2 with an IC50 value of 0.67 µM.1,2,3 It is a poor inhibitor of the organic cation transporters OCT1 and OCT2 (IC50 = 1.6 and 1.7 mM, respectively).4 It also acts as an agonist of TRPV2 (EC50 = 31.9 µM), eliciting nociceptive behavior under inflammatory conditions in mice. Formulations containing probenecid have been used in the treatment of gouty arthritis.5

    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. Robbins, N., Koch, S.E., Tranter, M., et al. The history and future of probenecid. Cardiovasc. Toxicol. 12(1), 1-9 (2012).