Probenecid

  • CAT Number: A000386
  • CAS Number: 57-66-9
  • Molecular Formula: C13H19NO4S
  • Molecular Weight: 285.4
  • Purity: ≥95%
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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.

Catalog Number A000386
CAS Number 57-66-9
Molecular Formula

C13H19NO4S

Purity 95%
Storage -20°C
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)
InChIKey DBABZHXKTCFAPX-UHFFFAOYSA-N
SMILES CCCN(CCC)S(=O)(=O)C1=CC=C(C=C1)C(=O)O
Reference

1: Nyberg M, Piil P, Kiehn OT, Maagaard C, Jørgensen TS, Egelund J, Isakson BE,
Nielsen MS, Gliemann L, Hellsten Y. Probenecid Inhibits α-Adrenergic
Receptor-Mediated Vasoconstriction in the Human Leg Vasculature. Hypertension.
2017 Oct 30. pii: HYPERTENSIONAHA.117.10251. doi:
10.1161/HYPERTENSIONAHA.117.10251. [Epub ahead of print] PubMed PMID: 29084879.

<br>
2: Zhang QS, Heng Y, Chen Y, Luo P, Wen L, Zhang Z, Yuan YH, Chen NH. A Novel
Bibenzyl Compound (20C) Protects Mice from
1-Methyl-4-Phenyl-1,2,3,6-Tetrahydropyridine/Probenecid Toxicity by Regulating
the α-Synuclein-Related Inflammatory Response. J Pharmacol Exp Ther. 2017
Nov;363(2):284-292. doi: 10.1124/jpet.117.244020. Epub 2017 Sep 14. PubMed PMID:
28912345.

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3: Clark RSB, Empey PE, Bay&#305;r H, Rosario BL, Poloyac SM, Kochanek PM, Nolin TD,
Au AK, Horvat CM, Wisniewski SR, Bell MJ. Phase I randomized clinical trial of
N-acetylcysteine in combination with an adjuvant probenecid for treatment of
severe traumatic brain injury in children. PLoS One. 2017 Jul 7;12(7):e0180280.
doi: 10.1371/journal.pone.0180280. eCollection 2017. PubMed PMID: 28686657;
PubMed Central PMCID: PMC5501440.
<br>

4: Hainz N, Becker P, Rapp D, Wagenpfeil S, Wonnenberg B, Beisswenger C,
Tschernig T, Meier C. Probenecid-treatment reduces demyelination induced by
cuprizone feeding. J Chem Neuroanat. 2017 Nov;85:21-26. doi:
10.1016/j.jchemneu.2017.06.003. Epub 2017 Jun 16. PubMed PMID: 28629631.
<br>

5: Ibrahim E, Aballa TC, Lynne CM, Brackett NL. Oral probenecid improves sperm
motility in men with spinal cord injury. J Spinal Cord Med. 2017 May 2:1-4. doi:
10.1080/10790268.2017.1320875. [Epub ahead of print] PubMed PMID: 28464732.

<br>
6: Rao Khandavilli UB, Bhogala BR, Maguire AR, Lawrence SE. Symmetry assisted
tuning of bending and brittle multi-component forms of probenecid. Chem Commun
(Camb). 2017 Mar 16;53(23):3381-3384. doi: 10.1039/c7cc01091e. PubMed PMID:
28265636.

<br>
7: Nataraj J, Manivasagam T, Justin Thenmozhi A, Essa MM. Neurotrophic Effect of
Asiatic acid, a Triterpene of Centella asiatica Against Chronic 1-Methyl 4-Phenyl
1, 2, 3, 6-Tetrahydropyridine Hydrochloride/Probenecid Mouse Model of Parkinson/’s
disease: The Role of MAPK, PI3K-Akt-GSK3β and mTOR Signalling Pathways. Neurochem
Res. 2017 May;42(5):1354-1365. doi: 10.1007/s11064-017-2183-2. Epub 2017 Feb 8.
PubMed PMID: 28181071.
<br>

8: Du L, Empey PE, Ji J, Chao H, Kochanek PM, Bay&#305;r 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 Oct
15;33(20):1913-1917. Epub 2016 Mar 22. PubMed PMID: 26830358; PubMed Central
PMCID: PMC5079409.
<br>

9: Gu PS, Moon M, Choi JG, Oh MS. Mulberry fruit ameliorates
Parkinson/’s-disease-related pathology by reducing α-synuclein and ubiquitin
levels in a 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine/probenecid model. J Nutr
Biochem. 2017 Jan;39:15-21. doi: 10.1016/j.jnutbio.2016.08.014. Epub 2016 Sep 22.
PubMed PMID: 27741433.

<br>
10: Ohashi A, Saeki Y, Harada T, Naito M, Takahashi T, Aizawa S, Hasegawa H.
Tetrahydrobiopterin Supplementation: Elevation of Tissue Biopterin Levels
Accompanied by a Relative Increase in Dihydrobiopterin in the Blood and the Role
of Probenecid-Sensitive Uptake in Scavenging Dihydrobiopterin in the Liver and
Kidney of Rats. PLoS One. 2016 Oct 6;11(10):e0164305. doi:
10.1371/journal.pone.0164305. eCollection 2016. PubMed PMID: 27711248; PubMed
Central PMCID: PMC5053593.

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