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MedKoo Cat#: 584393 | Name: Piribedil
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Description:

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

Piribedil is a dopamine D2 agonist. It is used in the treatment of Parkinson disease, particularly for alleviation of tremor. It has also been used for circulatory disorders and in other applications as a D2 agonist. Piribedil is a symptomatic treatment of PD either as monotherapy or as adjuvant therapy with other antiparkinsonian treatments.

Chemical Structure

Piribedil
Piribedil
CAS#3605-01-4

Theoretical Analysis

MedKoo Cat#: 584393

Name: Piribedil

CAS#: 3605-01-4

Chemical Formula: C16H18N4O2

Exact Mass: 298.1430

Molecular Weight: 298.35

Elemental Analysis: C, 64.41; H, 6.08; N, 18.78; O, 10.73

Price and Availability

Size Price Availability Quantity
1g USD 350.00 2 weeks
5g USD 650.00 2 Weeks
10g USD 950.00 2 Weeks
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Related CAS #
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Synonym
Piribedil; ET 495; ET-495; ET495; EU 4200; EU-4200; EU4200
IUPAC/Chemical Name
2-(4-Piperonyl-1-piperazinyl)pyrimidine
InChi Key
OQDPVLVUJFGPGQ-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H18N4O2/c1-4-17-16(18-5-1)20-8-6-19(7-9-20)11-13-2-3-14-15(10-13)22-12-21-14/h1-5,10H,6-9,11-12H2
SMILES Code
C1(N2CCN(CC3=CC4=C(C=C3)OCO4)CC2)=NC=CC=N1
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
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:
Piribedil is a potent and orally active dopamine D2 and dopamine D3 agonist. Piribedil is also a α2-adrenoceptors antagonist. Piribedil can inhibit MLL1 methyltransferase activity (EC50: 0.18 μM).
In vitro activity:
Piribedil specifically inhibited the proliferation of MLL-r cells by inducing cell-cycle arrest, apoptosis and myeloid differentiation with little toxicity to the non-MLL cells. Mechanism study showed Piribedil blocked the MLL1-WDR5 interaction and thus selectively reduced MLL1-dependent H3K4 methylation. Importantly, MLL1 depletion induced gene expression that was similar to that induced by Piribedil and rendered the MLL-r cells resistant to Piribedil-induced toxicity, revealing Piribedil exerted anti-leukemia effects by targeting MLL1. Furthermore, both the Piribedil treatment and MLL1 depletion sensitized the MLL-r cells to doxorubicin-induced apoptosis. Reference: Cancer Lett. 2018 Sep 1;431:150-160. https://pubmed.ncbi.nlm.nih.gov/29857126/
In vivo activity:
The aims of this study were therefore (1) to investigate the anti-dyskinetic effects of piribedil on L-DOPA-induced contralateral turning behaviour, locomotive dyskinesias (LD), axial dystonia (AD), orolingual dyskinesia (OD) and forelimb dyskinesia (FD) and (2) to compare these effects to the α(2) adrenoceptor antagonist, idazoxan, or the α(2) adrenoceptor agonist, clonidine. Rats were unilaterally lesioned with 6-hydroxydopamine (6-OHDA) and injected intraperitoneally twice daily with L-DOPA methylester (12.5 mg/kg) and benserazide (3.25 mg/kg). After 3 weeks, the effects of piribedil (5, 15, 40 mg/kg), clonidine (0.15 mg/kg), idazoxan (10 mg/kg) and combinations of these drugs were scored during 2 h. Pre-treatment with 5 and 40 mg/kg, but not 15 mg/kg, of piribedil reduced turning behaviour and AD, OD and FD, but piribedil increased LD at the 40 mg/kg doses compared to the L-DOPA group. Idazoxan induced similar effects as piribedil (40 mg/kg), except that it had no effect on LD. Idazoxan blocked the effect of piribedil on AD and FD. Reference: J Neural Transm (Vienna). 2013 Jan;120(1):31-6. https://pubmed.ncbi.nlm.nih.gov/22592937/
Solvent mg/mL mM comments
Solubility
DMF 10.0 33.52
DMF:PBS (pH 7.2) (1:6) 0.1 0.47
DMSO 32.4 108.74
Ethanol 32.0 107.26
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 298.35 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.

Recalculate based on batch purity %
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. Zhang X, Zheng X, Yang H, Yan J, Fu X, Wei R, Xu X, Zhang Z, Yu A, Zhou K, Ding J, Geng M, Huang X. Piribedil disrupts the MLL1-WDR5 interaction and sensitizes MLL-rearranged acute myeloid leukemia (AML) to doxorubicin-induced apoptosis. Cancer Lett. 2018 Sep 1;431:150-160. doi: 10.1016/j.canlet.2018.05.034. Epub 2018 May 30. PMID: 29857126. 2. Cagnotto A, Parotti L, Mennini T. In vitro affinity of piribedil for dopamine D3 receptor subtypes, an autoradiographic study. Eur J Pharmacol. 1996 Oct 10;313(1-2):63-7. doi: 10.1016/0014-2999(96)00503-1. PMID: 8905329. 3. Gerlach M, Halley P, Riederer P, van den Buuse M. The effect of piribedil on L-DOPA-induced dyskinesias in a rat model of Parkinson's disease: differential role of α(2) adrenergic mechanisms. J Neural Transm (Vienna). 2013 Jan;120(1):31-6. doi: 10.1007/s00702-012-0818-7. Epub 2012 May 17. PMID: 22592937. 4. Smith LA, Tel BC, Jackson MJ, Hansard MJ, Braceras R, Bonhomme C, Chezaubernard C, Del Signore S, Rose S, Jenner P. Repeated administration of piribedil induces less dyskinesia than L-dopa in MPTP-treated common marmosets: a behavioural and biochemical investigation. Mov Disord. 2002 Sep;17(5):887-901. doi: 10.1002/mds.10200. PMID: 12360537.
In vitro protocol:
1. Zhang X, Zheng X, Yang H, Yan J, Fu X, Wei R, Xu X, Zhang Z, Yu A, Zhou K, Ding J, Geng M, Huang X. Piribedil disrupts the MLL1-WDR5 interaction and sensitizes MLL-rearranged acute myeloid leukemia (AML) to doxorubicin-induced apoptosis. Cancer Lett. 2018 Sep 1;431:150-160. doi: 10.1016/j.canlet.2018.05.034. Epub 2018 May 30. PMID: 29857126. 2. Cagnotto A, Parotti L, Mennini T. In vitro affinity of piribedil for dopamine D3 receptor subtypes, an autoradiographic study. Eur J Pharmacol. 1996 Oct 10;313(1-2):63-7. doi: 10.1016/0014-2999(96)00503-1. PMID: 8905329.
In vivo protocol:
1. Gerlach M, Halley P, Riederer P, van den Buuse M. The effect of piribedil on L-DOPA-induced dyskinesias in a rat model of Parkinson's disease: differential role of α(2) adrenergic mechanisms. J Neural Transm (Vienna). 2013 Jan;120(1):31-6. doi: 10.1007/s00702-012-0818-7. Epub 2012 May 17. PMID: 22592937. 2. Smith LA, Tel BC, Jackson MJ, Hansard MJ, Braceras R, Bonhomme C, Chezaubernard C, Del Signore S, Rose S, Jenner P. Repeated administration of piribedil induces less dyskinesia than L-dopa in MPTP-treated common marmosets: a behavioural and biochemical investigation. Mov Disord. 2002 Sep;17(5):887-901. doi: 10.1002/mds.10200. PMID: 12360537.
1: Campos HM, Pereira RM, de Oliveira Ferreira PY, Uchenna N, Branco da Silva CR, Pruccoli L, Sanz G, Rodrigues MF, Vaz BG, Rivello BG, Batista da Rocha AL, de Carvalho FS, Oliveira GAR, Lião LM, Georg RC, Leite JA, Dos Santos FCA, Costa EA, Menegatti R, Tarozzi A, Ghedini PC. A novel arylpiperazine derivative (LQFM181) protects against neurotoxicity induced by 3- nitropropionic acid in in vitro and in vivo models. Chem Biol Interact. 2024 May 25;395:111026. doi: 10.1016/j.cbi.2024.111026. Epub 2024 Apr 26. PMID: 38679115. 2: Zalyalova ZA, Katunina EA, Pokhabov DV, Munasipova SE, Ermakova MM. Tremor- dominantnaya forma bolezni Parkinsona [Tremor-dominant form of Parkinson's disease]. Zh Nevrol Psikhiatr Im S S Korsakova. 2024;124(4):28-35. Russian. doi: 10.17116/jnevro202412404128. PMID: 38676674. 3: Ahizoune A, Ait Berri M. Delusional Infestation in Parkinson's Disease Secondary to Piribedil Escalation: An Uncommon Case Report. Cureus. 2024 Feb 5;16(2):e53631. doi: 10.7759/cureus.53631. PMID: 38449964; PMCID: PMC10917070. 4: Pokhabov DV, Tunik ME, Pokhabov DD, Katunina EA, Zalyalova ZA. Postural'naya ustoichivost' i khod'ba pri bolezni Parkinsona [Postural stability and walking in Parkinson's disease]. Zh Nevrol Psikhiatr Im S S Korsakova. 2023;123(11):29-32. Russian. doi: 10.17116/jnevro202312311129. PMID: 37994885. 5: Li W, Zhang H, Zhang Y, Wang K, Hui J, Yi Z. Comparison of the effectiveness, safety, and costs of anti-Parkinson drugs: A multiple-center retrospective study. CNS Neurosci Ther. 2024 Apr;30(4):e14531. doi: 10.1111/cns.14531. Epub 2023 Nov 20. PMID: 37983933; PMCID: PMC11017413. 6: Theleritis C, Siarkos K, Politis A, Smyrnis N, Papageorgiou C, Politis AM. A Systematic Review of Pharmacological Interventions for Apathy in Aging Neurocognitive Disorders. Brain Sci. 2023 Jul 12;13(7):1061. doi: 10.3390/brainsci13071061. PMID: 37508993; PMCID: PMC10377475. 7: Chen XT, Zhang Q, Chen FF, Wen SY, Zhou CQ. Comparative efficacy and safety of six non-ergot dopamine-receptor agonists in early Parkinson's disease: a systematic review and network meta-analysis. Front Neurol. 2023 Jun 16;14:1183823. doi: 10.3389/fneur.2023.1183823. PMID: 37396766; PMCID: PMC10312085. 8: Pilipovich AA, Vorob'eva OV. Vliyanie motornykh i vegetativnykh narushenii na vyrazhennost' bolevogo sindroma u patsientov s I—III stadiyami bolezni Parkinsona [Motor and autonomic disorders influence on pain syndrome of patients with Parkinson's disease of the I-III H&Y stages]. Zh Nevrol Psikhiatr Im S S Korsakova. 2023;123(4):59-67. Russian. doi: 10.17116/jnevro202312304159. PMID: 37084366. 9: Geng Y, Yates C, Peterson RT. Social behavioral profiling by unsupervised deep learning reveals a stimulative effect of dopamine D3 agonists on zebrafish sociality. Cell Rep Methods. 2023 Jan 5;3(1):100381. doi: 10.1016/j.crmeth.2022.100381. PMID: 36814839; PMCID: PMC9939379. 10: Pilipovich AA, Vorob'eva OV. Disfunktsiya verkhnikh otdelov zheludochno- kishechnogo trakta u patsientov na I—III stadiyakh bolezni Parkinsona i ee korrektsiya agonistami dofaminovykh retseptorov [Upper gastrointestinal tract dysfunction and its correction by dopamine agonists for patients with Parkinson's disease of I-III stage]. Zh Nevrol Psikhiatr Im S S Korsakova. 2022;122(11):86-93. Russian. doi: 10.17116/jnevro202212211186. PMID: 36440783. 11: Fan R, Kuai M, Lin D, Bauer F, Fang W. A General C-N Cross-Coupling to Synthesize Heteroaryl Amines Using a Palladacyclic N-Heterocyclic Carbene Precatalyst. Org Lett. 2022 Dec 2;24(47):8688-8693. doi: 10.1021/acs.orglett.2c03580. Epub 2022 Nov 20. PMID: 36403152. 12: Chen XT, Zhang Q, Wen SY, Chen FF, Zhou CQ. Efficacy and safety of non-ergot dopamine-receptor agonists as an adjunct to levodopa in advanced Parkinson's disease: A network meta-analysis. Eur J Neurol. 2023 Mar;30(3):762-773. doi: 10.1111/ene.15635. Epub 2022 Nov 30. PMID: 36380711; PMCID: PMC10099912. 13: Uppuluri CT, Ravi PR, Dalvi AV. Design and evaluation of thermo-responsive nasal in situ gelling system dispersed with piribedil loaded lecithin-chitosan hybrid nanoparticles for improved brain availability. Neuropharmacology. 2021 Dec 15;201:108832. doi: 10.1016/j.neuropharm.2021.108832. Epub 2021 Oct 8. PMID: 34627852. 14: Chen JJ, Chen YW, Zeng BY, Hung CM, Zeng BS, Stubbs B, Carvalho AF, Thompson T, Roerecke M, Su KP, Tu YK, Wu YC, Smith L, Chen TY, Lin PY, Liang CS, Hsu CW, Hsu SP, Kuo HC, Wu MK, Tseng PT. Efficacy of pharmacologic treatment in tinnitus patients without specific or treatable origin: A network meta-analysis of randomised controlled trials. EClinicalMedicine. 2021 Aug 13;39:101080. doi: 10.1016/j.eclinm.2021.101080. PMID: 34611615; PMCID: PMC8478678. 15: Uppuluri CT, Ravi PR, Dalvi AV. Design, optimization and pharmacokinetic evaluation of Piribedil loaded solid lipid nanoparticles dispersed in nasal in situ gelling system for effective management of Parkinson's disease. Int J Pharm. 2021 Sep 5;606:120881. doi: 10.1016/j.ijpharm.2021.120881. Epub 2021 Jul 14. PMID: 34273426. 16: Wahba MEK, El Wasseef D, El Sherbiny D. Studying the suitability of hybrid micelle liquid chromatography for estimating the lipophilicity of some partial dopamine agonists used to attain the reward circuit. R Soc Open Sci. 2021 May 26;8(5):202371. doi: 10.1098/rsos.202371. PMID: 34084546; PMCID: PMC8150020. 17: Wang Y, Lu Z, Xun G. Pathological gambling in a patient on piribedil: A case report. Medicine (Baltimore). 2021 Feb 12;100(6):e24568. doi: 10.1097/MD.0000000000024568. PMID: 33578553; PMCID: PMC7886474. 18: Zhang R, Li J, Wu Y, Liang S, Xu L. Association of Multiple Dopamine D3 Receptor Gene 3'UTR Polymorphisms with Susceptibility to Parkinson's Disease and Clinical Efficacy of Piribedil Therapy. Genet Test Mol Biomarkers. 2021 Jan;25(1):20-30. doi: 10.1089/gtmb.2020.0195. Epub 2020 Dec 28. PMID: 33372861. 19: Pilipovich AA, Vorob'eva OV. Umerennye kognitivnye rasstroistva: sovremennye aspekty diagnostiki i terapii [Mild cognitive impairment: modern aspects of diagnostics and therapy]. Zh Nevrol Psikhiatr Im S S Korsakova. 2020;120(11):124-130. Russian. doi: 10.17116/jnevro2020120111124. PMID: 33340307. 20: El Otmani H, Sabiry S, Bellakhdar S, El Moutawakil B, Abdoh Rafai M. Othello syndrome in Parkinson's disease: A diagnostic emergency of an underestimated condition. Rev Neurol (Paris). 2021 Jun;177(6):690-693. doi: 10.1016/j.neurol.2020.08.006. Epub 2020 Dec 1. PMID: 33276961.