Piribedil | CAS#3605-01-4 | dopamine D2 agonist

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

MedKoo CAT#: 584393

CAS#: 3605-01-4

Description: 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.

Chemical Structure

Piribedil

CAS# 3605-01-4

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 584393
Name: Piribedil
CAS#: 3605-01-4
Chemical Formula: C16H18N4O2
Exact Mass: 298.14
Molecular Weight: 298.346
Elemental Analysis: C, 64.41; H, 6.08; N, 18.78; O, 10.73

Price and Availability

Size	Price	Availability
1g	USD 250	2 weeks
5g	USD 550	2 Weeks
10g	USD 850	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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

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Product Data:

Product Data

Instruction:

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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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
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

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.

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.

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1: Eggert K, Öhlwein C, Kassubek J, Wolz M, Kupsch A, Ceballos-Baumann A, Ehret R, Polzer U, Klostermann F, Schwarz J, Fuchs G, Jost W, Albert A, Haag A, Hermsen A, Lohmüller K, Kuhn K, Wangemann M, Oertel WH; In Cooperation With the German Competence Network on Parkinson’s Disease. Influence of the nonergot dopamine agonist piribedil on vigilance in patients With Parkinson Disease and excessive daytime sleepiness (PiViCog-PD): an 11-week randomized comparison trial against pramipexole and ropinirole. Clin Neuropharmacol. 2014 Jul-Aug;37(4):116-22. doi: 10.1097/WNF.0000000000000041. PubMed PMID: 24992083.

2: Perez-Lloret S, Rascol O. Piribedil for the Treatment of Motor and Non-motor Symptoms of Parkinson Disease. CNS Drugs. 2016 Aug;30(8):703-17. doi: 10.1007/s40263-016-0360-5. Review. PubMed PMID: 27344665.

3: Thobois S, Lhommée E, Klinger H, Ardouin C, Schmitt E, Bichon A, Kistner A, Castrioto A, Xie J, Fraix V, Pelissier P, Chabardes S, Mertens P, Quesada JL, Bosson JL, Pollak P, Broussolle E, Krack P. Parkinsonian apathy responds to dopaminergic stimulation of D2/D3 receptors with piribedil. Brain. 2013 May;136(Pt 5):1568-77. doi: 10.1093/brain/awt067. Epub 2013 Mar 29. PubMed PMID: 23543483.

4: Micheli FE, Giugni JC, Espinosa ME, Calvo DS, Raina GB. Piribedil and pathological gambling in six parkinsonian patients. Arq Neuropsiquiatr. 2015 Feb;73(2):115-8. doi: 10.1590/0004-282X20140212. PubMed PMID: 25742580.

5: 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. PubMed PMID: 22592937.

6: Piribedil: sleep attacks, also in patients without Parkinson's disease. Prescrire Int. 2013 Nov;22(143):265. PubMed PMID: 24427837.

7: Il'nitskiĭ AN, Proshchaev KI, Shvartsman GI, Bakhmutova IuV, Pozdniakova NM, Krivetskiĭ VV, Varavina LIu. [The use of piribedil for the prevention of falls in elderly patients with metabolic syndrome]. Klin Med (Mosk). 2014;92(5):46-50. Russian. PubMed PMID: 25782306.

8: Altschuler RA, Wys N, Prieskorn D, Martin C, DeRemer S, Bledsoe S, Miller JM. Treatment with Piribedil and Memantine Reduces Noise-Induced Loss of Inner Hair Cell Synaptic Ribbons. Sci Rep. 2016 Sep 30;6:30821. doi: 10.1038/srep30821. PubMed PMID: 27686418; PubMed Central PMCID: PMC5043183.

9: Giugni JC, Tschopp L, Escalante V, Micheli F. Dose-dependent impulse control disorders in piribedil overdose. Clin Neuropharmacol. 2012 Jan-Feb;35(1):49-50. doi: 10.1097/WNF.0b013e31823d78ab. PubMed PMID: 22240861.

10: Gouraud A, Millaret A, Descotes J, Vial T; French Association of Regional Pharmacovigilance Centres. Piribedil-induced sleep attacks in patients without Parkinson disease: a case series. Clin Neuropharmacol. 2011 May-Jun;34(3):104-7. doi: 10.1097/WNF.0b013e31821f0d8b. Review. PubMed PMID: 21586915.

11: Fedorova NV, Kulua TK, Gubanova ЕN. [The use of piribedil in early and late stages of Parkinson's disease]. Zh Nevrol Psikhiatr Im S S Korsakova. 2015;115(10):96-98. doi: 10.17116/jnevro201511510196-98. Russian. PubMed PMID: 26525631.

12: de Azevedo AA, Langguth B, de Oliveira PM, Rodrigues Figueiredo R. Tinnitus treatment with piribedil guided by electrocochleography and acoustic otoemissions. Otol Neurotol. 2009 Aug;30(5):676-80. doi: 10.1097/MAO.0b013e3181ab8fd5. PubMed PMID: 19574947.

13: Smith LA, Jackson MG, Bonhomme C, Chezaubernard C, Pearce RK, Jenner P. Transdermal administration of piribedil reverses MPTP-induced motor deficits in the common marmoset. Clin Neuropharmacol. 2000 May-Jun;23(3):133-42. PubMed PMID: 10895396.

14: Rascol O, Dubois B, Caldas AC, Senn S, Del Signore S, Lees A; Parkinson REGAIN Study Group. Early piribedil monotherapy of Parkinson's disease: A planned seven-month report of the REGAIN study. Mov Disord. 2006 Dec;21(12):2110-5. PubMed PMID: 17013922.

15: Ziegler M, Castro-Caldas A, Del Signore S, Rascol O. Efficacy of piribedil as early combination to levodopa in patients with stable Parkinson's disease: a 6-month, randomized, placebo-controlled study. Mov Disord. 2003 Apr;18(4):418-25. PubMed PMID: 12671949.

16: Butterworth RF, Poignant JC, Barbeau A. Apomorphine and piribedil in rats: biochemical and pharmacologic studies. Adv Neurol. 1975;9:307-26. PubMed PMID: 1170716.

17: Kölle M, Lepping P, Kassubek J, Schönfeldt-Lecuona C, Freudenmann RW. Delusional infestation induced by piribedil add-on in Parkinson's disease. Pharmacopsychiatry. 2010 Aug;43(6):240-2. doi: 10.1055/s-0030-1261881. Epub 2010 Jul 7. PubMed PMID: 20614418.

18: Demirel M, Yazan Y, Müller RH, Kiliç F, Bozan B. Formulation and in vitro-in vivo evaluation of piribedil solid lipid micro- and nanoparticles. J Microencapsul. 2001 May-Jun;18(3):359-71. PubMed PMID: 11308226.

19: Callaghan N, Fitzpatrick E, O'Mahony JB. Piribedil (ET 495) in the treatment of Parkinson's disease combined with amantadine or levodopa. Acta Neurol Scand. 1975 Sep;52(3):179-86. PubMed PMID: 1098359.

20: 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. PubMed PMID: 12360537.

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