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MedKoo Cat#: 563043 | Name: Pramipexole Dihydrochloride
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Description:

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

Pramipexole Dihydrochloride is a D2/3 agonist. It acts by reducing mitochondrial ROS production and inhibiting the activation of apoptotic pathways.

Chemical Structure

Pramipexole Dihydrochloride
Pramipexole Dihydrochloride
CAS#191217-81-9 (2HCl hydrate)

Theoretical Analysis

MedKoo Cat#: 563043

Name: Pramipexole Dihydrochloride

CAS#: 191217-81-9 (2HCl hydrate)

Chemical Formula: C10H21Cl2N3OS

Exact Mass: 301.0782

Molecular Weight: 302.26

Elemental Analysis: C, 39.74; H, 7.00; Cl, 23.46; N, 13.90; O, 5.29; S, 10.61

Price and Availability

Size Price Availability Quantity
250mg USD 250.00 2 weeks
500mg USD 350.00 2 weeks
1g USD 550.00 2 Weeks
2g USD 750.00 2 Weeks
5g USD 1,250.00 2 Weeks
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Related CAS #
104632-26-0 (free base) 104632-25-9 (2HCl) 191217-81-9 (2HCl hydrate)
Synonym
Pramipexole Dihydrochloride Monohydrate; Pramipexole Dihydrochloride; Pramipexole 2HCl Monohydrate; Pramipexole 2HCl H2O;
IUPAC/Chemical Name
(S)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine dihydrochloride hydrate
InChi Key
APVQOOKHDZVJEX-QTPLPEIMSA-N
InChi Code
InChI=1S/C10H17N3S.2ClH.H2O/c1-2-5-12-7-3-4-8-9(6-7)14-10(11)13-8;;;/h7,12H,2-6H2,1H3,(H2,11,13);2*1H;1H2/t7-;;;/m0.../s1
SMILES Code
CCCN[C@H]1CCC(N=C(N)S2)=C2C1.O.Cl.Cl
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:
Pramipexole dihydrochloride hydrate is a selective and blood-brain barrier (BBB) penetrant dopamine D2-type receptor agonist, with Kis of 2.2 nM, 3.9 nM, 0.5 nM and 1.3 nM for D2-type receptor, D2, D3 and D4 receptors, respectively.
In vitro activity:
Pramipexole reduced levodopa-induced THir cell loss in a dose-dependent and saturable fashion (ED50 = 500 pM), its inactive stereoisomer was significantly less potent in this regard and pergolide and bromocriptine had negligible cytoprotective effects. Culture media from mesencephalic cultures incubated with pramipexole for 6 days increased THir cell counts in freshly harvested recipient cultures. The magnitude of this effect was directly proportional to the amount of pramipexole in the donor cultures and heat-inactivation of the media abolished the growth promoting effect. The results from this exploratory set of experiments suggest that pramipexole may be cytoprotective to dopamine neurons in tissue culture. Reference: J Neural Transm (Vienna). 1997;104(2-3):209-28. https://pubmed.ncbi.nlm.nih.gov/9203083/
In vivo activity:
This study examined the possible mitochondrial role of pramipexole in promoting neuroprotection following an ischemic stroke of rat. Western blotting was used to analyze the expression of various proteins such as Bax, Bcl-2 and cytochrome c Pramipexole promoted the neurological recovery as shown by the panel of neurobehavioral tests and TTC staining. Post-stroke treatment with pramipexole reduced levels of mitochondrial ROS and Ca2+ after ischemia. Pramipexole elevated the mitochondrial membrane potential and mitochondrial oxidative phosphorylation. Western blotting showed that pramipexole inhibited the transfer of cytochrome c from mitochondria to cytosol, and hence inhibited the mitochondrial permeability transition pore. Reference: Dis Model Mech. 2019 Aug 29;12(8):dmm033860. https://pubmed.ncbi.nlm.nih.gov/31235613/
Solvent mg/mL mM comments
Solubility
DMSO 41.0 135.65
Water 80.0 264.67
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 302.26 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. Okura T, Ito R, Ishiguro N, Tamai I, Deguchi Y. Blood-brain barrier transport of pramipexole, a dopamine D2 agonist. Life Sci. 2007 Apr 3;80(17):1564-71. doi: 10.1016/j.lfs.2007.01.035. Epub 2007 Jan 27. PMID: 17307202. 2. Carvey PM, Pieri S, Ling ZD. Attenuation of levodopa-induced toxicity in mesencephalic cultures by pramipexole. J Neural Transm (Vienna). 1997;104(2-3):209-28. doi: 10.1007/BF01273182. PMID: 9203083. 3. Kang X, Liu L, Wang W, Wang Y. Effects of different doses of dopamine receptor agonist pramipexole on neurobehaviors and changes of mitochondrial membrane potentials in rats with global cerebral ischemia-reperfusion injury. J Stroke Cerebrovasc Dis. 2023 Jul;32(7):107142. doi: 10.1016/j.jstrokecerebrovasdis.2023.107142. Epub 2023 Apr 25. PMID: 37105127. 4. Andrabi SS, Ali M, Tabassum H, Parveen S, Parvez S. Pramipexole prevents ischemic cell death via mitochondrial pathways in ischemic stroke. Dis Model Mech. 2019 Aug 29;12(8):dmm033860. doi: 10.1242/dmm.033860. PMID: 31235613; PMCID: PMC6737958.
In vitro protocol:
1. Okura T, Ito R, Ishiguro N, Tamai I, Deguchi Y. Blood-brain barrier transport of pramipexole, a dopamine D2 agonist. Life Sci. 2007 Apr 3;80(17):1564-71. doi: 10.1016/j.lfs.2007.01.035. Epub 2007 Jan 27. PMID: 17307202. 2. Carvey PM, Pieri S, Ling ZD. Attenuation of levodopa-induced toxicity in mesencephalic cultures by pramipexole. J Neural Transm (Vienna). 1997;104(2-3):209-28. doi: 10.1007/BF01273182. PMID: 9203083.
In vivo protocol:
1. Kang X, Liu L, Wang W, Wang Y. Effects of different doses of dopamine receptor agonist pramipexole on neurobehaviors and changes of mitochondrial membrane potentials in rats with global cerebral ischemia-reperfusion injury. J Stroke Cerebrovasc Dis. 2023 Jul;32(7):107142. doi: 10.1016/j.jstrokecerebrovasdis.2023.107142. Epub 2023 Apr 25. PMID: 37105127. 2. Andrabi SS, Ali M, Tabassum H, Parveen S, Parvez S. Pramipexole prevents ischemic cell death via mitochondrial pathways in ischemic stroke. Dis Model Mech. 2019 Aug 29;12(8):dmm033860. doi: 10.1242/dmm.033860. PMID: 31235613; PMCID: PMC6737958.
1: Trivedi R, Minglani VV, El-Gazzar AM, Batiha GE, Mahmoud MH, Patel M, Patel M. Optimization of Pramipexole-Loaded In Situ Thermosensitive Intranasal Gel for Parkinson's Disease. Pharmaceuticals (Basel). 2024 Jan 29;17(2):172. doi: 10.3390/ph17020172. PMID: 38399387; PMCID: PMC10891972. 2: Tjandrawinata RR, Cahyana AH, Nugroho AO, Adi IK, Talpaneni JSR. Structure Identification and Risk Assurance of Unknown Impurities in Pramipexole Oral Drug Formulation. Adv Pharmacol Pharm Sci. 2024 Feb 13;2024:5583526. doi: 10.1155/2024/5583526. PMID: 38379663; PMCID: PMC10878758. 3: Yang L, Zhang L, Luo Z. Comparative Pharmacokinetics and Bioequivalence Evaluation of Two Formulations of Pramipexole Dihydrochloride Extended-Release Tablets in Healthy Chinese Subjects Under Fasted and Fed States: A Randomized, Open-Label, Single-Dose, Two-Period Crossover Clinical Trial. Drug Des Devel Ther. 2023 Aug 15;17:2369-2381. doi: 10.2147/DDDT.S421449. PMID: 37600497; PMCID: PMC10439801. 4: Pamlényi K, Regdon G Jr, Jójárt-Laczkovich O, Nemes D, Bácskay I, Kristó K. Formulation and characterization of pramipexole containing buccal films for using in Parkinson's disease. Eur J Pharm Sci. 2023 Aug 1;187:106491. doi: 10.1016/j.ejps.2023.106491. Epub 2023 Jun 9. PMID: 37301240. 5: Saepang K, Li SK, Chantasart D. Passive and iontophoretic transport of pramipexole dihydrochloride across human skin microchannels created by microneedles in vitro. Int J Pharm. 2021 Nov 20;609:121092. doi: 10.1016/j.ijpharm.2021.121092. Epub 2021 Sep 14. PMID: 34530098. 6: Casadó-Anguera V, Moreno E, Sánchez-Soto M, Cai NS, Bonaventura J, Homar- Ruano P, Rubinstein M, Cortés A, Canela EI, Ferré S, Casadó V. Heteromerization between α2A adrenoceptors and different polymorphic variants of the dopamine D4 receptor determines pharmacological and functional differences. Implications for impulsive-control disorders. Pharmacol Res. 2021 Aug;170:105745. doi: 10.1016/j.phrs.2021.105745. Epub 2021 Jun 26. PMID: 34182128; PMCID: PMC9885860. 7: Singhal M, Serna C, Merino V, Kalia YN. Current profile controlled transdermal delivery of pramipexole from an iontophoretic patch system in vitro and in vivo. Eur J Pharm Biopharm. 2021 Sep;166:175-181. doi: 10.1016/j.ejpb.2021.06.010. Epub 2021 Jun 25. PMID: 34175373. 8: Saepang K, Li SK, Chantasart D. Effect of Pulsed Direct Current on Iontophoretic Delivery of Pramipexole across Human Epidermal Membrane In Vitro. Pharm Res. 2021 Jul;38(7):1187-1198. doi: 10.1007/s11095-021-03055-3. Epub 2021 Jun 16. PMID: 34136986. 9: Saepang K, Li SK, Chantasart D. Effect of pH on Iontophoretic Transport of Pramipexole Dihydrochloride across Human Epidermal Membrane. Pharm Res. 2021 Apr;38(4):657-668. doi: 10.1007/s11095-021-03001-3. Epub 2021 Apr 7. PMID: 33826056. 10: Luis-Ravelo D, Fumagallo-Reading F, Castro-Hernandez J, Barroso-Chinea P, Afonso-Oramas D, Febles-Casquero A, Cruz-Muros I, Salas-Hernandez J, Mesa- Infante V, Rodriguez-Nuñez J, Gonzalez-Hernandez T. Prolonged dopamine D3 receptor stimulation promotes dopamine transporter ubiquitination and degradation through a PKC-dependent mechanism. Pharmacol Res. 2021 Mar;165:105434. doi: 10.1016/j.phrs.2021.105434. Epub 2021 Jan 20. PMID: 33484816. 11: Liakos EV, Rekos K, Giannakoudakis DA, Mitropoulos AC, Fu J, Kyzas GZ. Activated Porous Carbon Derived from Tea and Plane Tree Leaves Biomass for the Removal of Pharmaceutical Compounds from Wastewaters. Antibiotics (Basel). 2021 Jan 11;10(1):65. doi: 10.3390/antibiotics10010065. PMID: 33440860; PMCID: PMC7827272. 12: Malikowska-Racia N, Sałat K, Nowaczyk A, Fijałkowski Ł, Popik P. Dopamine D2/D3 receptor agonists attenuate PTSD-like symptoms in mice exposed to single prolonged stress. Neuropharmacology. 2019 Sep 1;155:1-9. doi: 10.1016/j.neuropharm.2019.05.012. Epub 2019 May 11. PMID: 31085186. 13: Mohamed D, Hegazy MA, Elshahed MS, Toubar SS, Helmy MI. Novel contribution to the simultaneous monitoring of pramipexole dihydrochloride monohydrate and levodopa as co-administered drugs in human plasma utilizing UPLC-MS/MS. Eur J Mass Spectrom (Chichester). 2018 Oct;24(5):397-407. doi: 10.1177/1469066718788800. Epub 2018 Jul 17. PMID: 30012017. 14: Wang M, Fang S, Liang X. Natural deep eutectic solvents as eco-friendly and sustainable dilution medium for the determination of residual organic solvents in pharmaceuticals with static headspace-gas chromatography. J Pharm Biomed Anal. 2018 Sep 5;158:262-268. doi: 10.1016/j.jpba.2018.06.002. Epub 2018 Jun 4. PMID: 29890483. 15: Raj R, Wairkar S, Sridhar V, Gaud R. Pramipexole dihydrochloride loaded chitosan nanoparticles for nose to brain delivery: Development, characterization and in vivo anti-Parkinson activity. Int J Biol Macromol. 2018 Apr 1;109:27-35. doi: 10.1016/j.ijbiomac.2017.12.056. Epub 2017 Dec 13. PMID: 29247729. 16: Zhu J, Yu F. [Feeding difficulty and developmental delay for 8 months and nystagmus for 4 months in an infant]. Zhongguo Dang Dai Er Ke Za Zhi. 2017 Jan;19(1):68-72. Chinese. doi: 10.7499/j.issn.1008-8830.2017.01.011. PMID: 28100326; PMCID: PMC7390117. 17: Fenu S, Espa E, Pisanu A, Di Chiara G. In vivo dopamine agonist properties of rotigotine: Role of D1 and D2 receptors. Eur J Pharmacol. 2016 Oct 5;788:183-191. doi: 10.1016/j.ejphar.2016.06.035. Epub 2016 Jun 22. PMID: 27343381. 18: Bennett J, Burns J, Welch P, Bothwell R. Safety and Tolerability of R(+) Pramipexole in Mild-to-Moderate Alzheimer's Disease. J Alzheimers Dis. 2016;49(4):1179-87. doi: 10.3233/JAD-150788. PMID: 26682692; PMCID: PMC5862139. 19: Hoang MT, Ita KB, Bair DA. Solid Microneedles for Transdermal Delivery of Amantadine Hydrochloride and Pramipexole Dihydrochloride. Pharmaceutics. 2015 Sep 28;7(4):379-96. doi: 10.3390/pharmaceutics7040379. PMID: 26426039; PMCID: PMC4695825. 20: Brust TF, Hayes MP, Roman DL, Watts VJ. New functional activity of aripiprazole revealed: Robust antagonism of D2 dopamine receptor-stimulated Gβγ signaling. Biochem Pharmacol. 2015 Jan 1;93(1):85-91. doi: 10.1016/j.bcp.2014.10.014. Epub 2014 Nov 7. PMID: 25449598; PMCID: PMC4276521.