Mirapex

Base Information

• Chemical Name: Mirapex
• CAS No.: 104632-25-9
• Molecular Formula: C10H17N3S^.2(HCl)
• Molecular Weight: 284.253
• Hs Code.: 2934999090
• NSC Number: 760426
• ChEMBL ID: CHEMBL542257
• Mol file: 104632-25-9.mol

Synonyms:PRAMIPEXOLE HCl;Pramipexole diHCl;Mirapex;SND-919CL2Y;pramipexole-hcl;MLS001401423;SCHEMBL408536;CHEMBL542257;YLOYRMPMRZXEMW-FJXQXJEOSA-N;Pharmakon1600-01504202;(R)-Pramipexole (dihydrochloride);R-(+)-Pramipexole (dihydrochloride);KNS-760704 (dihydrochloride);NSC760426;CCG-100929;GS-3187;NC00179;SMR000469142;(6S)-N6-propyl-4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine hydrochloride;2,6-Benzothiazolediamine, 4,5,6,7-tetrahydro-N6-propyl-,dihydrochloride, (6S)-

Chemical Property of Mirapex

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 6.49E-06mmHg at 25°C
• Melting Point: 288-290 °C
• Boiling Point: 378 °C at 760 mmHg
• Flash Point: 182.4 °C
• PSA: 79.18000
• LogP: 4.15830
• Storage Temp.: Desiccate at RT
• Solubility.: H2O: >20mg/mL
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 247.0909965
• Heavy Atom Count: 15
• Complexity: 188

Purity/Quality:

99% ^*data from raw suppliers

Pramipexole dihydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCNC1CCC2=C(C1)SC(=N2)N.Cl
• Isomeric SMILES: CCCN[C@H]1CCC2=C(C1)SC(=N2)N.Cl
• Recent ClinicalTrials: Ophthalmologic Safety Study of Pramipexole Immediate Release (IR) Versus Ropinirole in Early Parkinson's Disease (PD) Patients
• Recent EU Clinical Trials: A Multicenter, Randomized, Double Blind, Pramipexole Controlled Pilot Study to Assess Efficacy and Safety of Pardoprunox as Adjunct Therapy to L-dopa in the Treatment of Patients with Parkinson’s Disease Experiencing Motor Fluctuations and Dyskinesia
• Uses: It is used for treating Parkinsonism. It can also be used as pharmaceutical raw materials. A dopamine-D2-receptor agonist. Antiparkinsonian A dopamine-D2-receptor agonist. Antiparkinsonian.
• Description: (S)-Pramipexole is a dopamine D2S, D2L, D3, and D4 receptor agonist (EC50s = 426.58, 338.84, 2.24, and 128.82 nM, respectively, in a [35S]GTPγS binding assay). It is also a partial agonist of α2A-adrenergic receptors (α2A-ARs; EC50 = 3,548.13 nM). (S)-Pramipexole is selective for dopamine D2-4 receptors (Kis = 954.99, 1,698.24, 12.59, 128.82 nM for for D2S, D2L, D3, and D4 receptors, respectively, in a radioligand binding assay) over D1 and D5 receptors (Kis = >10,000 nM for both). It prevents MPTP-induced decreases in the number of dopaminergic neurons in the substantia nigra pars compacta in common marmosets when administered at a dose of 60 μg/kg per day before, during, and after administration of MPTP. Formulations containing (S)-pramipexole have been used in the treatment of Parkinson''s disease and restless legs syndrome. Mirapex, an non ergot derivative, was launched in the US for treatment of Parkinson's disease. It can be prepared by two related routes, 5 steps and 3 steps, both involving an optical resolution with L-(+)-tartaric acid to afford the (S)-isomer. Mechanistically, it is a presynaptic dopamine D2 autoreceptor agonist which also activates D3-receptors. It is well absorbed from the GI and excreted in the urine essentially unchanged with a half-life of 8-12 hr. Mirapex had favorable effects on the symptoms without levodopa for patients with advanced PD and allowed a 27% reduction in use of levodopa in combination therapy. It had an adverse events profile similar to other dopamine agonists and in advanced patients reduced the mean "on-off" hr/day from 6 to 4. It was safe but not efficacious in all patients.
• Therapeutic Function: Antiparkinsonian, Antipsychotic

Technology Process of Mirapex

There total 22 articles about Mirapex which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

pramipexole (104632-26-0) → pramipexole dihydrochloride (104632-25-9,104617-85-8)

Guidance literature:

With hydrogenchloride; In water; acetone; at 0 - 3 ℃; for 2h; pH=1.5; Product distribution / selectivity;

Reference yield: 87.0%

(6S,7S)-2-amino-7-hydroxy-6-(propylamino)-4,5,6,7-tetrahydrobenzothiazole (1001648-71-0,1246818-51-8) → pramipexole dihydrochloride (104632-25-9,104617-85-8)

Guidance literature:

(6S,7S)-2-amino-7-hydroxy-6-(propylamino)-4,5,6,7-tetrahydrobenzothiazole; With hydrogenchloride; formic acid; In water;

With hydrogen; palladium on activated carbon; In water; Product distribution / selectivity;

Reference yield: 86.0%

2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole p-toluenesulfonic acid (943319-02-6) → pramipexole dihydrochloride (104632-25-9,104617-85-8)

Guidance literature:

With acetyl chloride; In isopropyl alcohol; at 5 - 20 ℃; for 12.5h;

upstream raw materials:

(6S,7S)-2-amino-7-hydroxy-6-(propylamino)-4,5,6,7-tetrahydrobenzothiazole

pramipexole

2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole p-toluenesulfonic acid

2,6-diamino-4,5,6,7-tetrahydro-benzthiazole

Downstream raw materials:

pramipexole

pramipexole dihydrochloride monohydrate

Refernces

• 1、 -. "Preparation method of pramipexole dihydrochloride". Paragraph 0017-0025. . Retrieved 2020/05/09.
• 2、 Ghasemi, Mohammad Hadi,Kowsari, Elaheh. "Convenient N-Alkylation of amines using an effective magnetically separable supported ionic liquid containing an anionic polyoxometalate". . p. 1957 - 1968. Retrieved 2017/02/15.