(6R)-6-N-propyl-4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine

• ChemBase ID: 296
• Molecular Formular: C10H17N3S
• Molecular Mass: 211.32708
• Monoisotopic Mass: 211.11431856
• SMILES: s1c2C[C@H](NCCC)CCc2nc1N
• Canonical SMILES: CCCN[C@@H]1CCc2c(C1)sc(n2)N
• InChI: InChI=1S/C10H17N3S/c1-2-5-12-7-3-4-8-9(6-7)14-10(11)13-8/h7,12H,2-6H2,1H3,(H2,11,13)/t7-/m1/s1
• InChIKey: FASDKYOPVNHBLU-SSDOTTSWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R)-6-N-propyl-4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine
• IUPAC Traditional name: mirapex
• Brand Name: Mirapex
• Synonyms: (6R)-6-N-propyl-4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine; Dexpramipexole; Furfuryl Acetate; Pramipexol [Spanish]; Pramipexole 2HCl Monohydrate; Pramipexole hydrochloride; Pramipexolum [Latin]; Pramipexol; pramipexole; Pramipexole; (R)-4,5,6,7-Tetrahydro-N6-propyl-2,6-benzothiazolediamine Dihydrochloride; R-(+)-Pramipexole Dihydrochloride; Dexpramipexole Dihydrochloride; (R)-Pramipexole Dihydrochloride

Database IDs

• CAS Number: 104632-26-0; 104632-28-2
• MDL Number: MFCD09033169
• PubChem SID: 160963759
• PubChem CID: 59868
• Chemspider ID: 54002
• Wikipedia Title: Dexpramipexole

CALCULATED PROPERTIES

JChem

• Acid pKa: 17.661047
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.5217185
• LogD (pH = 7.4): -0.98125774
• Log P: 1.7642827
• Molar Refractivity: 59.7672 cm^3
• Polarizability: 22.761166 Å^3
• Polar Surface Area: 50.94 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.18
• LOG S: -3.18
• Solubility (Water): 1.40e-01 g/l

PROPERTIES

Physical Property

• Solubility: 0.14 mg/mL [Predicted by ALOGPS]; DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 270-272°C (dec.)
• Hydrophobicity(logP): 0.4; 1.168

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

Product Information

• Purity: 95%

DETAILS

DrugBank - DB00413

• Drug Groups: approved; investigational
• Description: Pramipexole is a medication indicated for treating Parkinson's disease and restless legs syndrome (RLS). It is also sometimes used off-label as a treatment for cluster headache or to counteract the problems with low libido experienced by some users of SSRI antidepressant drugs. Pramipexole has shown robust effects on pilot studies in bipolar disorder. Pramipexole is classified as a non-ergoline dopamine agonist.
• Indication: For the treatment of signs and symptoms of idiopathic Parkinson's disease
• Pharmacology: Pramipexole is a nonergot dopamine agonist with high relative in vitro specificity and full intrinsic activity at the D2 subfamily of dopamine receptors, binding with higher affinity to D3 than to D2 or D4 receptor subtypes. The relevance of D3 receptor binding in Parkinson's disease is unknown. The precise mechanism of action of Pramipexole as a treatment for Parkinson's disease is unknown, although it is believed to be related to its ability to stimulate dopamine receptors in the striatum. This conclusion is supported by electrophysiologic studies in animals that have demonstrated that Pramipexole influences striatal neuronal firing rates via activation of dopamine receptors in the striatum and the substantia nigra, the site of neurons that send projections to the striatum.
• Affected Organisms: Humans and other mammals
• Biotransformation: No metabolites have been identified in plasma or urine.
• Absorption: Rapid. Absolute bioavailability is greater than 90%, indicating that pramipexole is well absorbed and undergoes little presystemic metabolism. Food does not affect the extent of absorption.
• Half Life: 8 hours
• Protein Binding: About 15% bound to plasma proteins.
• Elimination: Urinary excretion is the major route of pramipexole elimination, with 90% of a pramipexole dose recovered in urine, almost all as unchanged drug. Nonrenal routes may contribute to a small extent to pramipexole elimination, although no metabolites have been identified in plasma or urine.
• Distribution: * 500 L
• Clearance: * renal cl=400 mL/min
• References: Mierau J, Schneider FJ, Ensinger HA, Chio CL, Lajiness ME, Huff RM: Pramipexole binding and activation of cloned and expressed dopamine D2, D3 and D4 receptors. Eur J Pharmacol. 1995 Jun 23;290(1):29-36. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Toronto Research Chemicals - P700745

The opposite enantiomer of Pramipexole (P700755), a dopamine-D2-receptor agonist. Dexpramipexole is a low-molecular-weight, water-soluble, orally bioavailable, renally excreted compound with linear pharmacokinetics.

REFERENCES

• Mierau J, Schneider FJ, Ensinger HA, Chio CL, Lajiness ME, Huff RM: Pramipexole binding and activation of cloned and expressed dopamine D2, D3 and D4 receptors. Eur J Pharmacol. 1995 Jun 23;290(1):29-36. Pubmed
• Mierau, J., et al.: J. Med. Chem., 30, 494 (1987)
• Schilling, J.C., et al.: Clin. Pharmacol. Ther., 51, 541 (1987)
• Kieburtz, K., et al.: J. Am. Med. Assoc., 278, 125 (1997)