Pramipexole

Pramipexole

Clinical data
Trade names	Mirapex, Mirapexin, Sifrol
AHFS/Drugs.com	Monograph
MedlinePlus	a697029
Pregnancy category	AU: B3 US: C (Risk not ruled out)
Routes of administration	Oral
ATC code	N04BC05 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	>90%
Protein binding	15%
Biological half-life	8–12 hours
Excretion	Urine (90%), Feces (2%)
Identifiers
IUPAC name (S)-N  6-propyl-4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine
CAS Number	104632-26-0 Y
PubChem CID	119570
IUPHAR/BPS	953
DrugBank	DB00413 Y
ChemSpider	106770 Y
UNII	83619PEU5T
KEGG	D05575 Y
ChEBI	CHEBI:8356 Y
ChEMBL	CHEMBL301265 Y
ECHA InfoCard	100.124.761
Chemical and physical data
Formula	C10H17N3S
Molar mass	211.324 g/mol
3D model (Jmol)	Interactive image
SMILES n1c2c(sc1N)C[C@@H](NCCC)CC2
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-/m0/s1 Y Key:FASDKYOPVNHBLU-ZETCQYMHSA-N Y

Pramipexole (Mirapex, Mirapexin, Sifrol) is a dopamine agonist of the non-ergoline class indicated for treating Parkinson's disease (PD) and restless legs syndrome (RLS).

Pramipexole acts as a partial/full agonist at the following receptors:

Pramipexole also possesses low/insignificant affinity (500–10,000 nM) for the 5-HT_1A, 5-HT_1B, 5-HT_1D, and α₂-adrenergic receptors. It has negligible affinity (>10,000 nM) for the D₁, D₅, 5-HT₂, α₁-adrenergic, β-adrenergic, H₁, and mACh receptors. All sites assayed were done using human tissues.

While pramipexole is used clinically (see below), its D₃-preferring receptor binding profile has made it a popular tool compound for preclinical research. For example, pramipexole has been used (in combination with D₂- and or D₃-preferring antagonists) to discover the role of D₃ receptor function in rodent models and tasks for neuropsychiatric disorders. Of note, it appears that pramipexole, in addition to having effects on dopamine D₃ receptors, may also affect mitochondrial function via a mechanism that remains less understood. A pharmacological approach to separate dopaminergic from non-dopaminergic (e.g. mitochondrial) effects of pramipexole has been to study the effects of the R-stereoisomer of pramipexole (which has much lower affinity to the dopamine receptors when compared to the S-isomer) side-by-side with the effects of the S-isomer.