ContaminantDB: Pramipexole

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (14)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:26:50 UTC

Update Date

2026-05-14 16:38:03 UTC

Accession Number

CHEM002189

Identification

Common Name

Pramipexole

Class

Small Molecule

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.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Antidyskinetic
Antioxidant
Antiparkinson Agent
Dopamine Agonist
Drug
Free Radical Scavenger
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-Pramipexole	ChEBI
Pramipexol	ChEBI
Pramipexolum	ChEBI
2-Amino-4,5,6,7-tetrahydro-6-propylaminobenzothiazole	HMDB
Mirapex	HMDB
SND 919CL2X	HMDB
Dexpramipexole	HMDB
Pramipexol, (+-)-isomer	HMDB
Sifrole	HMDB
2-Amino-6-propylaminotetrahydrobenzothiazole	HMDB
SND-919	HMDB
Pramipexol dihydrobromide, (+-)-isomer	HMDB
Pramipexol dihydrochloride, (S)-isomer	HMDB
4,5,6,7-Tetrahydro-N6-propyl-2,6-benzothiazole-diamine	HMDB
6,7-Tetrahydro-N6-propyl-2,6-benzothiazolediamine dihydrochloride monohydrate	HMDB
SND-919CL2X	HMDB
SND919CL2X	HMDB
Pramipexol, (R)-isomer	HMDB
Pramipexole dihydrochloride	HMDB
Pramipexole dihydrochloride anhydrous	HMDB
2 Amino 6 propylaminotetrahydrobenzothiazole	HMDB
Pramipexole hydrochloride monohydrate	HMDB
Sifrol	HMDB
SND 919	HMDB

Chemical Formula

C₁₀H₁₇N₃S

Average Molecular Mass

211.327 g/mol

Monoisotopic Mass

211.114 g/mol

CAS Registry Number

104632-26-0

IUPAC Name

(6S)-N6-propyl-4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine

Traditional Name

pramipexole

SMILES

CCCN[C@H]1CCC2=C(C1)SC(N)=N2

InChI Identifier

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

InChI Key

FASDKYOPVNHBLU-ZETCQYMHSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Aralkylamines

Alternative Parents

Substituents

Aralkylamine
Heteroaromatic compound
Thiazole
Azole
Isothiourea
Azacycle
Organoheterocyclic compound
Secondary amine
Secondary aliphatic amine
Organopnictogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzothiazoles (CHEBI:8356 )
diamine (CHEBI:8356 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

dopamine agonist

Chemical Roles

radical scavenger

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	1.40e-01 g/L

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	2.18	ALOGPS
logP	1.76	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	17.66	ChemAxon
pKa (Strongest Basic)	10.31	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	50.94 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	59.77 m³·mol⁻¹	ChemAxon
Polarizability	24.47 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f89-5900000000-2f0a391f30cf7118b5c5	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0udi-1900000000-c299b6c1b06ed6f2a709	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-1290000000-bc573dbf2f8ee5b71096	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gvo-9730000000-fd8c10c012fd8fe62c74	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-8900000000-605ed0f5393829cb2bf3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0090000000-4cbc9934fb61d8772826	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-5490000000-7c5237ecb4da60355c97	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-ecd3da1b2e6cddd7b639	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0090000000-d53b4114529d172c6315	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0090000000-05098f8885ac070a5c36	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01tc-4900000000-1efa3719885d8a194bab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0090000000-8370021700e32bab5e81	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0090000000-8f12c031e88379040ad0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f79-2900000000-89ca482dc7e68f54ab38	Spectrum

Toxicity Profile

Route of Exposure

Oral, 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.

Mechanism of Toxicity

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.

Metabolism

No metabolites have been identified in plasma or urine. Route of 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. Half Life: 8 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the treatment of signs and symptoms of idiopathic Parkinson's disease

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

There is no known antidote for overdosage of a dopamine agonist. If signs of central nervous system stimulation are present, a phenothiazine or other butyrophenone neuroleptic agent may be indicated; the efficacy of such drugs in reversing the effects of overdosage has not been assessed. Management of overdose may require general supportive measures along with gastric lavage, intravenous fluids, and electrocardiogram monitoring. (3)

Concentrations

Not Available

External Links

DrugBank ID

DB00413

HMDB ID

HMDB0014557

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID