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pramipexole 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
	2233	104632-26-0

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: pramipexole hydrochloride pramipexole hydrochloride hydrate sifrol oprymea pramipexole (S)-Pramipexole mirapexin pramipexole dihydrochloride pramipexole dihydrochloride monohydrate pramipexole HCl pramipexol dihydrobromide	A dopamine agonist that binds with high selectivity and specificity to the D2 subfamily of dopamine receptors of which it has a preferential affinity to D3 receptors, and has full intrinsic activity. Pramipexole alleviates parkinsonian motor deficits by stimulation of dopamine receptors in the striatum. Animal studies have shown that pramipexole inhibits dopamine synthesis, release, and turnover. Molecular weight: 211.33 Formula: C10H17N3S CLOGP: 1.47 LIPINSKI: 0 HAC: 3 HDO: 2 TPSA: 50.94 ALOGS: -3.18 ROTB: 3 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

pramipexole hydrochloride
pramipexole hydrochloride hydrate
sifrol
oprymea
pramipexole
(S)-Pramipexole
mirapexin
pramipexole dihydrochloride
pramipexole dihydrochloride monohydrate
pramipexole HCl
pramipexol dihydrobromide

A dopamine agonist that binds with high selectivity and specificity to the D2 subfamily of dopamine receptors of which it has a preferential affinity to D3 receptors, and has full intrinsic activity. Pramipexole alleviates parkinsonian motor deficits by stimulation of dopamine receptors in the striatum. Animal studies have shown that pramipexole inhibits dopamine synthesis, release, and turnover.

Molecular weight: 211.33
Formula: C10H17N3S
CLOGP: 1.47
LIPINSKI: 0
HAC: 3
HDO: 2
TPSA: 50.94
ALOGS: -3.18
ROTB: 3

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
2.50	mg	O

ADMET properties:

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Property	Value	Reference
BA (Bioavailability)	93 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
EoM (Fraction excreted unchanged in urine)	90 %	Benet LZ, Broccatelli F, Oprea TI
CL (Clearance)	7.20 mL/min/kg	Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution)	7 L/kg	Lombardo F, Berellini G, Obach RS
BDDCS (Biopharmaceutical Drug Disposition Classification System)	3	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	20 mg/mL	Bocci G, Oprea TI, Benet LZ
t_half (Half-life)	12.40 hours	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.85 %	Lombardo F, Berellini G, Obach RS
MRTD (Maximum Recommended Therapeutic Daily Dose)	0.30 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

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Approvals:

Date	Agency	Company	Orphan
July 1, 1997	FDA	BOEHRINGER INGELHEIM
Sept. 12, 2008	EMA	KRKA, D.D., NOVO MESTO

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Gambling disorder	483.45	11.42	117	35180	1135	63452590
Dyskinesia	445.21	11.42	256	35041	31746	63421979
Impulse-control disorder	305.90	11.42	74	35223	716	63453009
Compulsive shopping	293.40	11.42	71	35226	688	63453037
On and off phenomenon	287.63	11.42	84	35213	1751	63451974
Hallucination	245.86	11.42	220	35077	54597	63399128
Hallucination, visual	183.07	11.42	121	35176	19177	63434548
Gambling	153.69	11.42	34	35263	212	63453513
Parkinsonism hyperpyrexia syndrome	146.07	11.42	30	35267	123	63453602
Dystonia	136.80	11.42	89	35208	13730	63439995

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Impulse-control disorder	787.58	13.47	178	21081	1123	34934549
Gambling disorder	616.76	13.47	153	21106	1507	34934165
Hypersexuality	592.02	13.47	145	21114	1348	34934324
Hallucination	487.66	13.47	333	20926	51165	34884507
Dyskinesia	387.10	13.47	213	21046	22200	34913472
On and off phenomenon	320.49	13.47	100	21159	2397	34933275
Dopamine dysregulation syndrome	231.01	13.47	54	21205	402	34935270
Hallucination, visual	211.87	13.47	133	21126	17658	34918014
Gambling	202.39	13.47	42	21217	164	34935508
Compulsive shopping	184.56	13.47	44	21215	360	34935312

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Impulse-control disorder	768.24	11.57	182	44340	1592	79698274
Gambling disorder	663.57	11.57	166	44356	1860	79698006
Dyskinesia	631.86	11.57	362	44160	44411	79655455
Hallucination	487.82	11.57	395	44127	85350	79614516
On and off phenomenon	432	11.57	131	44391	3109	79696757
Hypersexuality	405.65	11.57	108	44414	1572	79698294
Hallucination, visual	316.56	11.57	208	44314	32521	79667345
Compulsive shopping	282.94	11.57	70	44452	746	79699120
Dopamine dysregulation syndrome	249.90	11.57	58	44464	459	79699407
Parkinsonism hyperpyrexia syndrome	227.05	11.57	47	44475	201	79699665

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	N04BC05	NERVOUS SYSTEM ANTI-PARKINSON DRUGS DOPAMINERGIC AGENTS Dopamine agonists
CHEBI has role	CHEBI:48407	antiparkinson agent
CHEBI has role	CHEBI:48578	free radical scavengers
CHEBI has role	CHEBI:51065	Dopamine receptor agonist
CHEBI has role	CHEBI:66956	antidyskinetic agent
FDA EPC	N0000175768	Nonergot Dopamine Agonist
FDA MoA	N0000000117	Dopamine Agonists
MeSH PA	D018726	Anti-Dyskinesia Agents
MeSH PA	D000975	Antioxidants
MeSH PA	D000978	Antiparkinson Agents

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Restless legs	indication	32914008	DOID:0050425
Parkinson's disease	indication	49049000	DOID:14330
Fibromyalgia	off-label use	203082005	DOID:631
Hallucinations	contraindication	7011001
Dyskinesia	contraindication	9748009
Orthostatic hypotension	contraindication	28651003
Narcolepsy	contraindication	60380001	DOID:8986
Psychotic disorder	contraindication	69322001
Sleep apnea	contraindication	73430006	DOID:0050847
Kidney disease	contraindication	90708001	DOID:557

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	9.57	Basic
pKa2	5.18	Basic

Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
0.375MG	MIRAPEX ER	BOEHRINGER INGELHEIM	N022421	Feb. 19, 2010	RX	TABLET, EXTENDED RELEASE	ORAL	8679533	Sept. 8, 2029	TREATMENT OF PARKINSONS DISEASE
0.75MG	MIRAPEX ER	BOEHRINGER INGELHEIM	N022421	Feb. 19, 2010	RX	TABLET, EXTENDED RELEASE	ORAL	8679533	Sept. 8, 2029	TREATMENT OF PARKINSONS DISEASE
1.5MG	MIRAPEX ER	BOEHRINGER INGELHEIM	N022421	Feb. 19, 2010	RX	TABLET, EXTENDED RELEASE	ORAL	8679533	Sept. 8, 2029	TREATMENT OF PARKINSONS DISEASE
2.25MG	MIRAPEX ER	BOEHRINGER INGELHEIM	N022421	June 17, 2011	RX	TABLET, EXTENDED RELEASE	ORAL	8679533	Sept. 8, 2029	TREATMENT OF PARKINSONS DISEASE
3.75MG	MIRAPEX ER	BOEHRINGER INGELHEIM	N022421	June 17, 2011	RX	TABLET, EXTENDED RELEASE	ORAL	8679533	Sept. 8, 2029	TREATMENT OF PARKINSONS DISEASE
3MG	MIRAPEX ER	BOEHRINGER INGELHEIM	N022421	Feb. 19, 2010	RX	TABLET, EXTENDED RELEASE	ORAL	8679533	Sept. 8, 2029	TREATMENT OF PARKINSONS DISEASE
4.5MG	MIRAPEX ER	BOEHRINGER INGELHEIM	N022421	Feb. 19, 2010	RX	TABLET, EXTENDED RELEASE	ORAL	8679533	Sept. 8, 2029	TREATMENT OF PARKINSONS DISEASE

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Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
D(2) dopamine receptor	GPCR	P14416	DRD2_HUMAN	AGONIST	EC50	6.60	WOMBAT-PK	CHEMBL
Alpha-2A adrenergic receptor	GPCR	P08913	ADA2A_HUMAN		Ki	7.12	PDSP
5-hydroxytryptamine receptor 1A	GPCR	P08908	5HT1A_HUMAN		Ki	6.16	WOMBAT-PK
5-hydroxytryptamine receptor 2A	GPCR	P28223	5HT2A_HUMAN		EC50	5.93	CHEMBL
5-hydroxytryptamine receptor 7	GPCR	P34969	5HT7R_HUMAN		Ki	5.93	PDSP
Alpha-2B adrenergic receptor	GPCR	P18089	ADA2B_HUMAN		Ki	6.20	WOMBAT-PK
D(3) dopamine receptor	GPCR	P35462	DRD3_HUMAN	AGONIST	EC50	8.67	WOMBAT-PK
Histamine H1 receptor	GPCR	P35367	HRH1_HUMAN		Kd	8.35	CHEMBL
Histamine H2 receptor	GPCR	P25021	HRH2_HUMAN		Ki	5.57	PDSP
Histamine H4 receptor	GPCR	Q9H3N8	HRH4_HUMAN		Kd	7.80	CHEMBL

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External reference:

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ID	Source
006721	NDDF
006722	NDDF
108471007	SNOMEDCT_US
119570	PUBCHEM_CID
169631	MMSL
191217-81-9	SECONDARY_CAS_RN
23370	MMSL
236747	RXNORM
386852009	SNOMEDCT_US
4021042	VANDF

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Mirapex ER	HUMAN PRESCRIPTION DRUG LABEL	1	0597-0109	TABLET, EXTENDED RELEASE	0.38 mg	ORAL	NDA	32 sections
Mirapex ER	HUMAN PRESCRIPTION DRUG LABEL	1	0597-0109	TABLET, EXTENDED RELEASE	0.38 mg	ORAL	NDA	32 sections
Mirapex ER	HUMAN PRESCRIPTION DRUG LABEL	1	0597-0113	TABLET, EXTENDED RELEASE	1.50 mg	ORAL	NDA	32 sections
Mirapex ER	HUMAN PRESCRIPTION DRUG LABEL	1	0597-0113	TABLET, EXTENDED RELEASE	1.50 mg	ORAL	NDA	32 sections
Mirapex ER	HUMAN PRESCRIPTION DRUG LABEL	1	0597-0115	TABLET, EXTENDED RELEASE	3 mg	ORAL	NDA	32 sections
Mirapex ER	HUMAN PRESCRIPTION DRUG LABEL	1	0597-0115	TABLET, EXTENDED RELEASE	3 mg	ORAL	NDA	32 sections
Mirapex ER	HUMAN PRESCRIPTION DRUG LABEL	1	0597-0116	TABLET, EXTENDED RELEASE	4.50 mg	ORAL	NDA	32 sections
Mirapex ER	HUMAN PRESCRIPTION DRUG LABEL	1	0597-0116	TABLET, EXTENDED RELEASE	4.50 mg	ORAL	NDA	32 sections
Mirapex ER	HUMAN PRESCRIPTION DRUG LABEL	1	0597-0285	TABLET, EXTENDED RELEASE	0.75 mg	ORAL	NDA	32 sections
Mirapex ER	HUMAN PRESCRIPTION DRUG LABEL	1	0597-0285	TABLET, EXTENDED RELEASE	0.75 mg	ORAL	NDA	32 sections

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