FIPAMEZOLE

Investigational

Details

Stereochemistry	RACEMIC
Molecular Formula	C14H15FN2
Molecular Weight	230.2807
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC1(CC2=CC=C(F)C=C2C1)C3=CNC=N3

InChI

InChIKey=KXSUAWAUCNFBQJ-UHFFFAOYSA-N

InChI=1S/C14H15FN2/c1-2-14(13-8-16-9-17-13)6-10-3-4-12(15)5-11(10)7-14/h3-5,8-9H,2,6-7H2,1H3,(H,16,17)

HIDE SMILES / InChI

Molecular Formula	C14H15FN2
Molecular Weight	230.2807
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12889076 | https://www.ncbi.nlm.nih.gov/pubmed/22744665 | https://www.ncbi.nlm.nih.gov/pubmed/23917951 | http://adisinsight.springer.com/drugs/800012904

Fipamezole is a fluorine substituted imidazole compound with high antagonist specificity for the presynaptic alpha2-adrenoceptor. There were no significant differences between the affinity of Fipamezole for the different subtypes, thus characterizing Fipamezole as a non-subtype–selective alpha2 antagonist. Fipamezole had been in phase III clinical trials for the treatment of dyskinesia associated with Parkinson’s disease. Detected side effects are hypertension, nausea, vomiting, dysgeusia, facial flushing.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Alpha-2a adrenergic receptor 70 Target ID: CHEMBL1867 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12889076	Antagonist 2849	9.2 nM [Ki]
Alpha-2b adrenergic receptor 35 Target ID: CHEMBL1942 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12889076	Antagonist 2849	17.0 nM [Ki]
Alpha-2c adrenergic receptor 44 Target ID: CHEMBL1916 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12889076	Antagonist 2849	55.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Parkinson's disease 232 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12889076 https://www.ncbi.nlm.nih.gov/pubmed/22744665	Primary		Phase III 665	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY525995	https://www.001chemical.com/chem/150586-58-6
Achemica	ACMC-1BZQD	http://www.achemica.com/prodinfo/?id=76608
Alsachim	1720	http://www.alsachim.com/product-C2494-glo.bal-view.html
BLD Pharm	BD01277367	http://www.bldpharm.com/products/150586-58-6.html
BOC Sciences	150586-58-6	https://www.bocsci.com/4-2-ethyl-5-fluoro-1-3-dihydroinden-2-yl-3h-imidazole-cas-150586-58-6-item-244914.html
ChemMol	99047085	http://www.chemmol.com/chemmol/99047085.html
eNovation Chemicals	Y1075123	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y1075123
Molcore	MC525995	https://www.molcore.com/product/150586-58-6
MuseChem	M093957	https://www.musechem.com/product/M093957.html
Smolecule	S528011	http://www.smolecule.com/products/s528011
Synblock Inc	SB17014	http://www.synblock.com/product/150586-58-6.html
THE BioTek	bt-268117	https://www.thebiotek.com/product/inhibitors/bt-268117

PubMed

Title	Date	PubMed
Therapeutic strategies to prevent and manage dyskinesias in Parkinson's disease.	2015-02	25483147
Non-dopaminergic treatments for motor control in Parkinson's disease.	2013-09	23917951
[Pharmacotherapy of Parkinson's disease: progress or regress?].	2013-07-24	24018435
Randomized clinical trial of fipamezole for dyskinesia in Parkinson disease (FJORD study).	2012-07-10	22744665
The α₂ adrenergic antagonist fipamezole improves quality of levodopa action in Parkinsonian primates.	2010-10-15	20824735

Patents

Sample Use Guides

In Vivo Use Guide

30 mg, 60 mg or 90 mg three times per day for up to 28 days

Route of Administration: Oral

In Vitro Use Guide

Fipamezole had moderate affinity for histamine H1 and H3 receptors and the serotonin (5-HT) transporter (IC50s between 100 nM and 1 uM).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:34:02 GMT 2025` Edited by `admin` on `Mon Mar 31 21:34:02 GMT 2025`
Record UNII	T5RCK09KHV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FIPAMEZOLE

Official Name

English

fipamezole [INN]

Preferred Name

English

4-((2RS)-2-ETHYL-5-FLUOROINDAN-2-YL)-1H-IMIDAZOLE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29713