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Details

Stereochemistry RACEMIC
Molecular Formula C14H15FN2.ClH
Molecular Weight 266.742
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FIPAMEZOLE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=XAGTWPPXXHAZMK-UHFFFAOYSA-N
InChI=1S/C14H15FN2.ClH/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);1H

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 ( + / - )

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
9.2 nM [Ki]
17.0 nM [Ki]
55.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
The α₂ adrenergic antagonist fipamezole improves quality of levodopa action in Parkinsonian primates.
2010 Oct 15
Randomized clinical trial of fipamezole for dyskinesia in Parkinson disease (FJORD study).
2012 Jul 10
[Pharmacotherapy of Parkinson's disease: progress or regress?].
2013 Jul 24
Non-dopaminergic treatments for motor control in Parkinson's disease.
2013 Sep
Therapeutic strategies to prevent and manage dyskinesias in Parkinson's disease.
2015 Feb
Patents

Sample Use Guides

30 mg, 60 mg or 90 mg three times per day for up to 28 days
Route of Administration: Oral
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 Sat Dec 16 05:00:20 UTC 2023
Edited
by admin
on Sat Dec 16 05:00:20 UTC 2023
Record UNII
441J9148CQ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FIPAMEZOLE HYDROCHLORIDE
Common Name English
1H-IMIDAZOLE, 5-(2-ETHYL-5-FLUORO-2,3-DIHYDRO-1H-INDEN-2-YL)-, HYDROCHLORIDE (1:1)
Systematic Name English
MPV-1730 HYDROCHLORIDE
Common Name English
Code System Code Type Description
FDA UNII
441J9148CQ
Created by admin on Sat Dec 16 05:00:20 UTC 2023 , Edited by admin on Sat Dec 16 05:00:20 UTC 2023
PRIMARY
CAS
150586-72-4
Created by admin on Sat Dec 16 05:00:20 UTC 2023 , Edited by admin on Sat Dec 16 05:00:20 UTC 2023
PRIMARY
PUBCHEM
6918257
Created by admin on Sat Dec 16 05:00:20 UTC 2023 , Edited by admin on Sat Dec 16 05:00:20 UTC 2023
PRIMARY