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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 of FIPAMEZOLE

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

Description

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

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).