Flupentixol dihydrochlorideProduct ingredient for Flupentixol

Name
Flupentixol dihydrochloride
Drug Entry
Flupentixol

Flupentixol is an antipsychotic drug of the thioxanthene group. It exists in two geometric isomers, the trans(E) and pharmacologically active cis(Z) forms. Flupentixol decanoate is one of the active ingredients found in injectable drug formulations: it is produced by esterification of cis(Z)‐flupentixol with decanoic acid.1 Flupentixol is an antagonist of both D1 and D2 dopamine receptors.1

Available as oral tablets or long-acting intramuscular injections, flupentixol is marketed under brand names such as Depixol and Fluanxol. It is approved for use in Canada and other countries around the world, but not in the US. It is used for the management of chronic schizophrenia in patients whose main manifestations do not include excitement, agitation or hyperactivity.11 It has been marketed to manage symptoms of depression in patients who may or may not exhibit signs of anxiety.14 In combination with melitracen, flupentixol is used to manage symptoms of anxiety, depression, and asthenia.13

Accession Number
DBSALT000929
Structure
Synonyms
Flupentixol diHCl
UNII
96L0Z069N1
CAS Number
51529-01-2
Weight
Average: 507.44
Monoisotopic: 506.1173246
Chemical Formula
C23H27Cl2F3N2OS
InChI Key
IOVDQEIIMOZNNA-MHKBYHAFSA-N
InChI
InChI=1S/C23H25F3N2OS.2ClH/c24-23(25,26)17-7-8-22-20(16-17)18(19-4-1-2-6-21(19)30-22)5-3-9-27-10-12-28(13-11-27)14-15-29;;/h1-2,4-8,16,29H,3,9-15H2;2*1H/b18-5-;;
IUPAC Name
2-(4-{3-[(9Z)-2-(trifluoromethyl)-9H-thioxanthen-9-ylidene]propyl}piperazin-1-yl)ethan-1-ol dihydrochloride
SMILES
Cl.Cl.OCCN1CCN(CC\C=C2\C3=CC=CC=C3SC3=CC=C(C=C23)C(F)(F)F)CC1
PubChem Compound
10140115
ChemSpider
4445626
ChEBI
180489
ChEMBL
CHEMBL1496351
Predicted Properties
PropertyValueSource
Water Solubility0.00399 mg/mLALOGPS
logP4.56ALOGPS
logP4.5Chemaxon
logS-5ALOGPS
pKa (Strongest Acidic)15.59Chemaxon
pKa (Strongest Basic)8.03Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area26.71 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity128.17 m3·mol-1Chemaxon
Polarizability45.71 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleYesChemaxon