Lumateperone tosylateProduct ingredient for Lumateperone

Name
Lumateperone tosylate
Drug Entry
Lumateperone

Schizophrenia is a complex mental illness and impacts approximately 1% of the population.7 Although there are several antipsychotics including aripiprazole, paliperidone and clozapine available for clinical use, they are generally accompanied by significant metabolic and/or neurological adverse effects.1

Lumateperone is a newly approved 2nd generation antipsychotic currently indicated for the treatment of schizophrenia.1 It has a unique receptor binding profile and differs from other antipsychotics in that it modulates glutamate, serotonin and dopamine, which are all neurotransmitters that contribute to the pathophysiology of schizophrenia.1,5

The data so far indicates that lumateperone can alleviate both positive and negative symptoms of schizophrenia.1 Further, not only is the new antipsychotic selective for dopamine (D2) receptors in the mesolimbic and mesocortical brain regions, but it also has minimal off-target activity.1 Both characteristics lend to a more favourable adverse effect profile and ultimately safer drug.1,8

Accession Number
DBSALT001873
Structure
Synonyms
Lumateperone tosylate
UNII
JIE88N006O
CAS Number
1187020-80-9
Weight
Average: 565.7
Monoisotopic: 565.241055988
Chemical Formula
C31H36FN3O4S
InChI Key
LHAPOGAFBLSJJQ-GUTACTQSSA-N
InChI
InChI=1S/C24H28FN3O.C7H8O3S/c1-26-14-15-28-21-11-13-27(16-20(21)19-4-2-5-22(26)24(19)28)12-3-6-23(29)17-7-9-18(25)10-8-17;1-6-2-4-7(5-3-6)11(8,9)10/h2,4-5,7-10,20-21H,3,6,11-16H2,1H3;2-5H,1H3,(H,8,9,10)/t20-,21-;/m0./s1
IUPAC Name
1-(4-fluorophenyl)-4-[(10R,15S)-4-methyl-1,4,12-triazatetracyclo[7.6.1.0^{5,16}.0^{10,15}]hexadeca-5,7,9(16)-trien-12-yl]butan-1-one; 4-methylbenzene-1-sulfonic acid
SMILES
CC1=CC=C(C=C1)S(O)(=O)=O.[H][C@]12CCN(CCCC(=O)C3=CC=C(F)C=C3)C[C@@]1([H])C1=C3N2CCN(C)C3=CC=C1
ChemSpider
34235899
BindingDB
50007659
ChEMBL
CHEMBL3233142
Wikipedia
Lumateperone
Predicted Properties
PropertyValueSource
Water Solubility0.0805 mg/mLALOGPS
logP3.87ALOGPS
logP3.59ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)16.61ChemAxon
pKa (Strongest Basic)8.47ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.79 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity116.42 m3·mol-1ChemAxon
Polarizability43.16 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon