Structure

InChI Key KLBQZWRITKRQQV-UHFFFAOYSA-N
Smiles CSc1ccc2c(c1)N(CCC1CCCCN1C)c1ccccc1S2
InChI
InChI=1S/C21H26N2S2/c1-22-13-6-5-7-16(22)12-14-23-18-8-3-4-9-20(18)25-21-11-10-17(24-2)15-19(21)23/h3-4,8-11,15-16H,5-7,12-14H2,1-2H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C21H26N2S2
Molecular Weight 370.59
AlogP 5.89
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 4.0
Polar Surface Area 6.48
Molecular species BASE
Aromatic Rings 2.0
Heavy Atoms 25.0

Bioactivity

Mechanism of Action Action Reference
D2-like dopamine receptor antagonist ANTAGONIST ISBN DailyMed
Protein: Serotonin 2a (5-HT2a) receptor

Description: 5-hydroxytryptamine receptor 2A

Organism : Homo sapiens

P28223 ENSG00000102468
Protein: Serotonin 2c (5-HT2c) receptor

Description: 5-hydroxytryptamine receptor 2C

Organism : Homo sapiens

P28335 ENSG00000147246
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Kinase Protein Kinase CAMK protein kinase group CAMK protein kinase PIM family
- 6890 - - -
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 33-363 - 869 -
Ion channel Voltage-gated ion channel Voltage-gated calcium channel
- 1300-1300 - - -
Ion channel Voltage-gated ion channel Voltage-gated sodium channel
- 1830 - - 64
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Acetylcholine receptor
- 2-106 - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Adrenergic receptor
- 17-65 - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Dopamine receptor
- 3-60 - 8-27 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Histamine receptor
- 99 - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Serotonin receptor
- 18-60 - 70-181 -
Membrane receptor
- 3-60 - 70-181 -
Secreted protein
- - 6690 - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 4
- - - - 2
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 22
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 24330 - - -
Transporter
- 1300 - - 22
Assay Description Organism Bioactivity Reference
Binding affinity towards 5-hydroxytryptamine 2 receptor as antagonism of serotonin-induced contractions in rat jugular vein Rattus norvegicus 60.0 nM
Binding affinity towards 5-hydroxytryptamine 2 receptor was measured using radioligand ([3H]spiperone) binding assay None 18.0 nM
Binding affinity towards human 5-hydroxytryptamine 7 receptor Homo sapiens 70.0 nM
Displacement of [3H]WB-4101 from alpha-1 adrenergic receptor in rat brain Rattus norvegicus 17.0 nM
In vitro affinity for cortical alpha-1 adrenergic receptor labelled with [3H]WB-4101 None 65.0 nM
Inhibition of [3H]WB-4101 binding to rat cortical Alpha-1 adrenergic receptor in vitro None 65.0 nM
Displacement of [3H]cis-flupenthixol from Dopamine receptor D1 in rat brain Rattus norvegicus 80.0 nM
Affinity for displacement of [3H]WB-4101 labeled Dopamine receptor D1 None 17.3 nM
Compound was tested in vitro for its affinity towards rat striatal Dopamine receptor D2 labeled with [3H]- spiperone None 60.0 nM
Displacement of [3H]haloperidol from Dopamine receptor D2 in rat brain Rattus norvegicus 4.0 nM
Inhibition of [3H]spiperone binding to dopamine receptor from rat corpus striatal membranes None 85.0 nM
Binding affinity towards Dopamine receptor D2 None 27.0 nM
In vitro binding affinity against Dopamine receptor D2 by displacement of [3H]haloperidol from rat striatal membranes. None 2.8 nM
In vitro inhibitory against radioligand [3H]spiperone binding to rat striatal Dopamine receptor D2 None 60.0 nM
K+ channel blocking activity in human embryonic kidney cells expressing HERG Kv11.1 Homo sapiens 35.7 nM
Binding affinity against Histamine H1 receptor was measured using radioligand ([3H]pyrilamine) binding assay None 99.0 nM
Compound was evaluated for the inhibition of Locomotion-Screen falloff test, at dose (mg/Kg) = 10; 60-100% Mus musculus 60.0 %
Displacement of [3H]quinuclidinyl benzilate (QNB) from Muscarinic acetylcholine receptor in rat brain Rattus norvegicus 2.0 nM
Binding affinity against Muscarinic acetylcholine receptor was measured using radioligand ([3H]QNB) binding assay None 106.0 nM
Inhibition of human Potassium channel HERG expressed in mammalian cells Homo sapiens 363.08 nM
Inhibitory activity against Potassium channel HERG Homo sapiens 191.0 nM
Displacement of (+)-[3H]-3-PPP from rat cortical sigma site Cavia porcellus 750.0 nM
Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on voltage dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex at 10 uM Cavia porcellus 63.5 %
Inhibitory concentration against potassium channel HERG None 190.55 nM
Inhibition of partially open human voltage-gated potassium channel subunit Kv11.1 (ERG K+ channel) Homo sapiens 35.48 nM
Displacement of [3H]Astemizole from hERG expressed in HEK293 cells at 10 uM Homo sapiens 869.0 nM
Inhibition of wild type androgen receptor expressed in CV1 cells assessed as dihydrotestosterone-stimulated transactivation at 500 nM by CAT reporter gene assay None 2.4 %
Inhibition of human ERG channel Homo sapiens 33.2 nM Inhibition of human ERG channel Homo sapiens 33.2 nM
Inhibition of human ERG expressed in CHO cells by whole cell patch clamp technique Homo sapiens 363.08 nM
Inhibition of human ERG in MCF7 cells Homo sapiens 35.48 nM
Antagonist activity at human 5HT3A receptor expressed in HEK293 cells assessed as inhibition of serotonin-induced inward Na+ current at >= 10 uM Homo sapiens 50.0 %
Inhibition of NorA in Staphylococcus aureus 1199B assessed as reduction in ethidium bromide efflux at 50 uM by fluorimetry after 5 mins Staphylococcus aureus 88.0 %
Inhibition of human ERG Homo sapiens 95.5 nM
DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine) None 7.019 nM DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine) None 1.69 nM
DRUGMATRIX: Muscarinic M2 radioligand binding (ligand: [3H] N-Methylscopolamine) None 106.0 nM DRUGMATRIX: Muscarinic M2 radioligand binding (ligand: [3H] N-Methylscopolamine) None 38.0 nM
DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine) None 90.0 nM DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine) None 19.0 nM
DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine) None 80.0 nM DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine) None 11.0 nM
DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine) None 9.246 nM DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine) None 6.643 nM
DRUGMATRIX: Opiate kappa (OP2, KOP) radioligand binding (ligand: [3H] Diprenorphine) None 996.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: [3H] 8-OH-DPAT) None 60.0 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: [3H] 8-OH-DPAT) None 34.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: [3H] Ketanserin) None 4.366 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: [3H] Ketanserin) None 1.247 nM
DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 5.093 nM DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 2.062 nM
DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 4.692 nM DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 2.597 nM
DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) None 5.891 nM DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) None 2.895 nM
DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) None 133.0 nM DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) None 50.0 nM
DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscine) None 380.0 nM DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscine) None 174.0 nM
DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) None 171.0 nM DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) None 25.0 nM
DRUGMATRIX: Calcium Channel Type L, Benzothiazepine radioligand binding (ligand: [3H] Diltiazem) Rattus norvegicus 469.0 nM DRUGMATRIX: Calcium Channel Type L, Benzothiazepine radioligand binding (ligand: [3H] Diltiazem) Rattus norvegicus 417.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 129.0 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 82.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: [3H] Mesulergine) None 44.0 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: [3H] Mesulergine) None 23.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT6 radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 71.0 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT6 radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 33.0 nM
DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand binding (ligand: [3H] Paroxetine) None 751.0 nM DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand binding (ligand: [3H] Paroxetine) None 399.0 nM
DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) None 363.0 nM DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) None 153.0 nM
DRUGMATRIX: Sigma2 radioligand binding (ligand: [3H] Ifenprodil) Rattus norvegicus 845.0 nM DRUGMATRIX: Sigma2 radioligand binding (ligand: [3H] Ifenprodil) Rattus norvegicus 520.0 nM
DRUGMATRIX: Calcium Channel Type L, Phenylalkylamine radioligand binding (ligand: [3H] (-)-Desmethoxyverapamil (D-888)) Rattus norvegicus 443.0 nM DRUGMATRIX: Calcium Channel Type L, Phenylalkylamine radioligand binding (ligand: [3H] (-)-Desmethoxyverapamil (D-888)) Rattus norvegicus 431.0 nM
DRUGMATRIX: Dopamine D1 radioligand binding (ligand: [3H] SCH-23390) None 194.0 nM DRUGMATRIX: Dopamine D1 radioligand binding (ligand: [3H] SCH-23390) None 97.0 nM
DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone) None 35.0 nM DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone) None 12.0 nM
DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) None 9.892 nM DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) None 3.36 nM
DRUGMATRIX: Dopamine D4.2 radioligand binding (ligand: [3H] Spiperone) None 515.0 nM
DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) None 72.0 nM DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) None 8.412 nM
DRUGMATRIX: Histamine H2 radioligand binding (ligand: [125I] Aminopotentidine) None 950.0 nM DRUGMATRIX: Histamine H2 radioligand binding (ligand: [125I] Aminopotentidine) None 934.0 nM
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens 26.1 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 25.2 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 21.5 %
Neuroleptic activity in Sprague-Dawley rat assessed as inhibition of Sidman avoidance at 20 mg/kg, ip relative to control Rattus norvegicus 15.0 %
Cytotoxicity against african green monkey Vero cells assessed as reduction in cell viability by MTT assay Chlorocebus sabaeus 5.3 ug.mL-1
Inhibition of hERG K channel None 33.0 nM
Binding affinity to Wistar rat brain lipid by TRANSIL assay Rattus norvegicus 369.0 nM
Cytotoxicity against human MDM assessed as cell viability after 3 days by Alamar blue dye-based fluorocytometric analysis relative to control Homo sapiens 5.5 ug.mL-1
Cytotoxicity against human MRC5 cells assessed as decrease in cell viability after 24 hrs by resazurin reduction assay Homo sapiens 8.2 ug.mL-1
Cytotoxicity against mouse J774 cells assessed as decrease in cell viability after 24 hrs by resazurin reduction assay Mus musculus 4.1 ug.mL-1
Cytotoxicity against mouse L5178Y cells assessed as reduction in cell viability by MTT assay Mus musculus 12.72 nM
Cytotoxicity against multidrug resistance mouse L5178Y cells expressing human MDR1 assessed as reduction in cell viability by MTT assay Mus musculus 7.43 nM
Cytotoxicity against African green monkey Vero cells assessed as decrease in cell viability incubated for 72 hrs by resazurin assay Chlorocebus sabaeus 17.79 ug.mL-1
Displacement of [3H]-Raclopride from human D2 receptor (unknown origin) expressed in HEK293 cell membranes Homo sapiens 8.0 nM
Displacement of [3H]-Ketanserin from human 5HT2A receptor expressed in CHO-K1 cells Homo sapiens 84.0 nM
Displacement of [3H]-LSD from human 5HT6 receptor expressed in HEK293 cells Homo sapiens 71.0 nM
Displacement of [3H]-5-CT from human 5HT7 receptor expressed in HEK293 cells Homo sapiens 181.0 nM
Inhibition of NF-kappaB (unknown origin) at 5 uM relative to control Homo sapiens 85.0 %
Inhibition of NF-kappaB (unknown origin) assessed as reduction in IL-2 production at 5 uM by cell based assay relative to control Homo sapiens 95.0 %

Cross References

Resources Reference
ChEBI 9566
ChEMBL CHEMBL479
DrugBank DB00679
DrugCentral 2637
FDA SRS N3D6TG58NI
Human Metabolome Database HMDB0014817
Guide to Pharmacology 100
PharmGKB PA451666
SureChEMBL SCHEMBL9566