CHLORPROTHIXENE

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Trade Names
Synonyms
Status
Molecule Category Free-form
ATC N05AF03
UNII 9S7OD60EWP

Structure

InChI Key WSPOMRSOLSGNFJ-AUWJEWJLSA-N
Smiles CN(C)CC/C=C1/c2ccccc2Sc2ccc(Cl)cc21
InChI
InChI=1S/C18H18ClNS/c1-20(2)11-5-7-14-15-6-3-4-8-17(15)21-18-10-9-13(19)12-16(14)18/h3-4,6-10,12H,5,11H2,1-2H3/b14-7-

Physicochemical Descriptors

Property Name Value
Molecular Formula C18H18ClNS
Molecular Weight 315.87
AlogP 5.19
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 3.0
Polar Surface Area 3.24
Molecular species BASE
Aromatic Rings 2.0
Heavy Atoms 21.0

Bioactivity

Mechanism of Action Action Reference
Dopamine D2 receptor antagonist ANTAGONIST PubMed PubMed Wikipedia Wikipedia
Protein: Dopamine D2 receptor
Description: D(2) dopamine receptor
Organism : Homo sapiens
P14416 ENSG00000149295
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
Protein: Dopamine D3 receptor
Description: D(3) dopamine receptor
Organism : Homo sapiens
P35462 ENSG00000151577
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Ion channel Voltage-gated ion channel Voltage-gated sodium channel
- - - - 55
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Dopamine receptor
- - - 18 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Histamine receptor
- 1-871 - 4 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Serotonin receptor
- - - 3 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- 77800 - - 65
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 27470 - - -
Transporter
- 27470 - -
Assay Description Organism Bioactivity Reference
Binding affinity towards human 5-hydroxytryptamine 6 receptor None 3.0 nM
Binding affinity towards rat 5-hydroxytryptamine 7 receptor None 5.6 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 55.2 %
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens 65.4 %
Displacement of [3H]pyrilamine from human histamine H1 receptor expressed in CHO cells Homo sapiens 3.75 nM
Displacement of [3H]SCH23390 from human dopamine D1 receptor expressed in HEK cells Homo sapiens 18.0 nM
Displacement of [3H]SCH23390 from human dopamine D5 receptor expressed in HEK cells Homo sapiens 9.0 nM
Displacement of [3H]spiperone from human dopamine D2 receptor expressed in CHO cells Homo sapiens 2.96 nM
Displacement of [3H]spiperone from human dopamine D3 receptor expressed in CHO cells Homo sapiens 4.56 nM
TP_TRANSPORTER: increase in Calcein-AM intracellular accumulation (Calcein-AM: ? uM, Chlorprothixene: 100 uM) in MDR1-expressing MDCKII cells None 57.5 %
Antagonist activity at H1 receptor in human HeLa cells assessed as inhibition of histamine-induced Ca2+ release by using fura-2AM-based fluorescence assay Homo sapiens 1.0 nM Antagonist activity at H1 receptor in human HeLa cells assessed as inhibition of histamine-induced Ca2+ release by using fura-2AM-based fluorescence assay Homo sapiens 870.96 nM
Displacement of [3H]mepyramine from histamine H1 receptor in Sprague-Dawley rat brain membrane after 2 hr by scintillation counting Rattus norvegicus 1.072 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 24.0 %
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 -6.9 %
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 26.6 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 6.78 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.07 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.07 %

Related Entries

Cross References

Resources Reference
ChEBI 50931
ChEMBL CHEMBL908
DrugBank DB01239
DrugCentral 623
FDA SRS 9S7OD60EWP
KEGG C07953
PubChem 667467
SureChEMBL SCHEMBL94235
ZINC ZINC000000001137
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