FLUPHENAZINE

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Synonyms
Status
Molecule Category Free-form
ATC N05AB02
UNII S79426A41Z
EPA CompTox DTXSID2023068

Structure

InChI Key PLDUPXSUYLZYBN-UHFFFAOYSA-N
Smiles OCCN1CCN(CCCN2c3ccccc3Sc3ccc(C(F)(F)F)cc32)CC1
InChI
InChI=1S/C22H26F3N3OS/c23-22(24,25)17-6-7-21-19(16-17)28(18-4-1-2-5-20(18)30-21)9-3-8-26-10-12-27(13-11-26)14-15-29/h1-2,4-7,16,29H,3,8-15H2

Physicochemical Descriptors

Property Name Value
Molecular Formula C22H26F3N3OS
Molecular Weight 437.53
AlogP 4.31
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 6.0
Polar Surface Area 29.95
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 30.0
Assay Description Organism Bioactivity Reference
The compound was tested for adenylate cyclase activity in rat corpus striatum None 80.0 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 72.8 %
Binding affinity for human 5-hydroxytryptamine 6 receptor Homo sapiens 50.0 nM
Displacement of [3H]mibolerone from rat androgen receptor Rattus norvegicus 800.0 nM
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens 61.9 %
Displacement of [3H]pyrilamine from human histamine H1 receptor expressed in CHO cells Homo sapiens 40.0 nM
Displacement of [3H]SCH23390 from human dopamine D1 receptor expressed in HEK cells Homo sapiens 179.0 nM
Displacement of [3H]SCH23390 from human dopamine D5 receptor expressed in HEK cells Homo sapiens 21.0 nM
Displacement of [3H]spiperone from human dopamine D2 receptor expressed in CHO cells Homo sapiens 1.44 nM
Displacement of [3H]spiperone from human dopamine D3 receptor expressed in CHO cells Homo sapiens 3.21 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 75.0 %
DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine) None 646.0 nM
DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine) None 484.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: [3H] 8-OH-DPAT) None 939.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1B radioligand binding (ligand: [125I] Cyanopindolol) Rattus norvegicus 869.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: [3H] Ketanserin) None 5.104 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: [3H] Ketanserin) None 1.458 nM
DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 24.0 nM DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 9.578 nM
DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 34.0 nM DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 19.0 nM
DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) None 33.0 nM DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) None 16.0 nM
DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) None 215.0 nM DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) None 80.0 nM
DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscine) None 29.0 nM DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscine) None 13.0 nM
DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) None 154.0 nM DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) None 22.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 39.0 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 25.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: [3H] Mesulergine) None 67.0 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: [3H] Mesulergine) None 35.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT6 radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 52.0 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT6 radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 24.0 nM
DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand binding (ligand: [3H] Paroxetine) None 793.0 nM
DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) None 20.0 nM DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) None 8.575 nM
DRUGMATRIX: Sigma2 radioligand binding (ligand: [3H] Ifenprodil) Rattus norvegicus 158.0 nM DRUGMATRIX: Sigma2 radioligand binding (ligand: [3H] Ifenprodil) Rattus norvegicus 97.0 nM
DRUGMATRIX: Dopamine D1 radioligand binding (ligand: [3H] SCH-23390) None 23.0 nM DRUGMATRIX: Dopamine D1 radioligand binding (ligand: [3H] SCH-23390) None 11.0 nM
DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone) None 1.616 nM DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone) None 0.539 nM
DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) None 0.594 nM DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) None 0.202 nM
DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) None 40.0 nM DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) None 4.662 nM
Antagonist activity at dopamine receptor in Sprague-Dawley rat olfactory tubercles assessed as inhibition of dopamine-induced adenylate cyclase activity after 5 mins Rattus norvegicus 500.0 nM
Antagonist activity at dopamine receptor in Sprague-Dawley rat olfactory tubercles assessed as inhibition of adenylate cyclase activity at 10 uM after 5 mins Rattus norvegicus 10.0 %
DNDI: Malaria in Vitro, 72 hour Plasmodium falciparum 500.0 nM
Antiplasmodial activity against Plasmodium falciparum K1 at 0.002 to 100 ug/ml by serial drug dilution assay Plasmodium falciparum K1 500.0 nM

Related Entries

Cross References

Resources Reference
ChEBI 5123
ChEMBL CHEMBL726
DrugBank DB00623
DrugCentral 1212
FDA SRS S79426A41Z
Human Metabolome Database HMDB0014761
Guide to Pharmacology 204
KEGG C07010
PharmGKB PA449676
PubChem 3372
SureChEMBL SCHEMBL19221
ZINC ZINC000019203912
CONTENTS