CYPROHEPTADINE

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category Free-form
ATC R06AX02
UNII 2YHB6175DO
EPA CompTox DTXSID8022872

Structure

InChI Key JJCFRYNCJDLXIK-UHFFFAOYSA-N
Smiles CN1CCC(=C2c3ccccc3C=Cc3ccccc32)CC1
InChI
InChI=1S/C21H21N/c1-22-14-12-18(13-15-22)21-19-8-4-2-6-16(19)10-11-17-7-3-5-9-20(17)21/h2-11H,12-15H2,1H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C21H21N
Molecular Weight 287.41
AlogP 4.7
Hydrogen Bond Acceptor 1.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 0.0
Polar Surface Area 3.24
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 22.0
Assay Description Organism Bioactivity Reference
Binding affinity at serotonin 5-hydroxytryptamine 2 receptor by [3H]ketanserin displacement. None 3.1 nM
Binding affinity towards 5-hydroxytryptamine 2A receptor using [3H]ketanserin None 3.0 nM
Displacement of [3H]ketanserin from 5-hydroxytryptamine 2A receptor expressed NIH3T3 cells None 1.6 nM
Binding affinity against 5-hydroxytryptamine 2A receptor from rat forebrain using [3H]ketanserin as radioligand None 1.6 nM
Displacement of [3H]ketanserin from 5-hydroxytryptamine 2A receptor of rat brain cortex Rattus norvegicus 5.0 nM
Binding affinity to 5-hydroxytryptamine 2C receptor using [3H]Mesulergine as radioligand in stably transfected NIH3T3 cells None 11.0 nM
Binding affinity towards 5-hydroxytryptamine 2C receptor using [3H]mesulergine as radioligand None 11.0 nM
Affinity against 5-hydroxytryptamine receptor was determined in rat stomach fundus strip Rattus norvegicus 7.943 nM
Binding affinity towards 5-hydroxytryptamine 7 receptor None 50.12 nM
Non-selective inhibitory activity was determined against 5-hydroxytryptamine 7 receptor None 50.12 nM
Binding affinity to Dopamine receptor D2 using [3H]spiperone as radioligand in stably transfected NIH3T3 cells None 112.0 nM
Binding affinity at dopamine D2 receptor by [3H]spiperone displacement. None 140.0 nM
Displacement of [3H]- spiperone radioligand binding at the dopamine binding site of rat caudate None 63.0 nM
Binding affinity towards dopamine receptor D2 using [3H]spiperone as radioligand None 112.0 nM
Potency against histamine H1 receptor on guinea pig ileum Cavia porcellus 1.0 nM
Inhibition of [3H]mepyramine binding with histamine H1 receptor in guinea pig cerebellum membranes after 30 min Cavia porcellus 0.537 nM
Displacement of [3H]- QNB binding at the muscarinic-cholinergic binding site of rat brain S1 None 4.0 nM
Binding affinity to Norepinephrine transporter using [3H]-nisoxatine as radioligand in stably transfected NIH3T3 cells None 290.0 nM
Binding affinity towards Norepinephrine transporter using [3H]nisoxitine as radioligand None 290.0 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 83.0 %
Antiinflammatory activity against PLA2-induced Swiss mouse paw edema at 5 mg/kg, ip administered 30 mins before PLA2 challenge Mus musculus 82.0 %
Antiinflammatory activity against PLA2-induced Swiss mouse paw edema at 5 mg/kg, ip administered 60 mins before PLA2 challenge Mus musculus 82.0 %
Antiinflammatory activity against Naja mossambica PLA2-induced Swiss mouse paw edema assessed as inhibition of paw volume at 5 mg/kg, ip administered before 30 mins of PLA2 challenge measured after 30 mins relative to control Mus musculus 66.0 %
Antiinflammatory activity against Naja mossambica PLA2-induced Swiss mouse paw edema assessed as inhibition of paw volume at 5 mg/kg, ip administered before 30 mins of PLA2 challenge measured after 60 mins relative to control Mus musculus 63.0 %
DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine) None 16.0 nM DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine) None 3.943 nM
DRUGMATRIX: Muscarinic M2 radioligand binding (ligand: [3H] N-Methylscopolamine) None 35.0 nM DRUGMATRIX: Muscarinic M2 radioligand binding (ligand: [3H] N-Methylscopolamine) None 12.0 nM
DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine) None 46.0 nM DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine) None 9.655 nM
DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine) None 16.0 nM DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine) None 2.186 nM
DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine) None 3.835 nM DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine) None 2.755 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: [3H] 8-OH-DPAT) None 122.0 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: [3H] 8-OH-DPAT) None 70.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: [3H] Ketanserin) None 0.973 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: [3H] Ketanserin) None 0.278 nM
DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 241.0 nM DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 98.0 nM
DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 80.0 nM DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 44.0 nM
DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) None 107.0 nM DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) None 53.0 nM
DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) None 283.0 nM DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) None 106.0 nM
DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscine) None 38.0 nM DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscine) None 17.0 nM
DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) None 185.0 nM
DRUGMATRIX: Norepinephrine Transporter radioligand binding (ligand: [125I] RTI-55) None 564.0 nM DRUGMATRIX: Norepinephrine Transporter radioligand binding (ligand: [125I] RTI-55) None 559.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 9.441 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 6.008 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: [3H] Mesulergine) None 2.44 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: [3H] Mesulergine) None 1.278 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT6 radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 281.0 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT6 radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 130.0 nM
DRUGMATRIX: Calcium Channel Type L, Phenylalkylamine radioligand binding (ligand: [3H] (-)-Desmethoxyverapamil (D-888)) Rattus norvegicus 438.0 nM DRUGMATRIX: Calcium Channel Type L, Phenylalkylamine radioligand binding (ligand: [3H] (-)-Desmethoxyverapamil (D-888)) Rattus norvegicus 426.0 nM
DRUGMATRIX: Dopamine D1 radioligand binding (ligand: [3H] SCH-23390) None 158.0 nM DRUGMATRIX: Dopamine D1 radioligand binding (ligand: [3H] SCH-23390) None 79.0 nM
DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone) None 164.0 nM DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone) None 55.0 nM
DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) None 48.0 nM DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) None 16.0 nM
DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) None 3.7 nM DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) None 0.43 nM
DRUGMATRIX: Histamine H2 radioligand binding (ligand: [125I] Aminopotentidine) None 198.0 nM DRUGMATRIX: Histamine H2 radioligand binding (ligand: [125I] Aminopotentidine) None 195.0 nM
DRUGMATRIX: Imidazoline I2, Central radioligand binding (ligand: [3H] Idazoxan) Rattus norvegicus 871.0 nM
Inhibition of hypersensitive immune responses in rat passive cutaneous anaphylaxis model at 30 mg/kg Rattus norvegicus 69.0 %
Antagonist activity at 5HT2A receptor None 0.46 nM
Antiallergic activity in in guinea pig ileum strips assessed as inhibition of serotonin-induced anaphylaxis Cavia porcellus 0.04 ug.mL-1
Antiallergic activity in in guinea pig ileum strips assessed as inhibition of bradykinin-induced anaphylaxis Cavia porcellus 2.0 ug.mL-1
Antiallergic activity in in rat stomach strips assessed as inhibition of PGE2-induced anaphylaxis Rattus norvegicus 25.0 ug.mL-1
Antiallergic activity in in rat stomach strips assessed as inhibition of PGE2alpha-induced anaphylaxis Rattus norvegicus 65.0 ug.mL-1
Antiallergic activity in in guinea pig lung tissue assessed as inhibition of SRS-A production Cavia porcellus 1.0 ug.mL-1
Antiallergic activity in in rat stomach strips assessed as inhibition of PGE2-induced anaphylaxis at 25 ug/ml Rattus norvegicus 54.0 %
Antiallergic activity in in rat stomach strips assessed as inhibition of PGE2alpha-induced anaphylaxis at 25 ug/ml Rattus norvegicus 33.0 %
Antiallergic activity in in rat stomach strips assessed as inhibition of PGE2alpha-induced anaphylaxis at 100 ug/ml Rattus norvegicus 74.0 %
Antiallergic activity in in guinea pig lung tissue assessed as inhibition of SRS-A production at 1 ug/ml Cavia porcellus 62.0 %
Antiallergic activity in adrenalectomized Sprague-Dawley rat assessed as inhibition of egg albumin-induced passive cutaneous anaphylaxis reaction at 10 mg/kg, iv after 30 mins by Evans blue staining Rattus norvegicus 51.0 %
Antiallergic activity in adrenalectomized Sprague-Dawley rat assessed as inhibition of egg albumin-induced passive cutaneous anaphylaxis reaction at 3 mg/kg, iv after 30 mins by Evans blue staining Rattus norvegicus 30.0 %
Antiallergic activity in in guinea pig ileum strips assessed as inhibition of histamine-induced anaphylaxis Cavia porcellus 0.04 ug.mL-1
Displacement of [3H]ketanserin from Sprague-Dawley rat cerebral cortex 5-HT2A receptor after 30 mins by liquid scintillation counting analysis Rattus norvegicus 1.6 nM
Antiinflammatory activity in Wistar rat assessed as inhibition of dextran-induced paw edema administered orally 30 mins prior to dextran treatment measured after 3 hrs Rattus norvegicus 56.0 %
Displacement of [3H]5-HT from recombinant human 5-HT7 receptor expressed in African green monkey COS7 cells Homo sapiens 125.89 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 14.5 %
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 0.03 % 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 0.03 %

Related Entries

Cross References

Resources Reference
ChEBI 4046
ChEMBL CHEMBL516
DrugBank DB00434
DrugCentral 765
FDA SRS 2YHB6175DO
Human Metabolome Database HMDB0014578
Guide to Pharmacology 277
KEGG C06935
PDB C7H
PharmGKB PA164749366
PubChem 2913
SureChEMBL SCHEMBL4021
ZINC ZINC000000968264
CONTENTS