LORATADINE

/static/temp/default.svg Search structure
Synonyms
Status
ATC R06AX13
UNII 7AJO3BO7QN
EPA CompTox DTXSID2023224

Structure

InChI Key JCCNYMKQOSZNPW-UHFFFAOYSA-N
Smiles CCOC(=O)N1CCC(=C2c3ccc(Cl)cc3CCc3cccnc32)CC1
InChI
InChI=1S/C22H23ClN2O2/c1-2-27-22(26)25-12-9-15(10-13-25)20-19-8-7-18(23)14-17(19)6-5-16-4-3-11-24-21(16)20/h3-4,7-8,11,14H,2,5-6,9-10,12-13H2,1H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C22H23ClN2O2
Molecular Weight 382.89
AlogP 4.89
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 1.0
Polar Surface Area 42.43
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 27.0

Bioactivity

Mechanism of Action Action Reference
Histamine H1 receptor antagonist ANTAGONIST PubMed
Protein: Histamine H1 receptor
Description: Histamine H1 receptor
Organism : Homo sapiens
P35367 ENSG00000196639
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C19
- 2800 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C8
- 2950 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- - - - 30
Enzyme Hydrolase
- - - - 11
Ion channel Voltage-gated ion channel Potassium channels Two-pore domain potassium channel
- 63400 - - -
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 170-174 - - -
Ion channel Voltage-gated ion channel Voltage-gated calcium channel
- 11400 - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Histamine receptor
- 290 190 37-414 16-65
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group H Nuclear hormone receptor subfamily 1 group H member 4
- 3070 - - 73
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group I Nuclear hormone receptor subfamily 1 group I member 2
3000-12600 - - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC06 neurotransmitter transporter family
- 4000 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 43-101
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 52
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 12000 - - -
Assay Description Organism Bioactivity Reference
Histamine induced in lethality in guinea pigs at 8 hr after oral dose of 0.3 mg/kg Cavia porcellus 80.0 %
Tested for concentration required to inhibit H1 histamine -induced guinea pig ileum contraction Cavia porcellus 290.0 nM
K+ channel blocking activity in human embryonic kidney cells expressing HERG Kv11.1 Homo sapiens 173.0 nM
Binding affinity to histamine H1 receptor in rat brain membranes was evaluated using [3H]-pyrilamine as radioligand None 350.0 nM
Inhibition of human Potassium channel HERG expressed in mammalian cells Homo sapiens 169.82 nM
Tested at 10 (mg/kg) intravenous dose for percent inhibition of the arterial blood pressure in normotensive rats caused by histamine Rattus norvegicus 66.3 %
Binding affinity for H1 histamine receptor expressed in CHO cells None 37.0 nM
Binding affinity towards human histamine H1 receptor expressed in CHO-K1 cells Homo sapiens 414.0 nM
Inhibitory concentration against potassium channel HERG None 169.82 nM
Inhibitory concentration against histamine H1 receptor Homo sapiens 290.0 nM
Inhibition of CYP3A4 in human microsomes at 25 uM Homo sapiens 30.0 %
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens 51.8 %
Inhibition of human ERG expressed in CHO cells by whole cell patch clamp technique Homo sapiens 169.82 nM
Inhibition of human ERG in MCF7 cells Homo sapiens 173.78 nM
Antagonist activity at histamine H1 receptor in Dunkin-Hartley guinea pig ileum assessed as inhibition of histamine-induced contractions at 3 umol/L Cavia porcellus 15.67 %
Antagonist activity at histamine H1 receptor in Dunkin-Hartley guinea pig ileum assessed as inhibition of histamine-induced contractions at 10 umol/L Cavia porcellus 33.36 %
Antagonist activity at histamine H1 receptor in Dunkin-Hartley guinea pig ileum assessed as inhibition of histamine-induced contractions at 30 umol/L Cavia porcellus 64.7 %
Inhibition of human ERG Homo sapiens 173.78 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 245.0 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 156.0 nM
DRUGMATRIX: CYP450, 2C19 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) None 16.0 nM
DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) None 170.0 nM DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) None 20.0 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 43.2 %
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 45.0 %
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 28.1 %
Antagonist activity at human GTS-tagged FXR at 15 uM after 20 mins by TR-FRET assay Homo sapiens 72.5 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 101.04 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 83.88 %
Displacement of [3H]mepyramine from human histamine H1 receptor expressed in Sf9 cells by scintillation counting method Homo sapiens 311.0 nM
Inhibition of human FAAH using [ethanolamine 1-3H] substrate assessed as radioactivity at 10 uM by liquid scintillation counting analysis Homo sapiens 11.0 %
Antagonist activity at histamine H1 receptor in guinea pig jejunum assessed as reduction in histamine-induced contractions Cavia porcellus 72.44 nM
Inhibition of CYP2D6 in human liver microsomes using dextromethorphan as substrate after 8 mins by LC-MS/MS analysis Homo sapiens 100.0 nM
Antiallergic activity in DNP-BSA-stimulated rat RBL2H3 cells assessed as inhibition of anti-DNP-IgE-mediated degranulation by measuring beta-hexosaminidase activity at 20 microg/ml pre-incubated for 1 hr followed by DNP-BSA stimulation by fluorescence assay relative to control Rattus norvegicus 35.0 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 11.88 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 4.99 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 12.62 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 15.05 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 12.99 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 2.41 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans -7.17 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 91.35 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 10.95 %
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 -0.12 % 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 -0.12 %
Binding affinity to human H1 histamine receptor expressed in CHO cells after 1 hr by calcium 5 dye-based FLIPR assay Homo sapiens 190.0 nM

Environmental Exposure

Environmental Exposure Map
Countries
Slovenia

Cross References

Resources Reference
ChEBI 6538
ChEMBL CHEMBL998
DrugBank DB00455
DrugCentral 1605
FDA SRS 7AJO3BO7QN
Human Metabolome Database HMDB0005000
Guide to Pharmacology 7216
PharmGKB PA450266
SureChEMBL SCHEMBL4596
ZINC ZINC000000537931
CONTENTS