Compound Detail

CHEMBL998

LORATADINE

💊 Approved Drug

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💊 Approved Drug

CCOC(=O)N1CCC(=C2c3ccc(Cl)cc3CCc3cccnc32)CC1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL998
Name	LORATADINE
Phase	Approved
Structure Type	MOL
InChI Key	JCCNYMKQOSZNPW-UHFFFAOYSA-N
Therapeutic	✓ Yes
Active Moiety	CHEMBL1172

Known Names

Alavert BAY76-2211 Children's claritin Claritin Claritin hives relief Claritin hives relief reditab Claritin reditabs Clarityn Clarityn rapide Clarityne Hay-rite Loratadina +7 more

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

382.9

MW (Da)

4.89

ALogP

HBA

HBD

42.4

PSA (Å²)

0.70

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1993
Availability	OTC
Chirality	Achiral

Routes of Administration

Oral

Flags

Natural Product Prodrug

USAN Stem	-atadine
USAN Year	1986

Extended Properties

Molecular Formula	C22H23ClN2O2
MW	382.89
Aromatic Rings	2
Heavy Atoms	27
NP-Likeness	-0.74

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Histamine H1 receptor antagonist	ANTAGONIST	Histamine H1 receptor	✓	✓

Indications

Hypersensitivity Pruritus Rhinitis, Allergic, Perennial Rhinitis, Allergic, Seasonal Rhinitis, Allergic, Seasonal Urticaria Asthma Back Pain Breast Neoplasms Eosinophilic Esophagitis Lymphangioleiomyomatosis Severe Acute Respiratory Syndrome Arthritis, Rheumatoid Dermatitis, Atopic Multiple Sclerosis Lymphoma Multiple Myeloma

ATC Classification

R06AX13

loratadine

Level 1: RESPIRATORY SYSTEM

Level 2: ANTIHISTAMINES FOR SYSTEMIC USE

Activity Summary

IC50 40 meas. best 7.8

Ki 7 meas. best 7.7

EC50 6 meas. best 5.52

Kd 2 meas. best 7.14

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Cytochrome P450 2C19 CHEMBL3622	IC50	7.8	6.675	16.0	2
Histamine H1 receptor CHEMBL231	Ki	7.7	7.005	20.0	4
Histamine H1 receptor CHEMBL3943	Kd	7.14	7.14	72.4	1
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	6.81	6.81	156.0	1
Histamine H1 receptor CHEMBL231	IC50	6.77	6.655	170.0	2
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	6.77	6.4286	169.8	7
Histamine H1 receptor CHEMBL231	Kd	6.72	6.72	190.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	IC50	6.61	6.61	245.0	1
Cavia porcellus CHEMBL369	IC50	6.54	6.54	290.0	1
Histamine H1 receptor CHEMBL4701	Ki	6.46	6.46	350.0	1
Plasmodium falciparum CHEMBL364	IC50	5.7	5.1714	1995.3	7
Cytochrome P450 2C8 CHEMBL3721	IC50	5.53	5.53	2950.0	1
Nuclear receptor subfamily 1 group I member 2 CHEMBL3401	EC50	5.52	5.105	3000.0	4
Bile acid receptor CHEMBL2047	IC50	5.51	5.51	3070.0	1
Sodium-dependent neutral amino acid transporter B(0)AT2 CHEMBL3351189	IC50	5.4	5.4	4000.0	1
HT-29 CHEMBL384	IC50	5.21	5.21	6200.0	2
MCF7 CHEMBL387	IC50	5.12	5.12	7500.0	2
MDA-MB-231 CHEMBL400	IC50	5.08	5.08	8400.0	2
Trypanosoma cruzi CHEMBL368	EC50	5.05	5.05	9000.0	1
ATP-dependent translocase ABCB1 CHEMBL4302	IC50	4.94	4.94	11400.0	1
Voltage-gated L-type calcium channel CHEMBL2095229	IC50	4.94	4.94	11400.0	1
Bile salt export pump CHEMBL6020	IC50	4.92	4.92	12000.0	1
Unchecked CHEMBL612545	IC50	4.88	4.88	13300.0	1
SARS-CoV-2 CHEMBL4303835	IC50	4.82	4.82	15130.0	1
ADMET CHEMBL612558	EC50	4.77	4.77	17000.0	1
Trypanosoma cruzi CHEMBL368	IC50	4.64	4.64	23000.0	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	Ki	4.5	4.5	32022.8	1
Potassium channel subfamily K member 9 CHEMBL2321614	IC50	4.2	4.2	63400.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	11.1	ng.hr.mL-1	Homo sapiens
AUC	230.7	-	Chlorocebus sabaeus
CL	137.0	mL.min-1.g-1	Homo sapiens
Fu	0.12	-	Homo sapiens
T1/2	12.0	hr	Homo sapiens
Vd	120.0	L.kg-1	-

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Cytochrome P450 2C19	IC50	=	16.0	nM	7.8	DRUGMATRIX: CYP450, 2C19 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin)	-
Histamine H1 receptor	Ki	=	20.0	nM	7.7	DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine)	-
Histamine H1 receptor	Ki	=	37.0	nM	7.43	Binding affinity for H1 histamine receptor expressed in CHO cells	15771458
Histamine H1 receptor	Kd	=	72.44	nM	7.14	Antagonist activity at histamine H1 receptor in guinea pig jejunum assessed as r...	25752982
5-hydroxytryptamine receptor 2B	Ki	=	156.0	nM	6.81	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ...	-
Histamine H1 receptor	IC50	=	170.0	nM	6.77	DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine)	-
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	169.82	nM	6.77	Inhibition of human ERG expressed in CHO cells by whole cell patch clamp techniq...	18448342
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	169.82	nM	6.77	Inhibitory concentration against potassium channel HERG	15911273
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	169.82	nM	6.77	Inhibition of human Potassium channel HERG expressed in mammalian cells	12873512
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	173.78	nM	6.76	Inhibition of human ERG	21185626
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	173.78	nM	6.76	Inhibition of human ERG in MCF7 cells	19110341
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	173.0	nM	6.76	K+ channel blocking activity in human embryonic kidney cells expressing HERG Kv1...	12190308
Histamine H1 receptor	Kd	=	190.0	nM	6.72	Binding affinity to human H1 histamine receptor expressed in CHO cells after 1 h...	32462865
5-hydroxytryptamine receptor 2B	IC50	=	245.0	nM	6.61	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ...	-
Cavia porcellus	IC50	=	290.0	nM	6.54	Tested for concentration required to inhibit H1 histamine -induced guinea pig il...	7914928
Histamine H1 receptor	IC50	=	290.0	nM	6.54	Inhibitory concentration against histamine H1 receptor	16220969
Histamine H1 receptor	Ki	=	311.0	nM	6.51	Displacement of [3H]mepyramine from human histamine H1 receptor expressed in Sf9...	25318072
Histamine H1 receptor	Ki	=	350.0	nM	6.46	Binding affinity to histamine H1 receptor in rat brain membranes was evaluated u...	1671420
Histamine H1 receptor	Ki	=	414.0	nM	6.38	Binding affinity towards human histamine H1 receptor expressed in CHO-K1 cells	15482930
Plasmodium falciparum	IC50	=	1995.26	nM	5.7	Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g...	19734910

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	941
-	10.6019/CHEMBL4295262	Unchecked	28
16472241	10.2174/1570163043334794	Hepatotoxicity	18
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
25740159	10.1016/j.bmcl.2015.02.013	No relevant target	9
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
15771458	10.1021/jm049495j	Rattus norvegicus	7
20966043	10.1124/dmd.110.035105	Nuclear receptor subfamily 1 group I member 2	7
19734910	10.1038/nchembio.215	Plasmodium falciparum	7
32462865	10.1021/acs.jmedchem.0c00483	ADMET	6
15771458	10.1021/jm049495j	Cavia porcellus	5
7914928	10.1021/jm00043a009	Mus musculus	5
11602674	-	ATP-dependent translocase ABCB1	5
7914928	10.1021/jm00043a009	Rattus norvegicus	4
15771458	10.1021/jm049495j	No relevant target	4
25318072	10.1021/jm501086v	Sodium-dependent neutral amino acid transporter B(0)AT2	4
20110173	10.1016/j.bmc.2009.12.061	Histamine H1 receptor	3
15771458	10.1021/jm049495j	Canis familiaris	3
32353859	10.1038/s41586-020-2286-9	SARS-CoV-2	3

Data from ChEMBL 36 via Core Engine