LORATADINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H23ClN2O2
Molecular Weight	382.883
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CCOC(=O)N1CCC(CC1)=C2C3=C(CCC4=C2N=CC=C4)C=C(Cl)C=C3

InChI

InChIKey=JCCNYMKQOSZNPW-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C22H23ClN2O2
Molecular Weight	382.883
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

Loratadine is a derivative of azatadine and a second-generation histamine H1 receptor antagonist used in the treatment of allergic rhinitis and urticaria. Unlike most classical antihistamines (histamine H1 antagonists) it lacks central nervous system depressing effects such as drowsiness. Loratadine competes with free histamine and exhibits specific, selective peripheral H1 antagonistic activity. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms (eg. nasal congestion, watery eyes) brought on by histamine. Loratadine has low affinity for cholinergic receptors and does not exhibit any appreciable alpha-adrenergic blocking activity in-vitro. Loratadine also appears to suppress the release of histamine and leukotrienes from animal mast cells, and the release of leukotrienes from human lung fragments, although the clinical importance of this is unknown.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 315	Antagonist 2,778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Upper respiratory allergies 8	Primary		Approved 8,429	CLARITIN

C_max

Value	Dose	Analyte	Population
4 ng/mL	5 mg 1 times / day steady-state, oral	DESLORATADINE plasma	Homo sapiens
27.1 ng/mL	40 mg 1 times / day steady-state, oral	LORATADINE plasma	Homo sapiens
10.8 ng/mL	20 mg single, oral	LORATADINE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
56.9 ng × h/mL	5 mg 1 times / day steady-state, oral	DESLORATADINE plasma	Homo sapiens
96 ng × h/mL	40 mg 1 times / day steady-state, oral	LORATADINE plasma	Homo sapiens
34.4 ng × h/mL	20 mg single, oral	LORATADINE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
27 h	5 mg 1 times / day steady-state, oral	DESLORATADINE plasma	Homo sapiens
14.4 h	40 mg 1 times / day steady-state, oral	LORATADINE plasma	Homo sapiens
11 h	20 mg single, oral	LORATADINE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
84.5%	5 mg 1 times / day steady-state, oral		DESLORATADINE plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
10 mg 1 times / day multiple, oral Recommended	unhealthy, 29 n = 103	Other AEs: Somnolence, Headache...
5 mg 1 times / day multiple, oral Recommended	unhealthy, 3.6 n = 60	Other AEs: Fatigue, Fever...
10 mg 1 times / day multiple, oral Recommended	unhealthy, 35.3 n = 331	Other AEs: Headache...

Showing 1 to 3 of 3 entries

Previous1Next

AEs

Show entries

AE	Significance	Dose	Population
Somnolence	10%	10 mg 1 times / day multiple, oral Recommended	unhealthy, 29 n = 103
Dry mouth	4%	10 mg 1 times / day multiple, oral Recommended	unhealthy, 29 n = 103
Fatigue	5%	10 mg 1 times / day multiple, oral Recommended	unhealthy, 29 n = 103
Headache	9%	10 mg 1 times / day multiple, oral Recommended	unhealthy, 29 n = 103
Allergic rhinitis	2%	5 mg 1 times / day multiple, oral Recommended	unhealthy, 3.6 n = 60

Showing 1 to 5 of 24 entries

Previous1 2 3 4 5Next

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737 inhibitor 1,587	substrate 1,037 inhibitor 1,767 activator 22	substrate 1,217 inhibitor 1,852	inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 1,478 CYP1A2 1,524 CYP2C8 911 P-gp 1,461	CYP1A1 349 CYP2C19 991 CYP1A2 1,054 CYP2B6 664 CYP2C8 693 CYP3A5 395 P-gp 1,537	CYP3A1/2 3 CYP2B1 26 CYP2B2 15 CYP1A1 108

Drug as perpetrator

Show entries

Target	Modality	Activity
CYP1A1 218	inducer 1,573	no
CYP1A2 1,692	inhibitor 3,277	no
CYP2C9 1,819	inhibitor 3,277	no
CYP3A4 1,925	inhibitor 3,277	no
CYP2D6 1,891	inhibitor 3,277	yes [IC50 0.61 uM]

Showing 1 to 5 of 12 entries

Previous1 2 3Next

Drug as victim

Show entries

Target	Modality	Activity	Clinical evidence
CYP3A4 1,737	substrate 3,367	major	yes (co-administration study)
CYP1A1 349	substrate 3,367	minor
CYP1A2 1,054	substrate 3,367	minor
CYP2B6 664	substrate 3,367	minor
CYP2C19 991	substrate 3,367	minor

Showing 1 to 5 of 10 entries

Previous1 2Next

Tox targets

Show entries

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	inhibitor 1,626

Showing 1 to 1 of 1 entries

Previous1Next

Sourcing

Sourcing

Show entries

Vendor/Aggregator	ID	URL
001 Chemical	NO15960	https://www.001chemical.com/chem/79794-75-5
3B Scientific (Wuhan) Corp	3B2-0771	http://www.3bsc.com/index/pro_info.php?id=20127
3B Scientific (Wuhan) Corp	3B1-00337	http://www.3bsc.com/index/pro_info.php?id=20549
AA Blocks	AA00ICZV	https://www.aablocks.com/goods/Goods/detail?id=AA00ICZV
AEchem Scientific Corp., USA	AE1-019802	http://www.aechemsc.com/info_products/AE1-019802.php

Showing 1 to 5 of 77 entries

Previous1 2 3 4 5…16Next

PubMed

Show entries

Title	Date	PubMed
Double-blind trials of azelastine nasal spray monotherapy versus combination therapy with loratadine tablets and beclomethasone nasal spray in patients with seasonal allergic rhinitis. Rhinitis Study Groups.	1999 Jun	10400480
Antiallergic effects of H1-receptor antagonists.	2000	11291777
Cetirizine and loratadine: a comparison using the ED50 in skin reactions.	2000 Mar-Apr	10898119
Treatment of urticaria. An evidence-based evaluation of antihistamines.	2001	11702618
Desloratadine.	2001	11398910

Showing 1 to 5 of 21 entries

Previous1 2 3 4 5Next

Patents

Sample Use Guides

In Vivo Use Guide

Adults and children 6 years and over: 1 tablet daily; not more than 1 tablet in 24 hours

Route of Administration: Oral

In Vitro Use Guide

dose-dependent inhibition of histamine release was observed at loratadine dose above 7 UM. In the rat basophilic leukemia cells (RBL-2H3) experimental system, inhibition by loratadine increased when the concentration of extracellular Ca2+ was reduced from 1.8 to 0.45 mM. Loratadine also inhibited the Mn2+ influx into these cells, thus reflecting the Ca2+ influx.