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Details

Stereochemistry ACHIRAL
Molecular Formula C22H23ClN2O2.ClH
Molecular Weight 419.3449
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LORATADINE HYDROCHLORIDE

SMILES

CCOC(=O)N1CCC(=C2c3ccc(cc3CCc4cccnc42)Cl)CC1.Cl

InChI

InChIKey=DUWMKTXPAFUTGI-UHFFFAOYSA-N
InChI=1S/C22H23ClN2O2.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula C22H23ClN2O2
Molecular Weight 382.884
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Curator's Comment:: The second generation antihistamines were less soluble in lipid and thus less readily penetrated the blood-brain barrier

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CLARITIN

Approved Use

Uses temporarily relieves these symptoms due to hay fever or other upper respiratory allergies: •runny nose •itchy, watery eyes •sneezing •itching of the nose or throat

Launch Date

7.3457277E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
4 ng/mL
5 mg 1 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
DESLORATADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
27.1 ng/mL
40 mg 1 times / day steady-state, oral
dose: 40 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
LORATADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
10.8 ng/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LORATADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
56.9 ng × h/mL
5 mg 1 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
DESLORATADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
96 ng × h/mL
40 mg 1 times / day steady-state, oral
dose: 40 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
LORATADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
34.4 ng × h/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LORATADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
27 h
5 mg 1 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
DESLORATADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
14.4 h
40 mg 1 times / day steady-state, oral
dose: 40 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
LORATADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
11 h
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LORATADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
84.5%
5 mg 1 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
DESLORATADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy, 29
n = 103
Health Status: unhealthy
Condition: seasonal allergic rhinitis
Age Group: 29
Sex: M+F
Population Size: 103
Sources:
Other AEs: Somnolence, Headache...
Other AEs:
Somnolence (10%)
Headache (9%)
Fatigue (5%)
Dry mouth (4%)
Sources:
5 mg 1 times / day multiple, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Sources:
unhealthy, 3.6
n = 60
Health Status: unhealthy
Condition: seasonal allergic rhinitis
Age Group: 3.6
Sex: M+F
Population Size: 60
Sources:
Other AEs: Fatigue, Fever...
Other AEs:
Fatigue (2%)
Fever (7%)
Headache (5%)
Influenza-like symptoms (2%)
Constipation (2%)
Diarrhea (3%)
Dyspepsia (2%)
Loose stools (2%)
Stomatitis (2%)
Tooth disorder (2%)
Vomiting (5%)
Earache (2%)
Drowsiness (7%)
Infection viral (2%)
Allergic rhinitis (2%)
Coughing (3%)
Epistaxis (3%)
Pharyngitis (3%)
Rash (2%)
Sources:
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy, 35.3
n = 331
Health Status: unhealthy
Condition: seasonal allergic rhinitis
Age Group: 35.3
Sex: M+F
Population Size: 331
Sources:
Other AEs: Headache...
Other AEs:
Headache (4.2%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Somnolence 10%
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy, 29
n = 103
Health Status: unhealthy
Condition: seasonal allergic rhinitis
Age Group: 29
Sex: M+F
Population Size: 103
Sources:
Dry mouth 4%
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy, 29
n = 103
Health Status: unhealthy
Condition: seasonal allergic rhinitis
Age Group: 29
Sex: M+F
Population Size: 103
Sources:
Fatigue 5%
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy, 29
n = 103
Health Status: unhealthy
Condition: seasonal allergic rhinitis
Age Group: 29
Sex: M+F
Population Size: 103
Sources:
Headache 9%
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy, 29
n = 103
Health Status: unhealthy
Condition: seasonal allergic rhinitis
Age Group: 29
Sex: M+F
Population Size: 103
Sources:
Allergic rhinitis 2%
5 mg 1 times / day multiple, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Sources:
unhealthy, 3.6
n = 60
Health Status: unhealthy
Condition: seasonal allergic rhinitis
Age Group: 3.6
Sex: M+F
Population Size: 60
Sources:
Constipation 2%
5 mg 1 times / day multiple, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Sources:
unhealthy, 3.6
n = 60
Health Status: unhealthy
Condition: seasonal allergic rhinitis
Age Group: 3.6
Sex: M+F
Population Size: 60
Sources:
Dyspepsia 2%
5 mg 1 times / day multiple, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Sources:
unhealthy, 3.6
n = 60
Health Status: unhealthy
Condition: seasonal allergic rhinitis
Age Group: 3.6
Sex: M+F
Population Size: 60
Sources:
Earache 2%
5 mg 1 times / day multiple, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Sources:
unhealthy, 3.6
n = 60
Health Status: unhealthy
Condition: seasonal allergic rhinitis
Age Group: 3.6
Sex: M+F
Population Size: 60
Sources:
Fatigue 2%
5 mg 1 times / day multiple, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Sources:
unhealthy, 3.6
n = 60
Health Status: unhealthy
Condition: seasonal allergic rhinitis
Age Group: 3.6
Sex: M+F
Population Size: 60
Sources:
Infection viral 2%
5 mg 1 times / day multiple, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Sources:
unhealthy, 3.6
n = 60
Health Status: unhealthy
Condition: seasonal allergic rhinitis
Age Group: 3.6
Sex: M+F
Population Size: 60
Sources:
Influenza-like symptoms 2%
5 mg 1 times / day multiple, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Sources:
unhealthy, 3.6
n = 60
Health Status: unhealthy
Condition: seasonal allergic rhinitis
Age Group: 3.6
Sex: M+F
Population Size: 60
Sources:
Loose stools 2%
5 mg 1 times / day multiple, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Sources:
unhealthy, 3.6
n = 60
Health Status: unhealthy
Condition: seasonal allergic rhinitis
Age Group: 3.6
Sex: M+F
Population Size: 60
Sources:
Rash 2%
5 mg 1 times / day multiple, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Sources:
unhealthy, 3.6
n = 60
Health Status: unhealthy
Condition: seasonal allergic rhinitis
Age Group: 3.6
Sex: M+F
Population Size: 60
Sources:
Stomatitis 2%
5 mg 1 times / day multiple, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Sources:
unhealthy, 3.6
n = 60
Health Status: unhealthy
Condition: seasonal allergic rhinitis
Age Group: 3.6
Sex: M+F
Population Size: 60
Sources:
Tooth disorder 2%
5 mg 1 times / day multiple, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Sources:
unhealthy, 3.6
n = 60
Health Status: unhealthy
Condition: seasonal allergic rhinitis
Age Group: 3.6
Sex: M+F
Population Size: 60
Sources:
Coughing 3%
5 mg 1 times / day multiple, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Sources:
unhealthy, 3.6
n = 60
Health Status: unhealthy
Condition: seasonal allergic rhinitis
Age Group: 3.6
Sex: M+F
Population Size: 60
Sources:
Diarrhea 3%
5 mg 1 times / day multiple, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Sources:
unhealthy, 3.6
n = 60
Health Status: unhealthy
Condition: seasonal allergic rhinitis
Age Group: 3.6
Sex: M+F
Population Size: 60
Sources:
Epistaxis 3%
5 mg 1 times / day multiple, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Sources:
unhealthy, 3.6
n = 60
Health Status: unhealthy
Condition: seasonal allergic rhinitis
Age Group: 3.6
Sex: M+F
Population Size: 60
Sources:
Pharyngitis 3%
5 mg 1 times / day multiple, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Sources:
unhealthy, 3.6
n = 60
Health Status: unhealthy
Condition: seasonal allergic rhinitis
Age Group: 3.6
Sex: M+F
Population Size: 60
Sources:
Headache 5%
5 mg 1 times / day multiple, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Sources:
unhealthy, 3.6
n = 60
Health Status: unhealthy
Condition: seasonal allergic rhinitis
Age Group: 3.6
Sex: M+F
Population Size: 60
Sources:
Vomiting 5%
5 mg 1 times / day multiple, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Sources:
unhealthy, 3.6
n = 60
Health Status: unhealthy
Condition: seasonal allergic rhinitis
Age Group: 3.6
Sex: M+F
Population Size: 60
Sources:
Drowsiness 7%
5 mg 1 times / day multiple, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Sources:
unhealthy, 3.6
n = 60
Health Status: unhealthy
Condition: seasonal allergic rhinitis
Age Group: 3.6
Sex: M+F
Population Size: 60
Sources:
Fever 7%
5 mg 1 times / day multiple, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Sources:
unhealthy, 3.6
n = 60
Health Status: unhealthy
Condition: seasonal allergic rhinitis
Age Group: 3.6
Sex: M+F
Population Size: 60
Sources:
Headache 4.2%
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy, 35.3
n = 331
Health Status: unhealthy
Condition: seasonal allergic rhinitis
Age Group: 35.3
Sex: M+F
Population Size: 331
Sources:
OverviewDrug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
major
yes (co-administration study)
Comment: Coadministration with either ketoconazole, erythromycin (both CYP3A4 inhibitors) increased AUC of drug by 307%, 40%, respectively; coadministration with cimetidine (CYP2D6 and CYP3A4 inhibitor) increased AUC of drug by 103%
Page: 1.0
minor
minor
minor
minor
minor
minor
minor
minor
yes (co-administration study)
Comment: coadministration with cimetidine (CYP2D6 and CYP3A4 inhibitor) increased AUC of drug by 103%
Page: 1.0
yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Central nervous system effects of H1-receptor antagonists in the elderly.
1999 Feb
The acute and sub-chronic effects of levocetirizine, cetirizine, loratadine, promethazine and placebo on cognitive function, psychomotor performance, and weal and flare.
2001
[The effect of second generation histamine antagonists on the heart].
2001
Applications of new liquid chromatography-tandem mass spectrometry technologies for drug development support.
2001 Aug 10
Polarographic behaviour of loratadine and its direct determination in pharmaceutical formulation and human plasma by cathodic adsorptive stripping voltammetry.
2001 Jul
Evaluation of quality of life in children and teenagers with allergic rhinitis: adaptation and validation of the Rhinoconjunctivitis Quality of Life Questionnaire (RQLQ).
2001 Jul-Aug
Pharmacokinetic and safety profile of desloratadine and fexofenadine when coadministered with azithromycin: a randomized, placebo-controlled, parallel-group study.
2001 Mar
Synergistic antiallergic activity of combined histamine H1- and cysteinyl leukotriene1-receptor blockade in human bronchus.
2001 May 11
[Childhood asthma and viral infection: interactions and therapeutic possibilities].
2001 May-Jun
[Approaches to prevention and treatment of latex allergy].
2001 Nov-Dec
The costs of nonsedating antihistamine therapy for allergic rhinitis in managed care: an updated analysis.
2001 Oct
A double-blind, placebo-controlled, and randomized study of loratadine (Clarityne) syrup for the treatment of allergic rhinitis in children aged 3 to 12 years.
2001 Sep
Controlled clinical study of the efficacy of loratadine in Nigerian patients with allergic rhinitis.
2001 Sep
In vitro characterization of the inhibition profile of loratadine, desloratadine, and 3-OH-desloratadine for five human cytochrome P-450 enzymes.
2001 Sep
Clinical evidence for antileukotriene therapy in the management of allergic rhinitis.
2002 Apr
Comparison of five new antihistamines (H1-receptor antagonists) in patients with allergic rhinitis using nasal provocation studies and skin tests.
2002 Apr
Are antihistamines useful in managing asthma?
2002 Feb
Medical management of Cronkhite-Canada syndrome.
2002 Feb
Effect of desloratadine versus placebo on nasal airflow and subjective measures of nasal obstruction in subjects with grass pollen-induced allergic rhinitis in an allergen-exposure unit.
2002 Jun
Comparison of a nasal glucocorticoid, antileukotriene, and a combination of antileukotriene and antihistamine in the treatment of seasonal allergic rhinitis.
2002 Jun
LC determination of loratadine and related impurities.
2002 Jun 20
Fixed drug eruption due to loratadine.
2002 Mar
Med-psych drug-drug interactions update.
2002 Mar-Apr
Influence of zafirlukast and loratadine on exercise-induced bronchoconstriction.
2002 May
The cost of treating allergic rhinitis.
2002 May
Ventricular tachycardia following ingestion of a commonly used antihistamine.
2002 May 6
Patents

Sample Use Guides

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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 13:55:21 UTC 2021
Edited
by admin
on Sat Jun 26 13:55:21 UTC 2021
Record UNII
RTQ46SZY8H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LORATADINE HYDROCHLORIDE
Common Name English
1-PIPERIDINECARBOXYLIC ACID, 4-(8-CHLORO-5,6-DIHYDRO-11H-BENZO(5,6)CYCLOHEPTA(1,2-B)PYRIDIN-11-YLIDENE)-, ETHYL ESTER, HYDROCHLORIDE (1:1)
Common Name English
LORATADINE HYDROCHLORIDE [WHO-DD]
Common Name English
Code System Code Type Description
PUBCHEM
10112775
Created by admin on Sat Jun 26 13:55:21 UTC 2021 , Edited by admin on Sat Jun 26 13:55:21 UTC 2021
PRIMARY
FDA UNII
RTQ46SZY8H
Created by admin on Sat Jun 26 13:55:21 UTC 2021 , Edited by admin on Sat Jun 26 13:55:21 UTC 2021
PRIMARY
CAS
444995-23-7
Created by admin on Sat Jun 26 13:55:21 UTC 2021 , Edited by admin on Sat Jun 26 13:55:21 UTC 2021
PRIMARY
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INNOVATOR->PARENT
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