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Details

Stereochemistry ACHIRAL
Molecular Formula C19H19ClN2.C6H6O7.2Na
Molecular Weight 546.908
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DESLORATADINE CITRATE DISODIUM

SMILES

[Na+].[Na+].OC(=O)C(O)(CC([O-])=O)CC([O-])=O.ClC1=CC2=C(C=C1)C(=C3CCNCC3)C4=C(CC2)C=CC=N4

InChI

InChIKey=RDLARMRWOHXAFV-UHFFFAOYSA-L
InChI=1S/C19H19ClN2.C6H8O7.2Na/c20-16-5-6-17-15(12-16)4-3-14-2-1-9-22-19(14)18(17)13-7-10-21-11-8-13;7-3(8)1-6(13,5(11)12)2-4(9)10;;/h1-2,5-6,9,12,21H,3-4,7-8,10-11H2;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12);;/q;;2*+1/p-2

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021165s017,021300s014,021312s015,021563s003lbl.pdf

Desloratadine is an active, descarboethoxy metabolite of loratadine. It acts by selective inhibition of H1 histamine receptor and thus provides relief to patients with allergic rhinitis and chronic idiopathic urticaria. Desloratadine was approved by FDA and it is currently marketed under the name Clarinex (among the others).

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
CLARINEX

Approved Use

Desloratadine Tablets are indicated for: Seasonal Allergic Rhinitis, Perennial Allergic Rhinitis, Chronic Idiopathic Urticaria.

Launch Date

2001
Palliative
CLARINEX

Approved Use

Desloratadine Tablets are indicated for: Seasonal Allergic Rhinitis, Perennial Allergic Rhinitis, Chronic Idiopathic Urticaria.

Launch Date

2001
Palliative
CLARINEX

Approved Use

Desloratadine Tablets are indicated for: Seasonal Allergic Rhinitis, Perennial Allergic Rhinitis, Chronic Idiopathic Urticaria.

Launch Date

2001
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
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
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
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​
1.25 mg 1 times / day steady, oral
Dose: 1.25 mg, 1 times / day
Route: oral
Route: steady
Dose: 1.25 mg, 1 times / day
Sources: Page: p. 25
unhealthy, 2-11 years
n = 48
Health Status: unhealthy
Age Group: 2-11 years
Sex: M+F
Population Size: 48
Sources: Page: p. 25
Disc. AE: Somnolence, Abdominal pain...
AEs leading to
discontinuation/dose reduction:
Somnolence (1 patient)
Abdominal pain (1 patient)
Sources: Page: p. 25
45 mg 1 times / day multiple, oral
Highest studied dose
Dose: 45 mg, 1 times / day
Route: oral
Route: multiple
Dose: 45 mg, 1 times / day
Sources:
healthy, adult
Health Status: healthy
Age Group: adult
Sex: M+F
Sources:
AEs

AEs

AESignificanceDosePopulation
Abdominal pain 1 patient
Disc. AE
1.25 mg 1 times / day steady, oral
Dose: 1.25 mg, 1 times / day
Route: oral
Route: steady
Dose: 1.25 mg, 1 times / day
Sources: Page: p. 25
unhealthy, 2-11 years
n = 48
Health Status: unhealthy
Age Group: 2-11 years
Sex: M+F
Population Size: 48
Sources: Page: p. 25
Somnolence 1 patient
Disc. AE
1.25 mg 1 times / day steady, oral
Dose: 1.25 mg, 1 times / day
Route: oral
Route: steady
Dose: 1.25 mg, 1 times / day
Sources: Page: p. 25
unhealthy, 2-11 years
n = 48
Health Status: unhealthy
Age Group: 2-11 years
Sex: M+F
Population Size: 48
Sources: Page: p. 25
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
no
no
not significant [IC50 43 uM]
strong [Ki 1.3 uM]
weak [Inhibition 10 uM]
weak [Inhibition 10 uM]
weak [Inhibition 10 uM]
weak [Inhibition 10 uM]
weak [Inhibition 10 uM]
weak [Inhibition 10 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
likely
likely
likely
likely
no (pharmacogenomic study)
Comment: pharmacogenotype 2C19 does not correlate with systemic exposure
Page: 19.0
likely
no (pharmacogenomic study)
Comment: lack of correlation in between 2D6 genotype and 3-OH DCL formation
Page: 10.0
likely
weak (co-administration study)
Comment: Coadministration of ketonconazole, mean drug Cmax and AUC0-24 values at steady state were increased by 29-45% and 21-39%, respectively; Coadministration with erythromycin, mean drug Cmax and AUC 0-24 at steady state were increased by 24% and 14%, respectively.
Page: 10.0
yes
yes
weak (co-administration study)
Comment: Coadministration of ketonconazole, mean drug Cmax and AUC0-24 values at steady state were increased by 29-45% and 21-39%, respectively; Coadministration with erythromycin, mean drug Cmax and AUC 0-24 at steady state were increased by 24% and 14%, respectively.
Tox targets
PubMed

PubMed

TitleDatePubMed
Second-generation antihistamines in asthma therapy: is there a protective effect?
2002
Poor sleep and daytime somnolence in allergic rhinitis: significance of nasal congestion.
2002
Advances in allergy management.
2002
Therapeutic points of intervention and clinical implications: role of desloratadine.
2002
Investigation of an enhanced resolution triple quadrupole mass spectrometer for high-throughput liquid chromatography/tandem mass spectrometry assays.
2002
Comparative pharmacology of H1 antihistamines: clinical relevance.
2002 Dec 16
Treatment of allergic rhinitis.
2002 Dec 16
Clinical pharmacology of H1-antihistamines in the skin.
2002 Nov
Desloratidine for the treatment of chronic urticaria.
2002 Oct
Effects of fexofenadine and desloratadine on subjective and objective measures of nasal congestion in seasonal allergic rhinitis.
2002 Oct
Severe hepatotoxicity after application of desloratadine and fluconazole.
2003
Desloratadine: an update of its efficacy in the management of allergic disorders.
2003
Chronic urticaria: a role for newer immunomodulatory drugs?
2003
Comparative effects of desloratadine versus montelukast on asthma symptoms and use of beta 2-agonists in patients with seasonal allergic rhinitis and asthma.
2003 Apr
Efficacy and safety of desloratadine 5 mg once daily in the treatment of chronic idiopathic urticaria: a double-blind, randomized, placebo-controlled trial.
2003 Apr
Pharmacokinetic properties of single-dose loratadine and ambroxol alone and combined in tablet formulations in healthy men.
2003 Aug
Efficacy of azelastine nasal spray in patients with an unsatisfactory response to loratadine.
2003 Aug
Studies on performance and sleepiness with the H1-antihistamine, desloratadine.
2003 Aug
Assessing satisfaction with desloratadine and fexofenadine in allergy patients who report dissatisfaction with loratadine.
2003 Aug 13
Gateways to clinical trials.
2003 Dec
Interactions of olopatadine and selected antihistamines with model and natural membranes.
2003 Dec
Comparative in vivo bioactivity of modern H1-antihistamines on AMP challenge in atopic asthma.
2003 Feb
Desloratadine: a nonsedating antihistamine.
2003 Feb
Comparison of ketotifen fumarate ophthalmic solution alone, desloratadine alone, and their combination for inhibition of the signs and symptoms of seasonal allergic rhinoconjunctivitis in the conjunctival allergen challenge model: a double-masked, placebo- and active-controlled trial.
2003 Jul
Pharmacokinetics of loratadine and its active metabolite descarboethoxyloratadine in healthy Chinese subjects.
2003 Jul
Desloratadine inhibits allergen-induced airway inflammation and bronchial hyperresponsiveness and alters T-cell responses in murine models of asthma.
2003 Jul
Validation of a sensitive and automated 96-well solid-phase extraction liquid chromatography-tandem mass spectrometry method for the determination of desloratadine and 3-hydroxydesloratadine in human plasma.
2003 Jul 25
[Safety of new antihistamines].
2003 Jun
[Clinical aspects of anti-inflammatory action of antihistamines].
2003 Jun
The effects of histamine and leukotriene receptor antagonism on nasal mannitol challenge in allergic rhinitis.
2003 Jun
Effects of mediator antagonism on mannitol and adenosine monophosphate challenges.
2003 Jun
Comparison of the effects of desloratadine 5-mg daily and placebo on nasal airflow and seasonal allergic rhinitis symptoms induced by grass pollen exposure.
2003 Jun
Gateways to clinical trials. March 2003.
2003 Mar
Double-stranded RNA viruses in a mycocinogenic strain of Cystofilobasidium infirmominiatum.
2003 Mar
Decongestant effects of antihistamines: a class effect?
2003 Mar
P-glycoprotein limits the brain penetration of nonsedating but not sedating H1-antagonists.
2003 Mar
First do no harm: managing antihistamine impairment in patients with allergic rhinitis.
2003 May
Desloratadine for allergic rhinitis.
2003 Nov 15
Loratadine, desloratadine and pregnancy: don't use, risk of hypospadias.
2003 Oct
A comparison of the effect of diphenhydramine and desloratadine on vigilance and cognitive function during treatment of ragweed-induced allergic rhinitis.
2003 Oct
Efficacy and safety profile of fexofenadine HCl: a unique therapeutic option in H1-receptor antagonist treatment.
2003 Oct
Comparison of the effects of desloratadine and levocetirizine on histamine-induced wheal, flare and itch in human skin.
2003 Oct
Twenty-four-hour activity and consistency of activity of levocetirizine and desloratadine in the skin.
2003 Oct
Reliable and specific high-performance liquid chromatographic method for simultaneous determination of loratadine and its metabolite in human plasma.
2003 Oct 25
[Modern antihistaminics against allergic rhinitis. Better breathing without side effects].
2003 Oct 30
Improvements in simulated real-world relevant performance for patients with seasonal allergic rhinitis: impact of desloratadine.
2004 Apr
Inhibition of cold urticaria by desloratadine.
2004 Jan
Anti-inflammatory activity of H1-receptor antagonists: review of recent experimental research.
2004 Jan
Gateways to clinical trials.
2004 Jan-Feb
High-performance liquid chromatographic method for the bioequivalence evaluation of desloratadine fumarate tablets in dogs.
2004 Mar 10
Patents

Sample Use Guides

Adults and Adolescents 12 Years of Age and Over: take 5 mg tablet once daily. Children 6 to Years of Age: take 2.5 mg tablet once daily. Children 12 Months to 5 Years of Age: take 1.25 mg tablet once daily. Children 6 to 11 Months of Age: 1 mg tablet once daily.
Route of Administration: Oral
In Vitro Use Guide
Nasal epithelial cells (activated by 1 uM of histamine) were treated with 10 uM of desloratadine and the inhibitory activity of the drug on expression of ICAM-1 and HLA-DR was studied.
Name Type Language
DESLORATADINE CITRATE DISODIUM
Common Name English
1,2,3-PROPANETRICARBOXYLIC ACID, 2-HYDROXY-, SODIUM SALT, COMPD. WITH 8-CHLORO-6,11-DIHYDRO-11-(4-PIPERIDINYLIDENE)-5H-BENZO(5,6)CYCLOHEPTA(1,2-B)PYRIDINE (1:2:1)
Systematic Name English
Desloratadine citrate disodium [WHO-DD]
Common Name English
Code System Code Type Description
FDA UNII
CZ422FA2AK
Created by admin on Sat Dec 16 18:17:16 GMT 2023 , Edited by admin on Sat Dec 16 18:17:16 GMT 2023
PRIMARY
CAS
1602766-05-1
Created by admin on Sat Dec 16 18:17:16 GMT 2023 , Edited by admin on Sat Dec 16 18:17:16 GMT 2023
PRIMARY
SMS_ID
100000164231
Created by admin on Sat Dec 16 18:17:16 GMT 2023 , Edited by admin on Sat Dec 16 18:17:16 GMT 2023
PRIMARY
PUBCHEM
163203578
Created by admin on Sat Dec 16 18:17:16 GMT 2023 , Edited by admin on Sat Dec 16 18:17:16 GMT 2023
PRIMARY