DESLORATADINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H19ClN2
Molecular Weight	310.8212
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

c1cc2CCc3cc(ccc3C(=C4CCNCC4)c2nc1)Cl

InChI

InChIKey=JAUOIFJMECXRGI-UHFFFAOYSA-N

InChI=1S/C19H19ClN2/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/h1-2,5-6,9,12,21H,3-4,7-8,10-11H2

HIDE SMILES / InChI

Molecular Formula	C19H19ClN2
Molecular Weight	310.8212
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11243504
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).

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 300 Target ID: CHEMBL231 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021165s017,021300s014,021312s015,021563s003lbl.pdf	Antagonist 2577	Seasonal allergic rhinitis Perennial allergic rhinitis Chronic idiopathic urticaria	0.869999999999999996 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Seasonal allergic rhinitis 61 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021165s017,021300s014,021312s015,021563s003lbl.pdf	Palliative	Histamine H1 receptor	Approved 7997	CLARINEX Approved Use Desloratadine Tablets are indicated for: Seasonal Allergic Rhinitis, Perennial Allergic Rhinitis, Chronic Idiopathic Urticaria. Launch Date 1008892800000
Perennial allergic rhinitis 45 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021165s017,021300s014,021312s015,021563s003lbl.pdf	Palliative	Histamine H1 receptor	Approved 7997	CLARINEX Approved Use Desloratadine Tablets are indicated for: Seasonal Allergic Rhinitis, Perennial Allergic Rhinitis, Chronic Idiopathic Urticaria. Launch Date 1008892800000
Chronic idiopathic urticaria 10 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021165s017,021300s014,021312s015,021563s003lbl.pdf	Palliative	Histamine H1 receptor	Approved 7997	CLARINEX Approved Use Desloratadine Tablets are indicated for: Seasonal Allergic Rhinitis, Perennial Allergic Rhinitis, Chronic Idiopathic Urticaria. Launch Date 1008892800000

C_max

Value	Dose	Co-administered	Analyte	Population
4 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021165s017,021300s014,021312s015,021563s003lbl.pdf	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

Value	Dose	Co-administered	Analyte	Population
56.9 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021165s017,021300s014,021312s015,021563s003lbl.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
27 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021165s017,021300s014,021312s015,021563s003lbl.pdf	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
84.5% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021165s017,021300s014,021312s015,021563s003lbl.pdf	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

Dose	Population	Adverse 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021300s000_Clarinex_MedR.pdf	unhealthy, 2-11 years Health Status: unhealthy Age Group: 2-11 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021300s000_Clarinex_MedR.pdf	Disc. AE: Somnolence, Abdominal pain... AEs leading to discontinuation/dose reduction: Somnolence (1 patient) Abdominal pain (1 patient) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021300s000_Clarinex_MedR.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21165lbl.pdf	healthy, adult Health Status: healthy Age Group: adult Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21165lbl.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21165lbl.pdf

AEs

AE	Significance	Dose	Population
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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021300s000_Clarinex_MedR.pdf	unhealthy, 2-11 years Health Status: unhealthy Age Group: 2-11 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021300s000_Clarinex_MedR.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021300s000_Clarinex_MedR.pdf	unhealthy, 2-11 years Health Status: unhealthy Age Group: 2-11 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021300s000_Clarinex_MedR.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1470	inhibitor 1318	substrate 1038 inhibitor 1421	inhibitor 1360

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1268 CYP2C8 761 CYP2C19 1215 CYP2B6 679 CYP3A4/5 225 UGT1A1 174 UGT1A3 76 UGT1A4 67 UGT1A6 94 UGT1A9 102 UGT2B7 130 UGT2B10 24 UGT2B15 56 UGT2B17 13 UGT1A7 17 UGT1A8 29 UGT1A10 26 UGT2B4 20 P-gp 1089	CYP1A2 892 CYP2B6 575 CYP1A1 302 CYP2C19 830 UGT2B10 112 P-gp 1223

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1406	inhibitor 2614 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,5	no
CYP2C19 1277	inhibitor 2614 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,5	no
CYP2C8 810	inhibitor 2614 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,5	no
CYP2C9 1362	inhibitor 2614 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,5	no
UGT1A1 219	inhibitor 2614 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,6	no
UGT1A3 82	inhibitor 2614 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,6	no
UGT1A4 70	inhibitor 2614 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,6	no
UGT1A6 126	inhibitor 2614 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,6	no
UGT1A7 19	inhibitor 2614 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,6	no
UGT1A8 41	inhibitor 2614 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,6	no
UGT1A9 107	inhibitor 2614 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,6	no
UGT2B15 56	inhibitor 2614 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,6	no
UGT2B7 138	inhibitor 2614 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,6	no
P-gp 1255	inhibitor 2614 Sources: https://pubmed.ncbi.nlm.nih.gov/11454724/	not significant [IC50 43 uM]
UGT2B10 26	inhibitor 2614 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,6	strong [Ki 1.3 uM]
CYP2B6 845	inhibitor 2614 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,5	weak [Inhibition 10 uM]
CYP2D6 1455	inhibitor 2614 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,5	weak [Inhibition 10 uM]
CYP3A4/5 277	inhibitor 2614 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,5	weak [Inhibition 10 uM]
UGT1A10 35	inhibitor 2614 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,6	weak [Inhibition 10 uM]
UGT2B17 15	inhibitor 2614 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,6	weak [Inhibition 10 uM]
UGT2B4 20	inhibitor 2614 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,6	weak [Inhibition 10 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP1A1 302	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-165_Clarinex_biopharmr_P1.pdf#page=19 Page: 19	likely
CYP1A2 892	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-165_Clarinex_biopharmr_P1.pdf#page=10 Page: 10	likely
CYP2B6 575	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-165_Clarinex_biopharmr_P1.pdf#page=10 Page: 10	likely
CYP2C19 830	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-165_Clarinex_biopharmr_P1.pdf#page=19 Page: 19	likely	no (pharmacogenomic study) Comment: pharmacogenotype 2C19 does not correlate with systemic exposure Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-165_Clarinex_biopharmr_P1.pdf#page=19 Page: 19
CYP2D6 1038	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-165_Clarinex_biopharmr_P1.pdf#page=10 Page: 10	likely	no (pharmacogenomic study) Comment: lack of correlation in between 2D6 genotype and 3-OH DCL formation Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-165_Clarinex_biopharmr_P1.pdf#page=10 Page: 10
CYP3A4 1470	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-165_Clarinex_biopharmr_P1.pdf#page=10; https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-165_Clarinex_biopharmr_P1.pdf#page=33 Page: 10	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. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-165_Clarinex_biopharmr_P1.pdf#page=10; https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-165_Clarinex_biopharmr_P1.pdf#page=33 Page: 10
UGT2B10 112	substrate 2752 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 1	yes
P-gp 1223	substrate 2752 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6388404/	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. Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6388404/

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1392	inhibitor 1374 Sources: https://pubmed.ncbi.nlm.nih.gov/11243504/#:~:text=Preclinical%20studies%20also%20show%20that,in%20preclinical%20and%20clinical%20studies.

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:291342	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:291342
MolPort	MolPort-000-883-875	https://www.molport.com/shop/molecule-link/MolPort-000-883-875
ZINC	ZINC000000001261	http://zinc15.docking.org/substances/ZINC000000001261

PubMed

Title	Date	PubMed
Second-generation antihistamines in asthma therapy: is there a protective effect?	2002	14720073
Advances in allergy management.	2002	12492727
Impact and modulation of nasal obstruction.	2002	12492726
Chronic urticaria: impact of allergic inflammation.	2002	12492725
Therapeutic points of intervention and clinical implications: role of desloratadine.	2002	12492724
Investigation of an enhanced resolution triple quadrupole mass spectrometer for high-throughput liquid chromatography/tandem mass spectrometry assays.	2002	12391581
Desloratadine has no clinically relevant electrocardiographic or pharmacodynamic interactions with ketoconazole.	2002	12169045
Lack of clinically relevant interaction between desloratadine and erythromycin.	2002	12169044
Effect of race and sex on single and multiple dose pharmacokinetics of desloratadine.	2002	12169043
A pharmacokinetic profile of desloratadine in healthy adults, including elderly.	2002	12169042
Oral bioavailability of desloratadine is unaffected by food.	2002	12169041
Desloratadine demonstrates dose proportionality in healthy adults after single doses.	2002	12169040
Grapefruit juice reduces the oral bioavailability of fexofenadine but not desloratadine.	2002	11978146
Biochemical characterization of desloratadine, a potent antagonist of the human histamine H(1) receptor.	2002 Aug 9	12167464
The new antihistamines--desloratadine and levocetirizine: a review.	2002 Dec	12851991
[The place of new antihistamines in allergy management. Apropos of desloratadine].	2002 Dec	12575624
Comparative pharmacology of H1 antihistamines: clinical relevance.	2002 Dec 16	12517581
Treatment of allergic rhinitis.	2002 Dec 16	12517578
[The result of neglected or erroneous treatment. Mentally handicapped by hay fever].	2002 Jul 11	12198886
Gateways to clinical trials.	2002 May	12092009
Clinical pharmacology of H1-antihistamines in the skin.	2002 Nov	12417888
Desloratidine for the treatment of chronic urticaria.	2002 Oct	12548327
Desloratadine reduces allergen challenge-induced mucinous secretion and plasma exudation in allergic rhinitis.	2002 Oct	12392387
Effects of fexofenadine and desloratadine on subjective and objective measures of nasal congestion in seasonal allergic rhinitis.	2002 Oct	12372132
Efficacy of once-daily desloratadine/pseudoephedrine for relief of nasal congestion.	2002 Sep-Oct	12476542
Chronic urticaria: a role for newer immunomodulatory drugs?	2003	12688835
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	12664016
Efficacy of azelastine nasal spray in patients with an unsatisfactory response to loratadine.	2003 Aug	12952117
Studies on performance and sleepiness with the H1-antihistamine, desloratadine.	2003 Aug	12924753
Assessing satisfaction with desloratadine and fexofenadine in allergy patients who report dissatisfaction with loratadine.	2003 Aug 13	12917016
Gateways to clinical trials.	2003 Dec	14735233
Interactions of olopatadine and selected antihistamines with model and natural membranes.	2003 Dec	14704897
Comparative in vivo bioactivity of modern H1-antihistamines on AMP challenge in atopic asthma.	2003 Feb	12589354
Desloratadine: a nonsedating antihistamine.	2003 Feb	12549956
The effect of ketotifen on inflammatory markers in allergic conjunctivitis: an open, uncontrolled study.	2003 Jan 6	12515585
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	12946545
Desloratadine inhibits allergen-induced airway inflammation and bronchial hyperresponsiveness and alters T-cell responses in murine models of asthma.	2003 Jul	12847492
The effects of histamine and leukotriene receptor antagonism on nasal mannitol challenge in allergic rhinitis.	2003 Jun	12814463
Effects of mediator antagonism on mannitol and adenosine monophosphate challenges.	2003 Jun	12801313
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	12757447
Gateways to clinical trials. March 2003.	2003 Mar	12731460
Double-stranded RNA viruses in a mycocinogenic strain of Cystofilobasidium infirmominiatum.	2003 Mar	12702247
Efficacy and safety of desloratadine in the treatment of perennial allergic rhinitis.	2003 Mar	12642846
P-glycoprotein limits the brain penetration of nonsedating but not sedating H1-antagonists.	2003 Mar	12584158
[Multicenter study of the effectiveness and tolerability of desloratadine in seasonal allergic rhinitis].	2003 May 25	12847854
Efficacy and safety profile of fexofenadine HCl: a unique therapeutic option in H1-receptor antagonist treatment.	2003 Oct	14530791
Comparison of the effects of desloratadine and levocetirizine on histamine-induced wheal, flare and itch in human skin.	2003 Oct	14520518
Twenty-four-hour activity and consistency of activity of levocetirizine and desloratadine in the skin.	2003 Oct	12968983
Reliable and specific high-performance liquid chromatographic method for simultaneous determination of loratadine and its metabolite in human plasma.	2003 Oct 25	14552827
Gateways to clinical trials.	2004 Jan-Feb	14988742

Patents

Sample Use Guides

In Vivo Use Guide

Adults and Adolescents 12 Years of Age and Over:

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.

Substance Class	Chemical Created by `admin` on `Fri Jun 25 21:08:37 UTC 2021` Edited by `admin` on `Fri Jun 25 21:08:37 UTC 2021`
Record UNII	FVF865388R
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

DESLORATADINE

Official Name

English

LORATADINE RELATED COMPOUND A [USP]

Common Name

English

8-CHLORO-6,11-DIHYDRO-11-(4-PIPERIDINYLIDENE)-5H-BENZO(5,6)CYCLOHEPTA(1,2-BPYRIDINE

Common Name

English

DESLORATADINE RATIOPHARM (AUTHORIZED: RHINITIS, URTICARIA)

Brand Name

English

DESLORATADINE RATIOPHARM

Brand Name

English

8-CHLORO-6,11-DIHYDRO-11(4-PIPERIDYLIDENE)-5H-BENZO(5,6)CYCLOHEPTA(1,2-B) PYRIDINE

Common Name

English

DENOSIN

Brand Name

English

DESLORATADINE [INN]

Common Name

English

DASSELTA

Brand Name

English

NSC-759824

Code

English

DESLORATADINE [MART.]

Common Name

English

RUPATADINE FUMARATE IMPURITY B [EP]

Common Name

English

NEOCLARITYN

Brand Name

English

DESLORATADINE ACTAVIS (AUTHORIZED: RHINITIS, URTICARIA)

Brand Name

English

DESLORATADINE [MI]

Common Name

English

DESLORATADINE [VANDF]

Common Name

English

DESLORATADINE [USP-RS]

Common Name

English

LORATADINE SPECIFIED IMPURITY D [EP]

Common Name

English

DESLORATADINE [USP MONOGRAPH]

Common Name

English

CLARINEX

Brand Name

English

DESCARBOETHOXYLORATADINE

Common Name

English

DESLORATADINE ACTAVIS

Brand Name

English

DESLORATADINE TEVA (AUTHORIZED: RHINITIS, URTICARIA)

Brand Name

English

DESLORATADINE [ORANGE BOOK]

Common Name

English

8-CHLORO-6,11-DIHYDRO-11-(4-PIPERIDINYLIDENE)-5H-BENZO(5,6)CYCLOHEPTA(1,2B)PYRIDINE

Common Name

English

CLARINEX-D COMPONENT DESLORATADINE

Common Name

English

DESLORATADINE [WHO-DD]

Common Name

English

OPULIS

Brand Name

English

SCH-34117

Code

English

AZOMYR

Brand Name

English

ALLEX

Brand Name

English

DESLORATADINE TEVA

Brand Name

English

AERIUS

Brand Name

English

DESLORATADINE [JAN]

Common Name

English

LORATADINE RELATED COMPOUND A [USP-RS]

Common Name

English

DESLORATADINE [EMA EPAR]

Common Name

English

DESLORATADINE [EP MONOGRAPH]

Common Name

English

DESLORATADINE [USAN]

Common Name

English

DESLORATADINE COMPONENT OF CLARINEX-D

Common Name

English

Classification Tree Code System Code

EMA ASSESSMENT REPORTS

DESLORATADINE TEVA (AUTHORIZED: RHINITIS, ALLERGIC, SEASONAL)