DESLORATADINE HEMISULFATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	2C19H19ClN2.H2O4S
Molecular Weight	719.72
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OS(O)(=O)=O.ClC1=CC2=C(C=C1)C(=C3CCNCC3)C4=C(CC2)C=CC=N4.ClC5=CC6=C(C=C5)C(=C7CCNCC7)C8=C(CC6)C=CC=N8

InChI

InChIKey=BFUKZAZVGNXTDM-UHFFFAOYSA-N

InChI=1S/2C19H19ClN2.H2O4S/c2*20-16-5-6-17-15(12-16)4-3-14-2-1-9-22-19(14)18(17)13-7-10-21-11-8-13;1-5(2,3)4/h2*1-2,5-6,9,12,21H,3-4,7-8,10-11H2;(H2,1,2,3,4)

HIDE SMILES / InChI

Molecular Formula	C19H19ClN2
Molecular Weight	310.821
Charge	0
Count

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

Molecular Formula	H2O4S
Molecular Weight	98.078
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 312 Target ID: CHEMBL231 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021165s017,021300s014,021312s015,021563s003lbl.pdf	Antagonist 2737		0.87 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Seasonal allergic rhinitis 63 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021165s017,021300s014,021312s015,021563s003lbl.pdf	Palliative	Approved 8307	CLARINEX Approved Use Desloratadine Tablets are indicated for: Seasonal Allergic Rhinitis, Perennial Allergic Rhinitis, Chronic Idiopathic Urticaria. Launch Date 1.00889277E12
Perennial allergic rhinitis 47 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021165s017,021300s014,021312s015,021563s003lbl.pdf	Palliative	Approved 8307	CLARINEX Approved Use Desloratadine Tablets are indicated for: Seasonal Allergic Rhinitis, Perennial Allergic Rhinitis, Chronic Idiopathic Urticaria. Launch Date 1.00889277E12
Chronic idiopathic urticaria 11 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021165s017,021300s014,021312s015,021563s003lbl.pdf	Palliative	Approved 8307	CLARINEX Approved Use Desloratadine Tablets are indicated for: Seasonal Allergic Rhinitis, Perennial Allergic Rhinitis, Chronic Idiopathic Urticaria. Launch Date 1.00889277E12

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 Page: p. 25	unhealthy, 2-11 years n = 48 Health Status: unhealthy Age Group: 2-11 years Sex: M+F Population Size: 48 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021300s000_Clarinex_MedR.pdf Page: p. 25	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 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: 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 Page: p. 25	unhealthy, 2-11 years n = 48 Health Status: unhealthy Age Group: 2-11 years Sex: M+F Population Size: 48 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021300s000_Clarinex_MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021300s000_Clarinex_MedR.pdf Page: p. 25	unhealthy, 2-11 years n = 48 Health Status: unhealthy Age Group: 2-11 years Sex: M+F Population Size: 48 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021300s000_Clarinex_MedR.pdf Page: p. 25

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1670	inhibitor 1695	substrate 1168 inhibitor 1789	inhibitor 1570

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1463 CYP2C8 869 CYP2C19 1410 CYP2B6 770 CYP3A4/5 261 UGT1A1 200 UGT1A3 84 UGT1A4 76 UGT1A6 107 UGT1A9 115 UGT2B7 145 UGT2B10 25 UGT2B15 64 UGT2B17 18 UGT1A7 21 UGT1A8 36 UGT1A10 32 UGT2B4 19 P-gp 1401	CYP1A2 1013 CYP2B6 648 CYP1A1 344 CYP2C19 955 UGT2B10 127 P-gp 1491

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1620	inhibitor 3185 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,5	no
CYP2C19 1484	inhibitor 3185 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,5	no
CYP2C8 923	inhibitor 3185 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,5	no
CYP2C9 1747	inhibitor 3185 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,5	no
UGT1A1 249	inhibitor 3185 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,6	no
UGT1A3 93	inhibitor 3185 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,6	no
UGT1A4 79	inhibitor 3185 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,6	no
UGT1A6 139	inhibitor 3185 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,6	no
UGT1A7 23	inhibitor 3185 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,6	no
UGT1A8 48	inhibitor 3185 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,6	no
UGT1A9 120	inhibitor 3185 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,6	no
UGT2B15 64	inhibitor 3185 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,6	no
UGT2B7 156	inhibitor 3185 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,6	no
P-gp 1588	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/11454724/	not significant [IC50 43 uM]
UGT2B10 27	inhibitor 3185 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,6	strong [Ki 1.3 uM]
CYP2B6 946	inhibitor 3185 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,5	weak [Inhibition 10 uM]
CYP2D6 1826	inhibitor 3185 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,5	weak [Inhibition 10 uM]
CYP3A4/5 314	inhibitor 3185 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,5	weak [Inhibition 10 uM]
UGT1A10 41	inhibitor 3185 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,6	weak [Inhibition 10 uM]
UGT2B17 20	inhibitor 3185 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 4,6	weak [Inhibition 10 uM]
UGT2B4 19	inhibitor 3185 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 344	substrate 3264 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-165_Clarinex_biopharmr_P1.pdf#page=19 Page: 19.0	likely
CYP1A2 1013	substrate 3264 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-165_Clarinex_biopharmr_P1.pdf#page=10 Page: 10.0	likely
CYP2B6 648	substrate 3264 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-165_Clarinex_biopharmr_P1.pdf#page=10 Page: 10.0	likely
CYP2C19 955	substrate 3264 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-165_Clarinex_biopharmr_P1.pdf#page=19 Page: 19.0	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: 19.0
CYP2D6 1168	substrate 3264 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-165_Clarinex_biopharmr_P1.pdf#page=10 Page: 10.0	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: 10.0
CYP3A4 1670	substrate 3264 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: 10.0	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. 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: 10.0
UGT2B10 127	substrate 3264 Sources: https://dmd.aspetjournals.org/content/43/9/1294 Page: 1.0	yes
P-gp 1491	substrate 3264 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 1603	inhibitor 1584 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
ChemicalBook	CB3462564	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3462564
MolPort	MolPort-000-883-875	https://www.molport.com/shop/molecule-link/MolPort-000-883-875
Selleck Chemicals	desloratadine	http://www.selleckchem.com/products/desloratadine.html
ZINC	ZINC000000001261	http://zinc15.docking.org/substances/ZINC000000001261
eMolecules	877481	https://www.emolecules.com/cgi-bin/more?vid=877481

PubMed

Title	Date	PubMed
Sensitive liquid chromatography-tandem mass spectrometry method for the determination of loratadine and its major active metabolite descarboethoxyloratadine in human plasma.	2001 Apr 20	11358228
[A new antihistamine. Inhibiting inflammation in rhinorrhea and nasal congestion].	2001 Apr 5	11340914
Once-daily desloratadine improves the signs and symptoms of chronic idiopathic urticaria: a randomized, double-blind, placebo-controlled study.	2001 Jan	11277962
Investigation of an enhanced resolution triple quadrupole mass spectrometer for high-throughput liquid chromatography/tandem mass spectrometry assays.	2002	12391581
24-hour efficacy of once-daily desloratadine therapy in patients with seasonal allergic rhinitis [ISRCTN32042139].	2002 Aug 5	12162793
[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
Antihistamines in late-phase clinical development for allergic disease.	2002 Feb	11829715
Desloratidine for the treatment of chronic urticaria.	2002 Oct	12548327
Effects of fexofenadine and desloratadine on subjective and objective measures of nasal congestion in seasonal allergic rhinitis.	2002 Oct	12372132
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
Pharmacokinetic properties of single-dose loratadine and ambroxol alone and combined in tablet formulations in healthy men.	2003 Aug	14512130
Gateways to clinical trials.	2003 Dec	14735233
Interactions of olopatadine and selected antihistamines with model and natural membranes.	2003 Dec	14704897
Decongestant effects of antihistamines: a class effect?	2003 Mar	12642858
First do no harm: managing antihistamine impairment in patients with allergic rhinitis.	2003 May	12743547
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
Improvements in simulated real-world relevant performance for patients with seasonal allergic rhinitis: impact of desloratadine.	2004 Apr	15005765
Gateways to clinical trials.	2004 Jan-Feb	14988742
High-performance liquid chromatographic method for the bioequivalence evaluation of desloratadine fumarate tablets in dogs.	2004 Mar 10	15019035

Patents

Sample Use Guides

In Vivo Use Guide

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.

Substance Class	Chemical Created by `admin` on `Sat Dec 17 15:10:59 UTC 2022` Edited by `admin` on `Sat Dec 17 15:10:59 UTC 2022`
Record UNII	WGA590NHUY
Record Status	`Validated (UNII)`
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Name

Type

Language

DESLORATADINE HEMISULFATE

Common Name

English

Code System Code Type Description

FDA UNII

WGA590NHUY

Created by admin on Sat Dec 17 15:10:59 UTC 2022 , Edited by admin on Sat Dec 17 15:10:59 UTC 2022

PRIMARY

PUBCHEM

76960496

Created by admin on Sat Dec 17 15:10:59 UTC 2022 , Edited by admin on Sat Dec 17 15:10:59 UTC 2022

PRIMARY

EVMPD

SUB177343

Created by admin on Sat Dec 17 15:10:59 UTC 2022 , Edited by admin on Sat Dec 17 15:10:59 UTC 2022

PRIMARY

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Desloratadine

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					FVF865388R

Desloratadine

ACTIVE MOIETY

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/11243504Curator's Comment: description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021165s017,021300s014,021312s015,021563s003lbl.pdf

CNS Activity

Approval Year

Targets

Conditions

Approved Use

Launch Date

Approved Use

Launch Date

Approved Use

Launch Date

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

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

C_max

T_1/2

F_unbound

Drug as perpetrator