LEVOCETIRIZINE DIHYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H25ClN2O3.2ClH
Molecular Weight	461.81
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of LEVOCETIRIZINE DIHYDROCHLORIDE

SMILES

Cl.Cl.OC(=O)COCCN1CCN(CC1)[C@H](C2=CC=CC=C2)C3=CC=C(Cl)C=C3

InChI

InChIKey=PGLIUCLTXOYQMV-GHVWMZMZSA-N

InChI=1S/C21H25ClN2O3.2ClH/c22-19-8-6-18(7-9-19)21(17-4-2-1-3-5-17)24-12-10-23(11-13-24)14-15-27-16-20(25)26;;/h1-9,21H,10-16H2,(H,25,26);2*1H/t21-;;/m1../s1

HIDE SMILES / InChI

Description

Levocetirizine is the active enantiomer of cetirizine. It is inverse agonist of H1 receptors. Levocetirizine hydrochloride was approved for treatment of Allergic Rhinitis and Chronic Idiopathic Urticaria.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 315	Antagonist 2,778		3.0 nM [Ki]
Histamine H1 receptor 315	Inverse Agonist 80		6.0 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Seasonal allergic rhinitis 64	Palliative	Approved 8,429	XYZAL
Perennial allergic rhinitis 47	Palliative	Approved 8,429	XYZAL
Chronic idiopathic urticaria 11	Palliative	Approved 8,429	XYZAL
Allergic rhinitis 100	Primary	Approved 8,429	XYZAL
Chronic Idiopathic Urticaria 3	Primary	Approved 8,429	XYZAL
Dermatitis 10	Primary	Phase III 656	XYZAL

C_max

Value	Dose	Analyte	Population
0.17 μg/mL	5 mg single, oral	LEVOCETIRIZINE blood	Homo sapiens
0.27 μg/mL	5 mg single, oral	LEVOCETIRIZINE plasma	Homo sapiens
512.25 ng/mL	10 mg single, oral	LEVOCETIRIZINE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
0.97 μg × h/mL	5 mg single, oral	LEVOCETIRIZINE blood	Homo sapiens
2.31 μg × h/mL	5 mg single, oral	LEVOCETIRIZINE plasma	Homo sapiens
4136.4 ng × h/mL	10 mg single, oral	LEVOCETIRIZINE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
6.83 h	5 mg single, oral	LEVOCETIRIZINE blood	Homo sapiens
7.05 h	5 mg single, oral	LEVOCETIRIZINE plasma	Homo sapiens
7.76 h	10 mg single, oral	LEVOCETIRIZINE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
4.5%	5 mg single, oral		LEVOCETIRIZINE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
20 mg 1 times / day multiple, oral Highest studied dose	unhealthy, 18–60 years n = 13
5 mg 1 times / day steady, oral Recommended	unhealthy, 48-64 years n = 2	Disc. AE: Hepatotoxicity...
5 mg 1 times / day steady, oral Recommended	unhealthy, > 12 years n = 428	Disc. AE: Somnolence, Fatigue...

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AEs

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AE	Significance	Dose	Population
Hepatotoxicity	2 patients Disc. AE	5 mg 1 times / day steady, oral Recommended	unhealthy, 48-64 years n = 2
Asthenia	2.3% Disc. AE	5 mg 1 times / day steady, oral Recommended	unhealthy, > 12 years n = 428
Fatigue	2.3% Disc. AE	5 mg 1 times / day steady, oral Recommended	unhealthy, > 12 years n = 428
Somnolence	2.3% Disc. AE	5 mg 1 times / day steady, oral Recommended	unhealthy, > 12 years n = 428

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737 inhibitor 1,587 inducer 781	inhibitor 1,767 inducer 389	substrate 1,217 inhibitor 1,852	inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1,524 CYP2C19 1,478 CYP2E1 882 P-gp 1,461	P-gp 1,537 OATP1A2 62 OAT4 78 OATP1B1 406 OATP1B3 350	CYP1A2 701 UGT1A1 69

Drug as perpetrator

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Target	Modality	Activity
CYP1A2 1,692	inducer 1,573	no
CYP1A2 1,692	inhibitor 3,277	no
CYP2C19 1,553	inhibitor 3,277	no
CYP2C9 1,819	inducer 1,573	no
CYP2C9 1,819	inhibitor 3,277	no

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Drug as victim

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Target	Modality	Activity
OAT4 78	substrate 3,367	likely
OATP1A2 62	substrate 3,367	likely
CYP2D6 1,217	substrate 3,367	no
OATP1B1 406	substrate 3,367	no
OATP1B3 350	substrate 3,367	no

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Tox targets

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

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-6286	http://www.3bsc.com/index/pro_info.php?id=115439
Alfa Chemistry	130018-77-8	https://www.alfa-chemistry.com/levocetirizine-cas-130018-77-8-item-289953.htm
Alichem	139002959	http://www.alichem.com/en/products/130018-77-8.html
AvaChem Scientific	1666B	http://www.avachem.com/productSearch.asp?1666B
BLD Pharm	BD136222	http://www.bldpharm.com/products/130018-77-8.html

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PubMed

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Title	Date	PubMed
Absorption, distribution, metabolism and excretion of [14C]levocetirizine, the R enantiomer of cetirizine, in healthy volunteers.	2001 Oct	11758635
[The first case of lasting pigmented toxidermia induced by cetirizine (Zyrtec, Virlix) and ticlopidine].	2002 Apr	12055559
24-hour efficacy of once-daily desloratadine therapy in patients with seasonal allergic rhinitis [ISRCTN32042139].	2002 Aug 5	12162793
Antihistamines in late-phase clinical development for allergic disease.	2002 Feb	11829715
Lack of effect of single and repeated doses of levocetirizine, a new antihistamine drug, on cognitive and psychomotor functions in healthy volunteers.	2002 Jul	12100225

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Patents

Sample Use Guides

In Vivo Use Guide

Adults and children 12 years of age and older: 5 mg once daily in the evening. Children 6 to 11 years of age: 2.5 mg once daily in the evening. Children 6 months to 5 years of age: 1.25 mg (1/2 teaspoon oral solution)[2.5mL] once daily in the evening.

Route of Administration: Oral

In Vitro Use Guide

Eosinophils isolated from normal subjects were pre-incubated with a concentration range of levocetirizine (10(-6)-10(-10) m) or negative dilution control. Levocetirizine significantly inhibited resting eosinophil adhesion to recombinant human vascular cell adhesion molecule-1 (rhVCAM-1) with maximal effect at 10(-8) M with an EC(50) of 10(-9) m.

Show entries

Name

Type

Language

LEVOCETIRIZINE DIHYDROCHLORIDE

Official Name

English

Levocetirizine dihydrochloride [WHO-DD]

Common Name

English

LEVOCETIRIZINE DIHYDROCHLORIDE [USAN]

Common Name

English

LEVOCETIRIZINE HYDROCHLORIDE [MART.]

Common Name

English

CETIRIZINE (R)-FORM DIHYDROCHLORIDE

Common Name

English

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Classification Tree

Code System

Code

Immunotherapeutic Agent

NCI_THESAURUS

C29578

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Code System

Code

Type

Description

MERCK INDEX

m3291

PRIMARY

Merck Index

NSC

758898

PRIMARY

CAS

130018-87-0

PRIMARY

RXCUI

402349

PRIMARY

RxNorm

USAN

TT-55

PRIMARY

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ACTIVE MOIETY


					6U5EA9RT2O

LEVOCETIRIZINE

SUBSTANCE RECORD


					SOD6A38AGA

LEVOCETIRIZINE DIHYDROCHLORIDE

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator