Levocetirizine

Identification

Summary

Levocetirizine is an H1-receptor antagonist used to treat symptoms associated with chronic allergic rhinitis and uncomplicated cases of chronic idiopathic urticaria.

Brand Names
Xyzal
Generic Name
Levocetirizine
DrugBank Accession Number
DB06282
Background

Levocetirizine is a selective histamine H1 antagonist used to treat a variety of allergic symptoms.2,3,4 It is the R enantiomer of cetirizine.4 Levocetirizine has greater affinity for the histamine H1 receptor than cetirizine.4

Levocetirizine was granted FDA approval in 1995.4

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 388.89
Monoisotopic: 388.1553704
Chemical Formula
C21H25ClN2O3
Synonyms
  • 2-(2-{4-[(R)-(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)acetic acid
  • Levocetirizina
  • Levocetirizine

Pharmacology

Indication

Levocetirizine is indicated to treat symptoms of perennial allergic rhinitis and uncomplicated skin manifestations of chronic idiopathic urticaria.4 It is also used over the counter for a variety of mild allergy symptoms.2

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination for symptomatic treatment ofAllergic rhinitis (ar)Combination Product in combination with: Montelukast (DB00471)••• ••••••••••• ••••••• ••••••
Symptomatic treatment ofChronic idiopathic urticaria••••••••••••
Used in combination for symptomatic treatment ofCommon coldCombination Product in combination with: Dextromethorphan (DB00514), Ibuprofen (DB01050), Phenylephrine (DB00388)••• ••••••••••• •••••• ••••••
Used in combination for symptomatic treatment ofNasal congestionCombination Product in combination with: Pseudoephedrine (DB00852)••• ••••••••••
Used in combination for symptomatic treatment ofNasal congestionCombination Product in combination with: Pseudoephedrine (DB00852)••• ••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Levocetirizine is a second generation histamine H1 antagonist used to treat various allergic symptoms.2,3,4 It has a long duration of action as it is generally taken once daily, and a wide therapeutic window as animal studies show the maximal nonlethal dose is over 100x a normal dose.4 Patients are cautioned to avoid tasks that require complete alertness, avoid alertness, and use caution in patients with factors predisposing urinary retention.4

Mechanism of action

Levocetirizine selectively inhibits histamine H1 receptors.4 This action prevents histamine from activating this receptor and causing effects like smooth muscle contraction, increased permeability of vascular endothelium, histidine uptake in basophils, stimulation of cough receptors, and stimulation of flare responses in the nervous system.3

TargetActionsOrganism
AHistamine H1 receptor
antagonist
inhibitor
Humans
Absorption

Following a 5mg oral dose of levocetirizine, a Cmax of 0.27±0.04µg/mL with a Tmax of 0.75±0.50h.1 The AUC of levocetirizine is 2.31±0.50µg*h/mL.1 Taking levocetirizine with food does not affect the AUC but delays Tmax by 1.25 hours and lowers Cmax by 36%.4

Volume of distribution

The volume of distribution of levocetirizine is 0.33±0.02L/kg.1

Protein binding

Plasma protein binding of levocetirizine was on average 96.1% 1 hour post dose and 91.9% 6 hours post dose.1

Metabolism

Levocetirizine is poorly metabolized with 85.8% of an oral dose being excreted as the unchanged drug.1 Levocetirizine can be metabolized to a dihydrodiol (M2), an N-oxide (M3), a hydroxymethoxy derivative (M4), a hydroxy derivative (M5), an O-dealkylated derivative (M6), a taurine conjugate (M8), and an N-dealkylated and aromatic hydroxylated derivative (M9).1 The M5 metabolite can be glucuronidated to form the M1 metabolite and the M9 metabolite can form 4-chloro-4'-hydroxybenzhydryl mercapturates (M10a and M10b).1

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Route of elimination

168 hours post dose an average of 85.4% of a radiolabeled dose was recovered with an average of 80.8% in the urine and 9.5% in the feces.1 In the urine, 77% of the dose was recovered as unchanged drug, 0.5% as the M8 and M9 metabolites, 0.4% as the M10a metabolite, 0.4% as the M10b metabolite, 0.3% as the M3 metabolite, 0.3% as the M4 and M5 metabolite, 0.2% as the M2 metabolite, and 0.1% as the M1 metabolite.1 In the feces, 9.0% of the dose was recovered as unchanged drug, 1.0% as the M4 and M5 metabolite, and 0.1% as the M1 metabolite.1

Half-life

The average half life of levocetirizine is 7.05±1.54 hours.1

Clearance

The average clearance of levocetirizine is 0.57±0.18mL/min/kg.1

Adverse Effects
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Toxicity

Patients experiencing an overdose may present with drowsiness.4 Children may become agitated and restless before drowsiness.4 Patients should be treated with supportive measures.4 Dialysis will not assist in removing the drug from the body.4

The maximal nonlethal dose in mice and rats is 240mg/kg.4

Pathways
PathwayCategory
Levocetirizine H1-Antihistamine ActionDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Levocetirizine is combined with 1,2-Benzodiazepine.
AbacavirAbacavir may decrease the excretion rate of Levocetirizine which could result in a higher serum level.
AbametapirThe serum concentration of Levocetirizine can be increased when it is combined with Abametapir.
AceclofenacAceclofenac may decrease the excretion rate of Levocetirizine which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Levocetirizine which could result in a higher serum level.
Food Interactions
  • Avoid alcohol.
  • Take with or without food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Levocetirizine dihydrochlorideSOD6A38AGA130018-87-0PGLIUCLTXOYQMV-GHVWMZMZSA-N
Product Images
International/Other Brands
Xusal
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Levocetirizine DihydrochlorideSolution0.5 mg/1mLOralWinthrop U.S.2008-04-022017-01-31US flag
Levocetirizine DihydrochlorideTablet, film coated5 mg/1OralWinthrop U.S.2007-08-092015-10-31US flag
XyzalSolution0.5 mg/1mLOralPhysicians Total Care, Inc.2010-04-27Not applicableUS flag
XyzalTablet, film coated5 mg/1Oralsanofi-aventis U.S. LLC2017-07-24Not applicableUS flag
XyzalTablet, film coated5 mg/1OralUcb Inc2007-08-092019-01-19US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Levocetirizine dihydrochlorideTablet5 mg/1OralPhysicians Total Care, Inc.2010-12-30Not applicableUS flag
Levocetirizine DihydrochlorideTablet, film coated5 mg/1OralMicro Labs Limited2013-09-30Not applicableUS flag
Levocetirizine DihydrochlorideSolution0.5 mg/1mLOralApotex Corp.2017-10-262021-05-31US flag
Levocetirizine DihydrochlorideTablet, film coated5 mg/1OralNucare Pharmaceuticals,inc.2016-01-11Not applicableUS flag
Levocetirizine DihydrochlorideTablet5 mg/1Oralbryant ranch prepack2014-09-09Not applicableUS flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
24HR Allergy ReliefTablet, coated5 mg/1OralLEADER/ Cardinal Health 110, Inc.2018-03-12Not applicableUS flag
ALERINIT FILM-COATED TABLET 5MGTablet, film coated5.00 mgOralGOLDPLUS UNIVERSAL PTE LTD2021-08-31Not applicableSingapore flag
Allergy ReliefTablet, coated5 mg/1OralAlbertsons Companies2018-06-30Not applicableUS flag
Allergy ReliefTablet5 mg/1OralYYBA CORP2020-06-30Not applicableUS flag
Allergy ReliefTablet, film coated5 mg/1OralWalgreen Company2021-09-23Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AIRPASS 5/10 MG FILM KAPLI TABLET, 30 ADETLevocetirizine dihydrochloride (5 mg) + Montelukast (10 mg)Tablet, coatedOralCELTİS İLAÇ SAN. VE TİC. A.Ş.2011-02-23Not applicableTurkey flag
AIRPASS 5/10 MG FILM KAPLI TABLET, 90 ADETLevocetirizine dihydrochloride (5 mg) + Montelukast (10 mg)Tablet, coatedOralCELTİS İLAÇ SAN. VE TİC. A.Ş.2011-02-23Not applicableTurkey flag
ALERNESS MLevocetirizine dihydrochloride (2.5 mg) + Montelukast sodium (5 mg)Tablet, chewableOralTECNOQUIMICAS S.A.2023-10-09Not applicableColombia flag
ANTISS® DLevocetirizine dihydrochloride (0.05 g) + Phenylephrine hydrochloride (0.1 g)SolutionOralLABORATORIO FRANCO COLOMBIANO - LAFRANCOL S.A.S.2010-01-25Not applicableColombia flag
BREATHEZY - LLevocetirizine dihydrochloride (5 mg) + Montelukast sodium (10 mg)Tablet, coatedOralMsn Laboratories Private Limited2020-05-19Not applicableColombia flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AlloPAXLevocetirizine dihydrochloride (3 g/3g) + Loratadine (3 g/3g)KitTransdermalPharmaGenetico LLC2015-06-30Not applicableUS flag
Clobetasol Propionate 0.05% / Levocetirizine Dihydrochloride 2%Levocetirizine dihydrochloride (2 g/100g) + Clobetasol propionate (0.05 g/100g)ShampooTopicalSincerus Florida, LLC2019-05-17Not applicableUS flag
Hydrocortisone 2.5% / Levocetirizine Dihydrochloride 2%Levocetirizine dihydrochloride (2 g/100g) + Hydrocortisone (2.5 g/100g)CreamTopicalSincerus Florida, LLC2019-05-15Not applicableUS flag
Imiquimod 5% / Levocetirizine Dihydrochloride 1% / Niacinamide 2%Levocetirizine dihydrochloride (1 g/100g) + Imiquimod (5 g/100g) + Nicotinamide (2 g/100g)GelTopicalSincerus Florida, LLC2019-05-01Not applicableUS flag
Imiquimod 5% / Levocetirizine Dihydrochloride 1% / Tretinoin 0.05%Levocetirizine dihydrochloride (1 g/100g) + Imiquimod (5 g/100g) + Tretinoin (0.05 g/100g)GelTopicalSincerus Florida, LLC2019-05-01Not applicableUS flag

Categories

ATC Codes
R06AE09 — Levocetirizine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylmethanes
Direct Parent
Diphenylmethanes
Alternative Parents
N-alkylpiperazines / Chlorobenzenes / Aralkylamines / Aryl chlorides / Trialkylamines / Amino acids / Monocarboxylic acids and derivatives / Dialkyl ethers / Carboxylic acids / Azacyclic compounds
show 5 more
Substituents
1,4-diazinane / Amine / Amino acid / Amino acid or derivatives / Aralkylamine / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Carbonyl group
show 22 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
6U5EA9RT2O
CAS number
130018-77-8
InChI Key
ZKLPARSLTMPFCP-OAQYLSRUSA-N
InChI
InChI=1S/C21H25ClN2O3/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)/t21-/m1/s1
IUPAC Name
2-(2-{4-[(R)-(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)acetic acid
SMILES
OC(=O)COCCN1CCN(CC1)[C@H](C1=CC=CC=C1)C1=CC=C(Cl)C=C1

References

General References
  1. Benedetti MS, Plisnier M, Kaise J, Maier L, Baltes E, Arendt C, McCracken N: Absorption, distribution, metabolism and excretion of [14C]levocetirizine, the R enantiomer of cetirizine, in healthy volunteers. Eur J Clin Pharmacol. 2001 Oct;57(8):571-82. [Article]
  2. Mosges R, Konig V, Koberlein J: The effectiveness of levocetirizine in comparison with loratadine in treatment of allergic rhinitis--a meta-analysis. Allergol Int. 2011 Dec;60(4):541-6. doi: 10.2332/allergolint.10-OA-0300. Epub 2011 Sep 25. [Article]
  3. Desager JP, Horsmans Y: Pharmacokinetic-pharmacodynamic relationships of H1-antihistamines. Clin Pharmacokinet. 1995 May;28(5):419-32. doi: 10.2165/00003088-199528050-00006. [Article]
  4. FDA Approved Drug Products: Levocetirizine Dihydrochloride Tablets and Oral Solution [Link]
Human Metabolome Database
HMDB0240226
KEGG Drug
D07402
PubChem Compound
1549000
PubChem Substance
310264866
ChemSpider
1266001
BindingDB
85030
RxNav
356887
ChEBI
94559
ChEMBL
CHEMBL1201191
ZINC
ZINC000019364230
PDBe Ligand
LCR
Drugs.com
Drugs.com Drug Page
Wikipedia
Levocetirizine
PDB Entries
5dqf
FDA label
Download (167 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableAnti-allergic Agents1
4CompletedNot AvailablePerennial Allergic Rhinitis (PAR)1
4CompletedNot AvailableSeasonal Allergic Rhinitis1
4CompletedBasic ScienceHealthy Volunteers (HV)1
4CompletedTreatmentAllergic Reaction1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, film coatedOral5.00 mg
KitTransdermal
SolutionOral0.5 g
SolutionOral
SolutionOral0.050 g
CapsuleOral
Tablet5 mg
Tablet, film coatedOral
ShampooTopical
CapsuleOral5.00 mg
Tablet, orally disintegratingOral5 MG
Tablet, coatedOral
TabletOral
SolutionOral50 mg
SyrupOral
Tablet
GelTopical
SolutionOral0.505 g
TabletOral5.00 mg
Tablet, effervescentOral
SolutionOral50.000 mg
Tablet, effervescent5 mg
Tablet, chewableOral
PowderOral
TabletBuccal5 mg
SolutionOral0.05 g
SyrupOral
SolutionOral0.1 g
SyrupOral0.05 g
TabletOral5 mg
Tablet, film coatedOral
SolutionOral2.5 mg/5mL
Tablet, coatedOral5 mg/1
Tablet, film coatedOral5 mg/1
CreamTopical
CapsuleOral5 mg
TabletOral500000 mg
Tablet, film coatedOral5 mg/10mg
SolutionOral500 mg
SolutionOral5 mg
Capsule, liquid filledOral5 mg
SyrupOral50 mg
SyrupOral2.5 mg/5ml
SolutionOral500000 mg
TabletOral
KitTopical
SyrupOral0.1 g
Powder, for solutionOral
Capsule, liquid filledOral
Capsule, coatedOral
SolutionOral500.000 mg
SyrupOral50.000 mg
SolutionOral5.000 mg
TabletOral5.000 mg
SolutionOral0.5 MG/ML
SolutionOral0.5 mg/1mL
Solution / dropsOral5 MG/ML
TabletOral5 mg/1
SolutionOral5 mg/ml
SolutionOral0.50 mg/ml
SolutionOral500.00 mg
Tablet, film coatedOral5 mg
Tablet, coatedOral5 mg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5698558No1997-12-162013-03-24US flag
US8633194No2014-01-212027-10-16US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)205-208http://www.chemspider.com/Chemical-Structure.1266001.html
boiling point (°C)542.1http://www.chemspider.com/Chemical-Structure.1266001.html
Predicted Properties
PropertyValueSource
Water Solubility0.0658 mg/mLALOGPS
logP2.98ALOGPS
logP0.87Chemaxon
logS-3.8ALOGPS
pKa (Strongest Acidic)3.59Chemaxon
pKa (Strongest Basic)7.42Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area53.01 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity106.87 m3·mol-1Chemaxon
Polarizability41.93 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0019000000-e24b60aef9a19aa0ca89
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0090000000-4fbbabe7bf3d0ad4cab5
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0190000000-8783499dc5c2d31a3f7a
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0uxr-0790000000-4efaf73700a535eb98e9
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0920000000-f952b59e46cde6d2cfac
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0udi-0492000000-90537be4971a327c0fb1
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0009000000-68052b6766ed366c63e4
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-6029000000-096a770835329ffdc3ff
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uk9-0079000000-2d34cc42330f30041359
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0hj9-5059000000-73fb3a3e16673256f88e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udl-2590000000-7b8e2450b42ebd6f9a56
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-7290000000-5274772d061942672254
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-199.3624895
predicted
DarkChem Lite v0.1.0
[M-H]-186.19106
predicted
DeepCCS 1.0 (2019)
[M+H]+199.6626895
predicted
DarkChem Lite v0.1.0
[M+H]+188.54904
predicted
DeepCCS 1.0 (2019)
[M+Na]+199.5563895
predicted
DarkChem Lite v0.1.0
[M+Na]+195.66512
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
Inhibitor
General Function
Histamine receptor activity
Specific Function
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
Gene Name
HRH1
Uniprot ID
P35367
Uniprot Name
Histamine H1 receptor
Molecular Weight
55783.61 Da
References
  1. Ferrer M: Pharmacokinetic evaluation of levocetirizine. Expert Opin Drug Metab Toxicol. 2011 Aug;7(8):1035-47. doi: 10.1517/17425255.2011.590131. Epub 2011 Jun 4. [Article]
  2. Devillier P, Roche N, Faisy C: Clinical pharmacokinetics and pharmacodynamics of desloratadine, fexofenadine and levocetirizine : a comparative review. Clin Pharmacokinet. 2008;47(4):217-30. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. FDA Approved Drug Products: Levocetirizine Dihydrochloride Tablets and Oral Solution [Link]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Liu X, Du Y, Sun W, Kou J, Yu B: Study on the interaction of levocetirizine dihydrochloride with human serum albumin by molecular spectroscopy. Spectrochim Acta A Mol Biomol Spectrosc. 2009 Dec;74(5):1189-96. doi: 10.1016/j.saa.2009.09.033. Epub 2009 Oct 4. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds.
Gene Name
SLC22A11
Uniprot ID
Q9NSA0
Uniprot Name
Solute carrier family 22 member 11
Molecular Weight
59970.945 Da
References
  1. Noguchi S, Nishimura T, Mukaida S, Benet LZ, Nakashima E, Tomi M: Cellular Uptake of Levocetirizine by Organic Anion Transporter 4. J Pharm Sci. 2017 Sep;106(9):2895-2898. doi: 10.1016/j.xphs.2017.03.026. Epub 2017 Apr 4. [Article]

Drug created at March 19, 2008 16:21 / Updated at February 02, 2024 22:53