Identification

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Name
Loratadine
Accession Number
DB00455  (APRD00384)
Type
Small Molecule
Groups
Approved, Investigational
Description

Loratadine is a second generation antihistamine used to manage symptoms of allergic rhinitis. 5 Due to their lack of sedative and CNS adverse effects, loratadine along with other second generation antihistamines have become preferable over their 1st generation counterparts in many clinical situations. 7

Structure
Thumb
Synonyms
  • Loratadina
  • Loratadine
  • Loratadinum
External IDs
SCH-29851
Product Images
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
LoratadineTablet10 mg/1OralNorthwind Pharmaceuticals2014-10-27Not applicableUs
Loratadine Allergy ReliefTablet10 mg/1OralClinical Solutions Wholsesale2003-08-282017-06-28Us58118 052620180907 15195 15moc6t
Loratadine antihistamineTablet10 mg/1Oralbryant ranch prepack2008-10-15Not applicableUs63629 132920180907 15195 jyy17u
Loratadineantihistamine antihistamineTablet10 mg/1OralRemedy Repack2015-02-192017-01-23Us
Loratadineantihistamine antihistamineTablet10 mg/1OralRemedy Repack2013-05-292016-07-11Us
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
24 Hour Allergy ReliefTablet10 mg/1OralMeijer Distribution2014-12-30Not applicableUs
24 Hour Allergy RemedyTablet10 mgOralVita Health Products Inc2006-07-28Not applicableCanada
7 Select Allergy ReliefTablet10 mg/1Oral7 Eleven2014-05-14Not applicableUs
Alavert AllergyTablet10 mg/1OralLil' Drug Store Products, Inc.2010-02-222012-12-19Us
Alavert AllergyTablet, orally disintegrating10 mg/1OralWyeth Consumer Healthcare2002-12-192009-06-30Us
Alavert AllergyTablet, orally disintegrating10 mg/1OralWyeth Consumer Healthcare2002-12-192009-06-30Us
Alavert AllergyTablet, orally disintegrating10 mg/1OralWyeth Consumer Healthcare Llc2002-12-19Not applicableUs
Alavert AllergyTablet, orally disintegrating10 mg/1OralWyeth Consumer Healthcare Llc2002-12-19Not applicableUs
All Day Allergy ReliefTablet10 mg/1OralP & L Development, LLC2018-09-30Not applicableUs
Allegy Relief 24 hour non drowsyTablet10 mg/1OralHannaford Brothers Company2006-09-072012-03-09Us
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
12 Hour Allergy and CongestionLoratadine (5 mg/1) + Pseudoephedrine sulfate (120 mg/1)Tablet, film coated, extended releaseOralWalgreen Company2018-05-05Not applicableUs
Alavert Allergy Sinus D-12Loratadine (5 mg/1) + Pseudoephedrine sulfate (120 mg/1)Tablet, film coated, extended releaseOralWyeth Consumer Healthcare Llc2004-01-30Not applicableUs00573 2660 24 nlmimage10 8d46c6b6
Alavert Allergy Sinus D-12Loratadine (5 mg/1) + Pseudoephedrine sulfate (120 mg/1)Tablet, film coated, extended releaseOralPhysicians Total Care, Inc.2007-04-262012-06-30Us
ALLERCLEAR-D 24 HourLoratadine (10 mg/1) + Pseudoephedrine sulfate (240 mg/1)Tablet, extended releaseOralCostco Wholesale2016-03-012018-04-30Us
Allergy and Congestion ReliefLoratadine (5 mg/1) + Pseudoephedrine sulfate (120 mg/1)Tablet, extended releaseOralHyvee2012-03-192016-07-12Us
Allergy and Congestion ReliefLoratadine (10 mg/1) + Pseudoephedrine sulfate (240 mg/1)Tablet, extended releaseOralHyvee2003-06-302017-05-23Us
Allergy and Congestion ReliefLoratadine (5 mg/1) + Pseudoephedrine sulfate (120 mg/1)Tablet, film coated, extended releaseOralL. Perrigo Company2018-04-12Not applicableUs
Allergy and Congestion ReliefLoratadine (5 mg/1) + Pseudoephedrine sulfate (120 mg/1)Tablet, film coated, extended releaseOralKroger2018-05-18Not applicableUs
Allergy and Congestion ReliefLoratadine (10 mg/1) + Pseudoephedrine sulfate (240 mg/1)Tablet, film coatedOralHannaford Brothers Company2009-06-032014-03-12Us
Allergy and Congestion ReliefLoratadine (5 mg/1) + Pseudoephedrine sulfate (120 mg/1)Tablet, extended releaseOralSafeway2012-10-182014-12-09Us
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AlloPAXLoratadine (3 g/3g) + Levocetirizine dihydrochloride (3 g/3g)KitPharmaGenetico LLC2015-06-30Not applicableUs
Help I have allergiesLoratadine (10 mg/1)TabletOralHelp Remedies, Inc.2009-07-01Not applicableUs
LoratadineLoratadine (10 mg/1)TabletOralCardinal Health2013-06-14Not applicableUs
LoratadineLoratadine (10 mg/1)TabletOralRebel Distributors2010-01-21Not applicableUs51660 0526 05 nlmimage10 bf16dfa6
Nazirex Compounding KitLoratadine (1 g/1g) + Levocetirizine dihydrochloride (1 g/1g)KitTopicalAlvix Laboratories2015-03-182015-07-01Us
International/Other Brands
Aerotina / Alavert / Biloina / Civeran / Fristamin / Histaloran / Lomilan / Loracert / Loradex / Loranox / Lorastine / Loratyne / Loritine / Nularef / Restamine / Roletra / Sensibit
Categories
UNII
7AJO3BO7QN
CAS number
79794-75-5
Weight
Average: 382.883
Monoisotopic: 382.144805697
Chemical Formula
C22H23ClN2O2
InChI Key
JCCNYMKQOSZNPW-UHFFFAOYSA-N
InChI
InChI=1S/C22H23ClN2O2/c1-2-27-22(26)25-12-9-15(10-13-25)20-19-8-7-18(23)14-17(19)6-5-16-4-3-11-24-21(16)20/h3-4,7-8,11,14H,2,5-6,9-10,12-13H2,1H3
IUPAC Name
ethyl 4-{13-chloro-4-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}piperidine-1-carboxylate
SMILES
CCOC(=O)N1CCC(CC1)=C1C2=C(CCC3=C1N=CC=C3)C=C(Cl)C=C2

Pharmacology

Indication

Loratadine is a 2nd generation antihistamine and is typically used to manage symptoms of allergic rhinitis, wheal formation and urticaria.56 Unlike 1st generation antihistamines, loratadine is non-sedating since it has minimal effect on the central nervous system with only a small amount entering the brain. 6

Associated Conditions
Pharmacodynamics

As a 2nd generation antihistamine, loratadine is selective for peripheral H1 receptors allowing it to effectively treat patients with allergic rhinitis or chronic urticaria. 9 Loratadine demonstrates poor penetration into the blood brain barrier and lacks affinity for CNS receptors explaining it's lack of overall CNS depressant effects including drowsiness, sedation, and impaired psychomotor function. 9

Mechanism of action

Loratadine binds to H1 histamine receptors found on the surface of various cells including epithelial cells, endothelial cells, eosinophils, neutrophils, airway cells, and vascular smooth muscle cells. 7 H1 histamine receptors fall under the wider umbrella of G-protein coupled receptors, therefore there is a balance of the active and inactive forms of H1 receptors at baseline.8 Histamine causes cross linking on transmembrane domain sites III and V which stabilizes the active form of the receptor, while antihistamines bind at different sites on the H1 receptor, favouring the inactive form.7 Given the mechanism of action, Loratadine should be referred to as an "inverse agonist" rather than a "histamine antagonist". 78

TargetActionsOrganism
AHistamine H1 receptor
antagonist
Humans
UPotassium voltage-gated channel subfamily H member 2Not AvailableHumans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

Learn more
Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

Learn more
Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

Learn more
Absorption

Loratadine is rapidly absorbed and achieves peak plasma concentration in 1-2 hours, while it's main metabolite achieves peak plasma concentration in 3-4 hours.6

Volume of distribution

The volume of distribution of loratadine is 120 L/Kg. 14

Protein binding

97 - 99% of the loratadine is bound to plasma proteins.13

Metabolism

Loratadine undergoes extensive first pass metabolism in the liver and is primarily metabolized by CYP enzymes including CYP3A4, CYP2D6, CYP1A1, CYP2C19. CYP1A2, CYP2B6, CYP2C9 and CYP3A5 play a smaller role in loratadine metabolism. 1011 CYP3A4 and CYP2D6 are largely responsible for metabolizing loratadine to it's primary metabolite, descarbethoxyloratadine, which is more potent pharmacological activity compared to it's parent drug .611

Route of elimination

Over a 10 day period, 40% of loratadine is excreted in the urine, while 42% is eliminated in the faeces.13

Half life

The elimination half life is approximately 10 hours for loratadine and 20 hours for descarbethoxyloratadine.6

Clearance

Interestingly, P-glycoprotein appears to be involved in the clearance of many 2nd generation antihistamines including loratadine from the central nervous system. Since 1st generation antihistamines are not P-glycoprotein substrates, this may help explain the difference in central nervous system adverse effects. 14

Toxicity

Second generation antihistamines such as loratadine have very few adverse effects; however, insomnia, headache, fatigue, drowsiness and rash have been reported.7 Symptoms of loratadine overdose include gastrointestinal side effects, agitation, drowsiness, tachycardia, and headache. 7 It is advised to obtain an ECG in the event of loratadine overdose.7

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Loratadine H1-Antihistamine ActionDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be increased when combined with Loratadine.
(S)-WarfarinThe metabolism of (S)-Warfarin can be increased when combined with Loratadine.
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative and stimulatory activities of Loratadine.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may decrease the sedative and stimulatory activities of Loratadine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be increased when combined with Loratadine.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative and stimulatory activities of Loratadine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be increased when combined with Loratadine.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when Loratadine is combined with 4-Methoxyamphetamine.
5-androstenedioneThe metabolism of 5-androstenedione can be increased when combined with Loratadine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Loratadine is combined with 5-methoxy-N,N-dimethyltryptamine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

    Learn more
  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

    Learn more
  • Action
    Evidence Level

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

    Learn more
Food Interactions
  • Take on empty stomach: 1 hour before or 2 hours after meals.

References

Synthesis Reference

Alberto Stampa, Pelayo Camps, Gloria Rodriguez, Jordi Bosch, Maria del Carmen Onrubia, "Process for the preparation of loratadine." U.S. Patent US6084100, issued July 04, 2000.

US6084100
General References
  1. See S: Desloratadine for allergic rhinitis. Am Fam Physician. 2003 Nov 15;68(10):2015-6. [PubMed:14655812]
  2. Menardo JL, Horak F, Danzig MR, Czarlewski W: A review of loratadine in the treatment of patients with allergic bronchial asthma. Clin Ther. 1997 Nov-Dec;19(6):1278-93; discussion 1523-4. [PubMed:9444440]
  3. Howarth PH: Histamine and asthma: an appraisal based on specific H1-receptor antagonism. Clin Exp Allergy. 1990 Aug;20 Suppl 2:31-41. [PubMed:1977506]
  4. Baroody FM, Naclerio RM: Antiallergic effects of H1-receptor antagonists. Allergy. 2000;55 Suppl 64:17-27. [PubMed:11291777]
  5. Tenn MW, Steacy LM, Ng CC, Ellis AK: Onset of action for loratadine tablets for the symptomatic control of seasonal allergic rhinitis in adults challenged with ragweed pollen in the Environmental Exposure Unit: a post hoc analysis of total symptom score. Allergy Asthma Clin Immunol. 2018 Jan 16;14:5. doi: 10.1186/s13223-017-0227-4. eCollection 2018. [PubMed:29371864]
  6. Barenholtz HA, McLeod DC: Loratadine: a nonsedating antihistamine with once-daily dosing. DICP. 1989 Jun;23(6):445-50. [PubMed:2525847]
  7. Randall KL, Hawkins CA: Antihistamines and allergy. Aust Prescr. 2018 Apr;41(2):41-45. doi: 10.18773/austprescr.2018.013. Epub 2018 Apr 3. [PubMed:29670310]
  8. Church MK, Church DS: Pharmacology of antihistamines. Indian J Dermatol. 2013 May;58(3):219-24. doi: 10.4103/0019-5154.110832. [PubMed:23723474]
  9. Clissold SP, Sorkin EM, Goa KL: Loratadine. A preliminary review of its pharmacodynamic properties and therapeutic efficacy. Drugs. 1989 Jan;37(1):42-57. [PubMed:2523301]
  10. Ghosal A, Gupta S, Ramanathan R, Yuan Y, Lu X, Su AD, Alvarez N, Zbaida S, Chowdhury SK, Alton KB: Metabolism of loratadine and further characterization of its in vitro metabolites. Drug Metab Lett. 2009 Aug;3(3):162-70. Epub 2009 Aug 1. [PubMed:19702548]
  11. Zhang YF, Chen XY, Zhong DF, Dong YM: Pharmacokinetics of loratadine and its active metabolite descarboethoxyloratadine in healthy Chinese subjects. Acta Pharmacol Sin. 2003 Jul;24(7):715-8. [PubMed:12852841]
  12. Claritin Packaging Label [File]
  13. Claritin Product Monograph [File]
  14. Comparative Pharmacology of the H1 Antihistamines [File]
External Links
Human Metabolome Database
HMDB0005000
KEGG Drug
D00364
PubChem Compound
3957
PubChem Substance
46507853
ChemSpider
3820
BindingDB
22876
ChEBI
6538
ChEMBL
CHEMBL998
Therapeutic Targets Database
DAP000101
PharmGKB
PA450266
Wikipedia
Loratadine
ATC Codes
R06AX13 — Loratadine
AHFS Codes
  • 04:08.00 — Second Generation Antihistamines
FDA label
Download (232 KB)
MSDS
Download (51.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentProgressive Multiple Sclerosis1
1CompletedOtherHealthy Volunteers2
1CompletedTreatmentHistamine H1 Antagonists, Non-Sedating1
1TerminatedTreatmentRheumatoid Arthritis1
2CompletedTreatmentAdverse Drug Events / Allergic Rhinitis (AR) / Quality of Life1
2CompletedTreatmentAllergic Rhinitis (AR)2
2CompletedTreatmentBone Pain in Stage I - III Breast Cancer1
2CompletedTreatmentChronic Urticaria1
2CompletedTreatmentRhinitis, Allergic, Perennial1
2CompletedTreatmentRhinitis / Seasonal Rhinitis1
2RecruitingSupportive CareBone pain1
2RecruitingTreatmentTransplant, Kidney1
2Unknown StatusSupportive CarePegfilgrastim-induced Back and Leg Pain1
3CompletedTreatmentAllergic Rhinitis (AR)1
3CompletedTreatmentAllergies / Conjunctivitis / Rhinitis / Rhinoconjunctivitis2
3CompletedTreatmentModerate or Severe Submental Fullness1
3CompletedTreatmentPerennial Allergic Rhinitis (PAR)1
3CompletedTreatmentRhinitis, Allergic, Seasonal2
3CompletedTreatmentSeasonal Allergic Rhinitis (SAR)6
4CompletedOtherHealthy Volunteers1
4CompletedTreatmentAllergic Rhinitis (AR)1
4CompletedTreatmentAllergic Rhinitis (AR) / Pollen Allergy / Rhinitis, Allergic, Seasonal / Severe Acute Respiratory Syndrome1
4CompletedTreatmentPerennial Allergic Rhinitis (PAR)1
4CompletedTreatmentRhinitis2
4CompletedTreatmentRhinitis, Allergic, Perennial1
4CompletedTreatmentSeasonal Allergic Rhinitis (SAR)1
Not AvailableCompletedNot AvailableLeukemias / Malignant Lymphomas1
Not AvailableCompletedNot AvailablePruritus / Rhinitis, Allergic, Perennial / Rhinitis, Allergic, Seasonal / Urticarias1
Not AvailableNot Yet RecruitingTreatmentRhinitis, Allergic, Perennial1
Not AvailableRecruitingTreatmentMalignant Lymphomas1

Pharmacoeconomics

Manufacturers
  • Schering plough healthcare products inc
  • Taro pharmaceuticals usa inc
  • Apotex inc richmond hill
  • L perrigo co
  • Ranbaxy laboratories ltd
  • Silarx pharmaceuticals inc
  • Taro pharmaceutical industries ltd
  • Teva pharmaceuticals usa inc
  • Wockhardt eu operations (swiss) ag
  • Wyeth consumer healthcare
  • Impax laboratories inc
  • Watson laboratories inc florida
  • Apotex inc etobicoke site
  • Mylan pharmaceuticals inc
  • Perrigo co
  • Sandoz inc
Packagers
  • Amerisource Health Services Corp.
  • AstraZeneca Inc.
  • Cardinal Health
  • Catalent Pharma Solutions
  • Chain Drug
  • Concern Stirol
  • CVS Pharmacy
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • H.J. Harkins Co. Inc.
  • Major Pharmaceuticals
  • Merck & Co.
  • Neuman Distributors Inc.
  • Novartis AG
  • Nucare Pharmaceuticals Inc.
  • Patient First Corp.
  • PD-Rx Pharmaceuticals Inc.
  • Physicians Total Care Inc.
  • Prepak Systems Inc.
  • Prescript Pharmaceuticals
  • Professional Co.
  • S&P Healthcare
  • Southwood Pharmaceuticals
  • Walgreen Co.
  • West-Ward Pharmaceuticals
  • Wockhardt Ltd.
  • Wyeth Pharmaceuticals
Dosage forms
FormRouteStrength
Tablet, film coated, extended releaseOral
Tablet, film coatedOral
Kit
TabletOral10 mg
LiquidOral5 mg/5mL
Tablet, orally disintegratingOral10 mg/1
Tablet, extended releaseOral
Tablet, chewableOral5 mg/1
Tablet, multilayer, extended releaseOral
Tablet, orally disintegratingOral10 mg
Tablet, orally disintegratingOral5 mg
Tablet, orally disintegratingOral5 mg/1
SyrupOral1 mg
Capsule, liquid filledOral10 mg/1
SolutionOral5 mg/5mL
TabletOral10 mg/1
CapsuleOral10 mg
Tablet, film coatedOral10 mg/1
KitTopical
Prices
Unit descriptionCostUnit
Claritin 30 10 mg tablet Box29.99USD box
Lisinopril 100% powder21.6USD g
Zestril 40 mg tablet2.48USD tablet
Claritin-d 12 hour tablet sa2.46USD tablet
Prinivil 40 mg tablet2.4USD tablet
Zestril 30 mg tablet2.4USD tablet
Zestril 5 mg tablet1.54USD tablet
Lisinopril 30 mg tablet1.51USD tablet
Claritin 10 mg tablet1.48USD tablet
Claritin-d 24 hour tablet sa1.43USD tablet
Zestril 10 mg tablet1.43USD tablet
Claritin 10 mg reditabs1.4USD tablet
Lisinopril 40 mg tablet1.26USD tablet
Zestril 20 mg tablet1.25USD tablet
Prinivil 20 mg tablet1.23USD tablet
Prinivil 10 mg tablet1.15USD tablet
Loratadine-d 24hr tablet1.11USD tablet
Prinivil 5 mg tablet1.11USD tablet
Lisinopril 20 mg tablet1.07USD tablet
Child's claritin 5 mg tablet chew1.02USD tablet
Lisinopril 10 mg tablet0.99USD tablet
Lisinopril 5 mg tablet0.96USD tablet
CVS Pharmacy loratadine-d 24hr tablet0.89USD tablet
Zestril 2.5 mg tablet0.79USD tablet
Tavist nd 10 mg tablet0.74USD tablet
Wal-itin 10 mg tablet0.7USD tablet
Alavert d-12 allergy-sinus tablet0.68USD tablet
Alavert 10 mg tablet0.64USD tablet
Lisinopril 2.5 mg tablet0.64USD tablet
CVS Pharmacy loratadine 10 mg tablet0.52USD tablet
Loratadine 10 mg tablet0.47USD tablet
CVS Pharmacy allergy relief 10 mg tablet0.44USD tablet
Qc loratadine 10 mg tablet0.08USD tablet
Allergy relief 10 mg tablet0.07USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6132758No2000-10-172018-06-01Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)134-136 °Chttps://www.chemicalbook.com/ChemicalProductProperty_US_CB5283770.aspx
water solubility0.000011 mg/mlNot Available
logP5.20SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.0134 mg/mLALOGPS
logP4.8ALOGPS
logP4.55ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)4.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area42.43 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity116.98 m3·mol-1ChemAxon
Polarizability41.67 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9754
Caco-2 permeable-0.5488
P-glycoprotein substrateSubstrate0.7337
P-glycoprotein inhibitor IInhibitor0.9505
P-glycoprotein inhibitor IIInhibitor0.8387
Renal organic cation transporterNon-inhibitor0.5143
CYP450 2C9 substrateNon-substrate0.8197
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateSubstrate0.677
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorInhibitor0.8949
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorNon-inhibitor0.831
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9359
Ames testNon AMES toxic0.6884
CarcinogenicityNon-carcinogens0.915
BiodegradationNot ready biodegradable0.9963
Rat acute toxicity2.8964 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7531
hERG inhibition (predictor II)Inhibitor0.8456
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001r-1279000000-1c522c39e53b6bbfb9aa
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001r-0039000000-928ed9c6b46ba83ebe20
MS/MS Spectrum - , positiveLC-MS/MSsplash10-067r-1292000000-3869907bd01f927b6f22
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as benzocycloheptapyridines. These are aromatic compounds containing a benzene ring and a pyridine ring fused to a seven membered carbocycle.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzocycloheptapyridines
Sub Class
Not Available
Direct Parent
Benzocycloheptapyridines
Alternative Parents
Piperidinecarboxylic acids / Pyridines and derivatives / Benzenoids / Aryl chlorides / Heteroaromatic compounds / Carbamate esters / Organic carbonic acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds
show 4 more
Substituents
Benzocycloheptapyridine / Piperidinecarboxylic acid / Aryl chloride / Aryl halide / Piperidine / Pyridine / Benzenoid / Heteroaromatic compound / Carbamic acid ester / Carbonic acid derivative
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Details
1. Histamine H1 receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
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. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Cieslewicz G, Gondorowicz K, Grzelewska-Rzymowska I, Rozniecki J, Wojciechowska B: [Effect of loratadine--selective antagonist of histamine (H1) receptor--on allergen-induced bronchoconstriction in atopic asthmatics]. Pneumonol Alergol Pol. 1992;60(11-12):11-5. [PubMed:1303772]
  3. Cieslewicz G, Gondorowicz K, Grzelewska-Rzymowska I, Rozniecki J: [Effect of loratadine, selective antagonist of histamine H1 receptors, on histamine-induced bronchoconstriction]. Pneumonol Alergol Pol. 1995;63(5-6):281-5. [PubMed:7581058]
  4. Letari O, Miozzo A, Folco G, Belloni PA, Sala A, Rovati GE, Nicosia S: Effects of loratadine on cytosolic Ca2+ levels and leukotriene release: novel mechanisms of action independent of the anti-histamine activity. Eur J Pharmacol. 1994 Feb 15;266(3):219-27. [PubMed:8174605]
  5. Cavero I, Mestre M, Guillon JM, Heuillet E, Roach AG: Preclinical in vitro cardiac electrophysiology: a method of predicting arrhythmogenic potential of antihistamines in humans? Drug Saf. 1999;21 Suppl 1:19-31; discussion 81-7. [PubMed:10597865]
  6. Tamura T, Masaki S, Ohmori K, Karasawa A: Effect of olopatadine and other histamine H1 receptor antagonists on the skin inflammation induced by repeated topical application of oxazolone in mice. Pharmacology. 2005 Dec;75(1):45-52. Epub 2005 Jun 7. [PubMed:15942272]
  7. Grzelewska-Rzymowska I, Gondorowicz K, Cieslewicz G, Rozniecki J, Wojciechowska B: [Effect of loratadine (LO), a selective H1 antagonist, on histamine-induced bronchoconstriction]. Pneumonol Alergol Pol. 1992;60(11-12):16-21. [PubMed:1303773]
  8. Menardo JL, Horak F, Danzig MR, Czarlewski W: A review of loratadine in the treatment of patients with allergic bronchial asthma. Clin Ther. 1997 Nov-Dec;19(6):1278-93; discussion 1523-4. [PubMed:9444440]
  9. Howarth PH: Histamine and asthma: an appraisal based on specific H1-receptor antagonism. Clin Exp Allergy. 1990 Aug;20 Suppl 2:31-41. [PubMed:1977506]
  10. Baroody FM, Naclerio RM: Antiallergic effects of H1-receptor antagonists. Allergy. 2000;55 Suppl 64:17-27. [PubMed:11291777]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarization
Specific Function
Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the ...
Gene Name
KCNH2
Uniprot ID
Q12809
Uniprot Name
Potassium voltage-gated channel subfamily H member 2
Molecular Weight
126653.52 Da
References
  1. Crumb WJ Jr: Loratadine blockade of K(+) channels in human heart: comparison with terfenadine under physiological conditions. J Pharmacol Exp Ther. 2000 Jan;292(1):261-4. [PubMed:10604956]
  2. Taglialatela M, Pannaccione A, Castaldo P, Giorgio G, Zhou Z, January CT, Genovese A, Marone G, Annunziato L: Molecular basis for the lack of HERG K+ channel block-related cardiotoxicity by the H1 receptor blocker cetirizine compared with other second-generation antihistamines. Mol Pharmacol. 1998 Jul;54(1):113-21. [PubMed:9658196]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid 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 oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. [PubMed:15601807]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. Backman JT, Filppula AM, Niemi M, Neuvonen PJ: Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. doi: 10.1124/pr.115.011411. [PubMed:26721703]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
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. Warzecha H, Ferme D, Peer M, Frank A, Unger M: Bioconversion of the antihistaminc drug loratadine by tobacco cell suspension cultures expressing human cytochrome P450 3A4. J Biosci Bioeng. 2010 Mar;109(3):288-90. doi: 10.1016/j.jbiosc.2009.09.001. Epub 2009 Sep 29. [PubMed:20159579]
  2. Li C, Lee MY, Choi JS: Effects of silybinin, CYP3A4 and P-glycoprotein inhibitor in vitro, on the bioavailability of loratadine in rats. Pharmazie. 2010 Jul;65(7):510-4. [PubMed:20662320]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  4. Barecki ME, Casciano CN, Johnson WW, Clement RP: In vitro characterization of the inhibition profile of loratadine, desloratadine, and 3-OH-desloratadine for five human cytochrome P-450 enzymes. Drug Metab Dispos. 2001 Sep;29(9):1173-5. [PubMed:11502723]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Barecki ME, Casciano CN, Johnson WW, Clement RP: In vitro characterization of the inhibition profile of loratadine, desloratadine, and 3-OH-desloratadine for five human cytochrome P-450 enzymes. Drug Metab Dispos. 2001 Sep;29(9):1173-5. [PubMed:11502723]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. Hossain MA, Tran T, Chen T, Mikus G, Greenblatt DJ: Inhibition of human cytochromes P450 in vitro by ritonavir and cobicistat. J Pharm Pharmacol. 2017 Dec;69(12):1786-1793. doi: 10.1111/jphp.12820. Epub 2017 Sep 29. [PubMed:28960344]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Barecki ME, Casciano CN, Johnson WW, Clement RP: In vitro characterization of the inhibition profile of loratadine, desloratadine, and 3-OH-desloratadine for five human cytochrome P-450 enzymes. Drug Metab Dispos. 2001 Sep;29(9):1173-5. [PubMed:11502723]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. Yumibe N, Huie K, Chen KJ, Snow M, Clement RP, Cayen MN: Identification of human liver cytochrome P450 enzymes that metabolize the nonsedating antihistamine loratadine. Formation of descarboethoxyloratadine by CYP3A4 and CYP2D6. Biochem Pharmacol. 1996 Jan 26;51(2):165-72. [PubMed:8615885]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Vitamin d 24-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 oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Ghosal A, Gupta S, Ramanathan R, Yuan Y, Lu X, Su AD, Alvarez N, Zbaida S, Chowdhury SK, Alton KB: Metabolism of loratadine and further characterization of its in vitro metabolites. Drug Metab Lett. 2009 Aug;3(3):162-70. Epub 2009 Aug 1. [PubMed:19702548]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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 oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Ghosal A, Gupta S, Ramanathan R, Yuan Y, Lu X, Su AD, Alvarez N, Zbaida S, Chowdhury SK, Alton KB: Metabolism of loratadine and further characterization of its in vitro metabolites. Drug Metab Lett. 2009 Aug;3(3):162-70. Epub 2009 Aug 1. [PubMed:19702548]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Steroid 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 oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Ghosal A, Gupta S, Ramanathan R, Yuan Y, Lu X, Su AD, Alvarez N, Zbaida S, Chowdhury SK, Alton KB: Metabolism of loratadine and further characterization of its in vitro metabolites. Drug Metab Lett. 2009 Aug;3(3):162-70. Epub 2009 Aug 1. [PubMed:19702548]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Steroid 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 oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Ghosal A, Gupta S, Ramanathan R, Yuan Y, Lu X, Su AD, Alvarez N, Zbaida S, Chowdhury SK, Alton KB: Metabolism of loratadine and further characterization of its in vitro metabolites. Drug Metab Lett. 2009 Aug;3(3):162-70. Epub 2009 Aug 1. [PubMed:19702548]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Oxygen binding
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 oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Ghosal A, Gupta S, Ramanathan R, Yuan Y, Lu X, Su AD, Alvarez N, Zbaida S, Chowdhury SK, Alton KB: Metabolism of loratadine and further characterization of its in vitro metabolites. Drug Metab Lett. 2009 Aug;3(3):162-70. Epub 2009 Aug 1. [PubMed:19702548]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Wang EJ, Casciano CN, Clement RP, Johnson WW: Evaluation of the interaction of loratadine and desloratadine with P-glycoprotein. Drug Metab Dispos. 2001 Aug;29(8):1080-3. [PubMed:11454724]
  2. Comparative Pharmacology of the H1 Antihistamines [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Pedersen JM, Matsson P, Bergstrom CA, Hoogstraate J, Noren A, LeCluyse EL, Artursson P: Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43. doi: 10.1093/toxsci/kft197. Epub 2013 Sep 6. [PubMed:24014644]

Drug created on June 13, 2005 07:24 / Updated on May 21, 2019 12:06