Loratadine

Identification

Summary

Loratadine is a second generation antihistamine used to manage the symptoms of allergic rhinitis.

Brand Names
Alavert, Alavert D, Allerclear, Claritin, Claritin-D, Diphen, Loradamed, Wal-itin, Wal-itin D
Generic Name
Loratadine
DrugBank Accession Number
DB00455
Background

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

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 382.883
Monoisotopic: 382.144805697
Chemical Formula
C22H23ClN2O2
Synonyms
  • Loratadina
  • Loratadine
  • Loratadinum
External IDs
  • SCH-29851

Pharmacology

Indication

Loratadine is a 2nd generation antihistamine and is used to manage symptoms of allergic rhinitis, wheal formation, urticaria, and other allergic dermatologic conditions.5617

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Symptomatic treatment ofAllergic dermatologic disorders••• ••••••••••
Symptomatic treatment ofAllergic dermatologic disorders••• •••••••••• ••••••• ••••••• •••••• ••••••••••••••
Used in combination for symptomatic treatment ofAllergic rhinitis (ar)Combination Product in combination with: Pseudoephedrine (DB00852)••••••••••••••••••• ••••••• •••••••• •••••••
Used in combination for symptomatic treatment ofAllergic rhinitis (ar)Combination Product in combination with: Pseudoephedrine (DB00852), Acetaminophen (DB00316)••••••••••••••••••
Symptomatic treatment ofAllergic rhinitis (ar)••••••••••••••••••• ••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Like other 2nd generation antihistamines, loratadine is selective for peripheral H1 receptors.9 Loratadine does not penetrate effectively into the central nervous system and has poor affinity for CNS H1-receptors.9 These qualities result in a lack of CNS depressant effects such as drowsiness, sedation, and impaired psychomotor function.9

Mechanism of action

Histamine release is a key mediator in allergic rhinitis and urticaria.1278 As a result, loratadine exerts it's effect by targeting H1 histamine receptors.

Loratadine binds to H1 histamine receptors found on the surface of epithelial cells, endothelial cells, eosinophils, neutrophils, airway cells, and vascular smooth muscle cells among others.7 H1 histamine receptors fall under the wider umbrella of G-protein coupled receptors, and exist in a state of equilibrium between the active and inactive forms.78 Histamine binding to the H1-receptor facilitates cross linking between transmembrane domains III and V, stabilizing the active form of the receptor.78 On the other hand, antihistamines bind to a different site on the H1 receptor favouring the inactive form.78

Hence, loratadine can more accurately be classified as an "inverse agonist" as opposed to a "histamine antagonist", and can prevent or reduce the severity of histamine mediated symptoms.7817

TargetActionsOrganism
AHistamine H1 receptor
antagonist
Humans
UPotassium voltage-gated channel subfamily H member 2
antagonist
Humans
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

In the rapid dissolve formulation, the pharmacokinetic parameters of loratadine are as follows17: Cmax = 2.56 ng/ml, Tmax = 1.14 hrs, AUC = 6.14 ng x hr/ml.

In the rapid dissolve formulation, the pharmacokinetic parameters of descarboethoxyloratadine are as follows17: Cmax = 3.72 ng/ml, Tmax = 1.97 hr, AUC = 49.1 ng x hr/ml.

In the conventional formulation, the pharmacokinetic parameters of loratadine are as follows17: Cmax = 2.11 ng/ml, Tmax = 1.00 hr, AUC = 4.64 ng x hr/ml

In the conventional formulation, the pharmacokinetic parameters of descarboethoxyloratadine are as follows17: Cmax = 3.66 ng/ml, Tmax = 1.97 hr, AUC = 48.4 ng x hr/ml

Volume of distribution

The volume of distribution of loratadine is 120 L/Kg.18

Protein binding

97 - 99% of the loratadine is bound to plasma proteins.17

Metabolism

Loratadine undergoes extensive first pass metabolism in the liver and is primarily metabolized by CYP3A4, CYP2D6, CYP1A1 and CYP2C19. Less involved CYP enzymes include CYP1A2, CYP2B6, CYP2C8, CYP2C9 and CYP3A5.1011 CYP3A4 and CYP2D6 are mainly responsible for metabolizing loratadine to descarboethoxyloratadine.11 This primary metabolite is 4 times more pharmacologically active than loratadine.6

In addition, a study demonstrates that descarboethoxyloratadine is first glucuronidated by UGT2B10, then hydroxylated by CYP2C8 to form 3-hydroxydesloratadine.15 Further glucuronidation of 3-hydroxydesloratadine facilitates excretion.16

Hover over products below to view reaction partners

Route of elimination

Over a 10 day period, 40% of loratadine is excreted in the urine, and 42% is eliminated in the faeces.17

Half-life

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

Clearance

The clearance of loratadine after single oral doses of 20 mg and 40 mg are 12 L/h/kg and 9 L/h/kg respectively.9 P-glycoprotein is involved in the clearance of many 2nd generation antihistamines, including loratadine, from the central nervous system. 1st generation antihistamines are not cleared by P-glycoprotein, which may help explain why they have a different central nervous system adverse effect profile compared to their 2nd generation counterparts.1813 It appears that an antihistamine with higher affinity for p-glycoprotein will have a lower incidence of CNS adverse effects.14

Adverse Effects
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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

Pathways
PathwayCategory
Loratadine 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
AbametapirThe serum concentration of Loratadine can be increased when it is combined with Abametapir.
AclidiniumAclidinium may increase the anticholinergic activities of Loratadine.
AcrivastineThe risk or severity of QTc prolongation can be increased when Loratadine is combined with Acrivastine.
AdenosineThe risk or severity of QTc prolongation can be increased when Loratadine is combined with Adenosine.
AjmalineThe risk or severity of QTc prolongation can be increased when Loratadine is combined with Ajmaline.
Food Interactions
No interactions found.

Products

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Product Images
International/Other Brands
Aerotina / Alavert / Biloina / Civeran / Fristamin / Histaloran / Lomilan / Loracert / Loradex / Loranox / Lorastine / Loratyne / Loritine / Nularef / Restamine / Roletra / Sensibit
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
LoratadineTablet10 mg/1OralNorthwind Pharmaceuticals2014-10-27Not applicableUS flag
LoratadineTablet10 mg/1OralStrategic Sourcing Services, LLC2024-02-22Not applicableUS flag
Loratadine Allergy ReliefTablet10 mg/1OralClinical Solutions Wholsesale2003-08-282017-06-28US flag
Loratadine antihistamineTablet10 mg/1Oralbryant ranch prepack2008-10-15Not applicableUS flag
Loratadineantihistamine antihistamineTablet10 mg/1OralRemedy Repack2015-02-192017-01-23US flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
24 / 7 Life Non-Drowsy Allergy ReliefTablet10 mg/1OralLil' Drug Store Products, Inc.2020-12-17Not applicableUS flag
24 / 7 Life Non-Drowsy Allergy ReliefTablet10 mg/1OralLil' Drug Store Products, Inc.2022-10-24Not applicableUS flag
24 Hour Allergy ReliefTablet10 mg/1OralMeijer Distribution Inc2014-12-302016-05-21US flag
24 Hour Allergy RemedyTablet10 mgOralVita Health Products Inc2006-07-28Not applicableCanada flag
7 Select Allergy ReliefTablet10 mg/1Oral7-Eleven2014-05-142020-10-31US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
12 Hour Allergy and CongestionLoratadine (5 mg/1) + Pseudoephedrine sulfate (120 mg/1)Tablet, film coated, extended releaseOralWalgreen Company2018-05-05Not applicableUS flag
ADOREM GRIPA TABLETASLoratadine (5 mg) + Acetaminophen (500 mg) + Phenylephrine hydrochloride (10 mg)TabletOralLABORATORIOS SIEGFRIED S.A.S.2006-11-102010-06-18Colombia flag
Alavert Allergy and Congestion D-12 hourLoratadine (5 mg/1) + Pseudoephedrine sulfate (120 mg/1)Tablet, film coated, extended releaseOralFoundation Consumer Brands2021-12-15Not applicableUS flag
Alavert Allergy Sinus D-12Loratadine (5 mg/1) + Pseudoephedrine sulfate (120 mg/1)Tablet, film coated, extended releaseOralHaleon US Holdings LLC2004-01-30Not applicableUS flag
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 flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AlloPAXLoratadine (3 g/3g) + Levocetirizine dihydrochloride (3 g/3g)KitTransdermalPharmaGenetico LLC2015-06-30Not applicableUS flag
Help I have allergiesLoratadine (10 mg/1)TabletOralHelp Remedies, Inc.2009-07-01Not applicableUS flag
LoratadineLoratadine (10 mg/1)TabletOralRebel Distributors2010-01-21Not applicableUS flag
Nazirex Compounding KitLoratadine (1 g/1g) + Levocetirizine dihydrochloride (1 g/1g)KitTopicalAlvix Laboratories2015-03-182015-07-01US flag

Categories

ATC Codes
R06AX13 — Loratadine
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Benzocycloheptapyridine / Carbamic acid ester / Carbonic acid derivative / Carbonyl group / Heteroaromatic compound
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
7AJO3BO7QN
CAS number
79794-75-5
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[9.4.0.0^{3,8}]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

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. [Article]
  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. [Article]
  3. Howarth PH: Histamine and asthma: an appraisal based on specific H1-receptor antagonism. Clin Exp Allergy. 1990 Aug;20 Suppl 2:31-41. [Article]
  4. Baroody FM, Naclerio RM: Antiallergic effects of H1-receptor antagonists. Allergy. 2000;55 Suppl 64:17-27. [Article]
  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. [Article]
  6. Barenholtz HA, McLeod DC: Loratadine: a nonsedating antihistamine with once-daily dosing. DICP. 1989 Jun;23(6):445-50. [Article]
  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. [Article]
  8. Church MK, Church DS: Pharmacology of antihistamines. Indian J Dermatol. 2013 May;58(3):219-24. doi: 10.4103/0019-5154.110832. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  12. Naclerio RM: The role of histamine in allergic rhinitis. J Allergy Clin Immunol. 1990 Oct;86(4 Pt 2):628-32. doi: 10.1016/s0091-6749(05)80227-1. [Article]
  13. Obradovic T, Dobson GG, Shingaki T, Kungu T, Hidalgo IJ: Assessment of the first and second generation antihistamines brain penetration and role of P-glycoprotein. Pharm Res. 2007 Feb;24(2):318-27. doi: 10.1007/s11095-006-9149-4. Epub 2006 Dec 19. [Article]
  14. Conen S, Theunissen EL, Vermeeren A, van Ruitenbeek P, Stiers P, Mehta MA, Toennes SW, Ramaekers JG: The role of P-glycoprotein in CNS antihistamine effects. Psychopharmacology (Berl). 2013 Sep;229(1):9-19. doi: 10.1007/s00213-013-3075-z. Epub 2013 Apr 7. [Article]
  15. Kazmi F, Barbara JE, Yerino P, Parkinson A: A long-standing mystery solved: the formation of 3-hydroxydesloratadine is catalyzed by CYP2C8 but prior glucuronidation of desloratadine by UDP-glucuronosyltransferase 2B10 is an obligatory requirement. Drug Metab Dispos. 2015 Apr;43(4):523-33. doi: 10.1124/dmd.114.062620. Epub 2015 Jan 16. [Article]
  16. Aratyn-Schaus Y, Ramanathan R: Advances in high-resolution MS and hepatocyte models solve a long-standing metabolism challenge: the loratadine story. Bioanalysis. 2016 Aug;8(16):1645-62. doi: 10.4155/bio-2016-0094. Epub 2016 Jul 27. [Article]
  17. Health Canada Product Monograph: Claritin (loratadine) [Link]
  18. Comparative Pharmacology of the H1 Antihistamines [Link]
Human Metabolome Database
HMDB0005000
KEGG Drug
D00364
PubChem Compound
3957
PubChem Substance
46507853
ChemSpider
3820
BindingDB
22876
RxNav
28889
ChEBI
6538
ChEMBL
CHEMBL998
ZINC
ZINC000000537931
Therapeutic Targets Database
DAP000101
PharmGKB
PA450266
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Loratadine
MSDS
Download (51.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedOtherAllergic Rhinitis (AR)1
4CompletedOtherHealthy Volunteers (HV)1
4CompletedTreatmentAllergic Conjunctivitis (AC)1
4CompletedTreatmentAllergic Rhinitis (AR)2
4CompletedTreatmentAllergic Rhinitis (AR) / Allergy to Tree Pollen / Seasonal Allergic Rhinitis1

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, chewableBuccal10 mg
Tablet, film coated, extended releaseOral
SolutionOral1.000 mg
Tablet, film coatedOral
TabletOral
KitTransdermal
Tablet, effervescentOral
Tablet, orally disintegratingOral
SuspensionOral1 mg/ml
SolutionOral100.000 mg
SyrupOral100.000 mg
CapsuleOral
LiquidOral5 mg/5mL
Tablet, orally disintegratingOral10 mg/1
TabletOral
SyrupOral5 mg/5ml
Tablet, chewableOral5 mg/1
Tablet, multilayer, extended releaseOral
Tablet, chewableOral10 mg/1
KitOral
SyrupOral5 mg / 5 mL
Tablet, orally disintegratingOral10 mg
Tablet, orally disintegratingOral5 mg
Tablet, orally disintegratingOral5 mg/1
SyrupOral1 mg / mL
Film, solubleOral10 MG
Tablet, sugar coatedOral
Tablet, film coatedOral10 mg
SyrupOral
Capsule, liquid filledOral
Tablet, delayed releaseOral
Cream; kit; liquid; ointment; tablet; tablet, chewable; tablet, film coatedOral; Topical
SyrupOral0.100 g
SolutionOral
Tablet, effervescentOral10 MG
Tablet, film coatedOral
Tablet, film coatedOral5 MG
SolutionOral0.100 g
Tablet, film coatedOral10 mg/1
SolutionOral100 mg
SuspensionOral1 mg/1ml
SyrupOral0.10 g
TabletOral10.000 mg
GranuleOral
SolutionOral1 mg
SuspensionOral
SyrupOral1.0 mg/ml
TabletOral10.0 mg
TabletOral10 mg
TabletOral1000000 mg
SyrupOral100 mg
SyrupOral1 MG/ML
SolutionOral0.1 g
Tablet, solubleOral10 mg
SyrupOral0.1 g
Capsule, liquid filledOral10 mg/1
SolutionOral5 mg/5mL
TabletOral10 mg/1
TabletOral5 mg/1
Tablet, extended releaseOral
Capsule, coatedOral
CapsuleOral10 mg
SolutionOral100.00 mg
SolutionOral
KitTopical
TabletOral10 mg / tab
SyrupOral
TabletOral10000 MG
SuspensionOral
Powder, for solutionOral
Capsule, extended release
TabletOral10.00 mg
Tablet, solubleOral
Tablet, coatedOral
SyrupOral100.00 mg
SyrupOral5 ml/5ml
SyrupOral5 mg/5ml
Tablet, coatedOral10 mg
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)Region
US6132758No2000-10-172018-06-01US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)134-136 °Chttps://www.chemicalbook.com/ChemicalProductProperty_US_CB5283770.aspx
water solubility<1 mg/ml at 25°Chttps://www.chemicalbook.com/ChemicalProductProperty_US_CB5283770.aspx
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
Polarizability41.68 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-MSsplash10-004i-6059000000-3d596b5ab5499c4089ca
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-001r-0039000000-928ed9c6b46ba83ebe20
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0009000000-f3e737e148a290040627
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0009000000-4fb68fc54ede88aedd84
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001r-0019000000-b3e96b96dece1aa1dca6
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-5009000000-810a8984357284a1bd94
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004m-0291000000-02c910217527e79e158b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-8279000000-0c7d83062cbd60912af6
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-199.044604
predicted
DarkChem Lite v0.1.0
[M-H]-195.4247137
predicted
DarkChem Lite v0.1.0
[M-H]-187.70808
predicted
DeepCCS 1.0 (2019)
[M+H]+199.392804
predicted
DarkChem Lite v0.1.0
[M+H]+184.3887636
predicted
DarkChem Lite v0.1.0
[M+H]+190.0661
predicted
DeepCCS 1.0 (2019)
[M+Na]+199.309204
predicted
DarkChem Lite v0.1.0
[M+Na]+199.533504
predicted
DarkChem Lite v0.1.0
[M+Na]+197.12764
predicted
DeepCCS 1.0 (2019)

Targets

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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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  9. Howarth PH: Histamine and asthma: an appraisal based on specific H1-receptor antagonism. Clin Exp Allergy. 1990 Aug;20 Suppl 2:31-41. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
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. [Article]
  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. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
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. [Article]
  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. [Article]
  3. 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. [Article]
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. [Article]
  2. 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. [Article]
  3. Yin OQ, Shi XJ, Tomlinson B, Chow MS: Effect of cyp2d6*10 allele on the pharmacokinetics of loratadine in chinese subjects. Drug Metab Dispos. 2005 Sep;33(9):1283-7. doi: 10.1124/dmd.105.005025. Epub 2005 Jun 2. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
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. [Article]
  2. Aratyn-Schaus Y, Ramanathan R: Advances in high-resolution MS and hepatocyte models solve a long-standing metabolism challenge: the loratadine story. Bioanalysis. 2016 Aug;8(16):1645-62. doi: 10.4155/bio-2016-0094. Epub 2016 Jul 27. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
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. [Article]
  2. 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. [Article]
  3. Aratyn-Schaus Y, Ramanathan R: Advances in high-resolution MS and hepatocyte models solve a long-standing metabolism challenge: the loratadine story. Bioanalysis. 2016 Aug;8(16):1645-62. doi: 10.4155/bio-2016-0094. Epub 2016 Jul 27. [Article]
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. [Article]
  2. 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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Specific Function
Glucuronosyltransferase activity
Gene Name
UGT2B10
Uniprot ID
P36537
Uniprot Name
UDP-glucuronosyltransferase 2B10
Molecular Weight
60773.485 Da
References
  1. Kazmi F, Barbara JE, Yerino P, Parkinson A: A long-standing mystery solved: the formation of 3-hydroxydesloratadine is catalyzed by CYP2C8 but prior glucuronidation of desloratadine by UDP-glucuronosyltransferase 2B10 is an obligatory requirement. Drug Metab Dispos. 2015 Apr;43(4):523-33. doi: 10.1124/dmd.114.062620. Epub 2015 Jan 16. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da
References
  1. Aratyn-Schaus Y, Ramanathan R: Advances in high-resolution MS and hepatocyte models solve a long-standing metabolism challenge: the loratadine story. Bioanalysis. 2016 Aug;8(16):1645-62. doi: 10.4155/bio-2016-0094. Epub 2016 Jul 27. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative reg...
Gene Name
UGT1A3
Uniprot ID
P35503
Uniprot Name
UDP-glucuronosyltransferase 1-3
Molecular Weight
60337.835 Da
References
  1. Aratyn-Schaus Y, Ramanathan R: Advances in high-resolution MS and hepatocyte models solve a long-standing metabolism challenge: the loratadine story. Bioanalysis. 2016 Aug;8(16):1645-62. doi: 10.4155/bio-2016-0094. Epub 2016 Jul 27. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Glucuronosyltransferase activity
Specific Function
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xeno...
Gene Name
UGT2B15
Uniprot ID
P54855
Uniprot Name
UDP-glucuronosyltransferase 2B15
Molecular Weight
61035.815 Da
References
  1. Aratyn-Schaus Y, Ramanathan R: Advances in high-resolution MS and hepatocyte models solve a long-standing metabolism challenge: the loratadine story. Bioanalysis. 2016 Aug;8(16):1645-62. doi: 10.4155/bio-2016-0094. Epub 2016 Jul 27. [Article]

Transporters

Details
1. P-glycoprotein 1
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
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. [Article]
  2. Obradovic T, Dobson GG, Shingaki T, Kungu T, Hidalgo IJ: Assessment of the first and second generation antihistamines brain penetration and role of P-glycoprotein. Pharm Res. 2007 Feb;24(2):318-27. doi: 10.1007/s11095-006-9149-4. Epub 2006 Dec 19. [Article]
  3. Chen C, Hanson E, Watson JW, Lee JS: P-glycoprotein limits the brain penetration of nonsedating but not sedating H1-antagonists. Drug Metab Dispos. 2003 Mar;31(3):312-8. doi: 10.1124/dmd.31.3.312. [Article]
  4. 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. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48