Olopatadine

Identification

Summary

Olopatadine is a histamine H1 antagonist used to treat allergic conjunctivitis and rhinitis.

Brand Names
Pataday, Patanase, Patanol, Pazeo, Ryaltris
Generic Name
Olopatadine
DrugBank Accession Number
DB00768
Background

Olopatadine is a selective histamine H1 antagonist and mast cell stabilizer that works by attenuating inflammatory and allergic reactions. It is a structural analog of doxepin, which has a minimal anti-allergic activity.10 Olopatadine works by blocking the effects of histamine, which is a primary inflammatory mediator that causes inflammatory and allergic reactions. An ophthalmic solution of olopatadine was approved by the FDA and European Union for the treatment of seasonal and perennial allergic conjunctivitis in 1996 and 2002, respectively.2 In comparison to other anti-allergenic ophthalmic medications, olopatadine displays a good comfort and tolerability profile since it does not cause perturbation of cell membranes.6 Olopatadine is used for the symptomatic treatment of ocular itching associated with allergic conjunctivitis in ophthalmic formulations and seasonal allergic rhinitis in intranasal formulations. It is currently marketed under several brand names, including Pazeo, Patanase, and Opatanol.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 337.4122
Monoisotopic: 337.167793607
Chemical Formula
C21H23NO3
Synonyms
  • Olopatadin
  • Olopatadina
  • Olopatadine
  • Olopatadinum
External IDs
  • AL-4943A
  • ALO 4943 A
  • KW 4679

Pharmacology

Indication

Olopatadine is indicated for the symptomatic treatment of ocular itching associated with allergic conjunctivitis as ophthalmic solution.7

As a nasal spray, as a monotherapy or in combination with mometasone furoate, olopatadine is indicated for the symptomatic relief of seasonal allergic rhinitis in patients 12 years of age and older.8,12

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Symptomatic treatment ofAllergic conjunctivitis••••••••••••••••••••• ••••••••••
Symptomatic treatment ofAllergic rhinitis (ar)••••••••••••••••••••
Used in combination for symptomatic treatment ofSeasonal allergic rhinitisCombination Product in combination with: Mometasone furoate (DB14512)•••••••••••••••••• ••••••••••••••
Symptomatic treatment ofSeasonal allergic rhinitis•••••••••••••••••
Used in combination for symptomatic treatment ofModerate, severe seasonal allergic rhinitisCombination Product in combination with: Mometasone furoate (DB14512)•••••••••••••••••• ••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Inflammatory reactions in response to various stimuli are mediated by endogenous mediators and other pro-inflammatory factors. Histamine receptor activation and mast cell degranulation are primary mechanisms that cause inflammatory reactions such as ocular itching, hyperemia, chemosis, eyelid swelling, and tearing of seasonal allergic conjunctivitis.3 Olopatadine is an anti-allergenic molecule and mast cell stabilizer that inhibits the in vivo type 1 immediate hypersensitivity reaction.10 By blocking the effects of histamine, olopatadine works to reduce the symptoms of allergies and inflammation at various sites of administration, including the eyes and nose. It has shown to exert antihistaminic effects in isolated tissues, animal models, and humans.8 Olopatadine also demonstrated dose-dependent inhibition of immunologically-stimulated release of histamine from rat basophilic leukemia cells and human conjunctival mast cells in vitro.3 Olopatadine has a relatively rapid onset of action and prolonged duration, where it was shown to mediate anti-histaminic effects at 5 minutes to 24 hours post-administration.3

While olopatadine is a non-sedating antihistamine agent, there have been reports of somnolence in some patients taking nasal olopatadine during clinical trials.8 Temporary blurred vision or other visual disturbances were observed following ophthalmic administration. Olopatadine has negligible effects on alpha-adrenergic, dopamine, muscarinic type 1 and 2, and serotonin receptors.10 In clinical trials, there was no evidence of any effect of olopatadine on QT prolongation was observed following intranasal administration.8

Mechanism of action

Histamine is a biogenic vasoactive amine that binds to its receptors, which are G-protein coupled receptors. Signaling through the histamine H1 receptor is thought to primarily promote the activation of inflammatory reactions, such as allergy, asthma, and autoimmune diseases.4 H1 receptor signaling activates the intracellular transcription factors, such as IP3, PLC, PKC, DAG, and intracellular calcium ions, which all work to activate further downstream cascades. Activated downstream cascades lead to the production of cytokines, the release of mast cell inflammatory mediators, synthesis of prostacyclins, activation of platelet factor, as well as the synthesis of nitric oxide, arachidonic acid, and thromboxane, which all contribute to inflammatory reactions.4

Olopatadine is an anti-allergic molecule that works via several mechanisms. As a mast cell stabilizer, it stabilizes rodent basophils and human conjunctival mast cells and inhibits the immunologically-stimulated release of histamine.3 Olopatadine acts as an antagonist at the histamine H1 receptors with high selectivity, which is explained by a unique receptor binding pocket that consists of the aspartate residue in the third transmembrane helix and other sites in the H1 receptor.1 Upon binding, olopatadine blocks the H1 receptor signaling pathway, inhibiting the release of inflammatory mediators, such as tryptase, prostaglandin D2, TNF-alpha, as well as pro-inflammatory cytokines.10 It also decreases chemotaxis and inhibits eosinophil activation.7 In vitro, olopatadine was shown to inhibit epithelial cell intercellular adhesion molecule-1 (ICAM-1), which promotes the recruitment of migrating pro-inflammatory mediators.3

TargetActionsOrganism
AHistamine H1 receptor
antagonist
Humans
UHistamine H2 receptor
antagonist
Humans
UHistamine H3 receptor
antagonist
Humans
UProtein S100-A1
antagonist
Humans
UProtein S100-A12
antagonist
Humans
UProtein S100-B
other/unknown
Humans
UProtein S100-A13
other/unknown
Humans
UProtein S100-A2
antagonist
Humans
Absorption

Ocular administration of olopatadine in healthy subjects resulted in the Cmax of 1.6 ± 0.9 ng/mL, which was reached after about 2.0 hours. The AUC was 9.7 ± 4.4 ngxh/mL.7

The average absolute bioavaiability of intranasal olopatadine is about 57%. Following intranasal administration in healthy subjects, the Cmax of 6.0 ± 8.99 ng/mL at steady-state was reached between 30 minutes to 1 hour after twice daily intranasal administration. The average AUC was 66.0 ± 26.8 ng·h/mL. In patients with seasonal allergic rhinitis, the Cmax of 23.3 ± 6.2 ng/mL at steady-state was reached between 15 minutes and 2 hours post-dosing and the average AUC was 78.0 ± 13.9 ng·h/mL.8

Volume of distribution

In an open-label study consisting of healthy Chinese subjects receiving oral administration of olopatadine, the mean apparent volume of distribution was 133.83 L.5

Protein binding

About 55% of total olopatadine is bound to human serum proteins, with serum albumin being the primary protein of binding.8

Metabolism

Olopatadine undergoes hepatic metabolism in a non-extensive manner.8,9 Based on oral pharmacokinetic studies, there are at least 6 circulating metabolites in human plasma.8 Following topical ocular application of olopatadine, olopatadine N-oxide is formed by metabolism catalyzed by flavin-containing monooxygenase (FMO) 1 and 3 8 and was detected in the plasma after 4 hours post-dosing in less than 10% of the total plasma in half of the patients.7 Mono-desmethyl olopatadine, or N-desmethyl olopatadine, is formed by CYP3A4 8 and may be detected in minimal levels.7

Hover over products below to view reaction partners

Route of elimination

Olopatadine is mainly eliminated through urinary excretion. Following oral administration, about 70% and 17% of the total dose was recovered in the urine and feces, respectively.8

Half-life

Following ocular administration, the elimination half-life of olopatadine was 3.4 ± 1.2 hours. In oral pharmacokinetics study, the elimination half-life was reported to be 8 to 12 hours.9

Clearance

In an open-label study consisting of healthy Chinese subjects receiving oral administration of olopatadine, the mean apparent oral clearance (CL/F) was 23.45 L/h.5

Adverse Effects
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Toxicity

Based on the findings of an acute toxicity study in animals, the oral LD50 of olopatadine was >1150 mg/kg in mice and >3870 mg/kg in rats.10 The Lowest published toxic dose via the oral route was 20 mg/kg in rat and 0.1 mg/kg in mouse.MSDS

There are no known reports on overdosage following oral, ophthalmic, or intranasal administration of olopatadine. Likely symptoms of antihistamine overdose may include drowsiness in adults and, initially, agitation and restlessness, followed by drowsiness in children. In case of suspected overdose, supportive and symptomatic treatment is recommended.8

Pathways
PathwayCategory
Olopatadine 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
OxymetazolineThe absorption of Olopatadine can be decreased when combined with Oxymetazoline.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Olopatadine hydrochloride2XG66W44KF140462-76-6HVRLZEKDTUEKQH-NOILCQHBSA-N
International/Other Brands
Alchek (Apex) / Alerchek (Indoco) / Allelock (Dae Woong) / Patanol S (Alcon)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Act Olopatadine 0.1%Solution0.1 % w/vOphthalmicTEVA Canada Limited2013-12-062021-07-30Canada flag
Act Olopatadine 0.2%Solution0.2 % w/vOphthalmicTEVA Canada Limited2014-02-202021-07-30Canada flag
OlopatadineSolution0.1 % w/vOphthalmicSanis Health Inc2022-07-13Not applicableCanada flag
Olopatadine 0.2%Solution0.2 % w/vOphthalmicSanis Health IncNot applicableNot applicableCanada flag
Olopatadine Hydrochloride NasalSpray665 ug/1NasalPerrigo New York Inc.2015-04-012018-02-01US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-olopatadineSolution0.1 %OphthalmicApotex Corporation2013-07-26Not applicableCanada flag
Apo-olopatadineSolution0.2 % w/vOphthalmicApotex Corporation2014-04-10Not applicableCanada flag
Jamp-olopatadineSolution0.1 % w/vOphthalmicJamp Pharma Corporation2017-10-06Not applicableCanada flag
Mint-olopatadineSolution0.1 % w/vOphthalmicMint Pharmaceuticals Inc2014-07-29Not applicableCanada flag
Mint-olopatadine 0.2%Solution0.2 % w/vOphthalmicMint Pharmaceuticals Inc2021-12-17Not applicableCanada flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Clear Eyes Once Daily Eye Allergy Itch ReliefSolution / drops2 mg/1mLOphthalmicPrestige Brands Holdings, Inc.2021-09-15Not applicableUS flag
CVS Eye Allergy Itch Relief Once DailySolution2 mg/1mLOphthalmicCVS HEALTH CORP2020-09-20Not applicableUS flag
CVS Eye Allergy Itch Relief Twice DailySolution / drops1 mg/1mLOphthalmicCVS HEALTH CORP2020-09-20Not applicableUS flag
Eye Allergy Itch and Redness ReliefSolution / drops1 mg/1mLOphthalmicStrategic Sourcing Services LLC2021-03-15Not applicableUS flag
Eye Allergy Itch and Redness ReliefSolution / drops1 mg/1mLOphthalmicStrategic Sourcing Specialists, LLC2021-03-15Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
OFNOL FRESH % 0.1 + %0.15 STERİL OFTALMİK ÇÖZELTİ, 1 ADETOlopatadine hydrochloride (1.11 mg/mL) + Sodium hyaluronate (1.5 mg/mL)SolutionOphthalmicABDİ İBRAHİM İLAÇ SAN. VE TİC. A.Ş.2017-07-06Not applicableTurkey flag
RyaltrisOlopatadine hydrochloride (665 ug/1) + Mometasone furoate monohydrate (25 ug/1)Spray, meteredNasalHikma Specialty USA Inc.2022-08-15Not applicableUS flag
RyaltrisOlopatadine hydrochloride (665 mcg / act) + Mometasone furoate monohydrate (25 mcg / act)Spray, meteredNasalGlenmark Specialty Sa2023-03-17Not applicableCanada flag

Categories

ATC Codes
S01GX09 — OlopatadineR01AC08 — Olopatadine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as dibenzoxepines. These are compounds containing a dibenzoxepine moiety, which consists of two benzene connected by an oxazepine ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzoxepines
Sub Class
Dibenzoxepines
Direct Parent
Dibenzoxepines
Alternative Parents
Alkyl aryl ethers / Benzenoids / Trialkylamines / Amino acids / Oxacyclic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Alkyl aryl ether / Amine / Amino acid / Amino acid or derivatives / Aromatic heteropolycyclic compound / Benzenoid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Dibenzoxepine
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
D27V6190PM
CAS number
113806-05-6
InChI Key
JBIMVDZLSHOPLA-LSCVHKIXSA-N
InChI
InChI=1S/C21H23NO3/c1-22(2)11-5-8-18-17-7-4-3-6-16(17)14-25-20-10-9-15(12-19(18)20)13-21(23)24/h3-4,6-10,12H,5,11,13-14H2,1-2H3,(H,23,24)/b18-8-
IUPAC Name
2-[(2Z)-2-[3-(dimethylamino)propylidene]-9-oxatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3(8),4,6,11,13-hexaen-5-yl]acetic acid
SMILES
CN(C)CC\C=C1\C2=CC=CC=C2COC2=C1C=C(CC(O)=O)C=C2

References

Synthesis Reference

Thomas Bader, Hans-Ulrich Bichsel, Bruno Gilomen, Imelda Meyer-Wilmes, Mark Sundermeier, "Polymorphic forms of olopatadine hydrochloride and methods for producing olopatadine and salts thereof." U.S. Patent US20070232814, issued October 04, 2007.

US20070232814
General References
  1. Ohmori K, Hayashi K, Kaise T, Ohshima E, Kobayashi S, Yamazaki T, Mukouyama A: Pharmacological, pharmacokinetic and clinical properties of olopatadine hydrochloride, a new antiallergic drug. Jpn J Pharmacol. 2002 Apr;88(4):379-97. [Article]
  2. Ohmori K, Hasegawa K, Tamura T, Miyake K, Matsubara M, Masaki S, Karasawa A, Urayama N, Horikoshi K, Kajita J, Hasegawa M, Taniguchi K, Komada T, Kawamoto Y: Properties of olopatadine hydrochloride, a new antiallergic/antihistaminic drug. Arzneimittelforschung. 2004;54(12):809-29. [Article]
  3. Rosenwasser LJ, O'Brien T, Weyne J: Mast cell stabilization and anti-histamine effects of olopatadine ophthalmic solution: a review of pre-clinical and clinical research. Curr Med Res Opin. 2005 Sep;21(9):1377-87. doi: 10.1185/030079905X56547. [Article]
  4. Branco ACCC, Yoshikawa FSY, Pietrobon AJ, Sato MN: Role of Histamine in Modulating the Immune Response and Inflammation. Mediators Inflamm. 2018 Aug 27;2018:9524075. doi: 10.1155/2018/9524075. eCollection 2018. [Article]
  5. Chu NN, Chen WL, Xu HR, Li XN: Pharmacokinetics of orally administered single- and multiple-dose olopatadine in healthy Chinese subjects: an open-label study. Clin Drug Investig. 2009;29(7):451-457. doi: 10.2165/00044011-200929070-00003. [Article]
  6. Lichtenstein SJ, Abelson MB: Pharmacology, clinical efficacy and safety of olopatadine hydrochloride. Expert Rev Clin Immunol. 2006 May;2(3):341-51. doi: 10.1586/1744666X.2.3.341. [Article]
  7. FDA Approved Drug Products: PAZEO (olopatadine hydrochloride) ophthalmic solution [Link]
  8. FDA Approved Drug Products: PATANASE (olopatadine hydrochloride) Nasal Spray [Link]
  9. Opatanol, INN-olopatadine - European Medicines Agency - Europa EU [Link]
  10. OLOPATADINE - Product Monograph - Sandoz Canada Inc. [Link]
  11. Patanol (olopatadine hydrochloride ophthalmic solution) 0.1% - FDA Label [Link]
  12. FDA Approved Drug Products: Ryaltris (olopatadine hydrochloride/mometasone furoate monohydrate) nasal spray [Link]
  13. Health Canada Approved Drug Proucts: Ryaltris (olopatadine hydrochloride/mometasone furoate monohydrate) nasal spray [Link]
Human Metabolome Database
HMDB0014906
KEGG Compound
C07789
PubChem Compound
5281071
PubChem Substance
46506025
ChemSpider
4444528
BindingDB
50002096
RxNav
135391
ChEMBL
CHEMBL1189432
ZINC
ZINC000000001850
Therapeutic Targets Database
DAP001062
PharmGKB
PA450698
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Olopatadine
MSDS
Download (26.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableAllergic Conjunctivitis (AC)1
4CompletedNot AvailableSeasonal Allergic Rhinitis1
4CompletedDiagnosticAllergic Conjunctivitis (AC)2
4CompletedPreventionAllergic Conjunctivitis (AC)1
4CompletedTreatmentAllergic Conjunctivitis (AC)13

Pharmacoeconomics

Manufacturers
  • Alcon inc
  • Alcon laboratories inc
  • Alcon Laboratories, Inc.
Packagers
  • Alcon Laboratories
  • A-S Medication Solutions LLC
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Lake Erie Medical and Surgical Supply
  • Physicians Total Care Inc.
  • Redpharm Drug
Dosage Forms
FormRouteStrength
SolutionConjunctival; Ophthalmic2 mg
SolutionOphthalmic7 mg
SolutionOphthalmic700000 mg
SolutionOphthalmic1.00 mg/ml
SolutionOphthalmic2.00 mg/ml
SolutionOphthalmic0.1 %
SolutionConjunctival; Ophthalmic1 mg
Solution / dropsOphthalmic0.1 %
SolutionOphthalmic2.216 mg
SolutionOphthalmic2.000 mg
SolutionOphthalmic
Solution / dropsOphthalmic0.2 %
SolutionOphthalmic2 mg
SprayNasal6.65 mg/ml
Solution / dropsOphthalmic0.1 % w/v
SolutionOphthalmic1.000 mg
SolutionIntrasinal; Nasal600 mg
Solution / dropsOphthalmic1 mg/ml
SolutionOphthalmic1 mg
SolutionOphthalmic100000 mg
SolutionIntraocular; Ophthalmic2 mg
Solution / dropsOphthalmic1.0 mg/1mL
Solution / dropsOphthalmic2.0 mg/1mL
PowderNot applicable1 kg/1kg
SolutionOphthalmic2 mg/1mL
Solution / dropsOphthalmic1.11 mg/1mL
Spray, meteredNasal665 ug/100uL
SprayNasal665 ug/1
SolutionNot applicable2 mg/1mL
Tablet, coatedOral2.5 mg
Tablet, coatedOral5 mg
SolutionConjunctival; Ophthalmic200000 mg
SprayNasal6.65 %
Solution / dropsOphthalmic2 mg/1mL
SolutionOphthalmic1 mg/1mL
SolutionOphthalmic0.2 % w/v
Spray, meteredNasal600 ug/1
Spray, meteredNasal665 ug/1
Solution / dropsOphthalmic1 mg/1mL
SolutionOphthalmic0.2 %
SolutionOphthalmic1 mg/ml
SolutionOphthalmic; Topical2 mg
SolutionOphthalmic0.7 % w/v
SolutionOphthalmic7 mg/1mL
Solution / dropsOphthalmic
Solution / dropsOphthalmic7 mg/1ml
SolutionOphthalmic0.7 %
SolutionOphthalmic; Topical7.76 mg
SolutionOphthalmic1.108 mg
Spray, meteredNasal
SolutionOphthalmic0.1 % w/v
SolutionOphthalmic2.220 mg
SolutionConjunctival; Ophthalmic0.2 g
Prices
Unit descriptionCostUnit
Patanol 0.1% Solution 5ml Bottle111.2USD bottle
Pataday 0.2% eye drops52.98USD ml
Patanol 0.1% eye drops21.38USD ml
Patanase 0.6% nasal spray3.83USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5116863No1992-05-262010-12-18US flag
CA2195094No2002-02-262016-05-03Canada flag
CA1337603No1995-11-212012-11-21Canada flag
US6995186Yes2006-02-072024-05-12US flag
US7402609Yes2008-07-222022-12-19US flag
US8399508Yes2013-03-192023-03-17US flag
US7977376Yes2011-07-122023-08-02US flag
US8791154No2014-07-292032-05-19US flag
US5641805Yes1997-06-242015-12-06US flag
US9533053No2017-01-032032-05-19US flag
US10765686No2020-09-082034-09-04US flag
US10758550No2020-09-012034-09-04US flag
US10646500No2020-05-122034-09-04US flag
US10548907No2020-02-042034-09-04US flag
US10016443No2018-07-102034-09-04US flag
US10517880No2019-12-312034-09-04US flag
US9750754No2017-09-052034-09-04US flag
US9078923No2015-07-142034-09-04US flag
US9937189No2018-04-102034-09-04US flag
US10376526No2019-08-132034-09-04US flag
US9370483No2016-06-212034-09-04US flag
US10561672No2020-02-182034-09-04US flag
US11400101No2014-09-042034-09-04US flag
US11679210No2018-09-032038-09-03US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0313 mg/mLALOGPS
logP3.99ALOGPS
logP0.75Chemaxon
logS-4ALOGPS
pKa (Strongest Acidic)3.78Chemaxon
pKa (Strongest Basic)9.76Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area49.77 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity109.55 m3·mol-1Chemaxon
Polarizability37.44 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9747
Blood Brain Barrier+0.6925
Caco-2 permeable+0.7249
P-glycoprotein substrateSubstrate0.8607
P-glycoprotein inhibitor IInhibitor0.5948
P-glycoprotein inhibitor IINon-inhibitor0.8196
Renal organic cation transporterInhibitor0.5413
CYP450 2C9 substrateNon-substrate0.7691
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.7242
CYP450 1A2 substrateInhibitor0.7906
CYP450 2C9 inhibitorNon-inhibitor0.8316
CYP450 2D6 inhibitorInhibitor0.6567
CYP450 2C19 inhibitorNon-inhibitor0.8466
CYP450 3A4 inhibitorNon-inhibitor0.8222
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8676
Ames testNon AMES toxic0.8032
CarcinogenicityNon-carcinogens0.8499
BiodegradationNot ready biodegradable0.6088
Rat acute toxicity2.7626 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8082
hERG inhibition (predictor II)Inhibitor0.5
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-MSsplash10-0a4i-9041000000-136cb3971a95366a26d3
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0006-0090000000-8e3ac3f01c9b0f33191f
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0007-0090000000-ff327751665292322357
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00ke-0190000000-4ee44c0a1808c8f38f5f
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-014l-0490000000-af62db4d573fa623449b
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-014l-0690000000-855734373da970ef9009
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-014l-0970000000-10c3777ced99134b4960
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0009000000-edd957bf788fa0da1cd5
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0019000000-76019801740d70094185
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00kk-0593000000-0fb46422a259d1710df5
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-016s-0690000000-d2686bcc07833ec6a7c5
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0fw9-0690000000-20403692a9e2a6948063
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000i-0009000000-e2c029010aa3133274f8
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000i-1239000000-a4a1f419cb7782a025ae
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-015a-4890000000-5408d5e1274f9ec8ab42
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00lu-4970000000-5d3cad1a8e8d0b931c62
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00lu-4960000000-d57d90bc4e9b3f57c2fa
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0frx-5960000000-9b3e25cd1765878b5709
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-0469000000-a0b3c5cdd43e637acdec
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000l-0069000000-f6d969499ea492511ec5
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-1009000000-894ec6dcec6d6bf633f0
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000e-0092000000-9e0b51a0a42875e9bf72
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000m-0095000000-701d7923a690f475dd81
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-05as-1091000000-ddbab97af6cf793293c5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00uu-3192000000-5425ec5ce5117c932993
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]-197.8976199
predicted
DarkChem Lite v0.1.0
[M-H]-180.20973
predicted
DeepCCS 1.0 (2019)
[M+H]+198.3578199
predicted
DarkChem Lite v0.1.0
[M+H]+182.56772
predicted
DeepCCS 1.0 (2019)
[M+Na]+197.8179199
predicted
DarkChem Lite v0.1.0
[M+Na]+189.47931
predicted
DeepCCS 1.0 (2019)

Targets

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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. 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]
  2. Ohmori K, Hayashi K, Kaise T, Ohshima E, Kobayashi S, Yamazaki T, Mukouyama A: Pharmacological, pharmacokinetic and clinical properties of olopatadine hydrochloride, a new antiallergic drug. Jpn J Pharmacol. 2002 Apr;88(4):379-97. [Article]
  3. Yanni JM, Stephens DJ, Miller ST, Weimer LK, Graff G, Parnell D, Lang LS, Spellman JM, Brady MT, Gamache DA: The in vitro and in vivo ocular pharmacology of olopatadine (AL-4943A), an effective anti-allergic/antihistaminic agent. J Ocul Pharmacol Ther. 1996 Winter;12(4):389-400. [Article]
  4. Ohmori K, Hasegawa K, Tamura T, Miyake K, Matsubara M, Masaki S, Karasawa A, Urayama N, Horikoshi K, Kajita J, Hasegawa M, Taniguchi K, Komada T, Kawamoto Y: Properties of olopatadine hydrochloride, a new antiallergic/antihistaminic drug. Arzneimittelforschung. 2004;54(12):809-29. [Article]
  5. Ohmori K, Ikemura T, Kobayashi H, Mukouyama A: [Pharmacological, pharmacokinetic and clinical properties of olopatadine hydrochloride' (olopatadine), an antiallergic drug]. Nihon Yakurigaku Zasshi. 2001 Jul;118(1):51-8. [Article]
  6. Roland PS, Ryan MW, Wall GM: Olopatadine nasal spray for the treatment of seasonal allergic rhinitis in patients aged 6 years and older. Expert Opin Pharmacother. 2010 Jun;11(9):1559-67. doi: 10.1517/14656566.2010.485609. [Article]
  7. Kaliner MA, Oppenheimer J, Farrar JR: Comprehensive review of olopatadine: the molecule and its clinical entities. Allergy Asthma Proc. 2010 Mar-Apr;31(2):112-9. doi: 10.2500/aap.2010.31.3317. [Article]
  8. Roland PS, Marple BF, Wall GM: Olopatadine nasal spray for the treatment of allergic rhinitis. Expert Rev Clin Immunol. 2010 Mar;6(2):197-204. [Article]
  9. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Histamine receptor activity
Specific Function
The H2 subclass of histamine receptors mediates gastric acid secretion. Also appears to regulate gastrointestinal motility and intestinal secretion. Possible role in regulating cell growth and diff...
Gene Name
HRH2
Uniprot ID
P25021
Uniprot Name
Histamine H2 receptor
Molecular Weight
40097.65 Da
References
  1. Rosenwasser LJ, O'Brien T, Weyne J: Mast cell stabilization and anti-histamine effects of olopatadine ophthalmic solution: a review of pre-clinical and clinical research. Curr Med Res Opin. 2005 Sep;21(9):1377-87. doi: 10.1185/030079905X56547. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Histamine receptor activity
Specific Function
The H3 subclass of histamine receptors could mediate the histamine signals in CNS and peripheral nervous system. Signals through the inhibition of adenylate cyclase and displays high constitutive a...
Gene Name
HRH3
Uniprot ID
Q9Y5N1
Uniprot Name
Histamine H3 receptor
Molecular Weight
48670.81 Da
References
  1. Rosenwasser LJ, O'Brien T, Weyne J: Mast cell stabilization and anti-histamine effects of olopatadine ophthalmic solution: a review of pre-clinical and clinical research. Curr Med Res Opin. 2005 Sep;21(9):1377-87. doi: 10.1185/030079905X56547. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
S100 protein binding
Specific Function
Weakly binds calcium but binds zinc very tightly-distinct binding sites with different affinities exist for both ions on each monomer. Physiological concentrations of potassium ion antagonize the b...
Gene Name
S100A1
Uniprot ID
P23297
Uniprot Name
Protein S100-A1
Molecular Weight
10545.755 Da
References
  1. Okada M, Tokumitsu H, Kubota Y, Kobayashi R: Interaction of S100 proteins with the antiallergic drugs, olopatadine, amlexanox, and cromolyn: identification of putative drug binding sites on S100A1 protein. Biochem Biophys Res Commun. 2002 Apr 12;292(4):1023-30. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Zinc ion binding
Specific Function
S100A12 is a calcium-, zinc- and copper-binding protein which plays a prominent role in the regulation of inflammatory processes and immune response. Its proinflammatory activity involves recruitme...
Gene Name
S100A12
Uniprot ID
P80511
Uniprot Name
Protein S100-A12
Molecular Weight
10574.975 Da
References
  1. Kishimoto K, Kaneko S, Ohmori K, Tamura T, Hasegawa K: Olopatadine suppresses the migration of THP-1 monocytes induced by S100A12 protein. Mediators Inflamm. 2006;2006(1):42726. [Article]
  2. Okada M, Tokumitsu H, Kubota Y, Kobayashi R: Interaction of S100 proteins with the antiallergic drugs, olopatadine, amlexanox, and cromolyn: identification of putative drug binding sites on S100A1 protein. Biochem Biophys Res Commun. 2002 Apr 12;292(4):1023-30. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Other/unknown
General Function
Zinc ion binding
Specific Function
Weakly binds calcium but binds zinc very tightly-distinct binding sites with different affinities exist for both ions on each monomer. Physiological concentrations of potassium ion antagonize the b...
Gene Name
S100B
Uniprot ID
P04271
Uniprot Name
Protein S100-B
Molecular Weight
10712.985 Da
References
  1. Okada M, Tokumitsu H, Kubota Y, Kobayashi R: Interaction of S100 proteins with the antiallergic drugs, olopatadine, amlexanox, and cromolyn: identification of putative drug binding sites on S100A1 protein. Biochem Biophys Res Commun. 2002 Apr 12;292(4):1023-30. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Other/unknown
General Function
Zinc ion binding
Specific Function
Plays a role in the export of proteins that lack a signal peptide and are secreted by an alternative pathway. Binds two calcium ions per subunit. Binds one copper ion. Binding of one copper ion doe...
Gene Name
S100A13
Uniprot ID
Q99584
Uniprot Name
Protein S100-A13
Molecular Weight
11471.095 Da
References
  1. Okada M, Tokumitsu H, Kubota Y, Kobayashi R: Interaction of S100 proteins with the antiallergic drugs, olopatadine, amlexanox, and cromolyn: identification of putative drug binding sites on S100A1 protein. Biochem Biophys Res Commun. 2002 Apr 12;292(4):1023-30. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Identical protein binding
Specific Function
May function as calcium sensor and modulator, contributing to cellular calcium signaling. May function by interacting with other proteins, such as TPR-containing proteins, and indirectly play a rol...
Gene Name
S100A2
Uniprot ID
P29034
Uniprot Name
Protein S100-A2
Molecular Weight
11116.695 Da
References
  1. Okada M, Tokumitsu H, Kubota Y, Kobayashi R: Interaction of S100 proteins with the antiallergic drugs, olopatadine, amlexanox, and cromolyn: identification of putative drug binding sites on S100A1 protein. Biochem Biophys Res Commun. 2002 Apr 12;292(4):1023-30. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
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. Kajita J, Inano K, Fuse E, Kuwabara T, Kobayashi H: Effects of olopatadine, a new antiallergic agent, on human liver microsomal cytochrome P450 activities. Drug Metab Dispos. 2002 Dec;30(12):1504-11. doi: 10.1124/dmd.30.12.1504. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Nadp binding
Specific Function
This protein is involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. Form I catalyzes the N-oxygenation of secondary and tertiary amines.
Gene Name
FMO1
Uniprot ID
Q01740
Uniprot Name
Dimethylaniline monooxygenase [N-oxide-forming] 1
Molecular Weight
60310.285 Da
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Trimethylamine monooxygenase activity
Specific Function
Involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. It N-oxygenates primary aliphatic alkylamines as well as secondary and tertiary amines. Plays an impor...
Gene Name
FMO3
Uniprot ID
P31513
Uniprot Name
Dimethylaniline monooxygenase [N-oxide-forming] 3
Molecular Weight
60032.975 Da

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
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

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
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. Mimura N, Nagata Y, Kuwabara T, Kubo N, Fuse E: P-glycoprotein limits the brain penetration of olopatadine hydrochloride, H1-receptor antagonist. Drug Metab Pharmacokinet. 2008;23(2):106-14. [Article]

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