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Identification
NameOlopatadine
Accession NumberDB00768  (APRD00310)
Typesmall molecule
Groupsapproved
Description

Used to treat allergic conjunctivitis (itching eyes), olopatadine inhibits the release of histamine from mast cells. It is a relatively selective histamine H1 antagonist that inhibits the in vivo and in vitro type 1 immediate hypersensitivity reaction including inhibition of histamine induced effects on human conjunctival epithelial cells.

Structure
Thumb
Synonyms
SynonymLanguageCode
OlopatadinGermanINN
OlopatadinaSpanishINN
OlopatadineFrenchINN
OlopatadinumLatinINN
Salts
Name/CAS Structure Properties
Olopatadine Hydrochloride
Thumb
  • InChI Key: HVRLZEKDTUEKQH-NOILCQHBSA-N
  • Monoisotopic Mass: 373.144471346
  • Average Mass: 373.873
DBSALT000685
Brand names
NameCompany
AlchekApex
AlerchekIndoco
AllelockDae Woong
OpatanolAlcon
PatadayAlcon
PatanaseAlcon
PatanolAlcon
Patanol SAlcon
Brand mixturesNot Available
Categories
CAS number113806-05-6
WeightAverage: 337.4122
Monoisotopic: 337.167793607
Chemical FormulaC21H23NO3
InChI KeyInChIKey=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(11),3(8),4,6,12,14-hexaen-5-yl]acetic acid
SMILES
CN(C)CC\C=C1\C2=CC=CC=C2COC2=C1C=C(CC(O)=O)C=C2
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassBenzoxepines
SubclassDibenzoxepines
Direct parentDibenzoxepines
Alternative parentsAlkyl Aryl Ethers; Benzene and Substituted Derivatives; Tertiary Amines; Carboxylic Acids; Polyamines; Enolates
Substituentsalkyl aryl ether; benzene; tertiary amine; polyamine; enolate; carboxylic acid derivative; carboxylic acid; ether; amine; organonitrogen compound
Classification descriptionThis compound belongs to the dibenzoxepines. These are compounds containing a dibenzoxepine moiety, which consists of two benzene connected by an oxazepine ring.
Pharmacology
IndicationFor the treatment of ocular itching associated with allergic conjunctivitis.
PharmacodynamicsUsed to treat allergic conjunctivitis (itching eyes), olopatadine inhibits the release of histamine from mast cells. It is a relatively selective histamine H1 antagonist that inhibits the in vivo and in vitro type 1 immediate hypersensitivity reaction including inhibition of histamine induced effects on human conjunctival epithelial cells.
Mechanism of actionOlopatadine is a selective histamine H1 antagonist that binds to the histamine H1 receptor. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine. Olopatadine is devoid of effects on alpha-adrenergic, dopamine and muscarinic type 1 and 2 receptors.
AbsorptionOphthalmic use of olopatadine usually does not produce measurable plasma concentrations.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

The mono-desmethyl and the N-oxide metabolites have been detected at low concentrations in the urine.

SubstrateEnzymesProduct
Olopatadine
    Mono-desmethyl olopatadineDetails
    Olopatadine
      Olopatadine n-oxideDetails
      Route of eliminationElimination was predominantly through renal excretion.
      Half life3 hours
      ClearanceNot Available
      ToxicityNot Available
      Affected organisms
      • Humans and other mammals
      PathwaysNot Available
      SNP Mediated EffectsNot Available
      SNP Mediated Adverse Drug ReactionsNot Available
      ADMET
      Predicted ADMET features
      Property Value Probability
      Human Intestinal Absorption + 0.9747
      Blood Brain Barrier + 0.6925
      Caco-2 permeable + 0.7249
      P-glycoprotein substrate Substrate 0.8607
      P-glycoprotein inhibitor I Inhibitor 0.5948
      P-glycoprotein inhibitor II Non-inhibitor 0.8196
      Renal organic cation transporter Inhibitor 0.5413
      CYP450 2C9 substrate Non-substrate 0.7691
      CYP450 2D6 substrate Non-substrate 0.9116
      CYP450 3A4 substrate Substrate 0.7242
      CYP450 1A2 substrate Inhibitor 0.7906
      CYP450 2C9 substrate Non-inhibitor 0.8316
      CYP450 2D6 substrate Inhibitor 0.6567
      CYP450 2C19 substrate Non-inhibitor 0.8466
      CYP450 3A4 substrate Non-inhibitor 0.8222
      CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8676
      Ames test Non AMES toxic 0.8032
      Carcinogenicity Non-carcinogens 0.8499
      Biodegradation Not ready biodegradable 0.6088
      Rat acute toxicity 2.7626 LD50, mol/kg Not applicable
      hERG inhibition (predictor I) Weak inhibitor 0.8082
      hERG inhibition (predictor II) Inhibitor 0.5
      Pharmacoeconomics
      Manufacturers
      • Alcon inc
      • Alcon laboratories inc
      • Alcon Laboratories, Inc.
      Packagers
      Dosage forms
      FormRouteStrength
      LiquidOphthalmic
      Prices
      Unit descriptionCostUnit
      Patanol 0.1% Solution 5ml Bottle111.2USDbottle
      Pataday 0.2% eye drops52.98USDml
      Patanol 0.1% eye drops21.38USDml
      Patanase 0.6% nasal spray3.83USDg
      DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
      Patents
      CountryPatent NumberApprovedExpires (estimated)
      United States69951862004-05-122024-05-12
      United States51168631993-12-182010-12-18
      Canada21950942002-02-262016-05-03
      Canada13376031995-11-212012-11-21
      Properties
      Statesolid
      Experimental Properties
      PropertyValueSource
      melting point248 °CNot Available
      water solubilitySolubleNot Available
      logP3.4Not Available
      Predicted Properties
      PropertyValueSource
      water solubility3.13e-02 g/lALOGPS
      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 area49.77ChemAxon
      rotatable bond count5ChemAxon
      refractivity109.55ChemAxon
      polarizability37.44ChemAxon
      number of rings3ChemAxon
      bioavailability1ChemAxon
      rule of fiveYesChemAxon
      Ghose filterYesChemAxon
      Veber's ruleNoChemAxon
      MDDR-like ruleNoChemAxon
      Spectra
      SpectraNot Available
      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 Reference
      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. Pubmed
      2. 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. Pubmed
      3. 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. Pubmed
      4. Ohmori K, Ikemura T, Kobayashi H, Mukouyama A: [Pharmacological, pharmacokinetic and clinical properties of olopatadine hydrochloride’ (olopatadine), an antiallergic drug] Nippon Yakurigaku Zasshi. 2001 Jul;118(1):51-8. Pubmed
      5. Kaliner MA, Oppenheimer J, Farrar JR: Comprehensive review of olopatadine: the molecule and its clinical entities. Allergy Asthma Proc. 2010 Mar;31(2):112-9. Pubmed
      External Links
      ResourceLink
      KEGG CompoundC07789
      PubChem Compound5281071
      PubChem Substance46506025
      ChemSpider4444528
      Therapeutic Targets DatabaseDAP001062
      PharmGKBPA450698
      Drug Product Database2233143
      RxListhttp://www.rxlist.com/cgi/generic2/olopat.htm
      Drugs.comhttp://www.drugs.com/cdi/olopatadine-spray.html
      PDRhealthhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/pat1633.shtml
      WikipediaOlopatadine
      ATC CodesS01GX09R01AC08
      AHFS Codes
      • 04:00.00
      PDB EntriesNot Available
      FDA labelshow(114 KB)
      MSDSshow(57.6 KB)
      Interactions
      Drug InteractionsSearched, but no interactions found.
      Food InteractionsNot Available

      1. Histamine H1 receptor

      Kind: protein

      Organism: Human

      Pharmacological action: yes

      Actions: antagonist

      Components

      Name UniProt ID Details
      Histamine H1 receptor P35367 Details

      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. Pubmed
      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. Pubmed
      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. Pubmed
      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. Pubmed
      5. Ohmori K, Ikemura T, Kobayashi H, Mukouyama A: [Pharmacological, pharmacokinetic and clinical properties of olopatadine hydrochloride’ (olopatadine), an antiallergic drug] Nippon Yakurigaku Zasshi. 2001 Jul;118(1):51-8. Pubmed
      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. Pubmed
      7. Kaliner MA, Oppenheimer J, Farrar JR: Comprehensive review of olopatadine: the molecule and its clinical entities. Allergy Asthma Proc. 2010 Mar;31(2):112-9. Pubmed
      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. Pubmed
      9. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

      2. Protein S100-A1

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: antagonist

      Components

      Name UniProt ID Details
      Protein S100-A1 P23297 Details

      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. Pubmed

      3. Protein S100-A12

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: antagonist

      Components

      Name UniProt ID Details
      Protein S100-A12 P80511 Details

      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. Pubmed
      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. Pubmed

      4. Protein S100-B

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: other/unknown

      Components

      Name UniProt ID Details
      Protein S100-B P04271 Details

      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. Pubmed

      5. Protein S100-A13

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: other/unknown

      Components

      Name UniProt ID Details
      Protein S100-A13 Q99584 Details

      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. Pubmed

      6. Protein S100-A2

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: antagonist

      Components

      Name UniProt ID Details
      Protein S100-A2 P29034 Details

      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. Pubmed

      1. Cytochrome P450 3A4

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: substrate

      Components

      Name UniProt ID Details
      Cytochrome P450 3A4 P08684 Details

      References:

      1. 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. Epub 2009 Nov 24. Pubmed

      Comments
      Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:12