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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
OpatanolNot AvailableNot Available
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 KeyJBIMVDZLSHOPLA-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
Not Available
Mono-desmethyl olopatadineDetails
Olopatadine
Not Available
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

Targets

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

Enzymes

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

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