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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:47 UTC
HMDB IDHMDB0014906
Secondary Accession Numbers
  • HMDB14906
Metabolite Identification
Common NameOlopatadine
DescriptionOlopatadine, also known as opatanol, belongs to the class of organic compounds known as dibenzoxepines. Dibenzoxepines are compounds containing a dibenzoxepine moiety, which consists of two benzene connected by an oxazepine ring. Olopatadine is a very strong basic compound (based on its pKa). In humans, olopatadine is involved in olopatadine h1-antihistamine action. In 2016 it was the 269th most prescribed medication in the United States with more than a million prescriptions. Olopatadine is a potentially toxic compound. It is unclear if use during pregnancy or breastfeeding is safe. Pataday – now Pataday Once Daily Relief – was first approved by the FDA in 2004, as a prescription drug and was indicated for the treatment of ocular itching associated with allergic conjunctivitis. These drugs are mast cell stabilizers, which work by preventing the release of histamine and therefore prevent or control allergic disorders. Common side effects include headache, sore throat, eye discomfort, change in taste.
Structure
Data?1582753234
Synonyms
ValueSource
OpatanolHMDB
11-(3-(Dimethylamino)propylidene)-6,11-dihydrodibenz(b,e)oxepin-2-acetic acidHMDB
Hydrochloride, olopatadineHMDB
PatanolHMDB
Olopatadine hydrochlorideHMDB
Chemical FormulaC21H23NO3
Average Molecular Weight337.4122
Monoisotopic Molecular Weight337.167793607
IUPAC Name2-[(2Z)-2-[3-(dimethylamino)propylidene]-9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaen-5-yl]acetic acid
Traditional Namepatanol
CAS Registry Number113806-05-6
SMILES
CN(C)CC\C=C1\C2=CC=CC=C2COC2=C1C=C(CC(O)=O)C=C2
InChI Identifier
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-
InChI KeyJBIMVDZLSHOPLA-LSCVHKIXSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dibenzoxepines. Dibenzoxepines are compounds containing a dibenzoxepine moiety, which consists of two benzene connected by an oxazepine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzoxepines
Sub ClassDibenzoxepines
Direct ParentDibenzoxepines
Alternative Parents
Substituents
  • Dibenzoxepine
  • Alkyl aryl ether
  • Benzenoid
  • Amino acid or derivatives
  • Amino acid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point248 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.031 g/LNot Available
LogP3.4Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.031 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 Area49.77 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity109.55 m³·mol⁻¹ChemAxon
Polarizability37.44 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+182.02631661259
DarkChem[M-H]-180.79931661259
DeepCCS[M+H]+179.81630932474
DeepCCS[M-H]-177.45830932474
DeepCCS[M-2H]-211.10730932474
DeepCCS[M+Na]+186.33430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
OlopatadineCN(C)CC\C=C1\C2=CC=CC=C2COC2=C1C=C(CC(O)=O)C=C24277.8Standard polar33892256
OlopatadineCN(C)CC\C=C1\C2=CC=CC=C2COC2=C1C=C(CC(O)=O)C=C22650.2Standard non polar33892256
OlopatadineCN(C)CC\C=C1\C2=CC=CC=C2COC2=C1C=C(CC(O)=O)C=C22727.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Olopatadine,1TMS,isomer #1CN(C)CC/C=C1/C2=CC=CC=C2COC2=CC=C(CC(=O)O[Si](C)(C)C)C=C122897.5Semi standard non polar33892256
Olopatadine,1TBDMS,isomer #1CN(C)CC/C=C1/C2=CC=CC=C2COC2=CC=C(CC(=O)O[Si](C)(C)C(C)(C)C)C=C123147.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Olopatadine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9041000000-136cb3971a95366a26d32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Olopatadine GC-MS (1 TMS) - 70eV, Positivesplash10-0a4l-9013000000-f00dcdbf6710dd3469172017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Olopatadine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Olopatadine LC-ESI-QFT , negative-QTOFsplash10-0006-0090000000-8e3ac3f01c9b0f33191f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Olopatadine LC-ESI-QFT , negative-QTOFsplash10-0007-0090000000-ff3277516652923223572017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Olopatadine LC-ESI-QFT , negative-QTOFsplash10-00ke-0190000000-4ee44c0a1808c8f38f5f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Olopatadine LC-ESI-QFT , negative-QTOFsplash10-014l-0490000000-af62db4d573fa623449b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Olopatadine LC-ESI-QFT , negative-QTOFsplash10-014l-0690000000-855734373da970ef90092017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Olopatadine LC-ESI-QFT , negative-QTOFsplash10-014l-0970000000-10c3777ced99134b49602017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Olopatadine LC-ESI-QTOF , positive-QTOFsplash10-000i-0009000000-edd957bf788fa0da1cd52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Olopatadine LC-ESI-QTOF , positive-QTOFsplash10-000i-0019000000-76019801740d700941852017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Olopatadine LC-ESI-QTOF , positive-QTOFsplash10-00kk-0593000000-0fb46422a259d1710df52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Olopatadine LC-ESI-QTOF , positive-QTOFsplash10-016s-0690000000-d2686bcc07833ec6a7c52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Olopatadine LC-ESI-QTOF , positive-QTOFsplash10-0fw9-0690000000-20403692a9e2a69480632017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Olopatadine LC-ESI-QFT , positive-QTOFsplash10-000i-0009000000-e2c029010aa3133274f82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Olopatadine LC-ESI-QFT , positive-QTOFsplash10-000i-1239000000-a4a1f419cb7782a025ae2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Olopatadine LC-ESI-QFT , positive-QTOFsplash10-015a-4890000000-5408d5e1274f9ec8ab422017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Olopatadine LC-ESI-QFT , positive-QTOFsplash10-00lu-4970000000-5d3cad1a8e8d0b931c622017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Olopatadine LC-ESI-QFT , positive-QTOFsplash10-00lu-4960000000-d57d90bc4e9b3f57c2fa2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Olopatadine LC-ESI-QFT , positive-QTOFsplash10-0frx-5960000000-9b3e25cd1765878b57092017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Olopatadine , positive-QTOFsplash10-000i-0469000000-a0b3c5cdd43e637acdec2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Olopatadine 50V, Positive-QTOFsplash10-0fw9-0690000000-92c72fcd463bddb69fb72021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olopatadine 10V, Positive-QTOFsplash10-007c-0069000000-ad075b60f53c626584de2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olopatadine 20V, Positive-QTOFsplash10-0006-1092000000-e65d348c335d8045bdc42016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olopatadine 40V, Positive-QTOFsplash10-001i-5390000000-0f51723c50125d077c1a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olopatadine 10V, Negative-QTOFsplash10-000l-0059000000-41a44e955bced08fbc6f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olopatadine 20V, Negative-QTOFsplash10-000f-3098000000-a4e2e92bce8c77bb39a42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olopatadine 40V, Negative-QTOFsplash10-0a4i-9372000000-9b0ceee49e37310536022016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00768 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00768 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00768
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4444528
KEGG Compound IDC07789
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOlopatadine
METLIN IDNot Available
PubChem Compound5281071
PDB IDNot Available
ChEBI ID763382
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
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. [PubMed:12046981 ]
  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:8951675 ]
  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:15646365 ]
  4. 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. [PubMed:11496828 ]
  5. 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. [PubMed:20406593 ]

Enzymes

General function:
Involved in monooxygenase 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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
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 catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:
HRH1
Uniprot ID:
P35367
Molecular weight:
55783.6
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:15942272 ]
  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:12046981 ]
  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:8951675 ]
  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:15646365 ]
  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. [PubMed:11496828 ]
  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. [PubMed:20482305 ]
  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. [PubMed:20406593 ]
  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:20402382 ]
  9. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in calcium 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 binding of both divalent cations, especially affecting high-affinity calcium-binding sites. Binds to and initiates the activation of STK38 by releasing autoinhibitory intramolecular interactions within the kinase. Interaction with AGER after myocardial infarction may play a role in myocyte apoptosis by activating ERK1/2 and p53/TP53 signaling
Gene Name:
S100B
Uniprot ID:
P04271
Molecular weight:
10713.0
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:11944917 ]
General function:
Involved in calcium 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 binding of both divalent cations, especially affecting high-affinity calcium-binding sites
Gene Name:
S100A1
Uniprot ID:
P23297
Molecular weight:
10545.8
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:11944917 ]
General function:
Involved in calcium ion binding
Specific function:
May act as a modulator against excess calcium accumulation in normal human mammary epithelial cells. May also play a role in suppressing tumor cell growth
Gene Name:
S100A2
Uniprot ID:
P29034
Molecular weight:
11116.7
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:11944917 ]