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113806-05-6 molecular structure
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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

ChemBase ID: 648
Molecular Formular: C21H23NO3
Molecular Mass: 337.41222
Monoisotopic Mass: 337.1677936
SMILES and InChIs

SMILES:
O1c2c(/C(=C\CCN(C)C)/c3c(C1)cccc3)cc(cc2)CC(=O)O
Canonical SMILES:
CN(CC/C=C/1\c2cc(ccc2OCc2c1cccc2)CC(=O)O)C
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-
InChIKey:
JBIMVDZLSHOPLA-LSCVHKIXSA-N

Cite this record

CBID:648 http://www.chembase.cn/molecule-648.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
IUPAC Traditional name
[(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
Brand Name
Olopatadine Hydrochloride
Patanol
Synonyms
Olopatadine
CAS Number
113806-05-6
PubChem SID
46506025
160964111
PubChem CID
5281071

DATA SOURCES

DATA SOURCES

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Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 3.7840304  H Acceptors
H Donor LogD (pH = 5.5) 0.74022824 
LogD (pH = 7.4) 0.74543273  Log P 0.7462555 
Molar Refractivity 109.5524 cm3 Polarizability 38.300964 Å3
Polar Surface Area 49.77 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 3.99  LOG S -4.03 
Solubility (Water) 3.13e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
Soluble expand Show data source
Hydrophobicity(logP)
3.4 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00768 external link
Item Information
Drug Groups approved
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.
Indication For the treatment of ocular itching associated with allergic conjunctivitis.
Pharmacology 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.
Affected Organisms
Humans and other mammals
Biotransformation The mono-desmethyl and the N-oxide metabolites have been detected at low concentrations in the urine.
Absorption Ophthalmic use of olopatadine usually does not produce measurable plasma concentrations.
Half Life 3 hours
Elimination Elimination was predominantly through renal excretion.
References
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]
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]
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]
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]
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
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RxList
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REFERENCES

REFERENCES

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  • • 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
  • • 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
  • • 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
  • • 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
  • • 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
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