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: 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• CAS Number: 113806-05-6
• PubChem SID: 160964111; 46506025
• PubChem CID: 5281071

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.7840304
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.74022824
• LogD (pH = 7.4): 0.74543273
• Log P: 0.7462555
• Molar Refractivity: 109.5524 cm^3
• Polarizability: 38.300964 Å^3
• Polar Surface Area: 49.77 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.99
• LOG S: -4.03
• Solubility (Water): 3.13e-02 g/l

PROPERTIES

Physical Property

• Solubility: Soluble
• Hydrophobicity(logP): 3.4

DETAILS

DrugBank - DB00768

• 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: Wikipedia; RxList; PDRhealth; Drugs.com

REFERENCES

• 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