2-[(2Z)-2-[3-(dimethylamino)propylidene]-9-oxatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-5-yl]acetic acid hydrochloride

• ChemBase ID: 73044
• Molecular Formular: C21H24ClNO3
• Molecular Mass: 373.87316
• Monoisotopic Mass: 373.14447131
• SMILES: C\1(=C/CCN(C)C)/c2c(OCc3c1cccc3)ccc(c2)CC(=O)O.Cl
• Canonical SMILES: CN(CC/C=C/1\c2cc(ccc2OCc2c1cccc2)CC(=O)O)C.Cl
• InChI: InChI=1S/C21H23NO3.ClH/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);1H/b18-8-
• InChIKey: HVRLZEKDTUEKQH-NOILCQHBSA-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 hydrochloride; 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 hydrochloride
• 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 hydrochloride; [(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 hydrochloride; 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 hydrochloride
• Synonyms: (11Z)-11-[3-(Dimethylamino)propylidene]-6,11-dihydrodibenz[b,e]oxepin-2-acetic AcidHydrochloride; ALO 4943A; KW 4679; Patanol; Opatanol; Pataday; Patanase; Allelock; Olopatadine hydrochloride; Patanol S; Olopatadine Hydrochloride

Database IDs

• CAS Number: 140462-76-6
• PubChem SID: 162037964
• PubChem CID: 5282402

CALCULATED PROPERTIES

• 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

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water (Sparingly)
• Apperance: White Solid
• Melting Point: 242-245°C (dec.)

Safety Information

• Storage Condition: -20°C; Refrigerator

Pharmacology Properties

• Mechanism of Action: Histamine H1-receptor antagonist,; Mediator release inhibitor

Product Information

• Salt Data: HCl; hydrochloride
• Application(s): Antiallergic agent; Used in the treatment of allergic rhinitis, urticaria, allergic conjunctivitis and asthma

DETAILS

Selleck Chemicals - S2494

Research Area: Immunology
Biological Activity:
Olopatadine hydrochloride(Opatanol) is a histamine blocker and mast cell stabilizer with an IC50 of 559 µM for the release of histamine. Evaluation of the interaction of olopatadine with histamine receptors revealed a relatively high affinity for the H1 receptor (Ki = 31.6 nM, pKi = 7.5 ± 0.1) but lower affinities for H2 receptors (Ki = 100 µM, pKi = 4.0 ± 0.19) and H3 receptors (Ki = 79.4 µM, pKi = 4.1 ± 0.16,). The H1 selectivity of olopatadine was superior to that of other ocularly used anti-histamines studied, such as ketotifen, levocabastine, antazoline and pheniramine. [1][2]

Toronto Research Chemicals - O575000

Dual acting histamine H1-receptor antagonist and mast cell stabilizer. Antiallergic; antihistaminic.

REFERENCES

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• Sharif, N.A., et al.: J. Pharmacol. Exp. Ther., 278, 1252 (1995)
• Abelson, M.B., et al.: Am. J. Ophthalmol., 125, 797 (1995)
• Eur. Pat., 1987, Kyowa Hakko Kogyo, 235 796; CA, 108, 167330, (synth, pharmacol)
• Oshima, E. et al., J. Med. Chem., 1992, 35, 2074, (synth, cryst struct, pharmacol)
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• Sharif, N.A. et al., J. Pharmacol. Exp. Ther., 1996, 278, 1252, (pharmacol)
• Berdy, G.J. et al., Clin. Ther., 2000, 22, 826-833; 2001, 23, 1272-1280, (pharmacol)