2-[(2Z)-2-{3-[(2H3)methyl(methyl)amino]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: 175876
• Molecular Formular: C21H24ClNO3
• Molecular Mass: 373.87316
• Monoisotopic Mass: 373.14447131
• SMILES: C1Oc2c(/C(=C\CCN(C)C)/c3c1cccc3)cc(cc2)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-[(^2H₃)methyl(methyl)amino]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-[(^2H₃)methyl(methyl)amino]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-(Dimethyl-d3-amino)propylidene]-6,11-dihydrodibenz[b,e]oxepin-2-acetic Acid Hydrochloride; ALO 4943A-d3; Allelock-d3; KW 4679-d3; Opatanol-d3; Patanol-d3; Olopatadine-d3 Hydrochloride

Database IDs

• PubChem SID: 164231786
• PubChem CID: 71751324

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: Methanol; Water
• Apperance: Pale Grey Solid
• Melting Point: 230-234°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - O575002

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

REFERENCES

• Kamei, C., et al.: Arzneim.-Forsch., 45, 1005 (1995)
• Sharif, N.A., et al.: J. Pharmacol. Exp. Ther., 278, 1252 (1995)
• Abelson, M.B., et al.: Am. J. Ophthalmol., 125, 797 (1995)