3-[(2Z)-5-(carboxymethyl)-9-oxatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]-N,N-dimethylpropanamine oxide

• ChemBase ID: 175878
• Molecular Formular: C21H23NO4
• Molecular Mass: 353.41162
• Monoisotopic Mass: 353.16270822
• SMILES: C1Oc2c(/C(=C\CC[N+]([O-])(C)C)/c3c1cccc3)cc(cc2)CC(=O)O
• Canonical SMILES: OC(=O)Cc1ccc2c(c1)/C(=C\CC[N+](C)(C)[O-])/c1ccccc1CO2
• InChI: InChI=1S/C21H23NO4/c1-22(2,25)11-5-8-18-17-7-4-3-6-16(17)14-26-20-10-9-15(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: TXKZPVWYFNGMCP-LSCVHKIXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(2Z)-5-(carboxymethyl)-9-oxatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]-N,N-dimethylpropanamine oxide
• IUPAC Traditional name: 3-[(2Z)-5-(carboxymethyl)-9-oxatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]-N,N-dimethylpropanamine oxide
• Synonyms: 11-[3-(Dimethyloxidoamino)propylidene]-6,11-dihydrodibenz[b,e]oxepin-2-acetic Acid; Olopatadine N-Oxide

Database IDs

• CAS Number: 203188-31-2
• PubChem SID: 164231788
• PubChem CID: 9950431

CALCULATED PROPERTIES

• Acid pKa: 3.591094
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.6318724
• LogD (pH = 7.4): -0.9169198
• Log P: 1.888131
• Molar Refractivity: 111.5973 cm^3
• Polarizability: 38.42466 Å^3
• Polar Surface Area: 73.41 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 155-157°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - O575010

A metabolite of Olopatadine (M3). A dibenz[b,e]oxepin derivative as antiallergic agents, useful for treatment of asthma, allergic rhinitis, atopic dermatitis.

REFERENCES

• Mizuno, N., et al.: Drug Metabol. Pharmacokin., 17, 93 (2002)
• Polli, J., et al.: J. Pharm. Sci., 92, 2082 (2002)
• Tashiro, M., et al.: J. Clin. Pharmacol., 44, 890 (2002)
• Ohashi, R., et al.: Drug Metab. Disos., 34, 793 (2002)