2-{2-[3-(dimethylamino)propylidene]-9-oxatricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,11,13-hexaen-5-yl}acetic acid hydrochloride

• ChemBase ID: 154726
• Molecular Formular: C21H24ClNO3
• Molecular Mass: 373.87316
• Monoisotopic Mass: 373.14447131
• SMILES: CN(C)CC/C=C/1\c2ccccc2COc2c1cc(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
• InChIKey: HVRLZEKDTUEKQH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{2-[3-(dimethylamino)propylidene]-9-oxatricyclo[9.4.0.0^3,^8]pentadeca-1(15),3(8),4,6,11,13-hexaen-5-yl}acetic acid hydrochloride
• IUPAC Traditional name: {2-[3-(dimethylamino)propylidene]-9-oxatricyclo[9.4.0.0^3,^8]pentadeca-1(15),3(8),4,6,11,13-hexaen-5-yl}acetic acid hydrochloride
• Synonyms: (11Z)-11-[3-(Dimethylamino)propylidene]-6,11-dihydrodibenz[b,e]oxepin-2-acetic acid hydrochloride; AL-4943A; KW-4679; Opatanol; Patanol; Olopatadine hydrochloride

Database IDs

• CAS Number: 140462-76-6
• MDL Number: MFCD00875716
• PubChem SID: 162248864
• PubChem CID: 21893738

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: H2O: ≥20 mg/mL
• Apperance: solid

Safety Information

• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25-50
• Safety Statements: 45-61
• GHS Pictograms: GHS06; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H400
• GHS Precautionary statements: P273-P301 + P310
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C21H23NO3·HCl

DETAILS

Sigma Aldrich - O0391

Biochem/physiol Actions
Olopatadine is a histamine H1 receptor antagonist and mast cell stabilizer. The low level of occupancy H1 receptors in the brain explains the low sedation effect of olopatidine. It is believed that olopatidine is a substrate for P-glycoprotein, which limits its brain penetration.1