CAS 140462-76-6|Patanase|Olopatadine hydrochloride|Pataday|Opatanol|Allelock|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 ac...

General Information

Structure

Molecular Formula

C₂₁H₂₄ClNO₃

Molecular Mass

373.87316

Exact Mass

373.14447131

Charge

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

Canonic Smiles

CN(CC/C=C/1\c2cc(ccc2OCc2c1cccc2)CC(=O)O)C.Cl

Isomeric Smiles

C\1(=C/CCN(C)C)/c2c(OCc3c1cccc3)ccc(c2)CC(=O)O.Cl

Calculated Properties

JChem

Acid pKa

3.7840304

H Acceptors

H Donor

LogD (pH = 5.5)

0.74022824

LogD (pH = 7.4)

0.74543273

Log P

0.7462555

Molar Refractivity

109.5524

Polarizability

38.300964

Polar Surface Area

49.77

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Commercial Catalog

Academic Data

Data Source

Names and Identifiers

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 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 [(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

Synonyms

Olopatadine hydrochloridePatadayOpatanolAllelockPatanasePatanolPatanol SOlopatadine HydrochlorideKW 4679ALO 4943A(11Z)-11-[3-(Dimethylamino)propylidene]-6,11-dihydrodibenz[b,e]oxepin-2-acetic AcidHydrochloride

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[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-5-yl]acetic acid hydrochloride

Names and Identifiers

Registration numbers

CAS Number

140462-76-6

PubChem CID

5282402

PubChem SID

162037964

Registration numbers

Properties

Safety Information

Storage Condition

-20°C

Refrigerator

MSDS Link

Download link

Product Information

Salt Data

hydrochloride

HCl

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Used in the treatment of allergic rhinitis, urticaria, allergic conjunctivitis and asthma

Antiallergic agent

Pharmacology Properties

Histamine H1-receptor antagonist,

Mediator release inhibitor

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule 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]

TRC

O575000

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

Molecule Details

References

PubChem Literature

From Data Sources

• Sharif NA et al. J Pharmacol Exp Ther. 1996 Sep

• Kamei, C., et al.: Arzneim.-Forsch., 45, 1005 (1995)

• Abelson, M.B., et al.: Am. J. Ophthalmol., 125, 797 (1995)

• Sharif, N.A., et al.: J. Pharmacol. Exp. Ther., 278, 1252 (1995)

• Eur. Pat., 1987, Kyowa Hakko Kogyo, 235 796; CA, 108, 167330, (synth, pharmacol)

• Berdy, G.J. et al., Clin. Ther., 2000, 22, 826-833; 2001, 23, 1272-1280, (pharmacol)

• Ikemura, T. et al., Int. Arch. Allergy Appl. Immunol., 1996, 110, 57; 64, (pharmacol)

• Ikeda, K. et al., Int. Arch. Allergy Appl. Immunol., 1995, 106, 157, (pharmacol)

• Sharif, N.A. et al., J. Pharmacol. Exp. Ther., 1996, 278, 1252, (pharmacol)

• Oshima, E. et al., J. Med. Chem., 1992, 35, 2074, (synth, cryst struct, pharmacol)

References

Bioactivity

PubChem BioAssay

Bioactivity