CAS 113806-05-6|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|Olopatadine Hydrochloride|Patanol|[(2Z)-2-[3-(dimethylamin...

General Information

Structure

Molecular Formula

C₂₁H₂₃NO₃

Molecular Mass

337.41222

Exact Mass

337.1677936

Charge

InChI

InChI=1S/C21H23NO3/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)/b18-8-

InChIKey

JBIMVDZLSHOPLA-LSCVHKIXSA-N

Canonic Smiles

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

Isomeric Smiles

O1c2c(/C(=C\CCN(C)C)/c3c(C1)cccc3)cc(cc2)CC(=O)O

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

ALOGPS 2.1

Log P

3.99

LOG S

-4.03

Solubility (Water)

3.13e-02 g/l

Data Source

Academic Data

Data Source

Names and Identifiers

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

Brand Name

PatanolOlopatadine 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

Synonyms

Olopatadine

Names and Identifiers

Registration numbers

PubChem SID

16096411146506025

PubChem CID

5281071

CAS Number

113806-05-6

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

3.4

Solubility

Soluble

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB00768

Drug Groups

approved

Description

Used to treat allergic conjunctivitis (itching eyes), olopatadine inhibits the release of histamine from mast cells. It is a relatively selective histamine H1 antagonist that inhibits the in vivo and in vitro type 1 immediate hypersensitivity reaction including inhibition of histamine induced effects on human conjunctival epithelial cells.

Indication

For the treatment of ocular itching associated with allergic conjunctivitis.

Pharmacology

Affected Organisms

Humans and other mammals

Biotransformation

The mono-desmethyl and the N-oxide metabolites have been detected at low concentrations in the urine.

Absorption

Ophthalmic use of olopatadine usually does not produce measurable plasma concentrations.

Half Life

3 hours

Elimination

Elimination was predominantly through renal excretion.

References

• Ohmori K, Hayashi K, Kaise T, Ohshima E, Kobayashi S, Yamazaki T, Mukouyama A: Pharmacological, pharmacokinetic and clinical properties of olopatadine hydrochloride, a new antiallergic drug. Jpn J Pharmacol. 2002 Apr;88(4):379-97. [Pubmed]

• Yanni JM, Stephens DJ, Miller ST, Weimer LK, Graff G, Parnell D, Lang LS, Spellman JM, Brady MT, Gamache DA: The in vitro and in vivo ocular pharmacology of olopatadine (AL-4943A), an effective anti-allergic/antihistaminic agent. J Ocul Pharmacol Ther. 1996 Winter;12(4):389-400. [Pubmed]

• Ohmori K, Hasegawa K, Tamura T, Miyake K, Matsubara M, Masaki S, Karasawa A, Urayama N, Horikoshi K, Kajita J, Hasegawa M, Taniguchi K, Komada T, Kawamoto Y: Properties of olopatadine hydrochloride, a new antiallergic/antihistaminic drug. Arzneimittelforschung. 2004;54(12):809-29. [Pubmed]

• Ohmori K, Ikemura T, Kobayashi H, Mukouyama A: [Pharmacological, pharmacokinetic and clinical properties of olopatadine hydrochloride' (olopatadine), an antiallergic drug] Nippon Yakurigaku Zasshi. 2001 Jul;118(1):51-8. [Pubmed]

• Kaliner MA, Oppenheimer J, Farrar JR: Comprehensive review of olopatadine: the molecule and its clinical entities. Allergy Asthma Proc. 2010 Mar;31(2):112-9. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

Molecule Details

References

PubChem Literature

From Data Sources

• Kaliner MA, Oppenheimer J, Farrar JR: Comprehensive review of olopatadine: the molecule and its clinical entities. Allergy Asthma Proc. 2010 Mar;31(2):112-9. Pubmed

References

Bioactivity

PubChem BioAssay

Bioactivity

Navigation

General Information

Calculated Properties

• RDKit

• JChem

• ALOGPS 2.1

Data Source

• Academic Data

Names and Identifiers

• IUPAC name

• Brand Name

• IUPAC Traditional name

• Synonyms

Registration numbers

• PubChem SID

• PubChem CID

• CAS Number

• Physical Property

• DrugBank

• PubChem Literature

• From Data Sources

Bioactivity

• PubChem BioAssay

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

Brand Name

PatanolOlopatadine 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

Synonyms

Olopatadine

PubChem SID

16096411146506025

CAS Number

113806-05-6

Physical Property

Hydrophobicity(logP)

3.4

Solubility

Soluble

DrugBank

DB00768

Drug Groups

approved

Description

Indication

For the treatment of ocular itching associated with allergic conjunctivitis.

Pharmacology

Affected Organisms

Humans and other mammals

Biotransformation

The mono-desmethyl and the N-oxide metabolites have been detected at low concentrations in the urine.

Absorption

Ophthalmic use of olopatadine usually does not produce measurable plasma concentrations.

Half Life

3 hours

Elimination

Elimination was predominantly through renal excretion.

References

• Kaliner MA, Oppenheimer J, Farrar JR: Comprehensive review of olopatadine: the molecule and its clinical entities. Allergy Asthma Proc. 2010 Mar;31(2):112-9. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

From Data Sources

• Kaliner MA, Oppenheimer J, Farrar JR: Comprehensive review of olopatadine: the molecule and its clinical entities. Allergy Asthma Proc. 2010 Mar;31(2):112-9. Pubmed

Molecule

ID:648