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140462-76-6 molecular structure
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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

ChemBase ID: 73044
Molecular Formular: C21H24ClNO3
Molecular Mass: 373.87316
Monoisotopic Mass: 373.14447131
SMILES and InChIs

SMILES:
C\1(=C/CCN(C)C)/c2c(OCc3c1cccc3)ccc(c2)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

Cite this record

CBID:73044 http://www.chembase.cn/molecule-73044.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
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
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
IUPAC Traditional name
[(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[9.4.0.0^{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
Synonyms
(11Z)-11-[3-(Dimethylamino)propylidene]-6,11-dihydrodibenz[b,e]oxepin-2-acetic AcidHydrochloride
ALO 4943A
KW 4679
Patanol
Opatanol
Pataday
Patanase
Allelock
Olopatadine hydrochloride
Patanol S
Olopatadine Hydrochloride
CAS Number
140462-76-6
PubChem SID
162037964
PubChem CID
5282402

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 5282402 external link

CALCULATED PROPERTIES

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 cm3 Polarizability 38.300964 Å3
Polar Surface Area 49.77 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Methanol expand Show data source
Water (Sparingly) expand Show data source
Apperance
White Solid expand Show data source
Melting Point
242-245°C (dec.) expand Show data source
Storage Condition
-20°C expand Show data source
Refrigerator expand Show data source
MSDS Link
Download expand Show data source
Mechanism of Action
Histamine H1-receptor antagonist, expand Show data source
Mediator release inhibitor expand Show data source
Salt Data
HCl expand Show data source
hydrochloride expand Show data source
Certificate of Analysis
Download expand Show data source
Application(s)
Antiallergic agent expand Show data source
Used in the treatment of allergic rhinitis, urticaria, allergic conjunctivitis and asthma expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals TRC TRC
Selleck Chemicals - S2494 external link
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]
Toronto Research Chemicals - O575000 external link
Dual acting histamine H1-receptor antagonist and mast cell stabilizer. Antiallergic; antihistaminic.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Sharif NA et al. J Pharmacol Exp Ther. 1996 Sep
  • • 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)
  • • Eur. Pat., 1987, Kyowa Hakko Kogyo, 235 796; CA, 108, 167330, (synth, pharmacol)
  • • Oshima, E. et al., J. Med. Chem., 1992, 35, 2074, (synth, cryst struct, pharmacol)
  • • Ikeda, K. et al., Int. Arch. Allergy Appl. Immunol., 1995, 106, 157, (pharmacol)
  • • Ikemura, T. et al., Int. Arch. Allergy Appl. Immunol., 1996, 110, 57; 64, (pharmacol)
  • • Sharif, N.A. et al., J. Pharmacol. Exp. Ther., 1996, 278, 1252, (pharmacol)
  • • Berdy, G.J. et al., Clin. Ther., 2000, 22, 826-833; 2001, 23, 1272-1280, (pharmacol)
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PATENTS

PATENTS

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INTERNET

INTERNET

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