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29216-28-2 molecular structure
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10-{1-azabicyclo[2.2.2]octan-3-ylmethyl}-10H-phenothiazine

ChemBase ID: 942
Molecular Formular: C20H22N2S
Molecular Mass: 322.46708
Monoisotopic Mass: 322.15036971
SMILES and InChIs

SMILES:
S1c2c(N(CC3C4CCN(C3)CC4)c3c1cccc3)cccc2
Canonical SMILES:
c1ccc2c(c1)N(CC1CN3CCC1CC3)c1c(S2)cccc1
InChI:
InChI=1S/C20H22N2S/c1-3-7-19-17(5-1)22(18-6-2-4-8-20(18)23-19)14-16-13-21-11-9-15(16)10-12-21/h1-8,15-16H,9-14H2
InChIKey:
HOKDBMAJZXIPGC-UHFFFAOYSA-N

Cite this record

CBID:942 http://www.chembase.cn/molecule-942.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
10-{1-azabicyclo[2.2.2]octan-3-ylmethyl}-10H-phenothiazine
IUPAC Traditional name
quitadrill
mequitazine
10-{1-azabicyclo[2.2.2]octan-3-ylmethyl}-10H-phenothiazine
Brand Name
Butix
Instotal
Kitazemin
Metaplexan
Mircol
Primalan
Vigigan
Virginan
Zesulan
Synonyms
Mequitazina [INN-Spanish]
Mequitazina [Spanish]
Mequitazinum [INN-Latin]
Mequitazine
10-(1-Azabicyclo[2.2.2]oct-3-ylmethyl)-10H-phenothiazine
10-(3-Quinuclidinylmethyl)phenothiazine
Butix
LM 209
Metaplexan
Mircol
NSC 303612
Nipolazin
Primalan
Quitadrill
Zesulan
(R)-10-(1-Azabicyclo[2.2.2]oct-3-ylmethyl)-10H-phenothiazine
(+)-Mequitazine
(R)-(+)-Mequitazine
Instotal
Kitazemin
Mequitazinum
Vigigan
Virginan
Mequitazine
CAS Number
29216-28-2
147780-50-5
PubChem SID
46505779
160964405
PubChem CID
4066

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 1.2331452  LogD (pH = 7.4) 2.961917 
Log P 4.1948013  Molar Refractivity 99.0543 cm3
Polarizability 38.213127 Å3 Polar Surface Area 6.48 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 5.38  LOG S -4.91 
Solubility (Water) 4.01e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Methanol expand Show data source
Apperance
Crystalline Solid expand Show data source
White Solid expand Show data source
Melting Point
130-131°C expand Show data source
143-145°C expand Show data source
Hydrophobicity(logP)
4.7 expand Show data source
Storage Condition
Refrigerator expand Show data source
MSDS Link
Download expand Show data source
Mechanism of Action
Mequitazine binds to the histamine H1 receptor sites on effector cells in the gastrointestinal tract, blood vessels, and respiratory tract. expand Show data source
This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine expand Show data source
Certificate of Analysis
Download expand Show data source
Application(s)
Antiallergic agent expand Show data source

DETAILS

DETAILS

DrugBank DrugBank TRC TRC
DrugBank - DB01071 external link
Item Information
Drug Groups approved
Description Mequitazine is a histamine H1 antagonist (antihistamine). It competes with histamine for the normal H1-receptor sites on effector cells of the gastrointestinal tract, blood vessels and respiratory tract. It provides effective, temporary relief of sneezing, watery and itchy eyes, and runny nose due to hay fever and other upper respiratory allergies.
Indication For the treatment of Hay fever, urticaria (hives) and allergic rhinitis
Pharmacology In allergic reactions an allergen interacts with and cross-links surface IgE antibodies on mast cells and basophils. Once the mast cell-antibody-antigen complex is formed, a complex series of events occurs that eventually leads to cell-degranulation and the release of histamine (and other chemical mediators) from the mast cell or basophil. Once released, histamine can react with local or widespread tissues through histamine receptors. Histamine, acting on H1-receptors, produces pruritis, vasodilatation, hypotension, flushing, headache, tachycardia, and bronchoconstriction. Histamine also increases vascular permeability and potentiates pain. Mequitazine is a histamine H1 antagonist. It competes with histamine for the normal H1-receptor sites on effector cells of the gastrointestinal tract, blood vessels and respiratory tract. It provides effective, temporary relief of sneezing, watery and itchy eyes, and runny nose due to hay fever and other upper respiratory allergies.
Affected Organisms
Humans and other mammals
References
Ramirez Chanona N, del Rio Navarro BE, Perez Martin J: [Efficacy of mequitazine (Primalan) on the relief of symptoms of allergic rhinoconjunctivitis in children. Documented clinical experience] Rev Alerg Mex. 2005 Nov-Dec;52(6):221-5. [Pubmed]
Theunissen EL, Vermeeren A, van Oers AC, van Maris I, Ramaekers JG: A dose-ranging study of the effects of mequitazine on actual driving, memory and psychomotor performance as compared to dexchlorpheniramine, cetirizine and placebo. Clin Exp Allergy. 2004 Feb;34(2):250-8. [Pubmed]
Nakamura K, Yokoi T, Kodama T, Inoue K, Nagashima K, Shimada N, Shimizu T, Kamataki T: Oxidation of histamine H1 antagonist mequitazine is catalyzed by cytochrome P450 2D6 in human liver microsomes. J Pharmacol Exp Ther. 1998 Feb;284(2):437-42. [Pubmed]
Persi L, Dupin O, Arnaud B, Trinquand C, Michel FB, Bousquet J: Efficacy of mequitazine in comparison with placebo assessed by ocular challenge with allergen in allergic conjunctivitis. Allergy. 1997 Apr;52(4):451-4. [Pubmed]
External Links
Wikipedia
Toronto Research Chemicals - M225105 external link
R-Enantiomer of Mequitazine. It is an antihistamine.
Toronto Research Chemicals - M225110 external link
It is an antihistamine.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Ramirez Chanona N, del Rio Navarro BE, Perez Martin J: [Efficacy of mequitazine (Primalan) on the relief of symptoms of allergic rhinoconjunctivitis in children. Documented clinical experience] Rev Alerg Mex. 2005 Nov-Dec;52(6):221-5. Pubmed
  • • Theunissen EL, Vermeeren A, van Oers AC, van Maris I, Ramaekers JG: A dose-ranging study of the effects of mequitazine on actual driving, memory and psychomotor performance as compared to dexchlorpheniramine, cetirizine and placebo. Clin Exp Allergy. 2004 Feb;34(2):250-8. Pubmed
  • • Nakamura K, Yokoi T, Kodama T, Inoue K, Nagashima K, Shimada N, Shimizu T, Kamataki T: Oxidation of histamine H1 antagonist mequitazine is catalyzed by cytochrome P450 2D6 in human liver microsomes. J Pharmacol Exp Ther. 1998 Feb;284(2):437-42. Pubmed
  • • Persi L, Dupin O, Arnaud B, Trinquand C, Michel FB, Bousquet J: Efficacy of mequitazine in comparison with placebo assessed by ocular challenge with allergen in allergic conjunctivitis. Allergy. 1997 Apr;52(4):451-4. Pubmed
  • • Uzan, A., et al.: Xenobiotica, 6, 633 (1976)
  • • Persi, L., et al.: Alergy, 52, 451 (1976)
  • • Nakamura, K., et al.: J. Pharmacol. Exp. Ther., 284, 437 (1976)
  • • Theunissen, E., et al.: Clin. Exp. Allergy, 34, 250 (1976)
  • • Uzan, A., et al.: Xenobiotica, 6, 633 (1976)
  • • Persi, L., et al.: Alergy, 52, 451 (1976)
  • • Nakamura, K., et al.: J. Pharmacol. Exp. Ther., 284, 437 (1976)
  • • Theunissen, E., et al.: Clin. Exp. Allergy, 34, 250 (1976)
  • • Ger. Pat., 1970, 2 009 555; CA, 73, 131017r, (synth)
  • • Uzan, A. et al., Xenobiotica, 1976, 6, 633, (metab)
  • • Uzan, A. et al., J. Pharm. Pharmacol., 1979, 31, 701, (pharmacol)
  • • Ger. Pat., 1985, 3 509 460; CA, 104, 148890, (synth, Mequitazine)
  • • Criscuolo, M. et al., Eur. J. Pharmacol., 1986, 126, 81, (pharmacol, Mequitazine)
  • • Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 5665, (synonyms)
  • • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 942
  • • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, MCJ400
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PATENTS

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