Cetirizine

Names

[ Name ]:
Cetirizine

[Synonym ]:
Acetic acid, (2-(4-((4-chlorophenyl)phenylmethyl)-1-piperazinyl)ethoxy)-
(2-{4-[(4-Chlorophenyl)(phenyl)methyl]-1-piperazinyl}ethoxy)acetic acid
Reactine
CERTIRIZINE 2HCL
Zirtek
acetic acid, [2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-
Cetirizine
Ceterizine
[(2-{4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethyl)oxy]acetic acid
Acetic acid, 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-
vidix
P-071
MFCD00800721
(±)-[2-[4-[(4-Chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]acetic Acid
Cetrizinehydrochloride
Formistin
(2-{4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)acetic acid
UNII:YO7261ME24
Zyrlex
(±)-[2-[4-(p-Chloro-a-phenylbenzyl)-1-piperazinyl]ethoxy]acetic Acid

Biological Activity

[Description]:

Cetirizine, a second-generation antihistamine, is a major metabolite of hydroxyzine, and a racemic selective H1 receptor inverse agonist used in the treatment of allergies, hay fever, angioedema, and urticaria. IC50 value:Target: Histamine H1 receptorCetirizine crosses the blood-brain barrier only slightly, reducing the sedative side-effect common with older antihistamines. It has also been shown to inhibit eosinophil chemotaxis and LTB4 release. At a dosage of 20 mg, Boone et al. found that it inhibited the expression of VCAM-1 in patients with atopic dermatitis. The levorotary enantiomer of cetirizine, known as levocetirizine, is the more active form. From Wikipedia.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Histamine Receptor

Signaling Pathways >> Immunology/Inflammation >> Histamine Receptor

Research Areas >> Inflammation/Immunology

Natural Products >> Alkaloid

[References]

[1]. Hair PI, Scott LJ. Levocetirizine: a review of its use in the management of allergic rhinitis and skin allergies. Drugs. 2006;66(7):973-96.

[2]. Day JH, Ellis AK, Rafeiro E. Levocetirizine: a new selective H1 receptor antagonist for use in allergic disorders. Drugs Today (Barc). 2004 May;40(5):415-21.

[3]. Namazi MR. Cetirizine and allopurinol as novel weapons against cellular autoimmune disorders. Int Immunopharmacol. 2004 Mar;4(3):349-53.

[4]. Curran MP, Scott LJ, Perry CM. Cetirizine: a review of its use in allergic disorders. Drugs. 2004;64(5):523-61.

[5]. Portnoy JM, Dinakar C. Review of cetirizine hydrochloride for the treatment of allergic disorders. Expert Opin Pharmacother. 2004 Jan;5(1):125-35.

[6]. Huang L, et al. Sinomenine-induced histamine release-like anaphylactoid reactions are blocked by tranilast via inhibiting NF-κB signaling. Pharmacol Res. 2017 Aug 31. pii: S1043-6618(17)30796-X.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
542.1±45.0 °C at 760 mmHg

[ Melting Point ]:
110-115°C

[ Molecular Formula ]:
C₂₁H₂₅ClN₂O₃

[ Molecular Weight ]:
388.888

[ Flash Point ]:
281.6±28.7 °C

[ Exact Mass ]:
388.155365

[ PSA ]:
53.01000

[ LogP ]:
2.16

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.589

[ Storage condition ]:
2-8℃

[ Water Solubility ]:
101 mg/L

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AG0977500

CHEMICAL NAME :: Acetic acid, (2-(4-((4-chlorophenyl)phenylmethyl)-1-piperazinyl)et hoxy)-

CAS REGISTRY NUMBER :: 83881-51-0

LAST UPDATED :: 199606

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C21-H25-Cl-N2-O3

MOLECULAR WEIGHT :: 388.93

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 116 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #4525358

Safety Information

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R22

[ WGK Germany ]:
3

[ RTECS ]:
AG0977500

[ HS Code ]:
2933599090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933599090

[ Summary ]:
2933599090. other compounds containing a pyrimidine ring (whether or not hydrogenated) or piperazine ring in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%