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ChemicalBook > CAS DataBase List > Cetirizine dihydrochloride

Cetirizine dihydrochloride

Description References
Product Name
Cetirizine dihydrochloride
CAS No.
83881-52-1
Chemical Name
Cetirizine dihydrochloride
Synonyms
CETIRIZINE DIHYDROCHLORIDE;CETIRIZINE HCL;CETIRIZINE 2HCL;ZYRTEC;CETIRIZINE DI HCL;Triz;Certirizine;CETIRIZIN DIHYDROCHLORIDE;Cesta;Ryzen
CBNumber
CB6135030
Molecular Formula
C21H26Cl2N2O3
Formula Weight
425.35
MOL File
83881-52-1.mol
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Cetirizine dihydrochloride Property

Melting point:
110-115°C
storage temp. 
2-8°C
solubility 
H2O: soluble5mg/mL, clear
form 
powder
color 
white to beige
Water Solubility 
Soluble in water, DMSO, ethanol, and methanol.
Merck 
14,2022
BCS Class
1,3
Stability:
Hygroscopic
InChIKey
PGLIUCLTXOYQMV-UHFFFAOYSA-N
CAS DataBase Reference
83881-52-1(CAS DataBase Reference)
EPA Substance Registry System
Acetic acid, 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-, hydrochloride (1:2) (83881-52-1)
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Safety

Hazard Codes 
Xn,Xi
Risk Statements 
22-36/37/38
Safety Statements 
26-36
RIDADR 
3249
WGK Germany 
3
RTECS 
AG0977500
HazardClass 
6.1(b)
PackingGroup 
III
HS Code 
29339900
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
C-158
Product name
Cetirizine dihydrochloride solution
Purity
1.0?mg/mL in acetonitrile: water (9:1) (as free base), ampule of 1?mL, certified reference material, Cerilliant?
Packaging
1mL
Price
$134
Updated
2024/03/01
Sigma-Aldrich
Product number
BP837
Product name
Cetirizine hydrochloride
Purity
British Pharmacopoeia (BP) Reference Standard
Packaging
100MG
Price
$220
Updated
2024/03/01
Sigma-Aldrich
Product number
BP1081
Product name
Cetirizine impurity standard
Purity
British Pharmacopoeia (BP) Reference Standard
Packaging
50MG
Price
$229
Updated
2024/03/01
Sigma-Aldrich
Product number
89126
Product name
Cetirizin dihydrochloride
Purity
≥98.0% (HPLC)
Packaging
1G
Price
$86.3
Updated
2024/03/01
Sigma-Aldrich
Product number
1102929
Product name
Cetirizine dihydrochloride
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
250mg
Price
$436
Updated
2024/03/01
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Cetirizine dihydrochloride Chemical Properties,Usage,Production

Description

Cetirizine hydrochloride(83881-52-1) is an orally-active and selective histamine (H1)-receptor antagonist. It is a second-generation antihistamine and a human metabolite of hydroxyzine. Three important features of cetirizine are: a high specificity fort he H1-receptor; a low need for metabolism, and the existence of non-H1-dependent activities on cells involved in the pathogenesis of allergy.
Cetirizine is used to treat seasonal allergic rhinitis (SAR), perennial allergic rhinitis, useful in treating urticaria and atopic dermatitis. Cetirizine possesses also mild anti-inflammatory effects.

References

[1] E. J. Corey and Christopher J. Helal, Catalytic Enantioselective Synthesis of the Second-Generation Histamine Antagonist Cetirizine Hydrochloride, Tetrahedron Letters, 1996, vol. 37, 4837-4840
[2] Jay M. Portnoy and Chitra Dinakar, Review of cetirizine hydrochloride for the treatment of allergic disorders, Journal of Expert Opinion on Pharmacotherapy, 2004, vol. 5, 125-135

Description

Cetirizine hydrochloride is a once-daily, non-sedating antihistamine useful in the treatment of allergic rhinitis, urticaria and conjunctivitis. It is reported to be more effective than most other agents in this category such as terfenadine and astemizole.

Chemical Properties

Cetirizine Hydrochloride occurs as a white crystalline powder or crystalline solid. It is very soluble in water, and slightly soluble in ethanol (99.5). It dissolves in 0.1 mol/L hydrochloric acid TS. A solution of Cetirizine Hydrochloride (1 in 10) shows no optical rotation.

Originator

UCB (Belgium)

Uses

Cetirizine hydrochloride is a nonsedating type histamine H1-receptor antagonist. A major metabolite of Hydroxyzine. Pharmacological activity resides primarily in the (R)-isomer. It is Cetirizine is an antihistamine medicine that is effective in the treatment of allergic rhinitis, chronic urticaria, and pollen-induced asthma. Unlike many traditional antihistamines, it does not cause drowsiness or anticholinergic side effects.

Application

Cetirizine Hydrochloride may be used as a pharmaceutical reference standard for the determination of the analyte in pharmaceutical formulations by various chromatography techniques.

Definition

ChEBI: Cetirizine hydrochloride is a diarylmethane.

Indications

Cetirizine HCl (Zyrtec) is the carboxylic acid metabolite of hydroxyzine. It is a selective, peripheral H1 receptor antagonist. It is a long-lasting antihistamine. It does not appear to have the same adverse cardiac effects as the other nonsedating H1 antihistamines; however, additional data are required. Indicated for allergic rhinitis and chronic urticaria.

Manufacturing Process

Preparation of 2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]- ethoxy]acetic acid (cetirizine).
To a mixture of 50 g 2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]- ethanol and 225 ml of tert-butanol at 45°C under a nitrogen was added 21 g tert-BuOK. The temperature was raised to 75-80°C and the mixture was kept at this temperature. After 45 min was added 11 g sodium chloracetate; after 1.5 hour was added 5.2 g tert-BuOK; after 2 hours was added 5.64 g sodium chloracetate; after 2.5 hours was added 1.9 g tert-BuOK; after 3 hours was added 1.9 g sodium chloracetate; after 3.5 hours was added 0.8 g tert-BuOK; and after 4 hours was added 1.13 g sodium chloracetate. Then about 150 ml tert-butanol was distilled of, 190 ml of water was added and the distillation of tert-butanol was continued until the temperature of the vapour reaches 100°C. To the reaction mixture was added 60 ml of water and 8 ml concentrated hydrochloric acid to pH 8. Unreacted 2-[4-[(4-chlorophenyl) phenylmethyl]-1-piperazinyl]-ethanol was extracted with diethyl ether. The aqueous phase was acidified to pH 5 by addition of hydrochloric acid and extracted with dichloromethane (200 ml x 3). The extract was dried over MgSO4, filtered and concentrated in a rotary evaporator. An obtained oil was allowed to crystallize by addition of 150 ml of 2-butanone, yields of 2-[4-[(4- chlorophenyl)phenylmethyl]-1-piperazinyl]-ethoxy]acetic acid 55.5%, M.P. 146-148°C.
32.7 g 2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]-ethoxy]acetic acid was suspended in a mixture of 125 ml of water and 13.8 ml 37% aqueous hydrochloric acid. The mixture was concentrated in a rotary evaporator. An obtained oil was allowed to crystallize by addition of 245 ml of 2-butanone, yields of 2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]-ethoxy]acetic acid dihydrochloride 88%, M.P. 228.22°C.

brand name

Zyrtec (Pfizer).

Therapeutic Function

Antihistaminic; Antiallergic

General Description

Cetirizine hydrochloride, a second generation antihistaminic drug, is one of the carboxylated metabolites of hydroxyzine that can typically bind to histamine H1 receptor. It is effective against diseases such as urticaria, angioedema, allergies and hay fever.

Biological Activity

Histamine H 1 receptor antagonist that displays selectivity over other receptors at concentrations up to 10 μ M. A non-sedating antihistamine that inhibits histamine release and eosinophil chemotaxis during secondary phase allergic response. Inhibits activation of eosinophils, neutrophils and monocytes in vivo .

Biochem/physiol Actions

Cetirizine hydrochloride is an orally active and selective H1-receptor antagonist. Antihistaminic; Piperazines. Non-sedating type histamine H1-receptor antagonist; major metabolite of hydroxyzine. Pharmacological activity resides primarily in the (R)-isomer.

Side effects

There are many side effects of Cetirizine hydrochloride which can be classified into five levels including common side effects (10%), more common side effects (1%), rare side effects (0.1%), very rare side effects (0.01%) and other side effects.
Common side effects include: drowsiness, dizziness, headache, pharyngitis, rhinitis (children), diarrhoea (children), nausea, dry mouth, fatigue. More common side effects include: restlessness, paresthesia (tingling or numbness in the hands and feet), diarrhoea, stomach pain, pruritus (itching), rash, asthenia (unusual weakness), weakness.
Rare side effects include: hypersensitivity, aggression, confusion, depression, hallucinations, insomnia, convulsions, tachycardia (fast heartbeat), abnormal liver function, hives, oedema (swelling), weight gain. Very rare side effects: Thrombocytopenia (low platelet count), anaphylaxis, convulsions (uncontrolled body movements), gustatory disturbances (disturbances in taste or loss of taste), dyskinesia (dyskinesia (uncontrolled movements), dystonia (uncontrolled muscle spasms), syncope (fainting), ophthalmoplegia (uncontrolled circular movements of the eyes), angioedema (severe). allergic reaction that causes swelling of the face or throat), dysuria (pain when urinating), incontinence (bedwetting).
Other side effects include: increased appetite, suicidal thoughts, nightmares, amnesia, memory problems, dizziness (spinning sensation), inflammation of the liver, urinary retention (difficulty in urinating), pain in the joints, rash with pus-containing blisters, and severe itching after stopping the drug (pruritus).

Veterinary Drugs and Treatments

Cetirizine is a H1 receptor blocking antihistamine agent that may be useful for the adjunctive treatment of histamine-mediated pruritic conditions in dogs or cats.

Drug interactions

Potentially hazardous interactions with other drugs
Antivirals: concentration possibly increased by ritonavir.

Metabolism

Cetirizine does not undergo extensive first pass metabolism.
About two thirds of the dose is excreted unchanged in urine.

Dosage forms

5 to 10mg daily.

Cetirizine dihydrochloride Preparation Products And Raw materials

Raw materials

Preparation Products

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Cetirizine dihydrochloride Suppliers

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View Lastest Price from Cetirizine dihydrochloride manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Cetirizine hydrochloride 83881-52-1
Price
US $0.00-0.00/Kg/Drum
Min. Order
1KG
Purity
99%min
Supply Ability
500kgs
Release date
2021-07-12
Hebei Weibang Biotechnology Co., Ltd
Product
Cetirizine hydrochloride 83881-52-1
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
5tons
Release date
2024-12-04
Baoji Guokang Bio-Technology Co., Ltd.
Product
Cetirizine hydrochloride 83881-52-1
Price
US $550.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
1000kg
Release date
2021-06-03

83881-52-1, Cetirizine dihydrochlorideRelated Search:

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