Cetirizine dihydrochloride CAS 83881-52-1
Introduction：Basic information about Cetirizine dihydrochloride CAS 83881-52-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Cetirizine dihydrochloride Basic informationDescription References
| Product Name: | Cetirizine dihydrochloride |
| Synonyms: | (2-(4-((4-chlorophenyl)phenylmethyl)-1-piperazinyl)ethoxy)aceticaciddihydro;2-[2-[4-[(4-chlorophenyl)-phenyl-methyl]piperazin-1-yl]ethoxy]acetic acid dihydrochloride;Cetirizine Hydrochloride (250 mg);Alercet;Alerid;Cesta;Cetiriz;Cetrak |
| CAS: | 83881-52-1 |
| MF: | C21H26Cl2N2O3 |
| MW: | 425.35 |
| EINECS: | 620-533-8 |
| Product Categories: | API;Aromatics, Heterocycles, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals;DOPRAM;Intermediates & Fine Chemicals;Pharmaceuticals;Active Pharmaceutical Ingredients;Aromatics;Heterocycles;Metabolites & Impurities;Histamine receptor |
| Mol File: | 83881-52-1.mol |
Cetirizine dihydrochloride Chemical Properties
| 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 |
| InChI | InChI=1S/C21H25ClN2O3.ClH/c22-19-8-6-18(7-9-19)21(17-4-2-1-3-5-17)24-12-10-23(11-13-24)14-15-27-16-20(25)26;/h1-9,21H,10-16H2,(H,25,26);1H |
| InChIKey | PGLIUCLTXOYQMV-UHFFFAOYSA-N |
| SMILES | O=C(COCCN1CCN(C(C2=CC=CC=C2)C2=CC=C(Cl)C=C2)CC1)O.[H]Cl |
| 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) |
Safety Information
| 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 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral |
| 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 thetreatment of allergic rhinitis, urticaria and conjunctivitis. It is reported to be moreeffective 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 aselective, peripheral H1 receptor antagonist. It is a long-lasting antihistamine. Itdoes not appear to have the same adverse cardiac effects as the other nonsedatingH1 antihistamines; however, additional data are required. Indicated for allergicrhinitis 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 gtert-BuOK. The temperature was raised to 75-80°C and the mixture was keptat this temperature. After 45 min was added 11 g sodium chloracetate; after1.5 hour was added 5.2 g tert-BuOK; after 2 hours was added 5.64 g sodiumchloracetate; after 2.5 hours was added 1.9 g tert-BuOK; after 3 hours wasadded 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 mltert-butanol was distilled of, 190 ml of water was added and the distillation oftert-butanol was continued until the temperature of the vapour reaches100°C. To the reaction mixture was added 60 ml of water and 8 mlconcentrated hydrochloric acid to pH 8. Unreacted 2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]-ethanol was extracted with diethyl ether. Theaqueous phase was acidified to pH 5 by addition of hydrochloric acid andextracted with dichloromethane (200 ml x 3). The extract was dried overMgSO4, filtered and concentrated in a rotary evaporator. An obtained oil wasallowed 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 acidwas suspended in a mixture of 125 ml of water and 13.8 ml 37% aqueoushydrochloric acid. The mixture was concentrated in a rotary evaporator. Anobtained oil was allowed to crystallize by addition of 245 ml of 2-butanone,yields of 2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]-ethoxy]aceticacid 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 maybe useful for the adjunctive treatment of histamine-mediated pruriticconditions 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. |
| References | [1] Patent: EP1157016, 2003, B1. Location in patent: Page/Page column 5 [2] Patent: US2005/20608, 2005, A1. Location in patent: Page 5-6 [3] Patent: US2004/266787, 2004, A1. Location in patent: Page/Page column 6 |
Cetirizine dihydrochloride Preparation Products And Raw materials
| Raw materials | 4-[(4-CHLOROPHENYL)PHENYLMETHYL]-1-PIPERAZINEETHANOL DIHYDROCHLORIDE-->Potassium tert-butoxide-->Cetirizine-->Acetaldehyde, 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]--->Sodium chloroacetate-->Acetone-->Hydrochloric acid-->Water |
| Preparation Products | 1-Piperazineacetaldehyde-->Cetirizine |
