Cetirizine

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Cetirizine
Systematic (IUPAC) name
(±) - [2- [4- [ (4-chlorophenyl)phenylmethyl] -1- piperazinyl] ethoxy]acetic acid, dihydrochloride
Identifiers
CAS number 83881-51-0
ATC code R06AE07
PubChem 2678
DrugBank APRD00630
Chemical data
Formula C21H25ClN2O3 
Mol. mass 388.89
SMILES eMolecules & PubChem
Synonyms Alatrol, Alzene, Cetirizina MERCK, Cetirin, Cetzine Glaxo, Cetirizin, Humex, Letizen, Razene, Reactine, Zyrtec, Zirtec, Zodac, Zirtek, Zynor, Zyrlek, Zyllergy
Pharmacokinetic data
Bioavailability well absorbed
Protein binding 93% avg
Metabolism CYP3A4 (Cytochrome P450 3A4)
Half life 8.3 Hours
Excretion Hepatic, urine or excrement (Small amounts)
Therapeutic considerations
Licence data

US
Pregnancy cat.

B(US)
Legal status

GSL(UK) OTC(US) OTC in Canada
Routes Oral

Cetirizine hydrochloride, an antihistamine, (pronounced /sɛˈtɪrɨziːn/) 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. The structural similarity of cetirizine to hydroxyzine, and its derivation from piperazine, attribute similar adverse reactions and properties to other piperazine derivatives.

Formerly prescription-only in the US, cetirizine is now available over the counter.

Contents

[edit] Clinical description

[edit] Pharmacology

Cetirizine does not cross the blood-brain barrier effectively, eliminating the sedative side-effect common with older antihistamines.[1]

[edit] Administration method and metabolisation

Chewable, non-chewable, and syrup forms of cetirizine are similarly absorbed rapidly and effectively, with absorbed food minutely affecting the absorption rate which yields a peak serum level one hour after administration;[2] in a study of healthy volunteers prescribed 10mg tablets, once daily for 10 days, a mean peak serum level of 311 ng/mL was observed.[3] The metabolic effects of cetirizine are long acting; remaining in the system for a maximum of 21 hours before being excreted, the average elimination half-life is 8 hours.[2][3] 70% of the drug is excreted or eliminated by kidney function within 72 hours, and 10% is removed through urine or excrement;[2][3] of which, half is observed as unchanged cetirizine compound.[2][3] Like many other antihistamine medications, cetirizine is commonly prescribed in combination with pseudoephedrine hydrochloride, a decongestant. These combinations are marketed using the same brand name as the cetirizine with a "-D" suffix (Zyrtec-D, Virlix-D, etc.)

Additionally, cetirizine HCl not sold in combination with pseudoephedrine, is commonly known and marketed under the brand name, "Zyrtec." Formerly only available by a prescription, both Zyrtec and Zyrtec-D are currently available over the counter in the United States.[4]

[edit] Levo version

The levo, or active enantiomer, version of Cetirizine is known as Levocetirizine. It is marketed under the name of Xyzal and Xusal. It is claimed to have somewhat fewer side effects.

[edit] Clinical use

[edit] Kimura's disease

Cetirizine is an effective agent in the treatment of Kimura's disease, which mostly occurs in young Asian men, affecting the lymph nodes and soft tissue of the head and neck in the form of tumor-like lesions. Cetirizine's properties of being effective both in the treatment of pruritus and as an anti-inflammatory agent[5] make it suitable for the treatment of the pruritus associated with these lesions.[5] In a 2005 study, the American College of Rheumatology conducted treatments initially using prednisone, followed by steroid dosages and azathioprine, omeprazole, and calcium and vitamin D supplements over the course of two years.[6] The skin condition of the patient began to improve and the skin lesions lessened. However, there were symptoms of cushingoid and hirsutism observed before the patient was removed from the courses of steroids and placed on 10mg/day of cetirizine to prevent skin lesions;[6]an agent suitable for the treatment of pruritus associated with such lesions.[6] Asymptomatically, the patient's skin lesions disappeared after treatment with cetirizine, blood eosinophil counts became normal,[6] corticosteroid effects were resolved,[6] and a remission began within a period 2 months.[6] It is also thought that the inhibition of eosinophils may be the key to treatment of Kimura's disease due to the role of eosinophils, rather than other cells with regards to the lesions of the skin.[6]

[edit] References

  1. ^ Gupta, Anubha; Chatelain, Pierre; Massingham, Roy; Jonsson, E. Niclas; Hammarlund-Udenaes, Margareta (2005-11-22). "Brain Distribution of Cetirizine Enantiomers: Comparison of Three Different Tissue-to-Plasma Partition Coefficients: Kp, Kp,u, and Kp,uu". Drug Metabolism and Disposition 34: 318. doi:10.1124/dmd.105.007211. PMID 16303872. 
  2. ^ a b c d Anderson, P. O., Knoben, J. E., et al. (2002), p807
  3. ^ a b c d Pfizer Inc, et al. (2006), p3 -- Note; this appears as Page 2 in online print versions.
  4. ^ Payne, January W. "Over-the-Counter Zyrtec Is About to Arrive", U.S. News & World Report, 2008-01-09. 
  5. ^ a b Chetrit, E. B., Amir, G., Shalit, M. (2005), p1.
  6. ^ a b c d e f g Chetrit, E. B., Amir, G., Shalit, M. (2005), p2.

[edit] Books and journals

  1. Anderson, P. O., Knoben, J. E., et al. (2002) Handbook of clinical drug data 10th ed. McGraw-Hill International
  2. Pfizer Inc, et al. (2006) ZYRTEC (cetirizine hydrochloride) Tablets, Chewable Tablets and Syrup For Oral Use Pfizer Incorporated publications
  3. Chetrit, E. B., Amir, G., Shalit, M. (2005). Cetirizine: an effective agent in Kimura's Disease Arthritis & Rheumatism (Arthritis care & research) Vol 53, p117-118

[edit] External links


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Antihistamines (primarily R06)
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