Cetirizin

Cetirizin

(IUPAC) ime
(±)-[2-[4-[(4-hlorofenil)fenilmetil]-1- piperazinil]etoksi]sirćetna kiselina
Klinički podaci
Robne marke	Zyrtec
AHFS/Drugs.com	Monografija
MedlinePlus	a698026
Identifikatori
CAS broj	83881-51-0
ATC kod	R06AE07
PubChem[1][2]	2678
DrugBank	DB00341
ChemSpider[3]	2577
UNII	YO7261ME24^Y
KEGG[4]	D07662^Y
ChEBI	CHEBI:3561^Y
ChEMBL[5]	CHEMBL1000^Y
Hemijski podaci
Formula	C21H25ClN2O3
Mol. masa	388,89
SMILES	eMolekuli & PubHem
InChI InChI=1S/C21H25ClN2O3/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)^Y Key: ZKLPARSLTMPFCP-UHFFFAOYSA-N^Y
Sinonimi	Alerid, Alatrol, Alzene, Cetirizina, Cetirin, Cetzine, Cetirizin, Cezin, Histazine, Humex, Letizen, Razene, Reactine, Zyrtec, Zirtec, Zodac, Zirtek, Zynor, Zyrlek, Zyllergy
Farmakokinetički podaci
Bioraspoloživost	dobro se apsorbuje
Vezivanje za proteine plazme	~93%
Metabolizam	izlučuje se uglavnom nepromenjen
Poluvreme eliminacije	8,3 sata
Izlučivanje	Urin (uglavnom), hepatički ili fekalno
Farmakoinformacioni podaci
Licenca	US FDA:link
Trudnoća	B(US)
Pravni status	GSL (UK) OTC (SAD) na recept u Kanadi
Način primene	Oralno

Cetirizin je druga generacija antihistamina. On je glavni metabolit hidroksizina, i racemiski selectivni inverzni agonist H₁ receptora koji se koristi za tretman alergija, alergijskog rinitisa, angioedema, i urtikarija.

Farmakologija

Cetirizin u manjoj meri prolazi kroz krvno moždanu barijeru, tako da proizvodi relativno neznatne sedacione nuspojave za razliku od starijih antihistamina.^[6] On takođe inhibira eozinofilnu hemotaksu i LTB4 oslobađanje. Doze od 20 mg inhibiraju VCAM-1 izražavanje kod pacijenata sa atopičkim dermatitisom.^[7]

Levorotarni enantiomer cetirizina, poznat kao levocetirizin, je aktivniji.

Sinteza

Sledeća sinteza ovog jedinjenja je objavljena 1985.:^[8]

Reference

1. Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519.  edit
2. Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1. 
3. Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846.  edit
4. Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H. 
5. Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594.  edit
6. Gupta, A; Chatelain P, Massingham R, Jonsson EN, Hammarlund-Udenaes M (February 2006). „Brain distribution of cetirizine enantiomers: comparison of three different tissue-to-plasma partition coefficients: K(p), K(p,u), and K(p,uu)”. Drug Metab. Dispos. 34 (2): 318–23. DOI:10.1124/dmd.105.007211. PMID 16303872. 
7. Boone M, Lespagnard L, Renard N, Song M, Rihoux JP (July 2000). „Adhesion molecule profiles in atopic dermatitis vs. allergic contact dermatitis: pharmacological modulation by cetirizine”. J Eur Acad Dermatol Venereol 14 (4): 263–6. DOI:10.1046/j.1468-3083.2000.00017.x. PMID 11204513. Arhivirano iz originala na datum 2013-01-05. Pristupljeno 2009-11-19. 
8. US patent 4525358, Šablon:Cite patent/authors, "2-[4-(Diphenylmethyl)-1-piperazinyl]-acetic acids and their amides", issued 25. 06. 1985., assigned to UCB Pharmaceuticals, Inc 

Literatura

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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

Vanjske veze

• Zyrtec prescribing information Arhivirano 2007-09-27 na Wayback Machine-u
• List of brand names Arhivirano 2013-03-13 na Wayback Machine-u
• US FDA approves Zyrtec-D for over the counter sales
• US FDA approves Zyrtec for over the counter sales
• U.S. National Library of Medicine: Drug Information Portal - Cetirizine