Cetirizin
(Preusmjereno sa stranice Ketirizin)
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(IUPAC) ime | |||
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(±)-[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 ![]() | ||
KEGG[4] | D07662 ![]() | ||
ChEBI | CHEBI:3561 ![]() | ||
ChEMBL[5] | CHEMBL1000 ![]() | ||
Hemijski podaci | |||
Formula | C21H25ClN2O3 | ||
Mol. masa | 388,89 | ||
SMILES | eMolekuli & PubHem | ||
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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 | |||
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.
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.
Sledeća sinteza ovog jedinjenja je objavljena 1985.:[8]
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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 21948863.
- ↑ 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.
- ↑ 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.
- ↑ 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
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- Anderson, P. O., Knoben, J. E., et al. (2002) Handbook of clinical drug data 10th ed. McGraw-Hill International
- Pfizer Inc, et al. (2006) ZYRTEC (cetirizine hydrochloride) Tablets, Chewable Tablets and Syrup For Oral Use Pfizer Incorporated publications
- 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
- 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