Pimecrolimus 915751 221933222 2008-06-26T19:22:49Z ChemNerd 2246483 Quick-adding category "Macrolides" (using [[WP:HOTCAT|HotCat]]) {{drugbox | | IUPAC_name = (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)<br> -3-{(E)-2-[(1R,3R,4S)-4-Chloro-3<br> -methoxycyclohexyl]-1-methylvinyl}<br> -8-ethyl-5,6,8,11,12,13,14,15,16,17,18<br> ,19,24,25,26,26a-hexadecahydro<br> -5,19-dihydroxy-14,16-dimethoxy<br> -4,10,12,18-tetramethyl-15,19-epoxy<br> -3H-pyrido[2,1-c][1,4]oxaazacyclotricosine<br> -1,7,20,21(4H,23H)-tetrone | image = Pimecrolimus.svg | width = 250 | image2 = | CAS_number = 137071-32-0 | ATC_prefix = D11 | ATC_suffix = AX15 | PubChem = 6447131 | DrugBank = APRD01182 | C = 43 | H = 68 | Cl = 1 | N = 1 | O = 11 | molecular_weight = 810.453 g/mol | bioavailability = low systemic absorption | protein_bound =74%–87% | metabolism = Hepatic [[CYP3A]] | elimination_half-life = | excretion = | pregnancy_category = | legal_status = | routes_of_administration = topical }} '''Pimecrolimus''' is an [[immunomodulator|immunomodulating agent]] used in the treatment of [[atopic dermatitis]] (eczema). It is currently available as a topical cream, once marketed by [[Novartis]], (however [[Galderma]] will be promoting the molecule in Canada in early 2007) under the trade name '''Elidel'''. ==Pharmacology== Pimecrolimus is an [[ascomycin]] [[macrolactam]] derivative. It has been shown ''in vitro'' that pimecrolimus binds to macrophilin-12 and inhibits [[calcineurin]]. Thus pimecrolimus inhibits [[T-cell]] activation by inhibiting the synthesis and release of [[cytokines]] from T-cells. Pimecrolimus also prevents the release of inflammatory cytokines and mediators from [[mast cell]]s. ==Side effects== ''See also: [[Eczema#Immunomodulators|Immunomodulators in the treatment of eczema]]'' In January 2006, the United States [[Food and Drug Administration]] (FDA) announced that Elidel packaging would be required to carry a [[black box warning]] regarding the potential increased risk of [[lymph node]] or [[skin malignancy]], as for the similar drug [[tacrolimus]]. Whereas current practice by [[United Kingdom|UK]] dermatologists is not to consider this a significant real concern and they are increasingly recommending the use of such new drugs.<!-- --><ref name=BAD2002">{{cite web | author= N H Cox and Catherine H Smith | year = 2002 | month = December | url=http://www.bad.org.uk/healthcare/guidelines/Advice_re_topical_tacrolimus.doc | title =Advice to dermatologists re topical tacrolimus | format =DOC | work = Therapy Guidelines Committee | publisher = British Association of Dermatologists}}</ref> Dermatologists' and Allergists' professional societies, the [[American Academy of Dermatology]][http://www.medicalnewstoday.com/articles/21091.php], and the [[American Academy of Allergy, Asthma, and Immunology]], have protested the inclusion of the black box warning. The AAAAI states "None of the information provided for the cases of lymphoma associated with the use of topical pimecrolimus or tacrolimus in AD indicate or suggest a causal relationship."[http://www.aaaai.org/members/resources/calcineurin_task_force.pdf]. In light of the known side effects of steroids which are used first line for many dermatological conditions, many doctors prefer to use this drug instead. In practice, other doctors use the drug as a second-line remedy only after conventional methods of treatment have failed. ==Footnotes== <references/> ==External links== *[http://www.elidel.com Elidel] official homepage *[http://www.fda.gov/bbs/topics/news/2006/NEW01299.html FDA News] *[http://www.npsradar.org.au/site.php?page=1&content=/npsradar/content/pimecrolimus.html NPS RADAR] *[http://www.protopiclawyers.com Offers more information on possible cancer risks of Elidel (Pimecrolimus)] *[http://www.medicalnewstoday.com/articles/21091.php Article about American Academy of Dermatology speaking out against black box warning] *[http://www.aaaai.org/members/resources/calcineurin_task_force.pdf Report of the Calcineurin Task Force of the ACAAI and AAAAI] {{pharma-stub}} {{Other dermatological preparations}} [[Category:Immunosuppressive agents]] [[Category:Macrolides]] [[de:Pimecrolimus]] [[nl:Pimecrolimus]] [[pl:Pimekrolimus]] [[pt:Pimecrolimus]]