Tacrolimus

USDailyMed:Tacrolimus AU:C D11AH01(WHO)L04AD02(WHO) CA:℞-onlyUS:℞-onlyEU:Rx-onlyIn general: ℞ (Prescription only) (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,26aS)-8-allyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-{(E)-2-[(1R,3R,4R)-4-hydroxy-3-methylcyclohexyl]-1-methylvinyl}-14,16-dimethoxy-4,10,12,18-tetramethyl-15,19-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosane-1,7,20,21(4H,23H)-tetrone 104987-11-3Y 445643 DB00864Y 393220Y Y5L2157C4J D08556YD00107Y CHEBI:61049 ChEMBL269732Y FK5 (PDBe,RCSB PDB) DTXSID5046354 Interactive image C=CC[C@@H]1/C=C(\C)C[C@H](C)C[C@H](OC)[C@H]2O[C@@](O)(C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@H](/C(C)=C/[C@@H]3CC[C@@H](O)[C@H](OC)C3)[C@H](C)[C@@H](O)CC1=O)[C@H](C)C[C@@H]2OC InChI=1S/C44H69NO12/c1-10-13-31-19-25(2)18-26(3)20-37(54-8)40-38(55-9)22-28(5)44(52,57-40)41(49)42(50)45-17-12-11-14-32(45)43(51)56-39(29(6)34(47)24-35(31)48)27(4)21-30-15-16-33(46)36(23-30)53-7/h10,19,21,26,28-34,36-40,46-47,52H,1,11-18,20,22-24H2,2-9H3/b25-19+,27-21+/t26-,28+,29+,30-,31+,32-,33+,34-,36+,37-,38-,39+,40+,44+/m0/s1YKey:QJJXYPPXXYFBGM-LFZNUXCKSA-NY Tacrolimus, sold under the brand namePrografamong others, is animmunosuppressive drug. After anallogenicorgan transplant, the risk of organrejectionis moderate; tacrolimus is used to lower the risk of organ rejection. Tacrolimus is also sold as atopical medicationfor treating T cell-mediated diseases, such aseczemaandpsoriasis. For example, it is prescribed for severe refractoryuveitisafter abone marrowtransplant, exacerbations ofminimal change disease,Kimura's disease, andvitiligo. It can be used to treatdry eye syndromein cats and dogs. Tacrolimus inhibitscalcineurin, which is involved in the production ofinterleukin-2, amoleculethat promotes the development andproliferationofT cells, as part of the body's learned (oradaptive) immune response. Chemically, it is amacrolidelactonethat was first discovered in 1987, from the fermentation broth of aJapanesesoilsample that contained thebacteriumStreptomyces tsukubensis. It is on theWorld Health Organization's List of Essential Medicines.In 2021, it was the 296th most commonly prescribed medication in the United States, with more than 500,000 prescriptions.