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Tacrolimus
Tacrolimus
2D structure of tacrolimus
4LAX - Tacrolimus
3D structure of tacrolimus
[note 1]
Names
Synonyms (-)-FK 506, 8-deethyl-8-[but-3-enyl]-ascomycin, FK 506, FK506, Prograf
Brand names Adoport, Advagraf, Astagraf, Capexion, Modigraf, Perixis, Prograf, Protopic

IUPAC name
IUPAC name
(1R,9S,12S,13R,14S,17R,21S,23S,24R,25S,27R)-1,14-dihydroxy-12-[(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-17-(prop-2-en-1-yl)-11,28-dioxa-4-azatricyclo[22.3.1.0^{4,9}]octacos-18-ene-2,3,10,16-tetrone
Clinical information
Preg. cat.
AU: C
US: C
Legal status
AU: Prescription Only Medicine (S4)
CA: ℞-only
UK: POM
US: ℞-only
Routes Oral, IV, topical


Identifiers
ATC code D11AH01, L04AD02
ChemSpider 393220
DrugBank DB00864
PubChem 445643
MedlinePlus a601117
MeSH ID D016559
PDB IDs
PDBs
1BKF (RCSB, PDBe; X-ray)
1FKF (RCSB, PDBe; X-ray)
1FKJ (RCSB, PDBe; X-ray)
1TCO (RCSB, PDBe; X-ray)
1YAT (RCSB, PDBe; X-ray)
2VN1 (RCSB, PDBe; X-ray)
3IHZ (RCSB, PDBe; X-ray)
4DZ2 (RCSB, PDBe; X-ray)
4LAX (RCSB, PDBe; X-ray)
4NNR (RCSB, PDBe; X-ray)
External links
DailyMed tacrolimus search
Drugs.com international, monograph
Jmol 3D structure
Licensing data US FDA: link.
MSR monograph
emc tacrolimus search
TGA-eBS tacrolimus search
Chemical properties
Formula C44H69NO12
Mol. mass
Mol. mass for MFs
804.0182 g/mol
SMILES
SMILES
CO[C@@H]1C[C@@H](CC[C@H]1O)\C=C(/C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@]2(O)O[C@@H]([C@H](C[C@H]2C)OC)[C@H](C[C@@H](C)C\C(C)=C\[C@@H](CC=C)C(=O)C[C@H](O)[C@H]1C)OC
InChI
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/s1
InChIKey
InChIKey
QJJXYPPXXYFBGM-LFZNUXCKSA-N


Tacrolimus is a calcineurin inhibitor that acts by binding to FK506 binding protein (FKBP), the resulting complex in turn inhibits calcineurin. Tacrolimus is used to prevent organ rejection in organ (including intestine, liver, lung, kidney and pancreas) transplant recipients and is more frequently used than the older calcineurin inhibitor, ciclosporin, due to its superior safety and efficacy (leading to lower rejection rates).[1] It has been used in the management of autoimmune diseases like inflammatory bowel disease too and topical tacrolimus is used to treat severe atopic dermatitis.[2][3]


External linksEdit

NotesEdit

  1. Hydrogens are hidden; structure is based on:
    Bracher, A; Kozany, C; Hähle, A; Wild, P; Zacharias, M; Hausch, F (15 November 2013). "Crystal structures of the free and ligand-bound FK1-FK2 domain segment of FKBP52 reveal a flexible inter-domain hinge. ". Journal of Molecular Biology 425 (22): 4134-44. doi:10.1016/j.jmb.2013.07.041. PDB: 4LAX (RCSB PDB, PDBe)PMID 23933011.

Reference listEdit

  1. Barbarino, JM; Staatz, CE; Venkataramanan, R; Klein, TE; Altman, RB (October 2013). "PharmGKB summary: cyclosporine and tacrolimus pathways.". Pharmacogenetics and genomics 23 (10): 563–85. PMC 4119065. PMID 23922006. doi:10.1097/FPC.0b013e328364db84. 
  2. Gonzalez-Lama, Y; Gisbert, JP; Mate, J (October 2006). "The role of tacrolimus in inflammatory bowel disease: a systematic review.". Digestive Diseases and Sciences 51 (10): 1833–40. PMID 16964541. doi:10.1007/s10620-006-9209-y. 
  3. Brayfield, A, ed. (13 January 2014). "Tacrolimus". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 19 November 2014. 

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