FK506 (Tacrolimus)

SKU
F-1030
  • CAS:104987-11-3
  • Formula:C44H69NO12
  • MW:804.0 Da
  • Appearance:White powder
  • Purity:≥99%

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Product Name Qty
FK506 (Tacrolimus)
10 mg
$73.82
FK506 (Tacrolimus)
25 mg
$162.49
FK506 (Tacrolimus)
1 mg
$21.89
FK506 (Tacrolimus)
5 mg
$48.36

Description

TacrolimusFK-506 or Fujimycin is an immunosuppressive drug that is mainly used after allogeneic organ transplant to reduce the activity of the patient's immune system and so lower the risk of organ rejection. It is also used in a topical preparation in the treatment of atopic dermatitis (eczema), severe refractory uveitis after bone marrow transplants, and for the skin condition vitiligo.

Tacrolimus is a macrolide compound isolated from the bacterium Streptomyces tsukubaensis. In T-cells, activation of the T-cell receptor normally increases intracellular calcium, which acts via calmodulin to activate calcineurin. Calcineurin then dephosphorylates the transcription factor NF-AT (nuclear factor of activated T-cells), which moves to the nucleus of the T-cell and increases the activity of genes coding for IL-2 and related cytokines. Tacrolimus prevents the dephosphorylation of NF-AT. 

In detail, Tacrolimus reduces peptidyl-prolyl isomerase activity by binding to the immunophilin FKBP12 (FK506 binding protein) creating a new complex. This FKBP12-FK506 complex interacts with and inhibits calcineurin thus inhibiting both T-lymphotye signal transduction and IL-2 transcription. Although this activity is similar to cyclosporine, studies have shown that the incidence of acute rejection is reduced by tacrolimus use over cyclosporine.Although short-term immunosuppression concerning patient and graft survival is found to be similar between the two drugs, tacrolimus results in a more favorable lipid profile, and this may have important long-term implications given the prognostic influence of rejection on graft survival.

 

More Information
Alternate Name/Synonyms
Prograf; Protopic; Fujimycin; Tsukubaenolide; Modigraf; Advagraf; Protopy; Astagraf XL
SKU
F-1030
CAS #
104987-11-3
Chemical Name
(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-1,14-dihydroxy-12-[(E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-17-prop-2-enyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetron
Chemical Formula
C44H69NO12
Molecular Weight
804.0 Da
Appearance
White powder
Purity
≥99%
Solubility
Clear and colorless at 10 mg/ml DMSO or Ethanol
Melting Point
130-132°C
Storage Temp
-20°C
THERAPEUTIC AREA
Immunotherapy
USE
Tacrolimus, also known as fujimycin or FK506, is an immunosuppressive drug used mainly after allogeneic organ transplant to lower the risk of organ rejection. It achieves this by inhibiting the production of interleukin-2, a molecule that promotes the development and proliferation of T cells, which are vital to the body's learned (or adaptive) immune response. Tacrolimus is also used in the treatment of other T cell-mediated diseases such as eczema and psoriasis. (for which it is applied to the skin in a medicated ointment), severe refractory uveitis after bone marrow transplants, exacerbations of minimal change disease, Kimura's disease, and the skin condition vitiligo.
Merck Index
13.9117.2001
Handling
Avoid contact with skin, eyes, and personal clothing. Wash hands thoroughly after handling. Avoid breathing fumes. Use only with adequate ventilation. Wear suitable protective clothing, gloves, and eye/face protection. Keep away from sources of ignition. Minimize dust generation and accumulation. Keep container tightly closed. Open and handle container with care. Do not eat, drink, or smoke while handling.
Certificate of Analysis 1
Certificate of Analysis 2
Certificate of Analysis 3
GHS PICTOGRAMS
Handling Avoid contact with skin, eyes, and personal clothing. Wash hands thoroughly after handling. Avoid breathing fumes. Use only with adequate ventilation. Wear suitable protective clothing, gloves, and eye/face protection. Keep away from sources of ignition. Minimize dust generation and accumulation. Keep container tightly closed. Open and handle container with care. Do not eat, drink, or smoke while handling.
Citations Inhibition of the adrenomedullin/nitric oxide signaling pathway in early diabetic retinopathy
Zinc transporter ZIP8 (SLC39A8) and zinc influence IFN-gamma expression in activated human T cells
Compensatory Internalization of Pma1 in V-ATPase Mutants in Saccharomyces cerevisiae Requires Calcium- and Glucose-Sensitive Phosphatases
Target cell cyclophilins facilitate human papillomavirus type 16 infection
Muscarinic M(1) modulation of N and L types of calcium channels is mediated by protein kinase C in neostriatal neurons
Integration of chemical-genetic and genetic interaction data links bioactive compounds to cellular target pathways
Proline isomerization of histone H3 regulates lysine methylation and gene expression
Exploring the mode-of-action of bioactive compounds by chemical-genetic profiling in yeast
Yeast Miro GTPase, Gem1p, regulates mitochondrial morphology via a novel pathway
Global analysis of the evolution and mechanism of echinocandin resistance in Candida glabrata
Hsp90 governs dispersion and drug resistance of fungal biofilms
Global analysis of genetic circuitry and adaptive mechanisms enabling resistance to the azole antifungal drugs
Genetic and genomic architecture of the evolution of resistance to antifungal drug combinations
MHCI requires MEF2 transcription factors to negatively regulate synapse density during development and in disease
Nuclear factor of activated T-cells isoform c4 (NFATc4/NFAT3) as a mediator of antiapoptotic transcription in NMDA receptor-stimulated cortical neurons
The Down syndrome critical region protein RCAN1 regulates long-term potentiation and memory via inhibition of phosphatase signaling
Cholinergic axons modulate GABAergic signaling among hippocampal interneurons via postsynaptic alpha 7 nicotinic receptors
Dynamin-related protein 1 (Drp1)-mediated diastolic dysfunction in myocardial ischemia-reperfusion injury: therapeutic benefits of Drp1 inhibition to reduce mitochondrial fission
Prolonged infusion of inhibitors of calcineurin or L-type calcium channels does not block mossy fiber sprouting in a model of temporal lobe epilepsy
IL-6 plays a unique role in initiating c-Maf expression during early stage of CD4 T cell activation
Cholesterol efflux to apoA-I in ABCA1-expressing cells is regulated by Ca2+-dependent calcineurin signaling
The yeast PH domain proteins Slm1 and Slm2 are targets of sphingolipid signaling during the response to heat stress
Lysosomes integrate metabolic-inflammatory cross-talk in primary macrophage inflammasome activation
Neuronal calcium sensor-1 (Ncs1p) is up-regulated by calcineurin to promote Ca2+ tolerance in fission yeast
A positive feedback loop between glycogen synthase kinase 3beta and protein phosphatase 1 after stimulation of NR2B NMDA receptors in forebrain neurons
Initial calcium release from intracellular stores followed by calcium dysregulation is linked to secondary axotomy following transient axonal stretch injury
Pivotal advance: CEACAM1 is a negative coreceptor for the B cell receptor and promotes CD19-mediated adhesion of B cells in a PI3K-dependent manner
High Number of Activated CD8+ T Cells Targeting HIV Antigens Are Present in Cerebrospinal Fluid in Acute HIV Infection
Cyclosporin A treatment of Leishmania donovani reveals stage-specific functions of cyclophilins in parasite proliferation and viability
Immunophilin deficiency augments Ca2+-dependent glutamate release from mouse cortical astrocytes
Granule neurons in cerebellum express distinct splice variants of the inositol trisphosphate receptor that are modulated by calcium
Differential effects of FK506 on structural and functional axonal deficits after diffuse brain injury in the immature rat
The calcineurin inhibitor, FK506, does not alter glutamate transport in the ischaemic mouse retina
Biochemical and functional characterization of the actin-binding activity of the B subunit of yeast vacuolar H+-ATPase
Metabolic control of antifungal drug resistance
Calcineurin mediates AKT dephosphorylation in the ischemic rat retina
Calcium-dependent phosphorylation regulates neuronal stability and plasticity in a highly precise pacemaker nucleus
Upregulation of D2-class signaling in dopamine-denervated striatum is in part mediated by D3 receptors acting on Ca V 2.1 channels via PIP2 depletion
Effect of the calcineurin inhibitor FK506 on K+-Cl- cotransporter 2 expression in the mouse hippocampus after kainic acid-induced status epilepticus
Role of FK506 binding protein 12 in morphine-induced μ-opioid receptor internalization and desensitization
The capacity of Aspergillus niger to sense and respond to cell wall stress requires at least three transcription factors: RlmA, MsnA and CrzA
Application of Epstein-Barr Virus for Optimization of Immortalized B-lymphocyte Production as a Positive Control in Genetic Studies
Drp1 dephosphorylation in ATP depletion-induced mitochondrial injury and tubular cell apoptosis
Functional partitioning of epithelial protein kinase CaMKII in signal transduction
The role of nuclear factors of activated T-cells (NFAT) in neuronal death.
Regulation of IL-12p40 expression by HIV-Nef in human monocytic cells
Determining the mechanisms of resistance to drug combinations and their fitness effects in Candida albicans
Analysis of cell cycle surveillance mechanisms in meiosis
CALCIUM-MEDIATED CHANGE IN NEURONAL INTRINSIC EXCITABILITY IN WEAKLY ELECTRIC FISH: BIASING MECHANISMS OF HOMEOSTASIS FOR THOSE OF PLASTICITY
Regulation of IL-12 Family Cytokines in Normal and HIV-1-infected Human Monocytic Cells
Fitness trade-offs restrict the evolution of resistance to amphotericin B
The calcineurin pathway links hyperpolarization (Kir2.1)-induced Ca2+ signals to human myoblast differentiation and fusion
CpG protects human monocytic cells against HIV-Vpr-induced apoptosis by cellular inhibitor of apoptosis-2 through the calcium-activated JNK pathway in a TLR9-independent manner
IL-10 Regulation by HIV-Tat in Primary Human Monocytic Cells: Involvement of Calmodulin/Calmodulin-Dependent Protein Kinase-Activated p38 MAPK and Sp-1 and CREB-1 Transcription Factors
Phospholipase Cgamma activation drives increased production of autotaxin in endothelial cells and lysophosphatidic acid-dependent regression
Protein kinase C-dependent enhancement of activity of rat brain NCKX2 heterologously expressed in HEK293 cells
Distinct role of calmodulin and calmodulin-dependent protein kinase-II in lipopolysaccharide and tumor necrosis factor-alpha-mediated suppression of apoptosis and antiapoptotic c-IAP2 gene expression in human monocytic cells
Differential involvement of calmodulin-dependent protein kinase II-activated AP-1 and c-Jun N-terminal kinase-activated EGR-1 signaling pathways in tumor necrosis factor-alpha and lipopolysaccharide-induced CD44 expression in human monocytic cells
Dependence of electrical activity and calcium influx-controlled prolactin release on adenylyl cyclase signaling pathway in pituitary lactotrophs
Critical role of c-IAP-2 in mediating mechanisms of resistance to HIV-Vpr-induced apoptosis in human monocytic cells
Role of cofilin, an actin cytoskeletal protein, in ischemic conditions: potential therapeutic target for ischemic stroke
Large-scale identification and analysis of suppressive drug interactions
Induction of ABCA1 expression is correlated with increased CREB phosphorylation and altered cytokine secretion
A synergistic effect between PG490-88 and tacrolimus prolongs renal allograft survival in monkeys
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