Tacrolimus (FK-506, Fujimycin, FR900506, Prograf)

Alias: FR900506;FR 900506; FR-900506; FK 506; FK-506; FK506; fujimycin; Prograf; Protopic; Advagraf; Astagraf XL
Cat No.:V0183 Purity: ≥98%
Tacrolimus(FK506, Fujimycin, FR-900506, Prograf),a natural macrocyclic lactone isolated from the fungus Streptomyces tsukubaensis, is a potent immunosuppressive agentused with other medications to prevent rejection of organ (kidney, heart, liver) transplant.
Tacrolimus (FK-506, Fujimycin, FR900506, Prograf) Chemical Structure CAS No.: 104987-11-3
Product category: mTOR
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
10mg
50mg
100mg
250mg
500mg
1g
2g
Other Sizes

Other Forms of Tacrolimus (FK-506, Fujimycin, FR900506, Prograf):

  • Tacrolimus Monohydrate
  • Tacrolimus-13C,d2 (FK506-13C,d2; Fujimycin-13C,d2; FR900506-13C,d2)
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Purity: ≥98%

Product Description

Tacrolimus (FK506, Fujimycin, FR-900506, Prograf), a natural macrocyclic lactone isolated from the fungus Streptomyces tsukubaensis, is an effective immunosuppressive drug that works in conjunction with other drugs to prevent organ transplant rejection (kidney, heart, liver). It works by attaching to the FK506 binding protein (FKBP) and inhibiting calcineurin phosphatase, which prevents the signaling of T lymphocytes and the transcription of IL-2. Tacrolimus can lower the risk of organ rejection by reducing the patient's immune system's activity. Additionally, atopic dermatitis (eczema), severe refractory uveitis following bone marrow transplants, exacerbations of minimal change disease, TH2-mediated illnesses like Kimura's disease, and the skin condition vitiligo are all treated with it topically.

Biological Activity I Assay Protocols (From Reference)
Targets
FKBP12; calcineurin
ln Vitro
FK-506 and cyclosporin A block translocation of the cytoplasmic component without affecting synthesis of the nuclear subunit in T lymphocytes.[1] K-506 inhibits a Ca(2+)-dependent process necessary for the induction of interleukin-2 transcription, which stops T-cell proliferation. [2] Cyclophilins and FK 506-binding proteins (FKBPs) are two different families of intracellular proteins (immunophilins) that FK 506 binds to. At drug concentrations that prevent activated T cells from producing interleukin 2, FK-506 specifically inhibits cellular calcineurin. [3] By blocking the same subset of early calcium-associated events involved in lymphokine expression, apoptosis, and degranulation, FK-506 and CsA have nearly identical biological effects on cells. The FK-506 binding proteins (FKBPs), a family of intracellular receptors, are where FK-506 binds. [4]
ln Vivo
FK-506 results in increase in the paw and tail withdrawal threshold as revealed by behavioral pain assessment in rats against hyperalgesic and allodynic stimuli. Additionally, FK-506 lowers serum nitrate and thiobarbituric acid reactive substance (TBARS) levels. It also lowers tissue myeloperoxidase (MPO) and total calcium levels, while raising tissue reduced glutathione levels in rats. In rats with ischemia reperfusion (I/R), FK-506 reduces the progression of neuronal edema and axonal degeneration. [5]
Enzyme Assay
Tacrolimus (FK506) inhibits calcium-dependent events, such as IL-2 gene transcription, NO synthase activation, cell degranulation, and apoptosis. Tacrolimus also potentiates the actions of glucocorticoids and progesterone by binding to FKBPs contained within the hormone receptor complex, preventing degradation. The agent may enhance expression of the TGFβ-1 gene in a fashion analogous to that demonstrated for CsA. T cell proliferation in response to ligation of the T cell receptor is inhibited by Tacrolimus. Treatment with a low concentration of Tacrolimus (FK506,10 μg/L) does not significantly affect the proliferation of MH3924A cells (P=0.135). Upon treatment with higher concentrations of Tacrolimus (100-1,000 μg/L), the proliferation of MH3924A cells is significantly enhanced (P<0.01). However, when different concentrations of AMD3100 are combined with 100 μg/L Tacrolimus, the in vitro proliferation of MH3924A cells is increased (P<0.01).
Cell Assay
Cells were cultured in the presence of 10 nM FK 506 for 1 hr and washed, and phosphatase activity was measured in lysates.
Animal Protocol
Mice; Six-week-old male C57BL/6J mice are maintained in a temperature- and humidity-controlled room with a 12-h light-dark cycle. FTacrolimus 30 mg/kg is given orally to colitic mice (n=10) for either 7 or 14 days (Days 10 to 23) as part of the multiple dosing study. The same regimen is used to administer placebos to the control group (n = 10) and the normal group (n = 5). 10 mL/kg of placebo or tacrolimus is given. On the day after the final dose, mice are put to death by CO2 inhalation. For the single-dose study, colitic mice are given Tacrolimus or a placebo (n=8) orally once on Days 7, 10, 17, or 24. The same procedure is used to administer a placebo to normal mice (n = 4). Eight hours after dosing, mice are put to death by CO2 inhalation.
References

[1]. Nature . 1991 Aug 29;352(6338):803-7.

[2]. Nature . 1992 Jun 25;357(6380):692-4.

[3]. Proc Natl Acad Sci U S A . 1992 May 1;89(9):3686-90.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C44H69NO12
Molecular Weight
804.0182
Exact Mass
973.29551
Elemental Analysis
C, 57.92; H, 5.69; Cl, 3.64; F, 5.85; N, 7.19; O, 9.85; S, 9.87
CAS #
104987-11-3
Appearance
Solid powder
SMILES
C[C@@H]1C[C@@H]([C@@H]2[C@H](C[C@H]([C@@](O2)(C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@@H]([C@@H]([C@H](CC(=O)[C@@H](/C=C(/C1)\C)CC=C)O)C)/C(=C/[C@@H]4CC[C@H]([C@@H](C4)OC)O)/C)O)C)OC)OC
InChi Key
QJJXYPPXXYFBGM-LFZNUXCKSA-N
InChi Code
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
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-tetrone
Synonyms
FR900506;FR 900506; FR-900506; FK 506; FK-506; FK506; fujimycin; Prograf; Protopic; Advagraf; Astagraf XL
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: ~94 mg/mL (~116.9 mM)
Water: <1 mg/mL
Ethanol: ~83 mg/mL (~103.2 mM)
Solubility (In Vivo)
5% DMSO+corn oil: 15mg/mL (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.2438 mL 6.2188 mL 12.4375 mL
5 mM 0.2488 mL 1.2438 mL 2.4875 mL
10 mM 0.1244 mL 0.6219 mL 1.2438 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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Clinical Trial Information
NCT Number Status Interventions Conditions Sponsor/Collaborators Start Date Phases
NCT04645667 Recruiting Drug: Tacrolimus Acute GVHD UNC Lineberger Comprehensive
Cancer Center
February 1, 2021
NCT05744635 Recruiting Drug: Tacrolimus Liver Failure Chiesi Hungary Ltd. May 10, 2023
NCT03760263 Recruiting Drug: Tacrolimus Transplant;Failure,Kidney Sentara Norfolk General
Hospital
January 16, 2020 Phase 4
NCT04380311 Recruiting Device: Tacrolimus Dosing
Support Tool
Heart Transplant Failure
and Rejection
University of Utah May 1, 2020
NCT03438773 Recruiting Drug: Envarsus
Drug: Tacrolimus
Kidney Transplant Failure
and Rejection
California Institute of
Renal Research
July 11, 2018 Phase 1
Biological Data
  • MHY1485

    Failure of the increase of autophagic flux. PLoS One. 2012; 7(8): e43418.

  • MHY1485

    Inhibition of starvation-induced autophagic flux by MHY1485.

  • MHY1485

    Activation of mTOR by MHY1485.

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