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Tacrolimus structure
  • CAS No:


  • Formula:


  • Synonyms:

    Anhydrous Tacrolimus;Anhydrous, Tacrolimus;FK 506;FK-506;FK506;FR 900506;FR-900506;FR900506;Prograf;Prograft

  • Categories:

    Biochemical Engineering  >  Inhibitors

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Tacrolimus is a macrocyclic lactone with potent immunosuppressive properties. Tacrolimus binds to FK506 binding protein (FKBP) to form a complex and inhibits calcineurin phosphatase.

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Basic Attributes

  • 104987-11-3

  • C44H69NO12

  • 804.02

  • 803.481995

  • 178 Ų

  • 3.3

  • 1308068-626-2


  • 12

  • 3

  • 7


  • white solid

  • 1.2±0.1 g/cm3

  • 113-115°C

  • 2℃

  • 1.549

  • Freely soluble in DMSO or ethanol. Poorly soluble in water.soluble in dimethyl sulfoxide, ethanol, water, acetone, chloroform, ethyl acetate, ether, methanol and dimethyl formamide.DMSO: >3 mg/mL

  • −20°C

  • 8.37X10-32 mm Hg at 25 °C (est)

  • Stable under recommended storage conditions. /FK-506 monohydrate/

Safety Information

  • 6.1

  • UN 2811 6.1/PG 3

  • 3

  • 25-36/37/38-36-20/21/22-11

  • 45-36-26-36/37-16-60-20

  • KD4201200

  • T,Xi,Xn,F

  • P210-P280-P305 + P351 + P338

  • H225-H302 + H312 + H332-H319


For use after allogenic organ transplant to reduce the activity of the patient's immune system and so the risk of organ rejection. It was first approved by the FDA in 1994 for use in liver transplantation, this has been extended to include kidney, heart,

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Production Methods

Obtained from Streptomyces tsukubaensis fermentation. The fermentation process is as follows: 100m1 seed liquid (containing 1% glycerol, 1% corn starch, 0.5% glucose, 1% cottonseed powder, 0.5% corn dipping solution and 0.2% calcium carbonate, pH=6.5) is transferred into a 500ml bottle, in Sterilize at 120℃ for 30min. Access to a circle of S. cultivating through slopes. Tsukubaensis No. 9993 seeds were cultivated at 30°C for 4 days. The culture liquid was transferred into the 201. The same seed liquid was sterilized in a 30L fermentor at 120°C for 30 minutes, and cultured at 30°C for 2 days, blowing air 2L/min, stirring 300r/min. 16L of this culture liquid was implanted in 1600L fermentation liquid (containing 4.5% soluble starch, 1% corn steep liquid, 1% dry yeast, 0.1% calcium carbonate and 0.1% Adekancd, pH=6.8), which had been sterilized at 120℃ After 2000min of 2000L, the tank was fermented at 30°C, 170r/min stirring and 1600L/min air flow for 4 days. Separation: 1500L fermentation broth is filtered with the aid of 25kg diatomaceous earth. The filter cake was extracted with 500L of acetone, and the extract and filtrate (1350L) were combined and passed through a column filled with 100LDiaion HP-20 non-ionic absorption resin (Mitsubishi (product of 2hemical Industries Ltd, Japan). 300L of water and 300L of 50% acetone aqueous solution were used. After washing, it was eluted again with 75% acetone aqueous solution. The eluent was concentrated under reduced pressure to about 300 L of aqueous solution, and then extracted with 20 L of ethyl acetate three times. The extracts were combined and concentrated under reduced pressure to the remaining oil. The residue was mixed with twice the weight of acidic silica gel (special silica gelgrade 12, Fuji (product of 9evision Co, Japan)) and immersed in ethyl acetate. The solvent was distilled off, and the remaining dry powder was chromatographed on the same acidic silica gel column of 8L , Eluted with 30L n-hexane, 30L n-hexane and ethyl acetate (4:1) mixed solution, 30L ethyl acetate. Collect the eluate containing fujimycin and concentrate under reduced pressure. The oily residue and 2 times the weight of Acidic silica gel was mixed and immersed in ethyl acetate. The solvent was distilled off and the resulting dry powder was chromatographed on 3.5L acidic silica gel column with 10L n-hexane, 10L n-hexane and ethyl acetate (4:1) mixed solution, 10L ethyl acetate Ester elution. Collect the eluent containing fugilin and concentrate it under reduced pressure. The resulting yellow oily residue was dissolved in a mixed solution of 300 ml of n-hexane and ethyl acetate (1:1) using 2 L of silica gel (230-400 μm) , Merck Co., Ltd. IJSA product) column chromatography, eluting with n-hexane and ethyl acetate (first 10L 1:1, then 6L 1:2), 6L ethyl acetate. Collect the elution containing fujimycin The solution was concentrated under reduced pressure to obtain 34g of fucomycin as a white powder. It was dissolved in acetonitrile and concentrated under reduced pressure. The concentrated solution was left at 5°C overnight to obtain 22.7g of prismatic crystals. It was recrystallized from acetonitrile to obtain 13.6 g colorless prismatic crystal pure fujimycin.

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