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Tacrolimus Produkt Beschreibung

Tacrolimus Struktur
Englisch Name:
FK-506;Tacros;prograf;CS-1172;Advagraf;fr900506;Protopic;L 679934;TacroBell;Fujimycin

Tacrolimus Eigenschaften

871.7±75.0 °C(Predicted)
1.19±0.1 g/cm3(Predicted)
storage temp. 
DMSO: >3 mg/mL
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.
CAS Datenbank
104987-11-3(CAS DataBase Reference)
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher T,Xi,Xn,F
R-Sätze: 25-36/37/38-36-20/21/22-11
S-Sätze: 45-36-26-36/37-16-60-20
RIDADR  UN 2811 6.1/PG 3
WGK Germany  3
RTECS-Nr. KD4201200
HazardClass  6.1
HS Code  29349990
Bildanzeige (GHS)
Alarmwort Achtung
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H225 Flüssigkeit und Dampf leicht entzündbar. Entzündbare Flüssigkeiten Kategorie 2 Achtung P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H301 Giftig bei Verschlucken. Akute Toxizität oral Kategorie 3 Achtung P264, P270, P301+P310, P321, P330,P405, P501
H319 Verursacht schwere Augenreizung. Schwere Augenreizung Kategorie 2 Warnung P264, P280, P305+P351+P338,P337+P313P
P210 Von Hitze, heißen Oberflächen, Funken, offenen Flammen und anderen Zündquellenarten fernhalten. Nicht rauchen.
P264 Nach Gebrauch gründlich waschen.
P264 Nach Gebrauch gründlich waschen.
P270 Bei Gebrauch nicht essen, trinken oder rauchen.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P321 Besondere Behandlung
P305+P351+P338 BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.
P405 Unter Verschluss aufbewahren.

Tacrolimus Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:

R25:Giftig beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.

S-Sätze Betriebsanweisung:

S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.


Tacrolimus, isolated from the microorganism Streptomyces tsukubaensis, is a macrolide immunosuppressant developed by Fujisawa for organ transplantation. It displays similar but more potent immunosuppressive activity than cyclosporin. It inhibits both cell mediated and humoral immune responses. In animal models of organ transplantation, tacrolimus has been shown to prolong survival of hepatic, renal, cardiac, small intestine, pancreatic and skin allografts and to reverse cardiac and renal allograft rejection. It has been used effectively in humans as rescue or primary immunosuppressant therapy in liver or kidney transplantation. Compared to cyclosporin, tacrolimus causes reduced incidence of infectious complications and of hypertension and hypercholesterolemia for the allograft recipients. In common with cyclosporin, tacrolimus binds with high affinity to a family of cytoplasmic immunosuppressant binding proteins, the immunophilins. This tight complex is proposed as the biologically active moiety that interacts with intracellular molecules involved in signal transduction.It inhibits phosphatase activity of calcineurin, an action that may impair the generation and/or activation of nuclear transcription factors required for lymphokine (particularly interleukin-2) gene expression. Tacrolimus has also been reported to have potential in multiple sclerosis, psoriasis, rheumatoid arthritis and uveitis associated with Behcet‘s disease.

Chemische Eigenschaften

White Crystalline Solid


Fujisawa (Japan)


An immunosuppressant that blocks T cell proliferation in vitro by inhibiting the generation of several lymphokines, especially IL-2. Shown to inhibit the activity of FK-506 binding protein, thereby reversing its effects on sarcoplasmic reticulum Ca+2 release.


FK-506 (Tacrolimus) is a macrolide immunosuppressive drug that is mainly used after allogeneic organ transplant to reduce the activity of the patient's immune system


Tacrolimus (fujimycin) was discovered as a potent inhibitor of IL2 production in a targeted search for novel immunosuppressants. Tacrolimus acts by blocking T cell proliferation in vitro by inhibiting the generation of several lymphokines, notably the original target IL-2. Tacrolimus inhibits the activity of FK-506 binding protein, Ca2+-dependent phosphatase and calcineurin, and activates NF-κB through phosphorylation and degradation of IκBα.


treatment of Cushing's syndrome


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,


ChEBI: Tacrolimus is a macrolide containing a 23-membered lactone ring, originally isolated from the fermentation broth of a Japanese soil sample that contained the bacteria Streptomyces tsukubaensis.


Tacrolimus is a macrolide lactone originally derived from Streptomyces tsukubaensis. Although structurally unrelated to cyclosporine, tacrolimus has a very similar mechanism of action; that is, it blocks the production of proinflammatory cytokines by T lymphocytes by inhibiting calcineurin.Tacrolimus, however, appears to be 10 to 100 times as potent as an immunosuppressive. Oral tacrolimus (FK506) is used for prevention of organ rejection in recipients of renal and hepatic transplants.


Tacrolimus (Prograf) is a second-generation immunosuppressive agent that has been approved for use in liver transplantation. Its efficacy for other transplantations is being evaluated. It has properties similar to those of cyclosporine except that weight for weight it is 10 to 100 times more potent. It is a macrolide antibiotic that selectively inhibits transcription of a specific set of lymphokine genes in T lymphocytes (e.g., IL-2, IL-4, and interferon-) and binds to cytoplasmic proteins in lymphocytes. Although the binding proteins (cytophilins) for cyclosporine and tacrolimus are different, they share similar functions in that the cytophilins are important for the intracellular folding of proteins. It is speculated that these proteins are important in regulating gene expression in T lymphocytes and that both drugs somehow interfere in this process.
Absorption of tacrolimus from the gastrointestinal (GI) tract is variable. It is extensively metabolized in the liver and excreted in the urine.As with cyclosporine, nephrotoxicity is its principal side effect.

Manufacturing Process

The novel 17-allyl-1,14-dihydroxy-12-[2-(4-hydroxy-3-methoxycyclohexyl)-1- methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4- azatrcyclo[,9]octacos-18-ene-2,3,10,16-tetraone (FR-900506), substance can be produced by culturing a FR-900506 substance(s)-producing strain belonging to the genus Streptomyces (e.g. Streptomyces tsukubaensis No. 9993, FERM BP-927) in a nutrient medium.
A culture medium (160 ml) containing glycerin (1%), corn starch (1%), glucose (0.5%), cottonseed meal (1%), dried yeast (0.5%), corn steep liquor (0.5%) and calcium carbonate (0.2%) (adjusted to pH 6.5) was poured into each of ten 500 ml-Erlenmeyer flasks and sterilized at 120°C for 30 min. A loopful of slant culture of Streptomyces tsukubaensis No. 9993 was inoculated to each of the medium and cultured at 30°C for 4 days on a rotary shaker. The resultant culture was inoculated to a medium containing soluble starch (5%), peanut powder (0.5%), dried yeast (0.5%), gluten meal (0.5%), calcium carbonate (0.1%) and Adekanol (deforming agent, Trade Mark, maker Asasi Denka Co.) (0.1%) (150 liters) in a 200-liter jar-fermentor, which had been sterilized at 120°C for 20 min in advance, and cultured at 30C for 4 days under aeration of 150 liters/minutes and agitation of 250 rpm.
Isolation and Purification
The cultured broth thus obtained was filtered with an aid of diatomaseous earth (5 kg). The mycelial cake was extracted with acetone (50 liters), yielding 50 liters of the extract. The acetone extract from mycelium and the filtrate (135 L) were combined and passed through a column of a non-ionic adsorption resin "Diaion HP-20" (Trade Mark, maker Mitsubishi Chemical Industries Ltd.) (10 L). After washing with water (30 L) and 50 % aqueous acetone (30 L), elution was carried out with 75 aqueous acetone. The eluate (30 liters) was evaporated under reduced pressure to give residual water (2 L). This residue was extracted with ethyl acetate (2 L) three times. The ethyl acetate extract was concentrated under reduced pressure to give an oily residue. The oily residue was mixed with twice weight of acidic silica gel (special silica gel grade 12, maker Fuji Devison Co.), and this mixture was slurried in ethyl acetate. After evaporating the solvent, the resultant dry powder was subjected to column chromatography of the same acidic silica gel (800 ml) which was packed with n-hexane. The column was developed with nhexane (3 L), a mixture of n-hexane and ethyl acetate (4:1 v/v, 3 L) and ethyl acetate (3 L). The fractions containing the object compound were collected and concentrated under reduced pressure to give an oily residue. The oily residue was dissolved in a mixture of n-hexane and ethyl acetate (1:1 v/v, 30 ml) and subjected to column chromatography of silica gel (maker Merck Co., Ltd. 230-400 mesh) (500 ml) packed with the same solvents system. Elution was carried out with a mixture of n-hexane and ethyl acetate (1:1 v/v, 2 liters and 1:2 v/v, 1.5 L) and ethyl acetate (1.5 L). Fractions containing the first object compound were collected and concentrated under reduced pressure to give crude FR-900506 substance (3 g) in the form of yellowish powder.
This powder of the FR-900506 substance could be transformed into a form of white crystals by recrystallization thereof from acetonitrile. Melting point: 127°-129°C.


Prograf (Astellas); Protopic (Astellas).

Therapeutic Function


Clinical Use

A topical formulation (Protopic) has recently been approved for treatment of moderate to severe atopic dermatitis in children and adults who have not responded to other therapies. Levels of systemic absorption are low even when applied to a relatively large body surface area.


Local irritant reactions (burning, stinging, erythema) are a common side effect, but these usually resolve within the first few days of treatment. The major benefit of topical tacrolimus over topical corticosteroids is that tacrolimus does not cause atrophy, striae, or telangiectasia, even with chronic use.

Veterinary Drugs and Treatments

Tacrolimus has recently been studied at the University of Tennessee College of Veterinary Medicine where investigators found it equally effective as cyclosporine and effective for cyclosporine-resistant cases of KCS. It exerts its effects through a mechanism similar to that of cyclosporine, however exact mechanisms of action in causing tear production are still being determined.

Veterinary Drugs and Treatments

Tacrolimus ointment may be of benefit in veterinary patients in the adjunctive treatment of atopic dermatitis, discoid lupus erythematosus, pemphigus erythematosus or foliaceous, pinnal vascular disease, alopecia areata, vitiligo and for perianal fistulas (terminal phase or maintenance treatment after cyclosporine therapy). Unlike topical corticosteroids, tacrolimus or pimecrolimus do not have atrophogenic or metabolic effects associated with long-term or large area treatment.
Tacrolimus acts similarly as cyclosporine, namely inhibiting T-lymphocyte activation primarily by inhibiting the phosphatase activity of calcineurin. It also inhibits the release of inflammatory cytokines and mediators from mast cells and basophils.

Tacrolimus Upstream-Materialien And Downstream Produkte


Downstream Produkte

Tacrolimus Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 460)Lieferanten
Firmenname Telefon Fax E-Mail Land Produktkatalog Edge Rate
Henan Tianfu Chemical Co.,Ltd.
0371-55170693 CHINA 22624 55
0371-55170695 CHINA 20534 58
Casorganics US Corp
+17326109938 CHINA 175 58
Hubei Ipure Biology Co., Ltd
18062553746 +86 18062427325 (WhatsApp) CHINA 348 58
Wuhan ChemNorm Biotech Co.,Ltd.
18971486879 +86-27-8439 4403
+86-27-8439 4403 CHINA 2793 58
Capot Chemical Co.,Ltd.
+86(0)13336195806 +86-571-85586718
+86-571-85864795 China 19929 60
Hubei XinRunde Chemical Co., Ltd.
02783214688 CHINA 568 55
Nanjing Finetech Chemical Co., Ltd.
025-85710122 17714198479
025-85710122 CHINA 890 55
+86 21 5161 9050/ 5187 7795
+86 21 5161 9052/ 5187 7796 CHINA 24886 60
Anhui Royal Chemical Co., Ltd.
+86-025-86655873 CHINA 537 55

104987-11-3()Verwandte Suche:

  • (3S,4R,5S,8R,9E...5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(2-propen-1-yl)-15,19-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone
  • (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-Hexadecahydro-5,19-dihydroxy-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(2-propen-1-yl)-15,19-e
  • Tacrolimus solution
  • Tacrolimus, Prograf, FK506
  • Tacrolimus, 98.5%
  • FK-506, Streptomyces sp. - CAS 104987-11-3 - Calbiochem
  • (2-propenyl)-,(3s-(3r*(e(1s*,3s*,4s*)),4s*,5r*,8s*,9e,12r*,14r*,15s*,16r*,18s*
  • ,19s*,26ar*))-
  • 16-dimethoxy-4,10,12,18-tetramethyl-8-3-(2-(4-hydroxy-3-methoxycyclohexyl)-1
  • FK-506:FR-900506
  • Fujimycin Prozraf
  • Tacrolimus,micronisedandpharmagrade
  • REF DUPL: Tacrolimus
  • FK506(Tacrolimus)
  • Tacrolimus premix
  • (1R,9S,12S,13R,14S,17R,18E,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[^{4,9}]octacos-18-ene-2,3,10
  • Advagraf
  • TacroBell
  • TacroliMus-13CD2/FK-506-13CD2
  • FujiMycin, FK506, FR900506, Tskubaenolide
  • (3S,4R,5S,8R,9E...5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(2-propen-1-yl)-15,19-e
  • FK-506
  • FK-506, 99+%
  • 19-epoxy-3h-pyrido(2,1-c)(1,4)oxaazacyclotricosine-1,7,20,21(4h,23h)-tetrone,5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-(2-(4-hydroxy-3-methoxycyclohexyl)-14,16-dim
  • 6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-5
  • fr900506
  • prograf
  • tsukubaenolide
  • Fujimycin
  • CS-1172
  • Tacros
  • Cacrolimus
  • Tacrolimus (FK506)(free base)
  • Tacrolimus, ≥98%(HPLC)
  • Protopic
  • L 679934
  • 15,19-Epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone, 5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-[2-(4-hydroxy-3-methoxycyclohexyl)-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(2-propenyl)-, [3S-[3R*[E(1S*,3S*,4S*)],4S*,5R*,8S*,9E,12R*,14R*,15S*,16R*,18S*,19S*,26aR*]]-
  • Tacrolimus RS
  • tacrolimus (anhydrous)
  • 104987-11-3
  • 104987-11-3 ;109581-93-3
  • 109581-93-9
  • C44H69NO12xH2O
  • C44H69NO12
  • C44H69NO10
  • BioChemical
  • Cell Biology
  • Cell Signaling and Neuroscience
  • Kinase/Phosphatase Biology
  • Protein Phosphatase 2B (Calcineurin/PP2B)
  • Serine/Threonine Phosphatase Inhibitors
  • Inhibitors
  • Immunosuppressant.
  • Fujimycin, Prograf
  • antibiotic
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