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タクロリムス

タクロリムス 化学構造式
104987-11-3
CAS番号.
104987-11-3
化学名:
タクロリムス
别名:
FK506;タクロリムス MONOHYDRATE;FK-506 (タクロリムス);タクロリムス 溶液;FK506(タクロリムス);FK506【タクロリムス】
英語化学名:
Tacrolimus
英語别名:
FK-506;Tacros;prograf;CS-1172;Advagraf;fr900506;Protopic;L 679934;TacroBell;Fujimycin
CBNumber:
CB9772399
化学式:
C44H69NO12
分子量:
804.02
MOL File:
104987-11-3.mol

タクロリムス 物理性質

融点 :
113-115°C
沸点 :
871.7±75.0 °C(Predicted)
比重(密度) :
1.19±0.1 g/cm3(Predicted)
闪点 :
2℃
貯蔵温度 :
−20°C
溶解性:
DMSO: >3 mg/mL
酸解離定数(Pka):
9.97±0.70(Predicted)
外見 :
solid
色:
white
水溶解度 :
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.
InChIKey:
QJJXYPPXXYFBGM-LFZNUXCKSA-N
CAS データベース:
104987-11-3(CAS DataBase Reference)
安全性情報
  • リスクと安全性に関する声明
  • 危険有害性情報のコード(GHS)
主な危険性  T,Xi,Xn,F
Rフレーズ  25-36/37/38-36-20/21/22-11
Sフレーズ  45-36-26-36/37-16-60-20
RIDADR  UN 2811 6.1/PG 3
WGK Germany  3
RTECS 番号 KD4201200
国連危険物分類  6.1
HSコード  29349990
絵表示(GHS)
注意喚起語 Danger
危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード
H225 引火性の高い液体および蒸気 引火性液体 2 危険 P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H301 飲み込むと有毒 急性毒性、経口 3 危険 P264, P270, P301+P310, P321, P330,P405, P501
H319 強い眼刺激 眼に対する重篤な損傷性/眼刺激 性 2A 警告 P264, P280, P305+P351+P338,P337+P313P
注意書き
P210 熱/火花/裸火/高温のもののような着火源から遠ざ けること。-禁煙。
P264 取扱い後は皮膚をよく洗うこと。
P264 取扱い後は手や顔をよく洗うこと。
P270 この製品を使用する時に、飲食または喫煙をしないこ と。
P280 保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。
P305+P351+P338 眼に入った場合:水で数分間注意深く洗うこと。次にコ ンタクトレンズを着用していて容易に外せる場合は外す こと。その後も洗浄を続けること。
P321 特別な処置が必要である(このラベルの... を見よ)。
P405 施錠して保管すること。

タクロリムス 価格 もっと(17)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01BVI1563-1
FK-506
104987-11-3 1mg ¥16900 2018-12-26 購入
富士フイルム和光純薬株式会社(wako) W01BVI1563-10
FK-506
104987-11-3 10mg ¥53300 2018-12-26 購入
Sigma-Aldrich Japan T-049 タクロリムス 溶液 1.0?mg/mL in acetonitrile, ampule of 1?mL, certified reference material
Tacrolimus solution 1.0?mg/mL in acetonitrile, ampule of 1?mL, certified reference material
104987-11-3 1ml ¥57000 2018-12-25 購入
富士フイルム和光純薬株式会社(wako) W01LKTT0008 タクロリムス
Tacrolimus
104987-11-3 100mg ¥77200 2018-12-26 購入
富士フイルム和光純薬株式会社(wako) W01CAY10007965
FK-506
104987-11-3 100mg ¥90200 2018-12-26 購入

タクロリムス 化学特性,用途語,生産方法

外観

白色〜ほとんど白色, 結晶〜粉末

溶解性

アセトニトリルに溶ける。

用途

強 力 な 免疫抑制剤 で す。 FK506はFK506結合タンパク-12(FKBP12) と複合体を形成し、さらにカルシニューリン に結合し、IL-2、インターフェロンに代表さ れる種々のサイトカインの発現を抑制しま す。これにより細胞外性 T 細胞の分化増殖を 抑制します。

効能

抗アレルギー薬, 免疫抑制薬, カルシニューリン阻害薬

説明

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.

化学的特性

White Crystalline Solid

Originator

Fujisawa (Japan)

使用

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.

使用

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

使用

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.

使用

treatment of Cushing's syndrome

使用

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,

定義

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.

適応症

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.

適応症

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[22.3.1.04,9]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.
Fermentation
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.

brand name

Prograf (Astellas); Protopic (Astellas).

Therapeutic Function

Immunosuppressive

臨床応用

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.

副作用

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.

タクロリムス 上流と下流の製品情報

原材料

準備製品


タクロリムス 生産企業

Global( 458)Suppliers
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104987-11-3(タクロリムス)キーワード:


  • 104987-11-3
  • (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[22.3.1.0^{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
  • FUJIMYCIN;PROGRAF;FK506;TACROLIMUS
  • TACROLIMUS
  • 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
  • FK506
  • タクロリムス MONOHYDRATE
  • FK-506 (タクロリムス)
  • タクロリムス 溶液
  • FK506(タクロリムス)
  • FK506【タクロリムス】
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