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(-)-ラパマイシン

(-)-ラパマイシン 化学構造式
53123-88-9
  • CAS番号.53123-88-9
  • 化学名:(-)-ラパマイシン
  • 别名:シロリムス;ラパマイシン;(-)-ラパマイシン;抗生物質AY-22989;EZSOLUTION™ RAPAMYCIN;ラパマイシン(異性体混合物);シロリムス 溶液;ラパマイシン STREPTOMYCES HYGROSCOPICUS由来;ラパマイシン(異性体混合物)【シロリムス】;EZSolution™ ラパマイシン;シロリムス (JAN)
  • 英語化学名:Rapamycin
  • 英語别名:RPM;RAPA;BCAR2;CS-440;TRERF1;TREP132;RAPAMUNE;AY 22989;SIROLIMUS;RAPAMYCIN
  • CBNumber:CB0275190
  • Molecular Formula:C51H79NO13
  • Formula Weight:914.19
  • MOL File:53123-88-9.mol
(-)-ラパマイシン 物理性質
  • 融点  :183-185°C
  • 比旋光度  :D25 -58.2° (methanol)
  • 沸点  :799.83°C (rough estimate)
  • 比重(密度)  :1.0352 (rough estimate)
  • 蒸気圧 :0.56 hPa ( 20 °C)
  • 屈折率  :1.5280 (estimate)
  • 闪点  :87 °C
  • 貯蔵温度  :-20°C
  • 溶解性 :ethanol: soluble2MM
  • 酸解離定数(Pka) :10.40±0.70(Predicted)
  • 外見  :solution
  • 色 :colorless to yellow
  • 水溶解度  :Soluble in DMSO at 50mg/ml or methanol at 25mg/mlSoluble in alcohol, dimethyl sulfoxide and dimethyl formamide. Insoluble in water.
  • Sensitive  :Moisture Sensitive/Light Sensitive/Hygroscopic
  • Merck  :14,8114
  • CAS データベース :53123-88-9(CAS DataBase Reference)
安全性情報
危険有害性情報のコード(GHS)
  • 絵表示(GHS)
  • 注意喚起語Danger
  • 危険有害性情報
  • H225:引火性の高い液体および蒸気
  • H227:引火性液体
  • H319:強い眼刺激
  • 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。
  • 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。
  • P403+P235:換気の良い場所で保管すること。涼しいところに 置くこと。
(-)-ラパマイシン 価格 もっと(24)
  • メーカー: 富士フイルム和光純薬株式会社(wako)
  • 製品番号: W01LKTR0161
  • 製品説明 : ラパマイシン
  • 純度: Rapamycin
  • 包装: 1mg
  • 価格: ¥6500
  • 更新時間: 2021/03/23
  • 購入: 購入
  • メーカー: 富士フイルム和光純薬株式会社(wako)
  • 製品番号: W01LKTR0161
  • 製品説明 : ラパマイシン
  • 純度: Rapamycin
  • 包装: 10mg
  • 価格: ¥19800
  • 更新時間: 2021/03/23
  • 購入: 購入
  • メーカー: 富士フイルム和光純薬株式会社(wako)
  • 製品番号: W01LKTR0161
  • 製品説明 : 
  • 純度: Rapamycin
  • 包装: 100mg
  • 価格: ¥86100
  • 更新時間: 2021/03/23
  • 購入: 購入
  • メーカー: 東京化成工業
  • 製品番号: R0097
  • 製品説明 : ラパマイシン
  • 純度: Rapamycin >98.0%(HPLC)
  • 包装: 25mg
  • 価格: ¥27200
  • 更新時間: 2021/03/23
  • 購入: 購入
  • メーカー: Sigma-Aldrich Japan
  • 製品番号: R0395
  • 製品説明 : ラパマイシン Streptomyces hygroscopicus由来
  • 純度: Rapamycin from Streptomyces hygroscopicus≥95% (HPLC), powder
  • 包装: 1mg
  • 価格: ¥51440
  • 更新時間: 2021/03/23
  • 購入: 購入

(-)-ラパマイシン MSDS


Sirolimus

Rapamycin 化学特性,用途語,生産方法

  • 外観 白色〜褐色, 結晶性粉末〜粉末
  • 溶解性 メタノール溶状:試験適合
  • 用途 FK506 の構造類似体であ り、FK506 と同様に FK506 結合タンパク質 (FKBP)と結合しますが、FK506 とは異なり、 カルシニューリンの活性は阻害しません。ラ パマイシンと FKBP の複合体は mTOR に結 合し、mTOR のキナーゼ活性を阻害すること により、IL-2 からのシグナルを阻害します。
  • 用途 移植臓器拒絶の予防のため、リンパ脈管筋腫症の治療のために医学分野で使われている。ヒトにおいて免疫抑制機能を持ち、腎臓移植の拒絶の予防において特に有用である。インターロイキン-2(IL-2)の産生を低下させることによってT細胞およびB細胞の活性化を阻害する。冠動脈ステント(英語版)のコーティング剤としても使われている。
  • 効能 抗悪性腫瘍薬, 免疫抑制薬, mTOR阻害薬
  • 商品名 ラパリムス (ノーベルファーマ); ラパリムス (ノーベルファーマ)
  • 化学的特性 White to Off-White Solid
  • Originator Rapamune,Wyeth Laboratories,UK
  • 使用 Tool for immunochemistry.
  • 使用 A specific mTOR inhibitor with an IC50 of 0.1 nM.
  • 使用 antidepressant
  • 使用 immunosuppressant, antineoplastic; rapamycin
  • 使用 Rapamycin is a triene macrolide discovered in 1995 as a metabolite of Streptomyces hygroscopicus found in a soil obtained on Rapi Nui (Easter Island). Rapamycin displayed potent and selective antifungal activity, notably against Candida albicans. Interest in the metabolite waned until the structural relationship to the potent immunosuppressant fujimycin (Antibiotic FK506) was recognised in the mid-1980s. This recognition led to the re-discovery of rapamycin as a highly selective antitumour and immunosuppressant. Rapamycin inhibits the activity of the protein, mTOR (mammalian target of rapamycin) which functions in a signalling pathway to promote tumour growth. Rapamycin binds to a receptor protein (FKBP12). The rapamycin/FKB12 complex then binds to mTOR and prevents interaction of mTOR with target proteins in this signalling pathway.
  • 使用 DDP-4 inhibitor type 2 diabetes therapeutic
  • 使用 Rapamycin is a triene macrolide discovered in 1974 as a metabolite of Streptomyces hygroscopicus found in a soil obtained on Rapa Nui (Easter Island). Rapamycin displayed potent and selective antifungal activity, notably against Candida albicans. Interest in the metabolite waned until the structural relationship to the potent immunosuppressant fujimycin (Antibiotic FK506) was recognised in the mid-1980s. This recognition led to the re-discovery of rapamycin as a highly selective antitumor and immunosuppressant. Rapamycin inhibits the activity of the protein, mTOR (mammalian target of rapamycin) which functions in a signalling pathway to promote tumor growth. Rapamycin binds to a receptor protein (FKBP12). The rapamycin/FKB12 complex then binds to mTOR and prevents interaction of mTOR with target proteins in this signalling pathway.
  • 使用 Labelled Rapamycin. A triene macrolide antibiotic isolated from Streptomyces hygroscopicus. Name derived from the native word for Easter Island, Rapa?Nui. Used as an immunosuppressant; antirestenotic. This compound contains aproximately 2% d0.;Labeled Sir
  • 使用 Rapamycin is an immunosuppressant that is used primarily to prevent the rejection of organ and bone marrow transplant. It was first described as a potent inhibitor of IL-2 activation of lymphocytes (IC50 = 5 pM). It is now known that rapamycin specifically interacts with the cytosolic FK-binding protein 12 (FKBP12) to form a complex which inhibits the mammalian target of rapamycin (mTOR) pathway by directly binding to mTOR Complex 1 (mTORC1). Rapamycin and other inhibitors of mTORC1 signaling show potential in treating cancer, adipogenesis, diabetes, tuberous sclerosis, and cardiovascular disease.[Cayman Chemical]
  • 定義 ChEBI: A macrolide isolated from Streptomyces hygroscopicus consisting of a 29-membered ring containing 4 trans double bonds, three of which are conjugated. It is an antibiotic, immunosupressive and antineoplastic agent.
  • 適応症 Mechanistic target of rapamycin (mTOR) is a serine/threonine-specific protein kinase in the PI3/PI4-kinase family. mTOR was named after the natural macrolide rapamycin, also known as sirolimus, which was isolated from a soil sample from Easter Island in the 1970s and later evaluated as an immunosuppressive agent. The anticancer activity of rapamycin was discovered in the 1980s, although the mechanismof action and the identification of the rapamycin target, mTOR, were not elucidated until the 1990s. Rapamycin and its macrocyclic analogues, such as temsirolimus (Torisel(R), Wyeth/Pfizer) and everolimus (Afinitor(R), Novartis), are grouped as “rapalogs” that constitute the first-generation mTOR inhibitors.
    Rapamycin was approved by the US FDA in 1999 as an immunosuppressive agent to prevent organ rejection in patients receiving kidney transplants. Although a large number of clinical studies have been performed to evaluate the anticancer activities of sirolimus in different types of cancers, such as invasive bladder cancer, breast cancer, and leukemia, most studies show limited efficacy. Outside oncological indications, sirolimus was approved by FDA for the treatment of a rare progressive lung disease lymphangioleiomyomatosis in 2015. Temsirolimus was approved for the treatment of advanced RCC. Everolimus was approved in the EU for the prevention of organ rejection in heart and kidney transplant recipients before FDA approved it in 2009 for the treatment of advanced RCC resistant to sunitinib or sorafenib and for the treatment of advanced or metastatic gastrointestinal and lung tumors in 2016. Additionally, rapamycin and rapalogs are being investigated as antiaging therapeutics or for the treatment of age-related diseases. Studies have revealed that mTOR activity can be retained under hypoxic conditions via mutations in the PI3K pathway, leading to increased translation and hypoxic gene expression and tumor progression.
  • 適応症 Sirolimus (Rapamune) is structurally related to tacrolimus. It is approved for use as an adjunctive agent in combination with cyclosporine for prevention of acute renal allograft rejection. It blocks IL-2-dependent T-cell proliferation by inhibiting a cytoplasmic serine– threonine kinase. This mechanism of action is different from those of tacrolimus and cyclosporine. This allows sirolimus to augment the immunosuppressive effects of these drugs.
  • Manufacturing Process Streptomyces hygroscopicus NRRL 5491 was grown and maintained on oatmeal-tomato paste agar slants (T. G. Pridham et al.; Antibiotic Annual 1956-1957, Medical Encyclopedia Inc., New York, p. 947) and in Roux bottles containing the same medium. Good growth was obtained after 7 days of incubation at 28°C. Spores from one Roux bottle were washed off and suspended into 50 ml of sterile distilled water. This suspension was used to inoculate the first stage inoculum.The first-stage inoculum medium consisted of Emerson broth [R. L. Emerson et al., J. Bacteriol, 52, 357 (1946)] 0.4% peptone, 0.4% sodium chloride, 0.25% yeast extract and 1% glucose; pH 7.0; flasks containing the above medium were inoculated with 1 % of the spore suspension described above. The inoculated flasks were incubated for 30 hours at 28°C on a reciprocating shaker set at 65 r.p.m. (4 inch stroke).
    Production stage
    The production stage was run in 250-liter New Brunswick fermenters Model F- 250, equipped with automatic antifoam addition system and pH recordercontroller. The fermenters were charged with 160 L of an aqueous production medium consisting of the following constituents: 1.0% soluble starch; 0.5% (NH4)2SO4; 0.5% K2HPO4; 1.5% glucose (Cerelose); 0.025% MgSO4; 0.005% ZnSO4; 0.001% MnSO4; 0.002% FeSO47H2O; 0.2% CaCO3; 0.5% "Blackstrap" molasses; 0.5% hydrolyzed casein; 0.2% lard oil; pH 7.1 to 7.3 of first stage inoculum. Incubation temperature: 28°C; aeration: 0.5 vol/vol/min; agitation: 250 r.p.m. The fermenters were sterilized at 121°C for 45 min, cooled and inoculated with one flask inoculum).
    A titre of ca. 20 μg/ml, determined by microbiological assay on agar plates seeded with Candida albicans, was reached in 5 days. The fermentation was stopped. The fermentation mixture was extracted twice with 1 v/v of nbutanol. The combined butanol extracts were washed with 1 v/v of water, dried with anhydrous sodium sulfate and evaporated to dryness under reduced pressure to yield a residue. The oily residue was extracted 3 times with 2 L of methanol. The combined methanol extracts were passed through diatomaceous earth (Celite) and evaporated to dryness to yield an oily residue containing crude Rapamycin.
  • brand name Rapamune (Wyeth).
  • Therapeutic Function Immunosuppressive, Antifungal
  • 生物活性 Antifungal and immunosuppressant. Specific inhibitor of mTOR (mammalian target of Rapamycin). Complexes with FKBP-12 and binds mTOR inhibiting its activity. Inhibits interleukin-2-induced phosphorylation and activation of p70 S6 kinase.
(-)-ラパマイシン 上流と下流の製品情報
原材料
準備製品
(-)-ラパマイシン 生産企業
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53123-88-9, (-)-ラパマイシン キーワード:
  • 53123-88-9
  • AY 22989
  • 23,27-EPOXY-3H-PYRIDO(2,1-C)(1,4)OXAAZACYCLOHENTRIACONTINE
  • NSC-226080
  • RAPA
  • RAPAMUNE
  • RAPAMYCIN
  • RAPAMYCIN, STREPTOMYCES HYGROSCOPICUS
  • RPM
  • SIROLIMUS
  • antibioticay22989
  • (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34aS)-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-Hexadecahydro-9,27-dihydroxy-3-[(1R)-2-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethyl]-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-23,27-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclohentriacontine-1,5,11,28,29(4H,6H,31H)-pentone
  • RAPAMYCIN FROM STREPTOMYCESHYGROSCOPICUS RESEARCH GRADE
  • Rapamycin from Streptomyces hygroscopicus,23,27-Epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclohentriacontine, AY 22989, Sirolimus
  • (1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-dihydroxy-12-[(2R)-1-[(1S,3R,4R)-4-hydroxy-3-Methoxycyclohexyl]propan-2-yl]-19,30-diMethoxy-15,17,21,23,29,35-hexaMethyl-11,36-dioxa-4-azatricyclo[30.3.1.0^{4,9}]hexatriaconta-16,24,26,28-te
  • (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34aS)-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-Hexadecahydro-9,27-dihydroxy-3-[(1R)-2-[(1S,3R,4R)-4-hydroxy-3-Methoxycyclohexyl]-1-Methylethyl]-10,21-diMethoxy-6,8,12,14,20,26-hexaMethy
  • RapaMycin RapaMuneTM
  • RapaMycin-d3 (SiroliMus-d3)
  • SiroliMus, AY 22989, SIIA 9268A
  • RapaMicin(siroliMus )
  • AY 22989,NSC-2260804
  • Sirolimus Rapamicin(sirolimus )
  • Rapamycin Sirolimus 23,27-Epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclohentriacontine
  • Rapamycin 23,27-Epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclohentriacontine
  • NSC-2260804
  • Rapamycin?Impurity
  • Rapamycin - CAS 53123-88-9 - Calbiochem
  • Rapmycin/Sirolimus
  • Rapamycin(mixture of isomers)
  • Rapamycin(mixture of isomers) [Sirolimus]
  • CS-440
  • シロリムス
  • ラパマイシン
  • (-)-ラパマイシン
  • 抗生物質AY-22989
  • EZSOLUTION™ RAPAMYCIN
  • ラパマイシン(異性体混合物)
  • シロリムス 溶液
  • ラパマイシン STREPTOMYCES HYGROSCOPICUS由来
  • ラパマイシン(異性体混合物)【シロリムス】
  • EZSolution™ ラパマイシン
  • シロリムス (JAN)
  • マクロライド系抗生物質
  • 免疫抑制薬