ChemicalBook
Chinese Japanese Germany Korea

Rapamycin

Indications and Usage Mechanisms of Action Application Adverse reactions
Rapamycin
Rapamycin structure
CAS No.
53123-88-9
Chemical Name:
Rapamycin
Synonyms
RPM;RAPA;BCAR2;CS-440;TRERF1;TREP132;AY 22989;RAPAMUNE;RAPAMYCIN;SIROLIMUS
CBNumber:
CB0275190
Molecular Formula:
C51H79NO13
Formula Weight:
914.18
MOL File:
53123-88-9.mol

Rapamycin Properties

Melting point:
183-185°C
alpha 
D25 -58.2° (methanol)
Boiling point:
799.83°C (rough estimate)
Density 
1.0352 (rough estimate)
vapor pressure 
0.56 hPa ( 20 °C)
refractive index 
1.5280 (estimate)
Flash point:
87 °C
storage temp. 
-20°C
solubility 
ethanol: soluble2MM
pka
10.40±0.70(Predicted)
form 
solution
color 
colorless to yellow
Water Solubility 
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 DataBase Reference
53123-88-9(CAS DataBase Reference)
EWG's Food Scores
1
FDA UNII
W36ZG6FT64
NCI Dictionary of Cancer Terms
Rapamune; rapamycin; sirolimus
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS02,GHS07
Signal word  Danger
Hazard statements  H227-H225-H302+H312+H332-H319
Precautionary statements  P210e-P280a-P370+P378a-P403+P235-P501a-P210-P280-P305+P351+P338
Hazard Codes  Xi,Xn,F
Risk Statements  36/38-36-20/21/22-11
Safety Statements  22-24/25-37/39-26-36/37-16
RIDADR  UN 1648 3 / PGII
WGK Germany  2
RTECS  VE6250000
Autoignition Temperature 301 °C
HS Code  29349990
Toxicity LD50 in mice (mg/kg): 600 i.p.; >2,500 orally (Vézina)

Rapamycin price More Price(17)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 553210 Rapamycin 53123-88-9 1mg $261 2019-12-02 Buy
Sigma-Aldrich 37094 Rapamycin VETRANAL 53123-88-9 10mg $489 2019-12-02 Buy
TCI Chemical R0097 Rapamycin >98.0%(HPLC) 53123-88-9 25mg $233 2020-06-24 Buy
Alfa Aesar J62473 Rapamycin, 99+% 53123-88-9 100mg $175 2020-06-24 Buy
Alfa Aesar J62473 Rapamycin, 99+% 53123-88-9 50mg $105 2020-06-24 Buy

Rapamycin Chemical Properties,Uses,Production

Indications and Usage

Rapamycin (Rapa, or Sirolimus) is a new form of macrolide immunosuppressive agent. It is a white solid crystal. Its melting point is 183-185℃ and it is lipophilic. It is soluble in methanol, ethanol, acetone, chloroform, and other organic solvents, very slightly soluble in water, and almost insoluble in ether. It was first discovered in 1975 on the Chilean Easter Island as a secondary metabolite secreted by soil Streptomyces, and its chemical structure is that of a three-polyene macrolide compound.
Rapamycin is a new form of immunosuppressive agent with good curative effects, low toxicity, and no nephrotoxicity. It can be used to maintain the immunity of transplant organs (especially in kidney transplants) to alleviate immunological rejections after organ transplant surgeries. The latest research has shown that Rapamycin can also be used to treat Alzheimer’s. When used on afflicted lab rats, it had a memory-restoring effect. Rapamycin oral tablets can be taken with grapefruit juice to treat melanoma (a type of benign tumor common among Western populations), dramatically increase other chemotherapy drugs’ anticancer effects, and extend patient survival. Rapamycin is a mammalian target of rapamycin (mTOR) targeting inhibitor, which can treat tumors that are related to this pathway including kidney cancer, lymphoma, lung cancer, liver cancer, breast cancer, neuroendocrine carcinoma, gastric cancer, etc. Its curative effects are especially strong for the rare diseases LAM (lymphangiomyomatosis) and TSC (tuberous sclerosis).

Mechanisms of Action

Rapamycin is a type of macrolide antibiotic and has a similar structure to Prograf (FK506), but has very different immunosuppressing mechanisms. FK506 suppresses T lymph cells from proliferating from G0 to G1 stage, while RAPA uses different cytokine receptors to block signal transduction, thus preventing T lymph cells and other cells from proliferating from G1 to S stage. Compared to Prograf, Rapamycin can block the signal transduction pathways of the calcium dependency and calcium non-dependency of T lymph cells and B lymph cells.

Application

As an mTOR inhibitor, sirolimus has a broad spectrum of activity that has demonstrated the ability to inhibit inflammation, proliferation, angiogenesis, fibrosis, and hyperpermeability. Sirolimus currently has multiple uses in the prevention of rejection in organ transplantation and, recently, in the treatment of advanced renal cell carcinoma. Sirolimus-eluting cardiac stents have been shown to limit the rate of overgrowth of tissue and thus prevent coronary restenosis. Early studies suggest that it may be an effective agent for controlling severe uveitis and that it may also have a role in treating agerelated macular degeneration.

Adverse reactions

Rapamycin has similar side effects to those of Prograf. Many clinical trials have found that its side effects are dose dependent and reversible. A treatment dosage of Rapamycin has not been found to lead to any significant nephrotoxicity or gingival hyperplasia. Its main toxic side effects include: headache, nausea, dizziness, nosebleed, and join pain. Laboratory inspections for anomalies found: thrombocytopenia, decreased white blood cells, decreased hemoglobin, hypertriglyceridemia, hypercholesterolemia, hyperglycemia, increased liver enzymes (SGOT, SGPT), increased lactate dehydrogenase, hypokalemia, hypokalemia, etc. Rapamycin may lead to puffiness of eyelids and lead to lowered plasma phosphate levels. Similar to other immunosuppressants, Rapamycin may also increase the chance of infection, with reports of increased tendency towards pneumonia.

Chemical Properties

White to Off-White Solid

Uses

Tool for immunochemistry.

Uses

A specific mTOR inhibitor with an IC50 of 0.1 nM.

Uses

antidepressant

Uses

immunosuppressant, antineoplastic; rapamycin

Uses

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.

Uses

DDP-4 inhibitor type 2 diabetes therapeutic

Uses

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.

Uses

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

Uses

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]

Definition

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.

Indications

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.

Indications

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.

brand name

Rapamune (Wyeth).

Biological Activity

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.

Rapamycin Preparation Products And Raw materials

Raw materials

Preparation Products


Rapamycin Suppliers

Global( 495)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Shanghai Arbor Chemical Co., Ltd.
021-60451682
021-60451683 act@arborchemical.com CHINA 906 58
Beijing Yibai Biotechnology Co., Ltd
0086-182-6772-3597
sales03@yibaibiotech.com CHINA 420 58
SHANDONG ZHI SHANG CHEMICAL CO.LTD
+86 18953170293
+86 0531-67809011 sales@sdzschem.com CHINA 2995 58
Haihang Industry Co.,Ltd
86-531-88032799
+86 531 8582 1093 export@haihangchem.com CHINA 10171 58
Capot Chemical Co.,Ltd.
+86-571-85586718
+86-571-85864795 sales@capotchem.com China 19929 60
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22626 55
Nanjing ChemLin Chemical Industry Co., Ltd.
025-83697070
product@chemlin.com.cn CHINA 3014 60
Hubei XinRunde Chemical Co., Ltd.
+8615102730682
02783214688 bruce@xrdchem.cn CHINA 568 55
ATK CHEMICAL COMPANY LIMITED
+86 21 5161 9050/ 5187 7795
+86 21 5161 9052/ 5187 7796 ivan@atkchemical.com CHINA 24723 60
AB PharmaTech,LLC
323-480-4688
323-480-4688 sales01@abpharmatechusa.com United States 989 55

Related articles


View Lastest Price from Rapamycin manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2019-03-04 Sirolimus
53123-88-9
US $0.00 / kg 5g 98 100kg Jinan Shengqi pharmaceutical Co,Ltd
2019-07-17 rapamycin 53123-88-9
53123-88-9
US $110.00 / g 1g ≥98% 1000.00 kgs NanJing Spring & Autumn Biological Engineering CO., LTD.
2019-08-16 Rapamycin Sirolimus
53123-88-9
US $0.00-0.00 / KG 1g 99% 50kg/month Beijing Yibai Biotechnology Co., Ltd

53123-88-9(Rapamycin)Related Search:


Copyright 2017 © ChemicalBook. All rights reserved