ChemicalBook
Chinese Japanese Germany Korea

Rapamycin

Indications and Usage Mechanisms of Action Adverse reactions
Rapamycin
Rapamycin structure
CAS No.
53123-88-9
Chemical Name:
Rapamycin
Synonyms
RPM;RAPA;BCAR2;TRERF1;TREP132;AY 22989;RAPAMUNE;SIROLIMUS;RAPAMYCIN;sila9268a
CBNumber:
CB0275190
Molecular Formula:
C51H79NO13
Formula Weight:
914.18
MOL File:
53123-88-9.mol

Rapamycin Properties

Melting point:
183-185°C
Boiling point:
799.83°C (rough estimate)
alpha 
D25 -58.2° (methanol)
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
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)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
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
Hazardous Substances Data 53123-88-9(Hazardous Substances Data)
Toxicity LD50 in mice (mg/kg): 600 i.p.; >2,500 orally (Vézina)
Symbol(GHS):
Signal word: Danger
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H225 Highly Flammable liquid and vapour Flammable liquids Category 2 Danger P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H227 Combustible liquid Flammable liquids Category 4 Warning P210, P280, P370+P378, P403+P235,P501
H319 Causes serious eye irritation Serious eye damage/eye irritation Category 2A Warning P264, P280, P305+P351+P338,P337+P313P
Precautionary statements:
P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P403+P235 Store in a well-ventilated place. Keep cool.

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 2018-11-20 Buy
Sigma-Aldrich 37094 Rapamycin VETRANAL 53123-88-9 10mg $433 2018-11-20 Buy
TCI Chemical R0097 Rapamycin >98.0%(HPLC) 53123-88-9 25mg $233 2018-11-22 Buy
Alfa Aesar J62473 Rapamycin, 99+% 53123-88-9 100mg $162 2018-11-13 Buy
Alfa Aesar J62473 Rapamycin, 99+% 53123-88-9 50mg $97 2018-11-13 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.

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

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

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.

Uses

Tool for immunochemistry.

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.

brand name

Rapamune (Wyeth).

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]

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( 411)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Shanghai Arbor Chemical Co., Ltd.
021-60451682
021-60451683 act@arborchemical.com CHINA 905 58
Capot Chemical Co.,Ltd.
+86 (0)571-855 867 18
+86 (0)571-858 647 95 sales@capotchem.com China 19954 60
Henan DaKen Chemical CO.,LTD.
+86-371-55531817
info@dakenchem.com CHINA 22043 58
Hebei Jiangkai Trading Co., Ltd
0086-17197824289/17197824028
alice@hbjkai.com CHINA 277 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 20786 55
Mainchem Co., Ltd.
+86-0592-6210733
+86-0592-6210733 sales@mainchem.com CHINA 32651 55
Nanjing ChemLin Chemical Industry Co., Ltd.
025-83697070;product@chemlin.com.cn
product@chemlin.com.cn CHINA 3015 60
Hubei XinRunde Chemical Co., Ltd.
+8615102730682; +8618874586545
02783214688 bruce@xrdchem.cn CHINA 552 55
ATK CHEMICAL COMPANY LIMITED
+86 21 5161 9050/ 5187 7795
+86 21 5161 9052/ 5187 7796 ivan@atkchemical.com CHINA 16534 60
AB PharmaTech,LLC
323-480-4688
323-480-4688 sales01@abpharmatechusa.com United States 991 55

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
2018-12-16 Rapamycin
53123-88-9
US $7.00 / kg 1kg 99% 100kg career henan chemical co
2018-07-27 DAMASCONE
23726-91-2
US $80.00-350.00 / KG 1KG 99.5% 10000kg career henan chemical co

53123-88-9(Rapamycin)Related Search:


Copyright 2017 © ChemicalBook. All rights reserved