description in vivo Indications and Usage Mechanisms of Action Application Adverse reactions
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Rapamycin

description in vivo Indications and Usage Mechanisms of Action Application Adverse reactions
Product Name
Rapamycin
CAS No.
53123-88-9
Chemical Name
Rapamycin
Synonyms
SIROLIMUS;RAPAMUNE;RAPA;Sirolomus;Rapamycin/Sirolimus CAS 53123-88-9;Rapamycin from Streptomyces hygroscopicus,23,27-Epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclohentriacontine, AY 22989, Sirolimus;RPM;BCAR2;CS-440;TRERF1
CBNumber
CB0275190
Molecular Formula
C51H79NO13
Formula Weight
914.17
MOL File
53123-88-9.mol
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Rapamycin Property

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
pka
10.40±0.70(Predicted)
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
Stability:
Stable for 2 years? from date of purchase as supplied.? Solutions in DMSO or ethanol may be stored at -20°C for up to 2 months.
CAS DataBase Reference
53123-88-9(CAS DataBase Reference)
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Safety

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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H351Suspected of causing cancer

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
S-015
Product name
Sirolimus solution
Purity
1.0?mg/mL in acetonitrile, ampule of 1?mL, certified reference material, Cerilliant?
Packaging
1ML
Price
$258
Updated
2024/03/01
Sigma-Aldrich
Product number
R8781
Product name
Rapamycin
Purity
Ready Made Solution, 2.5?mg/mL in DMSO (2.74 mM), from Streptomyces hygroscopicus
Packaging
200μL
Price
$303
Updated
2024/03/01
Sigma-Aldrich
Product number
553210
Product name
Rapamycin - CAS 53123-88-9 - Calbiochem
Purity
Rapamycin, CAS 53123-88-9, is an immunosuppressant that selectively inhibits mTOR and blocks the subsequent activation of p70 S6 kinase (IC?? = 50 pM).
Packaging
100μg
Price
$57.3
Updated
2024/03/01
Sigma-Aldrich
Product number
553210
Product name
Rapamycin
Packaging
1mg
Price
$352
Updated
2024/03/01
Sigma-Aldrich
Product number
37094
Product name
Rapamycin
Purity
VETRANAL
Packaging
10mg
Price
$595
Updated
2024/03/01
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Rapamycin Chemical Properties,Usage,Production

description

Rapamycin (also known as Sirolimus) is macrocyclic lactone produced by the bacterium Streptomyces hygroscopicus isolated from soil samples from Easter Island. Rapamycin is an antifungal agent with immunosuppressive properties. Rapamycin has antirejection properties without the side effects associated with other antirejection agents. Rapamycin binds to a specific protein, Target of Rapamycin (TOR). TOR is serine/threonine kinase. TOR (mTOR) forms two major complexes: mTORC1,and mTORC2. The mTORC1 consists of mTOR, Raptor, mLST8, FKBP38, PRAS40, and Deptor, and through specific binding of rapamycin to FKBP12, rapamycin inhibits the activity of mTORC1 leading to a decrease in protein synthesis, increased autophagy and inhibition of cell growth.

in vivo

Rapamycin (2.0 mg/kg; intraperitoneal injection; every other day; 28 days) alone has a moderate inhibitory effect. However, the combination of Metformin and Rapamycin exerts a significantly increased inhibition of tumor growth compared with the control group, the Rapamycin monotherapy group and the Metformin monotherapy group.

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.

Description

Rapamycin is a member of the macrolide immunosuppressant family and a FRAP inhibitor. Rapamycin exhibits binding and inhibitory actions to the FK506 binding protein (FKBP5) proline rotamase via simultaneous binding by FKBP12 and FRAP. FRAP (RAFT1) proteins exhibit homology to PI 4- and PI 3-kinases, which have PI 4-kinase and autophosphorylating activities. The rapamycin/FKBP complex does not inhibit the FRAP PI 4-kinase activity, but does inhibit FRAP autophosphorylation. Rapamycin is unique in its ability to inhibit lymphokine induced cell proliferation at the G1 and S phase as well as an irreversible cellular arrest at the G1 phase in S. cerevisiae cells. Rapamycin also exhibits selective signal blocking leading to the activation of p70/85 S6 kinase, which is potentially due to the inhibition of FRAP autophosphorylation or protein kinase activity. Rapamycin also exhibits Angiogenesis inhibition, possibly through the inhibition of the Akt pathway. Rapamycin is an inhibitor of mTOR. Rapamycin is also known as Rapamune, 23,27-Epoxy-3H-pyrido[2,1-c] oxaazacyclohentriacontine, AY 22989, and mTOR Inhibitor I.

Chemical Properties

White to Off-White Solid

Originator

Rapamune,Wyeth Laboratories,UK

Occurrence

Rapamycin was first discovered in 1972 in the soil of Easter Island produced by a bacterium called Streptomyces hygroscopicus. It takes its name from Rapa Nui, the indigenous name for the island. It is known clinically as sirolimus or Rapamune.

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]

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

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.

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.

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

General Description

Rapamycin is an anti-fungal antibiotic isolated from Streptomyces hygroscopicus. This antibiotic is active against all strains of Candida albicans. It blocks the signal transduction pathways required for the activation of T-helper cells.

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.

Biochem/physiol Actions

Rapamycin is a macrocyclic triene antibiotic possessing potent immunosuppressant and anticancer activity. It forms a complex with FKBP12 that binds to and inhibits the molecular target of rapamycin (mTOR). mTOR is a member of the phosphoinositide kinase-related kinase (PIKK) family that enhances cellular proliferation via the phosphoinositol 3-kinase/Akt signaling pathway. Inhibition of this pathway by rapamycin blocks downstream elements that result in cell cycle arrest in G1. The effectors of mTOR action include 4EBP1 and S6K1.

Clinical Use

Immunosuppressant:
Prophylaxis of transplant allograft rejection

in vitro

Rapamycin (12.5-100 nM; 24 hours) treatment exerts modest inhibitory effect on lung cancer cell proliferation in a dose-dependent manner in all cell lines (A549, SPC-A-1, 95D and NCI-H446 cells) tested, achieving about 30-40% reduction in cell proliferation at 100 nM vs. ~10% reduction at 12.5 nM.
Lung cancer cell line 95D cells are exposed to Rapamycin (10 nM, 20 nM) and RP-56976 (1 nM, 10 nM) alone or in combination (Rapamycin 20 nM+ RP-56976 10 nM). After 24 hours exposure to Rapamycin or RP-56976 alone does not significantly alter the level of expression or phosphorylation of ERK1/2, whereas cells treated with the combination of Rapamycin with RP-56976 exhibit a marked reduction in the phosphorylation levels of ERK1/2.

Drug interactions

Potentially hazardous interactions with other drugs
Antibacterials: concentration increased by clarithromycin - avoid; concentration of both drugs increased with erythromycin; concentration reduced by rifampicin and rifabutin - avoid.
Antifungals: concentration increased by itraconazole, fluconazole, ketoconazole, micafungin, miconazole,posaconazole and voriconazole - avoid with itraconazole, ketoconazole and voriconazole.
Antivirals: concentration possibly increased by atazanavir, boceprevir and lopinavir; concentration of both drugs increased with telaprevir, reduce dose of sirolimus; concomitant use with dasabuvir plus ombitasvir/paritaprevir/ritonavir is not recommended unless the benefits outweigh the risks, if used together administer sirolimus 0.2 mg twice a week (every 3 or 4 days on the same two days each week). Sirolimus blood concentrations should be monitored every 4-7 days until 3 consecutive trough levels have shown stable concentrations of sirolimus. Sirolimus dose and/or dosing frequency should be adjusted as needed.
Calcium-channel blockers: concentration increased by diltiazem; concentration of both drugs increased with verapamil.
Ciclosporin: increased absorption of sirolimus - give sirolimus 4 hours after ciclosporin; sirolimus concentration increased; long-term concomitant administration may be associated with deterioration in renal function.
Cytotoxics: use crizotinib with caution.
Grapefruit juice: concentration of sirolimus increased - avoid.
Mycophenolate: concomitant use of mycophenolate and sirolimus increases plasma levels of both sirolimus and mycophenolic acid.

Metabolism

Sirolimus is metabolised by the cytochrome P450 isoenzyme CYP3A4. Metabolism occurs by demethylation or hydroxylation, and the majority of a dose is excreted via the faeces.

storage

-20°C

References

1) Kay et al. (1991) Inhibition of T and B lymphocyte proliferation by rapamycin. Immunology, 72 544 2) Mita et al., (2003) The molecular target of rapamycin (mTOR) as a therapeutic target against cancer; Cancer Biol. Ther., 2(4 Suppl 1) S169 3) Lamming et al. ( 2012). Rapamycin-induced insulin resistance is mediated by mTORC2 loss and uncoupled from longevity; Science, 335 1638 4) Sarkar et al. (2009), Rapamycin and mTOR-independent autophagy inducers ameliorate toxicity of polyglutamine-expanded huntingtin and related proteinopathies; Cell Death and Differ., 16 46

Rapamycin Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Rapamycin manufacturers

Hebei Dangtong Import and export Co LTD
Product
Rapamycin 53123-88-9
Price
US $43.00-35.00/grams
Min. Order
10grams
Purity
99%
Supply Ability
100tons
Release date
2023-02-22
Sigma Audley
Product
Rapamycin 53123-88-9
Price
US $35.00-25.00/kg
Min. Order
1kg
Purity
99.8%
Supply Ability
200tons/year
Release date
2024-03-14
Shanghai Affida new material science and technology center
Product
Rapamycin 53123-88-9
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99
Supply Ability
9000kg/per week
Release date
2024-03-13

53123-88-9, RapamycinRelated Search:


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