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English name: Rapamycin
CAS number : 53123-88-9
Molecular formula: C51H79NO13
Molecular weight: 914.17
EINECS Number: 610-965-5
Related categories:
crude drug; immunosuppressant; Scientific research reagent; Fermentation class; Antibiotics class; Small-molecule inhibitors, natural products; Pharmaceutical API; acridine; intermediate; Small-molecule inhibitors; raw material; antibiotic; Traditional Chinese medicine control product; Analytical standards; plant extracts; control article; biochemical reagent; Medical intermediates; Microbial metabolites; good merchantable quality; rapamycin; Antitumor drugs and immunosuppressive agents; inhibitor; chemical reagent; Analytical reagent standards; antineoplastic; Chemical products-Organic chemicals; materia medica; Pharmaceutical and chemical industry; Cell biological reagents; materia medica; Standard products-Traditional Chinese medicine standard products; Synthetic material intermediate; ActivePharmaceuticalIngredients; Immunosuppressant; AllInhiChemicalbookbitors; Inhibitors; Intermediates&FineChemicals; Pharmaceuticals; Cytokinesignaling; Signalling; API; ChiralReagents; Heterocycles; Inhibitor; VIVACTIL; antibiotic; 11; chemical raw material; Chemical reagent-scientific research reagent; Other chemical products; Antidrug intermediate; Other categories; Fine chemical products; General biochemical reagent-Antibiotics; reagent; Kit-Cell analysis kit; Everolimus Impurities; chemical reagent; 53123-88-9; Biological buffer series; Advantage of the main products
The Mol file: 53123-88-9.mol
Structural formula:
The nature of rapamycin
Melting point: 183-185 C
Boiling point: 799.83 C (roughestimate)
Specific rotation: D25-58.2 (methanol)
Density: 1.0352 (roughestimate)
Steam pressure: 0.56 hPa (20Chemicalbook C)
Refractive index: 1.5280 (estimate)
Flash point: 87 C
Storage conditions: -20 C
Solubility: Ethanol: soluble, 2MM
Morphology: The solution may become dark during storage
Aciity coefficient (pK a): 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.
sensibility:Moisture Sensitive/Light Sensitive/Hygroscopic
Merck:14,8114
Stability: The DMSO or ethanol solution at-20 C can be stored for up to 2 months.
Use and synthesis method of rapamycin
Immunosuppressant
Rapamycin (RAPA) is a new macrolide immunosuppressor agent, which is a white solid crystal with a melting point of 183-185℃, lipophilic, dissolved in methanol, ethanol, acetone, chloroform and other organic solvents, very slightly soluble in water and almost insoluble in ether. As early as the 1970s was developed, at first as a low toxicity antifungal drugs, found in 1977 with immunosuppressive effect, in 1989 began the RAPA as a treatment of organ transplantation rejection of new drugs, from animal experiments and clinical application of Chemicalbook effect, is a good curative effect, low toxicity, no renal toxicity of new immunosuppressive agents. It is now often used as an immune-maintenance drug (especially kidney transplantation) to slow immune rejection after organ transplantation, but scientists recently found another use: to treat Alzheimer's disease (Alzheimer's). To their interest, the main ingredient of rapamycin is also found in bacterial products in isolated soil on Easter Island, and new experiments showed restoring the defect.
Rapamycin is a macrolide antibiotic with a similar structure to plector (FK506), but has very different mechanisms of immunosuppression. FK506 Inbits the proliferation of T lymphocytes from G0 to G1 phase, while RAPA blocks signaling through different Chemicalbook cytokine receptors and blocks the progression of T lymphocytes and other cells from G1 to S phase, compared with FK506, RAPA blocks the calcium-dependent and calcium-independent signaling pathways of T lymphocytes and B lymphocytes.
Medical researchers at the University of Chicago used commercially available rapamycin oral tablets and grapefruit juice to treat melanoma (a common malignancy in Europe), greatly improving the anticancer effects of other chemotherapy drugs and thus prolonging survival. Studies have shown that rapamycin is easily decomposed by enzymes after entering the digestive tract, while the Chemicalbook grapefruit juice contains a lot of furanocoumarins, which can inhibit the destruction of digestive tract enzymes on rapamycin, so it can improve the bioavailability of rapamycin. It is said that the earliest Dutch doctors have found that grapefruit juice has the effect of improving the oral absorption effect, and now doctors in European and American countries apply it to rapamycin preparation.
Discover history
Rapamycin (also known as "sirolimus") is a secondary metabolite secreted by soil streptomycetes first discovered in 1975. Its chemical structure belongs to the "Chemicalbook ester" compound. Due to the low yield of rapamycin fermentation and the complex extraction process, the product was developed and listed by the American Household Chemical company until 1999, and then listed in more than a dozen countries in Europe and the United States.
At the time, the Food and Drug Administration (FDA) approved rapamycin not as an antimicrobial but as an "immunosuppressant agent."This is because rapamycin shows potent immunosuppressive effects in clinical trials, replacing cyclosporin Chemicalbook, which has been clinically known for more than 30 years. Moreover, compared with cyclosporine, rapamycin oral liquid is administered in a smaller dose (only 2~3mg per time), has stronger anti-rejection effect, and fewer side effects. Therefore, rapamycin has quickly become a common oral immunosuppressive agent in organ transplants all over the world since its launch.
Targeted agents for cancer therapy
In recent years, studies have found that the target of rapamycin (mTOR), as an intracellular kinase, its conduction pathway abnormalities can induce a variety of diseases. As a targeted inhibitor of mTOR, rapamycin is able to treat tumors closely related to this pathway including renal, lymphatic Chemicalbook, lung, liver, breast, neuroendocrine carcinoma, and gastric cancer. In particular, the treatment of LAM (lymphangiomyomatosis) and TSC (tuberous sclerosis) is more obvious, and LAM and TSC can also be considered as neoplastic diseases to some extent.
Side effect
Rapamycin (RAPA) has similar side effects to FK506. The side effects have been found to be dose-dependent and reversible. The therapeutic dose of RAPA has not been found to have significant nephrotoxicity without gingival hyperplasia. The main toxic side effects include: headache, nausea, dizziness, epistaxis, and joint pain. Abnormal laboratory tests included: thrombocytopenia, leukocytopenia, decreased hemoglobin, hypertriglyceridemia, hypercholesterolemia, hyperglycemia, elevated liver enzyme Chemicalbook (SGOT, SGPT), elevated lactate dehydrogenase, hypokalemia, hypomagnesemia, etc. RAPA administration was recently reported to produce eyelid edema, and the reason for the lower plasma phosphate level is thought to be the prolonged excretion of phosphate in autotransplanted kidneys by RAPA-based immunosuppressive therapy. Like other immunosuppressive agents, RAPA has an increased chance of infection, with a particularly reported tendency to increase pneumonia, but the occurrence of other opportunistic infections is not significantly different from CsA.
Use as
Immunosuppressant
Use
A triene macrolide antibiotic isolated from Streptomyces hygroscopicus,antirestenotic. Sirolimus (lNN/USAN ), also known as rapamycin, is anumramusuppressant drug used to prevent rejection in organ transplantation; it is especially useful in kidney transplants
Members of the macrolide immunosuppressant family. FRAP inhibitor. Binds to and inhibits the target molecule of rapamycin (mTOR). A potent immunosuppressant with anticancer activity.
Security information
Hazmat signs Xi, Xn, F
Hazard category code 36 / 38-36-20 / 21 / 22-11
Safety instructions: 22-24Chemicalbook / 25-37 / 39-26-36 / 37-16
Dangerous Goods Transport No. UN16483 / PGII
WGKGermany2
RTECS No:VE6250000
Spontaneous combustion temperature: 301 C
Customs code: 2:9349990
Toxic substance data: 53123-88-9 (HazardousSubstancChemicalbookesData)
Toxicity: LD50inmice(mg/kg):600i.p.;> 2,500orally (Vezina)
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