Rapamycin, Immunosuppressive Antibiotic

SKU
R-1018
  • CAS:53123-88-9
  • Formula:C51H79NO13
  • MW:914.2 Da
  • Appearance:White powder
  • Purity:≥99%

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Product Name Qty
Rapamycin, Immunosuppressive Antibiotic
5 mg
$70.34
Rapamycin, Streptomyces hygroscopicus
5x1 mg
$81.16
Rapamycin, Immunosuppressive Antibiotic
25 mg
$227.24

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. 

Applications

Recent studies and investigation in mice have demonstrated the potential of Rapamycin to slow aging. Rapamycin is being tested in dogs for its anti-aging properties.

 

Additional Reading - Rapamycin: Most Commonly Asked Questions

 

 

More Information
Alternate Name/Synonyms
Sirolimus; Rapamune; Sirolimusum
SKU
R-1018
CAS #
53123-88-9
Chemical Name
(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[30.3.1.04,9]hexatriaconta-16,24,26,28-tetra
Chemical Formula
C51H79NO13
Molecular Weight
914.2 Da
Appearance
White powder
Purity
≥99%
Solubility
Clear colorless solution at 50 mg/mL in Ethanol or DMSO
Melting Point
183-184°C
Preparation
N/A
Storage Temp
-20°C
THERAPEUTIC AREA
Autoimmune Diseases; Infectious Diseases
USE
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. It 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. Angiogenesis inhibition is also exhibited, possibly through the inhibition of the Akt pathway. Rapamycin is an inhibitor of mTOR.
Merck Index
13.8202.2001
MDL NUMBER
MFCD00867594
CHEMACX
X1000584-2
INCHI
InChI=1S/C51H79NO13/c1-30-16-12-11-13-17-31(2)42(61-8)28-38-21-19-36(7)51(60,65-38)48(57)49(58)52-23-15-14-18-39(52)50(59)64-43(33(4)26-37-20-22-40(53)44(27-37)62-9)29-41(54)32(3)25-35(6)46(56)47(63-10)45(55)34(5)24-30/h11-13,16-17,25,30,32-34,36-40,42-44,46-47,53,56,60H,14-15,18-24,26-29H2,1-10H3/b13-11+,16-12+,31-17+,35-25+/t30-,32-,33-,34-,36-,37+,38+,39+,40-,42+,43+,44-,46-,47+,51-/m1/s1
SMILES
C[C@@H]1CC[C@H]2C[C@@H](/C(=C/C=C/C=C/[C@H](C[C@H](C(=O)[C@@H]([C@@H](/C(=C/[C@H](C(=O)C[C@H](OC(=O)[C@@H]3CCCCN3C(=O)C(=O)[C@@]1(O2)O)[C@H](C)C[C@@H]4CC[C@H]([C@@H](C4)OC)O)C)/C)O)OC)C)C)/C)OC
RTECS
VE6250000
Handling
Corrosive hazard. Wear protective gloves/clothing and eye/face protection. Handle in accordance with good industrial hygiene and safety practice.
Certificate of Analysis 1
Certificate of Analysis 2
Certificate of Analysis 3
GHS PICTOGRAMS
Handling Corrosive hazard. Wear protective gloves/clothing and eye/face protection. Handle in accordance with good industrial hygiene and safety practice.
Citations RNA Polymerase III Output Is Functionally Linked to tRNA Dimethyl-G26 Modification
A molecular barcoded yeast ORF library enables mode-of-action analysis of bioactive compounds
Therapeutic effect of rapamycin on gallbladder cancer in a transgenic mouse model
Identification of autophagosome-associated proteins and regulators by quantitative proteomic analysis and genetic screens
Genetic interactions of MAF1 identify a role for Med20 in transcriptional repression of ribosomal protein genes
Disrupting function of FK506-binding protein 1b/12.6 induces the Ca²+-dysregulation aging phenotype in hippocampal neurons
Ca2+-dependent reduction of IK1 in rat ventricular cells: a novel paradigm for arrhythmia in heart failure?
Mechanisms of Resistance to NTRK Inhibitors and Therapeutic Strategies in NTRK1-Rearranged Cancers
Activating the translational repressor 4E-BP or reducing S6K-GSK3β activity prevents accelerated axon growth induced by hyperactive mTOR in vivo
Thoracic aortic disease in tuberous sclerosis complex: molecular pathogenesis and potential therapies in Tsc2+/- mice
Analysis of the oestrogen response in an angiomyolipoma derived xenograft model
Avian reovirus nonstructural protein p17-induced G(2)/M cell cycle arrest and host cellular protein translation shutoff involve activation of p53-dependent pathways
Lack of tRNA-i6A modification causes mitochondrial-like metabolic deficiency in S. pombe by limiting activity of cytosolic tRNATyr, not mito-tRNA
Folic acid delays development of atherosclerosis in low-density lipoprotein receptor-deficient mice
Lack of tRNA modification isopentenyl-A37 alters mRNA decoding and causes metabolic deficiencies in fission yeast
Durability of stentless bioprostheses for right ventricular outflow tract reconstruction
Adverse effects of local or systemic application of rapamycin for the prevention of neointimal hyperplasia
Proteasomal degradation of Sfp1 contributes to the repression of ribosome biogenesis during starvation and is mediated by the proteasome activator Blm10
Prolonged survival of composite facial allografts in non-human primates associated with posttransplant lymphoproliferative disorder
The putative ABC transporter encoded by the orf19.4531 plays a role in the sensitivity of Candida albicans cells to azole antifungal drugs
CaTip41 regulates protein phosphatase 2A activity, CaRad53 deactivation and the recovery of DNA damage-induced filamentation to yeast form in Candida albicans
The putative transcription factor CaRtg3 is involved in tolerance to cations and antifungal drugs as well as serum-induced filamentation in Candida albicans
Genetic interactions between protein phosphatases CaPtc2p and CaPph3p in response to genotoxins and rapamycin in Candida albicans
The protein kinase CaSch9p is required for the cell growth, filamentation and virulence in the human fungal pathogen Candida albicans
The MAP kinase-activated protein kinase Rck2p plays a role in rapamycin sensitivity in Saccharomyces cerevisiae and Candida albicans
Identification and characterization of a functional Candida albicans homolog of the Saccharomyces cerevisiae TCO89 gene
AMP-activated protein kinase facilitates avian reovirus to induce mitogen-activated protein kinase (MAPK) p38 and MAPK kinase 3/6 signalling that is beneficial for virus replication
Avian reovirus influences phosphorylation of several factors involved in host protein translation including eukaryotic translation elongation factor 2 (eEF2) in Vero cells
Rapamycin-mediated mTOR inhibition attenuates survivin and sensitizes glioblastoma cells to radiation therapy
Antirestenotic effects of a novel polymer-coated d-24851 eluting stent. Experimental data in a rabbit iliac artery model
Fucoidan film safely inhibits surgical adhesions in a rat model
Identification of phosphatase 2A-like Sit4-mediated signalling and ubiquitin-dependent protein sorting as modulators of caffeine sensitivity in S. cerevisiae
Inhibitors of phosphatidylinositol 3-kinase and mTOR but not Akt enhance replication of bovine ephemeral fever virus
Rapamycin inhibits CaCl2-induced thoracic aortic aneurysm formation in rats through mTOR-mediated suppression of proinflammatory mediators
Regulation and localization of ribosomal protein S6 kinase 1 isoforms
Testing intravitreal toxicity of rapamycin in rabbit eyes
Mitochondrial dysfunction in some triple-negative breast cancer cell lines: role of mTOR pathway and therapeutic potential
Autophagy regulates the stemness of cervical cancer stem cells
A Role of CREB in BRCA1 Constitutive Promoter Activity and Aromatase Basal Expression
Efeito protetor da N-acetilcisteína na evolução precoce de receptores de transplante renal com doador falecido
Autophagy regulates homeostasis of pluripotency-associated proteins in hESCs
Evaluation of the Abbott ARCHITECT i2000 sirolimus assay and comparison with the Abbott IMx sirolimus assay and an established liquid chromatography-tandem mass spectrometry method
MEK-ERK1/2-dependent FLNA overexpression promotes abnormal dendritic patterning in tuberous sclerosis independent of mTOR
Hyaluronic acid-based hydrogels as 3D matrices for in vitro evaluation of chemotherapeutic drugs using poorly adherent prostate cancer cells
Hypervascularization in mTOR-dependent focal and global cortical malformations displays differential rapamycin sensitivity
Sirolimus oral absorption in rats is increased by ketoconazole but is not affected by D-alpha-tocopheryl poly(ethylene glycol 1000) succinate
The BEACH Domain Is Critical for Blue Cheese Function in a Spatial and Epistatic Autophagy Hierarchy
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