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Merck

R0395

Rapamycin

from Streptomyces hygroscopicus, ≥95% (HPLC), powder, mTOR inhibitor

Synonym(s):

23,27-Epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclohentriacontine, AY 22989, Sirolimus

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About This Item

Empirical Formula (Hill Notation):
C51H79NO13
CAS Number:
53123-88-9
Molecular Weight:
914.17
UNSPSC Code:
12352200
PubChem Substance ID:
57654583
NACRES:
NA.77
MDL number:
MFCD00867594

Key Documents

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Product Name

Rapamycin from Streptomyces hygroscopicus, ≥95% (HPLC), powder

SMILES string

CO[C@@H]1C[C@@H](CC[C@H]1O)C[C@@H](C)[C@@H]2CC(=O)[C@H](C)\C=C(C)\[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)\C=C\C=C\C=C(C)\[C@H](C[C@@H]3CC[C@@H](C)[C@@](O)(O3)C(=O)C(=O)N4CCCC[C@H]4C(=O)O2)OC

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

InChI key

QFJCIRLUMZQUOT-HPLJOQBZSA-N

assay

≥95% (HPLC)

form

powder

color

off-white

solubility

ethanol: 2 mM
DMSO: soluble

antibiotic activity spectrum

fungi
yeast

mode of action

enzyme | inhibits
protein synthesis | interferes

storage temp.

−20°C

Quality Level

300

Gene Information

human ... FKBP1A(2280)

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Features and Benefits

This compound is featured on the PKB/Akt page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Application

Rapamycin from Streptomyces hygroscopicus has been used:
  •  to treat BV2 cells or BV2-LC3 cells for autophagy assay
  • as an autophagy activator in the bone marrow mesenchymal stem cells (BM-MSCs) transfected with lentivirus carrier of small interfering RNA for FOXO3 (siFOXO3) to study the effects of Forkhead Box O3 (FOXO3) on the autophagy of BM-MSCs
  • to pre-incubate villi to inhibit the mammalian target of rapamycin complex 1 (mTORC1) signaling

Biochem/physiol Actions

A macrocyclic triene antibiotic that binds to and inhibits the molecular target of rapamycin (mTOR). It forms a complex with FKBP12 that binds to and inhibits the molecular target of rapamycin (mTOR). Rapamycin is a potent immunosuppressant and has anticancer activity.

General description

Chemical structure: macrolide
Rapamycin is derived from Streptomyces hygroscopicus . It can inhibit viral replication. This natural anti-fungal antibiotic is a proven anti-aging agent. Rapamycin significantly inhibits mTORC1 regardless of age. It suppresses protein kinase C activity and enhances ion transport in A6 cells. It also suppresses the immune response in membrane and cytosolic preparations. Additionally, it has specific effects on the translation of endogenous mRNAs and inhibits the translation of 5′TOP mRNAs by blocking p70s6k activation in the signaling pathway. Rapamycin exhibits antineoplastic properties.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.Keep in a dry place

pictograms

Health hazard
GHS08

signalword

Warning

Hazard Classifications

Carc. 2 - Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 2

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
049M4018V
049M4020V
14180807
077M4007V
066M4047V

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Line Heylen et al.
Clinical infectious diseases : an official publication of the Infectious Diseases Society of America, 60(10), 1505-1511 (2015-02-15)
Transplant recipients are at risk for invasive aspergillosis (IA), associated with a significant mortality rate. Renal transplant-specific risk factors have not been established. Forty-one adult kidney transplant recipients diagnosed with proven or probable IA from 1995 through 2013 were identified
Marlous J Groenewoud et al.
Open biology, 3(12), 130185-130185 (2013-12-20)
Mitochondrial dysfunction has been associated with various diseases, such as cancer, myopathies, neurodegeneration and obesity. Mitochondrial homoeostasis is achieved by mechanisms that adapt the number of mitochondria to that required for energy production and for the supply of metabolic intermediates
Stephanie James et al.
The American journal of tropical medicine and hygiene, 90(1), 6-10 (2013-11-28)
As global efforts to eliminate malaria intensify, accurate information on vector populations and transmission dynamics is critical for directing control efforts, developing new control tools, and predicting the effects of these interventions under various conditions. Currently available sampling tools for
A V Tinker et al.
Gynecologic oncology, 130(2), 269-274 (2013-05-16)
HPV infection has been associated with deregulation of the PI3K-Akt-mTOR pathway in invasive cervical carcinomas. This 2-stage phase II study assessed the activity of the mTOR inhibitor, temsirolimus, in patients with measurable metastatic and/or locally advanced, recurrent carcinoma of the
Benjamin Albert et al.
The Journal of cell biology, 202(2), 201-210 (2013-07-24)
Chromosomes architecture is viewed as a key component of gene regulation, but principles of chromosomal folding remain elusive. Here we used high-throughput live cell microscopy to characterize the conformation and dynamics of the longest chromosome of Saccharomyces cerevisiae (XII). Chromosome
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