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R0395 Sigma-Aldrich

Rapamycin from Streptomyces hygroscopicus

≥95% (HPLC), powder

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

  • CAS Number 53123-88-9

  • Empirical Formula (Hill Notation) C51H79NO13

  • Molecular Weight 914.17

  •  MDL number MFCD00867594

  •  PubChem Substance ID 57654583

  •  NACRES NA.77

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Properties

Related Categories Antibiotics, Antibiotics A to Z, Antibiotics N-S, Antibiotics by Application, Antibiotics by Mechanism of Action,
Quality Level   300
assay   ≥95% (HPLC)
form   powder
color   off-white
solubility   ethanol: 2 mM
  DMSO: soluble
Mode of action   enzyme | inhibits
  protein synthesis | interferes
antibiotic activity spectrum   fungi
  yeast
originator   Pfizer
storage temp.   −20°C
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
Gene Information   human ... FKBP1A(2280)

Description

General description

Chemical structure: macrolide

Packaging

1 mg in glass bottle

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.

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.

This compound was developed by Pfizer. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Other Notes

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

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 2
RTECS 
VE6250000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Frequently Asked Questions

Which document(s) contains shelf-life or expiration date information for a given product?
If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.
How do I get lot-specific information or a Certificate of Analysis?
The lot specific COA document can be found by entering the lot number above under the "Documents" section.
What is the solubility of Product R0395, Rapamycin?
Rapamycin is soluble in DMSO and in methanol (each at 25 mg/mL) and in ethanol(2 mM). It is insoluble in water. Additional solubility information is in the product information sheet (under Documents, above).
How should we store solutions of Product R0395, Rapamycin?
Rokaw, M.D. et al. J. Biol. Chem. 271, 32468 (1996) described storage of a 2 mM solution of rapamycin in ethanol at -70 °C which was diluted into serum-free media before use. Unless otherwise noted for other solvents, it may be best to prepare solutions fresh and protected from light. Please refer to our product information sheet at our website.
What is the shelf life of Product R0395, Rapamycin, as received?
The product has a recommended retest date of 2 years but the actual recommended retest date for each lot is on the Certificate of Analysis.We guarantee the quality of the product through this date for unopened bottles stored at -20 °C.
What are the extinction coefficient values forProduct R0395, Rapamycin, solutions?
The E1% extinction coefficient values in 95% ethanol at 267 nm, 277 nm and 288 nm have been reported and are listed in the product information sheet (under Documents, above).
How do I find price and availability?
There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote. USA customers: 1-800-325-3010 or view local office numbers.
What is the Department of Transportation shipping information for this product?
Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
My question is not addressed here, how can I contact Technical Service for assistance?
Ask a Scientist here.
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Peer-Reviewed Papers
15

References

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