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Merck

37094

Rapamycin

VETRANAL®, analytical standard

Synonym(s):

Sirolimus

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About This Item

Empirical Formula (Hill Notation):
C51H79NO13
CAS Number:
53123-88-9
Molecular Weight:
914.17
NACRES:
NA.24
PubChem Substance ID:
329755624
UNSPSC Code:
41116107
MDL number:
MFCD00867594

Product Name

Rapamycin, VETRANAL®, analytical standard

InChI key

QFJCIRLUMZQUOT-HPLJOQBZSA-N

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

grade

analytical standard

product line

VETRANAL®

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

forensics and toxicology
pharmaceutical (small molecule)

format

neat

storage temp.

−20°C

Quality Level

100

Gene Information

human ... FKBP1A(2280)

Related Categories

Application

The analytical standard can be used as follows:
  • Electrochemical determination of rapamycin using boron-doped diamond electrode and differential pulse voltammetry (DPV) in human urine, serum, and blood samples
  • Simultaneous determination of six immunosuppressants from whole blood samples by high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) technique combined with modified QuEChERS method

General description

Rapamycin belongs to the macrolide class of antibiotics obtained from the bacterium Streptomyces hygroscopicus. It was first used as an anti-fungal agent but later also found use as an immunosuppressant and potential anti-cancer drug. It acts by preventing the activity of serine/threonine kinase and subsequently blocking the cytokine-driven T cell proliferation.

Other Notes

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Legal Information

VETRANAL is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Health hazard
GHS08

signalword

Warning

Hazard Classifications

Carc. 2 - Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 2

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN2230
BCCL3594
BCCJ2791
BCCG2865
BCCD5607

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Complications in Surgery (2006)
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Journal of virology, 93(17) (2019-06-14)
The Us11 protein encoded by herpes simplex virus 1 (HSV-1) functions to impair autophagy; however, the molecular mechanisms of this inhibition remain to be fully established. Here, we report that the Us11 protein targets tripartite motif protein 23 (TRIM23), which
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
Carrie L Lucas et al.
Nature immunology, 15(1), 88-97 (2013-10-30)
The p110δ subunit of phosphatidylinositol-3-OH kinase (PI(3)K) is selectively expressed in leukocytes and is critical for lymphocyte biology. Here we report fourteen patients from seven families who were heterozygous for three different germline, gain-of-function mutations in PIK3CD (which encodes p110δ).
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