53123-88-9 Rapamycin AKSci C593
 
 
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  C593    AKSci Reference Standard
Rapamycin
, 98% (HPLC)
 
Sirolimus
23,27-Epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclohentriacontine




IDENTITY
CAS Number:53123-88-9
MDL Number:MFCD00867594
MF:C51H79NO13
MW:914.17
SPECIFICATIONS & PROPERTIES
Purity:98% (HPLC)
Spectra:FT-IR, LCMS, HPLC, Polarimetry
Physical Form:White to off-white powder
Melting Point:183-194°C
Optical Rotation:-145 to -155° (c=0.472, MeOH)
Long-Term Storage:Store long-term at -20°C

BIOLOGICAL INFO
Solubility:DMSO: 20mg/mL; H2O: <1mg/mL; EtOH: 4mg/mL
Application(s):Specific Mammalian target of Rapamycin (mTOR) inhibitor
Form:Free Base

REVIEW

 An immunosuppressant drug used to prevent rejection in organ transplantation. Sirolimus inhibits the response to interleukin-2 (IL-2), and thereby blocks activation of T and B cells. In contrast, tacrolimus inhibits the secretion of IL-2. The mode of action of sirolimus is to bind the cytosolic protein FK-binding protein 12 (FKBP12) in a manner similar to tacrolimus. Unlike the tacrolimus-FKBP12 complex which inhibits calcineurin (PP2B), though, the sirolimus-FKBP12 complex inhibits the mammalian target of rapamycin (mTOR) pathway by directly binding the mTOR Complex1 (mTORC1).

REFERENCES
[1]Pagano, Thomas G.; Magnetic Resonance in Chemistry 2005, V43(2), P174-175; (2) Ley, Steven V.; Chemistry--A European Journal 2009, V15(12), P2874-2914.
[2] V?zina C, Kudelski A, Sehgal SN (October 1975). Rapamycin (AY-22,989), a new antifungal antibiotic. J. Antibiot. 28 (10): 721u20136. PMID 1102508.
[3] Pritchard DI (2005). Sourcing a chemical succession for cyclosporin from parasites and human pathogens. Drug Discovery Today 10 (10): 688-691. doi:10.1016/S1359-6446(05)03395-7. PMID 15896681.
[4] McAlister VC, Mahalati K, Peltekian KM, Fraser A, MacDonald AS. (June 2002). A clinical pharmacokinetic study of tacrolimus and sirolimus combination immunosuppression comparing simultaneous to separated administration.. Ther Drug Monit. 24 (3): 346-50. PMID 12021624.

GHS

Pictograms

Signal Word
Warning

Hazard Statements
H315; H319; H335

Precautionary Statements
P261; P264; P271; P280; P302+P352; P304+P340; P305+P351+P338; P312; P321; P332+P313; P337+P313; P362; P403+P233; P405; P501


Current as of July 2, 2020

AKSci Reference Standards are high-purity, low-impurity compounds suitable for use as standards.


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CATEGORIES

 APIs and Bioactives > Immunomodulators


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