Rapamycin
Molecular Formula
C51H79NO13
M.W.
914.20
CAS number
53123-88-9
Source
Streptomyces hygroscopicus subsp hygroscopicus
Fermentek product Code
RAP-001
Appearance
Off-white to slight yellow powder
Purity by HPLC
≥98% ; refer to CoA for more data
Purity By TLC
≥98% ; refer to CoA for more data
Melting point
178-185°C
Solubility test
Clear colorless solution at 200mg/ml DMSO
Names and identifiers

Synonyms: RAPA, Rapamune, Sirolimus, RPM, Antibiotic AY 22989

RTECS: VE6250000

EU number
610-965-5
Description

Rapamycin (Sirolimus) is a macrolide compound that acts by selectively blocking the transcriptional activation of cytokines thereby inhibiting cytokine production. It is bioactive only when bound to IMMUNOPHILINS. Sirolimus (Rapamycin) is a potent immunosuppressant. Sirolimus (Rapamycin) possesses both antifungal and antineoplastic properties.

InChl Key
QFJCIRLUMZQUOT-HPLJOQBZSA-N
Canonical SMILES
CC1CCC2CC(C(=CC=CC=CC(CC(C(=O)C(C(C(=CC(C(=O)CC(OC(=O)C3CCCCN3C(=O)C(=O)C1(O2)O)C(C)CC4CCC(C(C4)OC)O)C)C)O)OC)C)C)C)OC
Isomeric 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
Solubility ( literature )

Methanol, DMSO

Compound Classification

macrolide immunosuppressor

Storage, handling
-20°C. Protect from light and moisture. Hygroscopic.
Applications

Research applications: Rapamycin Sirolimus inhibits cell motility by suppression of mTOR-mediated S6K1 and 4E-BP1 pathways. Rapamycin Sirolimus inhibits T-lymphocyte activation / proliferation occuring in response to antigenic and cytokine (Interleukin IL-2, IL-4, and IL-15) stimulation by a mechanism that is distinct from that of other immunosuppressing agents. Sirolimus also inhibits antibody production.

Ingredient type
Fermentek product
Available since
Title
Transport information
Value
Not hazardous for transport
Signal to sort
R