Rapamycin

Molecular Formula

C51H79NO13

M.W.

914.17

CAS number

53123-88-9

Details

Source

Streptomyces hygroscopicus subsp hygroscopicus

Fermentek product Code

RAP-001

Specifications

Appearance

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

170-185°C

Solubility test

Clear colorless solution at 200mg/ml DMSO

Chemical identification

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

Further Information

Solubility ( literature )

Methanol, DMSO

Compound Classification

macrolide immunosuppressor

Storage, handling

-20°C. Protect from light and moisture. Hygroscopic.

Retest time

3 Years

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.

Composition

Ingredient type

Fermentek product

Special Info

Available since

2004