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Laporolimus
Laporolimus
Rapamycin, 42-cyclohexanecarboxylate
CAS 1504576-27-5
MF C58H89NO14 MW 1024.3 g/mol
[(1R,2R,4S)-4-[(2R)-2-[(1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-dihydroxy-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-2,3,10,14,20-pentaoxo-11,36-dioxa-4-azatricyclo[30.3.1.04,9]hexatriaconta-16,24,26,28-tetraen-12-yl]propyl]-2-methoxycyclohexyl] cyclohexanecarboxylate
(1R,2R,4S)-4-{(2R)-2-[(3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34aS)-9,27-dihydroxy-10,21-dimethoxy6,8,12,14,20,26-hexamethyl-1,5,11,28,29-pentaoxo1,4,5,6,9,10,11,12,13,14,21,22,23,24,25,26,27,28,29,3
1,32,33,34,34a-tetracosahydro-3H-23,27-epoxypyrido[2,1-c][1,4]oxazacyclohentriacontin-3-yl]propyl}-2-methoxycyclohexyl
cyclohexanecarboxylate
immunosuppressant, CRC-015, CRC 015, F5041W3RVA, Rapamycin, 42-cyclohexanecarboxylate
Laporolimus is an experimental immunosuppressant compound that acts as an mTOR (mechanistic target of rapamycin) pathway inhibitor. It is chemically classified as a macrolide derivative and is also known by its chemical synonym, rapamycin 42-cyclohexanecarboxylate.
Currently, Laporolimus is designated for research use only and has not been approved for clinical medical applications in humans or animals.
Key Technical Details
- Mechanism of Action: It blocks the mTOR signaling pathway, which is responsible for regulating cell growth, proliferation, and immune cell activation.
Distinguishing Laporolimus from Clinical Alternatives
Because it ends with the suffix -limus, it shares structural and nomenclature similarities with widely used clinical immunosuppressants. However, its legal status and development stage differ significantly:
| Drug Name | Clinical Availability | Primary Mechanism | Primary Uses |
|---|---|---|---|
| Laporolimus | None (Research Only) | mTOR Inhibitor | Laboratory research |
| Sirolimus (Rapamycin) | Approved | mTOR Inhibitor | Transplant rejection, coating coronary stents |
| Tacrolimus | Approved | Calcineurin Inhibitor | Organ transplant prophylaxis, severe eczema |
If you are researching this compound for a laboratory study, you can review its structural data and biochemical properties via the PubChem Laporolimus Compound Page
Laporolimus (CAS 1504576-27-5) is an immunosuppressive agent and mTOR inhibitor structurally derived from rapamycin as a cyclohexanecarboxylate derivative. Its total chemical synthesis is highly complex, typically achieved via semisynthesis starting from natural macrolides produced by Streptomyces fermentation.
Semisynthetic Pathway
Because the core macrocyclic lactone (a 36-membered polyketide ring) is incredibly challenging to build from scratch, researchers and pharmaceutical manufacturers rely on a derivatization approach:
- Fermentation: The baseline macrolide is produced via large-scale fermentation of Streptomyces hygroscopicus (similar to the base rapamycin process).
- Purification: The naturally produced macrocyclic core is isolated and purified from the fermentation broth using column chromatography.
- Esterification: The C-42 hydroxyl group of the macrolide core is selectively protected and subjected to acylation with a cyclohexanecarboxylic acid derivative (or reactive cyclohexanecarbonyl chloride).
- Deprotection & Purification: The C-42 cyclohexanecarboxylate is then deprotected and purified via preparative chromatography to yield pure laporolimus.
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