Laporolimus

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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[30.3.1.0^4,9]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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