LGM Pharma

Sirolimus

CAS No: 53123-88-9

Sirolimus

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Product Details:

CAS No: 53123-88-9
AHFS Codes: 92:00.00
Synonyms:
  • (-)-Rapamycin
  • Rapamycin
ATC code: L04AA10
Molecular Weight: 914.1719 g/mol
PubChem: 5284616
Chemical Formula: C24H32O4S
DrugBank: DB00877 (APRD00178, DB02439)
Assay/Purity: Typically NLT 98%
IUPAC Name: (1R,9S,12S,15R,18R,19R,21R,23S,30S,32S,35R)-1,18-dihydroxy-12-[(2S)-1-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl]-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.0^{4,9}]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone
SMILES: [H][C,,]1(C[C,H](C)[C,]2([H])CC(=O)[C,H](C)C=C(C)[C,,H](O)[C,,H](OC)C(=O)[C,H](C)C[C,H](C)C=CC=CC=C(C)[C,H](C[C,]3([H])CC[C,,H](C)[C,,](O)(O3)C(=O)C(=O)N3CCCC[C,,]3([H])C(=O)O2)OC)CC[C,,H](O)[C,,H](C1)OC
InChl: QFJCIRLUMZQUOT-KLHQEZAJSA-N

Additional Details: [+]

Indication: For the prophylaxis of organ rejection in patients receiving renal transplants.
Pharmacodynamics: Sirolimus, a macrocyclic lactone produced by Streptomyces hygroscopicus, is an immunosuppressive agent indicated for the prophylaxis of organ rejection in patients receiving renal transplants. It is recommended that sirolimus be used in a regimen with cyclosporine and corticosteroids.
Mode of Action: Sirolimus inhibits T lymphocyte activation and proliferation that occurs 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 immunosuppressants. Sirolimus also inhibits antibody production. In cells, sirolimus binds to the immunophilin, FK Binding Protein-12 (FKBP-12), to generate an immunosuppressive complex. The sirolimus:FKBP-12 complex has no effect on calcineurin activity. This complex binds to and inhibits the activation of the mammalian Target Of Rapamycin (mTOR), a key regulatory kinase. This inhibition suppresses cytokine-driven T-cell proliferation, inhibiting the progression from the G1 to the S phase of the cell cycle.
General Reference:
  1. Pritchard DI: Sourcing a chemical succession for cyclosporin from parasites and human pathogens. Drug Discov Today. 2005 May 15;10(10):688-91. Pubmed
  2. Shuchman M: Trading restenosis for thrombosis? New questions about drug-eluting stents. N Engl J Med. 2006 Nov 9;355(19):1949-52. Pubmed
  3. Sun SY, Rosenberg LM, Wang X, Zhou Z, Yue P, Fu H, Khuri FR: Activation of Akt and eIF4E survival pathways by rapamycin-mediated mammalian target of rapamycin inhibition. Cancer Res. 2005 Aug 15;65(16):7052-8. Pubmed
  4. Chan S: Targeting the mammalian target of rapamycin (mTOR): a new approach to treating cancer. Br J Cancer. 2004 Oct 18;91(8):1420-4. Pubmed
  5. Graziani EI: Recent advances in the chemistry, biosynthesis and pharmacology of rapamycin analogs. Nat Prod Rep. 2009 May;26(5):602-9. Epub 2009 Mar 5. Pubmed

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