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QuickView for Sirolimus (compound)

Summary
General Info

PubChem

PubChem Compound 313006

PubChem Compound 313006

Name:	Sirolimus
PubChem Compound ID:	313006
Description:	A macrolide compound obtained from Streptomyces hygroscopicus that acts by selectively blocking the transcriptional activation of cytokines thereby inhibiting cytokine production. It is bioactive only when bound to IMMUNOPHILINS. Sirolimus is a potent immunosuppressant and possesses both antifungal and antineoplastic properties.
Molecular formula:	C₅₁H₇₉NO₁₃
Molecular weight:	914.172 g/mol
Synonyms:	NCI60_001851

DrugBank

Identification

Name:	Sirolimus
Name (isomeric):	DB00877
Drug Type:	small molecule
Description:	A macrolide compound obtained from Streptomyces hygroscopicus that acts by selectively blocking the transcriptional activation of cytokines thereby inhibiting cytokine production. It is bioactive only when bound to IMMUNOPHILINS. Sirolimus is a potent immunosuppressant and possesses both antifungal and antineoplastic properties.
Synonyms:	Antibiotic AY 22989; rapamycin
Brand:	Rapamune, Rapamycin
Category:	Anti-Bacterial Agents, Antifungal Agents, Antifungals, Macrolides, Antibiotics, Antineoplastic, Immunosuppressive Agents
CAS number:	53123-88-9

Pharmacology

Indication:	For the prophylaxis of organ rejection in patients receiving renal transplants.
Pharmacology:	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.
Mechanism 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-... show more » 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. show less «
Protein binding:	92%
Half Life:	57-63 hours
Affected organisms:	Humans and other mammals

Interactions

Drug interaction:

Itraconazole	Itraconazole may increase the effect and toxicity of sirolimus.
Trastuzumab	Trastuzumab may increase the risk of neutropenia and anemia. Monitor closely for signs and symptoms of adverse events.
Trandolapril	Increased risk of angioedema. Monitor for signs and symptoms of facial and systemic edema and/or erythema.
Erythromycin	The macrolide, erythromycin, may increase the serum concentration of sirolimus.
Clarithromycin	The macrolide, clarithromycin, may increase the serum concentration of sirolimus.

Targets

Serine/threonine-protein kinase mTOR

FK506-binding protein 1A

Heparin-binding growth factor 2

Enzymes

Cytochrome P450 3A4

Cytochrome P450 3A5

Cytochrome P450 3A7

Transporters

Multidrug resistance protein 1

Solute carrier organic anion transporter family member 1B1

Multidrug and toxin extrusion protein 1