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Namespace Prefixes

PrefixIRI
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Statements

Subject Item
n2:DB00877
rdf:type
n3:Drug
n3: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. [PubChem]
n3:dosage
n4:271B558B-363D-11E5-9242-09173F13E4C5 n4:271B558C-363D-11E5-9242-09173F13E4C5 n4:271B558D-363D-11E5-9242-09173F13E4C5 n4:271B558E-363D-11E5-9242-09173F13E4C5 n4:271B558F-363D-11E5-9242-09173F13E4C5 n4:271B5590-363D-11E5-9242-09173F13E4C5 n4:271B5591-363D-11E5-9242-09173F13E4C5 n4:271B558A-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# Pritchard DI: Sourcing a chemical succession for cyclosporin from parasites and human pathogens. Drug Discov Today. 2005 May 15;10(10):688-91. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15896681 # Shuchman M: Trading restenosis for thrombosis? New questions about drug-eluting stents. N Engl J Med. 2006 Nov 9;355(19):1949-52. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17093244 # 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":http://www.ncbi.nlm.nih.gov/pubmed/16103051 # 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":http://www.ncbi.nlm.nih.gov/pubmed/15365568 # 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":http://www.ncbi.nlm.nih.gov/pubmed/19387497
n3:group
approved investigational
n3:halfLife
57-63 hours
n3:indication
For the prophylaxis of organ rejection in patients receiving renal transplants.
n3:manufacturer
n9:271B5585-363D-11E5-9242-09173F13E4C5
owl:sameAs
n7:DB00877 n8:DB00877
dcterms:title
Sirolimus
adms:identifier
n12:50240955 n13:9168 n17:ARD n18:Sirolimus n19:PA451365 n20:C07909 n21:D00753 n22:DB00877
n3:mechanismOfAction
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.
n3:packager
n9:271B5584-363D-11E5-9242-09173F13E4C5 n9:271B5582-363D-11E5-9242-09173F13E4C5 n9:271B5583-363D-11E5-9242-09173F13E4C5 n9:271B5581-363D-11E5-9242-09173F13E4C5 n9:271B5580-363D-11E5-9242-09173F13E4C5 n9:271B557F-363D-11E5-9242-09173F13E4C5
n3:patent
n5:2293793 n5:2103571 n5:5212155 n5:5989591
n3:synonym
Rapamycin (-)-Rapamycin
n14:hasAHFSCode
n15:92-00-00
n3:proteinBinding
92%
n3:synthesisReference
Madhup K. Dhaon, Chi-nung Hsiao, Subhash R. Patel, Peter J. Bonk, Sanjay R. Chemburkar, Yong Y. Chen, "One pot synthesis of tetrazole derivatives of sirolimus." U.S. Patent US20080167335, issued July 10, 2008.
n24:hasConcept
n25:M0029863
foaf:page
n27:sirolimus.html n28:sirolimus.htm
n3:IUPAC-Name
n10:271B5596-363D-11E5-9242-09173F13E4C5
n3:InChI
n10:271B559C-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n10:271B559B-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n10:271B5598-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n10:271B5599-363D-11E5-9242-09173F13E4C5
n3:SMILES
n10:271B559A-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n10:271B5594-363D-11E5-9242-09173F13E4C5
n3:logP
n10:271B5592-363D-11E5-9242-09173F13E4C5 n10:271B5595-363D-11E5-9242-09173F13E4C5 n10:271B55AC-363D-11E5-9242-09173F13E4C5
n3:logS
n10:271B5593-363D-11E5-9242-09173F13E4C5
n14:hasATCCode
n29:L04AA10
n3:H-Bond-Acceptor-Count
n10:271B55A2-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n10:271B55A3-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n10:271B559D-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n10:271B559E-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n10:271B55A0-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n10:271B559F-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n10:271B55A1-363D-11E5-9242-09173F13E4C5
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
53123-88-9
n3:category
n3:containedIn
n23:271B5586-363D-11E5-9242-09173F13E4C5 n23:271B5589-363D-11E5-9242-09173F13E4C5 n23:271B5587-363D-11E5-9242-09173F13E4C5 n23:271B5588-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n10:271B55A8-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n10:271B55AA-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n10:271B55AB-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n10:271B55A7-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n10:271B55A6-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n10:271B55A9-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n10:271B5597-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n10:271B55A4-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n10:271B55A5-363D-11E5-9242-09173F13E4C5