s
sirolimus
Immunosuppressive medicine used to prevent rejection of transplanted organs
Also known as rapamycin · WY-090217 · AY-22989 · (-)-rapamycin
- Formula
- C₅₁H₇₉NO₁₃
1
- C₅₁H₇₉NO₁₃
- Mass
- 913.5551 Da
1
- 913.5551 Da
Overview
Chemistry
All data
140 statements · 61% with external sources · numbers in brackets are citations
- World Health Organisation international non-proprietary name
- sirolimus language: English, French
2
Sources- 1.Stated in ChEMBL“Sirolimus”Retrieved 2016-01-19
- 2.Stated in Recommended INN: List 34
- sirólimus
1
- sirolimusum
1
- sirolimus language: English, French
- Canonical SMILES
- CC1CCC2CC(C(=CC=CC=CC(CC(C(=O)C(C(C(=CC(C(=O)CC(OC(=O)C3CCCCN3C(=O)C(=O)C1(O2)O)C(C)CC4CCC(C(C4)OC)O)C)C)O)OC)C)C)C)OC
1
- CC1CCC2CC(C(=CC=CC=CC(CC(C(=O)C(C(C(=CC(C(=O)CC(OC(=O)C3CCCCN3C(=O)C(=O)C1(O2)O)C(C)CC4CCC(C(C4)OC)O)C)C)O)OC)C)C)C)OC
- Medical condition treated
- pachyonychia congenita
- lymphangioleiomyomatosis
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- renal cell carcinoma
- transplant rejection
- graft-versus-host disease
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- Defined daily dose
- 3 milligram route of administration: oral administration
- Isomeric SMILES
- CO[C@@H]1C[C@H](C[C@@H](C)[C@@H]2CC(=O)[C@H](C)\C=C(C)\[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)\C=C\C=C\C=C(C)\[C@H](C[C@@H]3CC[C@@H](C)[C@@](O)(O3)C(=O)C(=O)N4CCCC[C@H]4C(=O)O2)OC)CC[C@H]1O
1
Sources- 1.Stated in Global Substance Registration SystemRetrieved 2018-02-14
- CO[C@@H]1C[C@H](C[C@@H](C)[C@@H]2CC(=O)[C@H](C)\C=C(C)\[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)\C=C\C=C\C=C(C)\[C@H](C[C@@H]3CC[C@@H](C)[C@@](O)(O3)C(=O)C(=O)N4CCCC[C@H]4C(=O)O2)OC)CC[C@H]1O
- Physically interacts with
- FKBP prolyl isomerase 1A subject has role: enzyme inhibitor
1
- FKBP prolyl isomerase 1A subject has role: enzyme inhibitor
- Part of
- cellular response to rapamycin subject has role: reactant
1
- response to rapamycin subject has role: reactant
1
- cellular response to rapamycin subject has role: reactant
- Found in taxon
- Streptomyces hygroscopicus
19
Sources- 1.Stated in Incorporation of acetate, propionate, and methionine into rapamycin by Streptomyces hygroscopicus
- 2.Stated in Rapamycin (AY-22,989), a new antifungal antibiotic. II. Fermentation, isolation and characterization.
- 3.Stated in Secretion of FK506/FK520 and rapamycin by Streptomyces inhibits the growth of competing Saccharomyces cerevisiae and Cryptococcus neoformans
- 4.Stated in Cytochrome p450 complement (CYPome) of the avermectin-producer Streptomyces avermitilis and comparison to that of Streptomyces coelicolor A3(2).
- 5.Stated in Organization of the biosynthetic gene cluster for the macrolide concanamycin A in Streptomyces neyagawaensis ATCC 27449.
- 6.Stated in A combined approach of classical mutagenesis and rational metabolic engineering improves rapamycin biosynthesis and provides insights into methylmalonyl-CoA precursor supply pathway in Streptomyces hygroscopicus ATCC 29253
- Streptomyces iranensis
16
Sources- 1.Stated in Secretion of FK506/FK520 and rapamycin by Streptomyces inhibits the growth of competing Saccharomyces cerevisiae and Cryptococcus neoformans
- 2.Stated in Cytochrome p450 complement (CYPome) of the avermectin-producer Streptomyces avermitilis and comparison to that of Streptomyces coelicolor A3(2).
- 3.Stated in Organization of the biosynthetic gene cluster for the macrolide concanamycin A in Streptomyces neyagawaensis ATCC 27449.
- 4.Stated in A combined approach of classical mutagenesis and rational metabolic engineering improves rapamycin biosynthesis and provides insights into methylmalonyl-CoA precursor supply pathway in Streptomyces hygroscopicus ATCC 29253
- 5.Stated in Waking up Streptomyces secondary metabolism by constitutive expression of activators or genetic disruption of repressors
- 6.Stated in Effects of dissolved oxygen level on rapamycin production by pellet-form of Streptomyces hygroscopicus
- Streptomyces rapamycinicus
16
Sources- 1.Stated in Secretion of FK506/FK520 and rapamycin by Streptomyces inhibits the growth of competing Saccharomyces cerevisiae and Cryptococcus neoformans
- 2.Stated in Cytochrome p450 complement (CYPome) of the avermectin-producer Streptomyces avermitilis and comparison to that of Streptomyces coelicolor A3(2).
- 3.Stated in Organization of the biosynthetic gene cluster for the macrolide concanamycin A in Streptomyces neyagawaensis ATCC 27449.
- 4.Stated in A combined approach of classical mutagenesis and rational metabolic engineering improves rapamycin biosynthesis and provides insights into methylmalonyl-CoA precursor supply pathway in Streptomyces hygroscopicus ATCC 29253
- 5.Stated in Waking up Streptomyces secondary metabolism by constitutive expression of activators or genetic disruption of repressors
- 6.Stated in Effects of dissolved oxygen level on rapamycin production by pellet-form of Streptomyces hygroscopicus
- Purpureocillium
- Ophiocordyceps
- Streptomyces hygroscopicus
- Has use
- medication
2
Sources- 1.Stated in DrugBank“Sirolimus”
- 2.“Rapamycin can add years to your life, or none at all – it’s a lottery | New Scientist”newscientist.com/article/2516893-rapamycin-can-add-years-to-your-life-or-none-at-all-its-a-lotteryRetrieved 2026-02-25
- chemical probe
- biological research
- medication
- Legal status (medicine)
- boxed warning
1
Sources- 1.“FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.”nctr-crs.fda.gov/fdalabel/ui/spl-summaries/criteria/343802
- boxed warning
- Significant drug interaction
- diltiazem side effect: leukopenia
- diltiazem side effect: anemia
- diltiazem side effect: thrombocytopenia
- diltiazem side effect: Achor-Smith syndrom
- diltiazem side effect: diarrhea
- itraconazole side effect: leukopenia
- itraconazole side effect: anemia
- itraconazole side effect: thrombocytopenia
Show 27 moreShow less
- itraconazole side effect: Achor-Smith syndrom
- itraconazole side effect: diarrhea
- erythromycin side effect: leukopenia
- erythromycin side effect: anemia
- erythromycin side effect: thrombocytopenia
- erythromycin side effect: Achor-Smith syndrom
- erythromycin side effect: diarrhea
- ritonavir side effect: leukopenia
- ritonavir side effect: anemia
- ritonavir side effect: thrombocytopenia
- ritonavir side effect: Achor-Smith syndrom
- ritonavir side effect: diarrhea
- fluconazole side effect: leukopenia
- fluconazole side effect: anemia
- fluconazole side effect: thrombocytopenia
- fluconazole side effect: Achor-Smith syndrom
- fluconazole side effect: diarrhea
- cyclosporine side effect: leukopenia
- cyclosporine side effect: anemia
- cyclosporine side effect: thrombocytopenia
- cyclosporine side effect: Achor-Smith syndrom
- cyclosporine side effect: diarrhea
- ketoconazole side effect: leukopenia
- ketoconazole side effect: anemia
- ketoconazole side effect: thrombocytopenia
- ketoconazole side effect: Achor-Smith syndrom
- ketoconazole side effect: diarrhea
On other databases
48 identifiers linking sirolimus across the web's reference databases
- ATC codeL04AA10
- CAS Registry Number53123-88-9
- ChEBI ID9168
- ChEMBL IDCHEMBL413
- ChemSpider ID10482078
- DeCS ID33809
- DrugBank IDDB00877
- DrugCentral ID2446
- DSSTOX compound identifierDTXCID503582
- DSSTox substance IDDTXSID5023582
- EC number610-965-5
- ECHA Substance Infocard ID100.107.147
- Encyclopædia Britannica Online IDscience/rapamycin
- Freebase ID/m/02m01g
- Guide to Pharmacology Ligand ID6031
- HSDB ID7284
- InChIInChI=1S/C51H79NO13/c1-30-16-12-11-13-17-31(2)42(61-8)28-38-21-19-36(7)51(60,65-38)48(57)49(58)52-23-15-14-18-39(52)50(59)64-43(33(4)26-37-20-22-40(53)44(27-37)62-9)29-41(54)32(3)25-35(6)46(56)47(63-10)45(55)34(5)24-30/h11-13,16-17,25,30,32-34,36-40,42-44,46-47,53,56,60H,14-15,18-24,26-29H2,1-10H3/b13-11+,16-12+,31-17+,35-25+/t30-,32-,33-,34-,36-,37+,38+,39+,40-,42+,43+,44-,46-,47+,51-/m1/s1
- InChIKeyQFJCIRLUMZQUOT-HPLJOQBZSA-N
- J-GLOBAL ID200907050996917166
- J9U entity ID987007542160305171
- KEGG IDC07909
- KNApSAcK IDC00018055
- Library of Congress Authorities IDsh2001005861
- LIPID MAPS IDLMPK06000003
- MedlinePlus drug identifiera602026
- MeSH descriptor IDD020123
- MeSH tree codeD02.540.505.760
- Microsoft Academic ID (discontinued)2777921159
- Natural Product Atlas IDNPA000414
- NCI Thesaurus IDC1212
- NDF-RT IDN0000148624
- NE.se IDsirolimus
- Nikkaji IDJ137.896A
- NSC number226080
- OpenAlex IDC2777921159
- PatientsLikeMe treatment IDsirolimus
- PDB ligand IDRAP
- Probes And Drugs IDPD003301
- PubChem CID5284616
- RxNorm CUI35302
- SureChEMBL ID3463
- UniChem compound ID123924
- UNIIW36ZG6FT64
- UNSPSC code51201515
- Wellcome Collection concept IDmuudk6xc
- WikiProjectMed IDSirolimus
- World Health Organisation international non-proprietary name numeric ID7104
- Yale LUX IDconcept/d39adf49-2a29-472d-bec6-ce4fadd58fca