FANDOM


Sirolimus
Sirolimus
2D structure of sirolimus
Sirolimus
3D structure of sirolimus
Names
Synonyms AY-022989, AY-22989, NSC-226080, Rapamycin, WY-090217
Brand names Rapamune

IUPAC name
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
Clinical information
Preg. cat.
AU: C
US: C
Legal status
AU: Prescription Only Medicine (S4)
CA: ℞-only
UK: POM
US: ℞-only
Routes Oral


Identifiers
ATC code L04AA10
ChemSpider 10482078
DrugBank DB00877
PubChem 5284616
MedlinePlus a602026
MeSH ID D020123
PDB IDs
PDBs
1C9H (RCSB, PDBe; X-ray)
1FAP (RCSB, PDBe; X-ray)
1FKB (RCSB, PDBe; X-ray)
1PKB (RCSB, PDBe; X-ray)
2DG3 (RCSB, PDBe; X-ray)
4DRH (RCSB, PDBe; X-ray)
4DRI (RCSB, PDBe; X-ray)
4DRJ (RCSB, PDBe; X-ray)
External links
DailyMed sirolimus search
Drugs.com international, monograph
Jmol 3D structure
Licensing data EU EMA: link.
US FDA: link.
MSR monograph
emc sirolimus search
TGA-eBS sirolimus search
Chemical properties
Formula C51H79NO13
Mol. mass
Mol. mass for MFs
914.1719 g/mol
SMILES
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=C\C=C\C=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
InChI
InChI
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
InChIKey
InChIKey
QFJCIRLUMZQUOT-KLHQEZAJSA-N


Sirolimus is a macrolide mTOR inhibitor originally isolated from Streptomyces hygroscopicus with antibacterialantifungal, antineoplastic, antiviral  and immunosuppressant effects.[1][2] It is widely used to prevent organ rejection (especially kidney), when combined with a corticosteroids (e.g., prednisone) and ciclosporin.[1] It can also be used in the prevention and management of graft-versus-host disease (GVHD).[2]




External linksEdit

Reference listEdit

  1. 1.0 1.1 Brayfield, A, ed. (12 December 2013). "Sirolimus". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 15 December 2014. 
  2. 2.0 2.1 Abouelnasr, A; Roy, J; Cohen, S; Kiss, T; Lachance, S (January 2013). "Defining the role of sirolimus in the management of graft-versus-host disease: from prophylaxis to treatment.". Biology of Blood and Marrow Transplantation 19 (1): 12–21. PMID 22771839. doi:10.1016/j.bbmt.2012.06.020. 
Antineoplastic and immunomodulating agents (ATC:L)
Antineoplastic agents (L01)
(A)
N. mustards
(AA)
OZPPs Cyclophosphamide, ifosfamide, trofosfamide
PhDs Bendamustine, chlorambucil, melphalan, prednimustine
Other Chlormethine
Alkyl sulfonates
(AB)
Busulfan, mannosulfan, treosulfan
Ethylene imines
(AC)
Carboquone, thiotepa, triaziquone
Nitrosoureas
(AD)
Acyclical Carmustine, ranimustine
Cyclical Fotemustine, lomustine, semustine
Sugars Nimustine, streptozocin
Methylating-As
(AX, XB01)
Dacarbazine, procarbazine, temozolomide
Epoxides
(AG, AX)
Etoglucid, mitobronitol
Others
(AX, XX)
Altretamine, pipobroman
Antimetabolites
(B)
Folic acid-As
(BA)
DHFR-Is Aminopterin, methotrexate, pemetrexed, pralatrexate
TS-Is Pemetrexed, raltitrexed
Purine-As
(BB)
ADA-I Penostatin
RNR-Is Cladribine, clofarabine, fludarabine
G-Ds Mercaptopurine, tioguanine
Pyrimidine-As (BC) DMT-Is Azacitidine, decitabine
DPM-I Cytarabine, enocitabine
RNR-I Gemcitabine
TS-Is Capecitabine, carmofur, floxuridine, fluorouracil, tegafur
Others
(XX05)
RNR-I Hydroxycarbamide
Natural products
(C)
Vinca alkaloids (CA) Vinblastine, vincristine, vindesine, vinflunine, vinorelbine, vintafolide
Podophyllotoxins (CB) Etoposide, teniposide
Colchicine-D
(CC)
Demecolcine
Taxanes
(CD)
Cabazitaxel, docetaxel, paclitaxel, paclitaxel poliglumex
Camptothecins (XX) Irinotecan, topotecan
Other
(CX, XX)
Omacetaxine mepesuccinate, trabectedin
(D) Actinomycines (DA) Dactinomycin
Anthraquinones
(DB)
Cyclines Aclarubicin, amrubicin, daunorubicin, doxorubicin, epirubicin, idarubicin, pirarubicin, pixantrone, sabarubicin, valrubicin, zorubicin
CDs Mitoxantrone, pixantrone
Others
(DC)
Bleomycin, ixabepilone, mitomycin, peplomycin, plicamycin, zinostatin
Others
(X)
Pt compounds
(XA)
Carboplatin, cisplatin, eptaplatin, nedaplatin, oxaliplatin, picoplatin, polyplatillen, satraplatin
Monoclonal antibodies
(-mab)
(XC)
Chimeric
(-tuxi-)
Cetuximab, brentuximab vedotin, rituximab, siltuximab
Human
(-mu-, others)
Ipilimumab, nivolumab, ofatumumab, panitumumab, ramucirumab
Humanized
(-zu-)
Alemtuzumab, bevacizumab, gemtuzumab, mogamulizumab, nimotuzumab, obinutuzumab, pertuzumab, trastuzumab, trastuzumab emtansine
Murine
(-mo-, -axo-[n 1])
Catumaxomab, ibritumomab, tositumomab
PK inhibitors
(XE)
BRAF
(-rafenib)
Dabrafenib, vemurafenib
mTOR
(-rolimus)
Everolimus, ridaforolimus, temsirolimus
TK
(-nib)
Afatinib, axitinib, bosutinib, crizotinib, dasatinib, erlotinib, gefitinib, ibrutinib, imatinib, lapatinib, masitinib, nilotinib, pazopanib, ponatinib, regorafenib, ruxolitinib, sorafenib, sunitinib, trametinib, vandetanib
Others
(XX)
HDAC-Is Panobinostat, romidepsin, vorinostat
Microtubule Is Eribulin, estramustine
Oligo-/poly-mers Oblimersen, sizofiran
Proteasome Is
(-zomib)
Bortezomib, carfilzomib
Proteins Aflibercept, asparaginase, denileukin diftitox, endostatin, pegaspargase
Retinoids Alitretinoin, bexarotene, tamibarotene, tretinoin
TII Is Amsacrine, sobuzoxane
M enzyme Is Aceglatone, anagrelide, ubenimex
Others Arsenic trioxide, celecoxib, lonidamine, masoprocol, miltefosine, mitoguazone, mitotane, sitimagene ceradenovec
Endocrine therapy (L02)
Hormones and RAs
(A)
Oestrogens
(AA)
Diethylstilbestrol, ethinylestradiol, fosfestrol, polyestradiol phosphate
Progestogens
(AB)
Medroxyprogesterone, megestrol, gestonorone
GnRH analogues
(AE)
Buserelin, goserelin, histrelin, leuprorelin, triptorelin
Hormones antagonists and RAs
(B)
Anti-oestrogens
(BA)
Fulvestrant, tamoxifen, toremifene
Anti-androgens
(BB)
Bicalutamide, flutamide, nilutamide
Aromatase inhibitors
(BG)
Aminoglutethimide, anastrozole, exemestane, formestane, letrozole, vorozole
Others
(BX)
Abarelix, abiraterone, degarelix.
Immunostimulants (L03, L03A)
Colony-stimulating factors (CSFs)
(A)
G- Filgrastim (lipegfilgrastim, pegfilgrastim), lenograstim
GM- Molgramostim, sargramostim
Others Ancestim, mirimostim, thrombopoietin
Interferons (IFNs)
(B)
Alfa Interferon alfa-2a (peginterferon alfa-2a, peginterferon alfa-2a combinations), interferon alfa-2b (albinterferon alfa-2b, peginterferon alfa-2b, peginterferon alfa-2a combinations), interferon alfacon-1, interferon alfa-n1, interferon alfa natural
Beta Interferon beta-1a, interferon beta-1b, interferon beta natural
Gamma Interferon gamma
Interleukins (ILs)
(C)
Aldesleukin (IL-2), oprelvekin (IL-11)
Others
(AX)
Endogenous Histamine dihydrochloride, pegademase, tasonermin, thymopentin
Vaccines/
antigens
BCG vaccines, melanoma vaccine, mifamurtide, sipuleucel-T, vitespen
Polymers Lentinan, Poly I:C, Poly ICLC
Others Cridanimod, glatiramer acetate, pidotimod, plerixafor, roquinimex
Immunosuppressants (L04, L04A)
Selective agents
(A)
Antibodies Human mAbs Belimumab
Humanized mAbs Eculizumab, efalizumab, natalizumab
Murine mAbs Muromonab-CD3
Polyclonal Antithymocyte immunoglobulin
FPs Abatacept, alefacept, belatacept
mTOR inhibitors
(-rolimus)
Everolimus, sirolimus
IL-2 inhibitors
(-imus)
Abetimus, gusperimus
AMs Leflunomide, mycophenolic acid, teriflunomide
Others Apremilast, fingolimod, tofacitinib
TNF-α inhibitors
(B)
FPs Etanercept
mAbs Adalimumab, afelimomab, certolizumab pegol, golimumab, infliximab.
Interleukin inhibitors
(C)
IL-1 Anakinra, canakinumab, rilonacept
IL-2 Basiliximab, daclizumab
IL-5 Mepolizumab
IL-6 Siltuximab, tocilizumab, ustekinumab
IL-12 Briakinumab, ustekinumab
IL-17A Secukinumab
Calcineurin inhibitors
(D)
Cyclophilin-B
(-closporin)
Ciclosporin, voclosporin
FKBP12-binding
(-crolimus)
Pimecrolimus, tacrolimus
Others
(X)
Antimetabolites Azathioprine, fludarabine, mercaptopurine, methotrexate
IMiDs Lenalidomide, pomalidomide, thalidomide
Others Cyclophosphamide, mitoxantrone, pirfenidone
  1. Murine/rat hybrids

Ad blocker interference detected!


Wikia is a free-to-use site that makes money from advertising. We have a modified experience for viewers using ad blockers

Wikia is not accessible if you’ve made further modifications. Remove the custom ad blocker rule(s) and the page will load as expected.