Everolimus

Everolimus
Clinical data
Pronunciation	Everolimus /ˌɛvəˈroʊləməs/
Trade names	Afinitor, Zortress
Other names	42-O-(2-hydroxyethyl)rapamycin, RAD001
AHFS/Drugs.com	Monograph
MedlinePlus	a609032
License data	US DailyMed: Everolimus;
Pregnancy; category	AU: C; ;
Routes of; administration	By mouth
ATC code	L01EG02 (WHO) L04AH02 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); UK: ; US: WARNINGRx-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Elimination half-life	~30 hours
Identifiers
	IUPAC name Dihydroxy-12-[(2R)-1-[(1S,3R,4R)-4-(2-hydroxyethoxy)-3-methoxycyclohexyl]propan-2-yl]-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.0 hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone;
CAS Number	159351-69-6 ;
PubChem CID	6442177;
DrugBank	DB01590 ;
ChemSpider	21106307 ;
UNII	9HW64Q8G6G;
KEGG	D02714 ;
ChEBI	CHEBI:68478;
ChEMBL	ChEMBL1908360 ;
CompTox Dashboard (EPA)	DTXSID0040599 ;
ECHA InfoCard	100.149.896
Chemical and physical data
Formula	C53H83NO14
Molar mass	958.240 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES OCCO[C@@H]1CC[C@H](C[C@H]1OC)C[C@@H](C)[C@@H]4CC(=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](OC)C[C@@H]2CC[C@@H](C)[C@@](O)(O2)C(=O)C(=O)N3CCCC[C@H]3C(=O)O4;
	InChI InChI=1S/C53H83NO14/c1-32-16-12-11-13-17-33(2)44(63-8)30-40-21-19-38(7)53(62,68-40)50(59)51(60)54-23-15-14-18-41(54)52(61)67-45(35(4)28-39-20-22-43(66-25-24-55)46(29-39)64-9)31-42(56)34(3)27-37(6)48(58)49(65-10)47(57)36(5)26-32/h11-13,16-17,27,32,34-36,38-41,43-46,48-49,55,58,62H,14-15,18-26,28-31H2,1-10H3/b13-11+,16-12+,33-17+,37-27+/t32-,34-,35-,36-,38-,39+,40+,41+,43-,44+,45+,46-,48-,49+,53-/m1/s1 ; Key:HKVAMNSJSFKALM-GKUWKFKPSA-N ;
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Everolimus, sold under the brand name Afinitor among others, is a medication used as an immunosuppressant to prevent rejection of organ transplants^[10] and as a targeted therapy in the treatment of renal cell cancer and other tumours.^[11]

This compound also has a use in cardiovascular drug-eluting stent technologies to inhibit restenosis.^{[medical citation needed]}

It is the 40-O-(2-hydroxyethyl) derivative of sirolimus and works similarly to sirolimus as an inhibitor of mammalian target of rapamycin (mTOR).^[12]

It is marketed by Novartis under the trade names Zortress (US) and Certican (European Union and other countries) in transplantation medicine, and as Afinitor (general tumours) and Votubia (tumours as a result of Tuberous Sclerosis Complex (TSC)) in oncology.^{[citation needed]}

It is on the World Health Organization's List of Essential Medicines.^[13] It is available as a generic medication.^[14]

^ Use During Pregnancy and Breastfeeding
^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
^ "Summary of Product Characteristics (SmPC) - (emc)". Certican Tablets. 15 January 2021. Retrieved 30 December 2021.
^ "Afinitor- everolimus tablet Afinitor Disperz- everolimus tablet, for suspension". DailyMed. Retrieved 30 December 2021.
^ "Zortress- everolimus tablet". DailyMed. Retrieved 30 December 2021.
^ "Afinitor EPAR". European Medicines Agency. 17 September 2018. Retrieved 30 December 2021.
^ "Votubia EPAR". European Medicines Agency. 17 September 2018. Retrieved 30 December 2021.
^ Formica RN, Lorber KM, Friedman AL, Bia MJ, Lakkis F, Smith JD, Lorber MI (March 2004). "The evolving experience using everolimus in clinical transplantation". Transplantation Proceedings. 36 (2 Suppl): 495S–499S. doi:10.1016/j.transproceed.2004.01.015. PMID 15041395.
^ Tedesco-Silva H, Saliba F, Barten MJ, De Simone P, Potena L, Gottlieb J, et al. (January 2022). "An overview of the efficacy and safety of everolimus in adult solid organ transplant recipients". Transplantation Reviews. 36 (1): 100655. doi:10.1016/j.trre.2021.100655. hdl:10230/53730. PMID 34696930. S2CID 239887236.
^ Hasskarl J (2018). "Everolimus". Small Molecules in Oncology. Recent Results in Cancer Research. Vol. 211. pp. 101–123. doi:10.1007/978-3-319-91442-8_8. ISBN 978-3-319-91441-1. PMID 30069763. {{cite book}}: |journal= ignored (help)
^ Hasskarl J (2018). "Everolimus". In Martens UM (ed.). Small Molecules in Oncology (Third ed.). Heidelberg: Springer. p. 101-124. ISBN 978-3-319-91442-8.
^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
^ "First Generic Drug Approvals". U.S. Food and Drug Administration (FDA). 15 November 2021. Retrieved 30 December 2021.

[Drugs.com_pregnancy-1] Use During Pregnancy and Breastfeeding

[FDA-AllBoxedWarnings-2] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.

[3] "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.

[4] "Summary of Product Characteristics (SmPC) - (emc)". Certican Tablets. 15 January 2021. Retrieved 30 December 2021.

[Afinitor_FDA_label-5] "Afinitor- everolimus tablet Afinitor Disperz- everolimus tablet, for suspension". DailyMed. Retrieved 30 December 2021.

[Zortress_FDA_label-6] "Zortress- everolimus tablet". DailyMed. Retrieved 30 December 2021.

[Afinitor_EPAR-7] "Afinitor EPAR". European Medicines Agency. 17 September 2018. Retrieved 30 December 2021.

[Votubia_EPAR-8] "Votubia EPAR". European Medicines Agency. 17 September 2018. Retrieved 30 December 2021.

[9] Formica RN, Lorber KM, Friedman AL, Bia MJ, Lakkis F, Smith JD, Lorber MI (March 2004). "The evolving experience using everolimus in clinical transplantation". Transplantation Proceedings. 36 (2 Suppl): 495S–499S. doi:10.1016/j.transproceed.2004.01.015. PMID 15041395.

[Tedesco-Silva_2022-10] Tedesco-Silva H, Saliba F, Barten MJ, De Simone P, Potena L, Gottlieb J, et al. (January 2022). "An overview of the efficacy and safety of everolimus in adult solid organ transplant recipients". Transplantation Reviews. 36 (1): 100655. doi:10.1016/j.trre.2021.100655. hdl:10230/53730. PMID 34696930. S2CID 239887236.

[Hasskarl_2018-11] Hasskarl J (2018). "Everolimus". Small Molecules in Oncology. Recent Results in Cancer Research. Vol. 211. pp. 101–123. doi:10.1007/978-3-319-91442-8_8. ISBN 978-3-319-91441-1. PMID 30069763. {{cite book}}: |journal= ignored (help)

[12] Hasskarl J (2018). "Everolimus". In Martens UM (ed.). Small Molecules in Oncology (Third ed.). Heidelberg: Springer. p. 101-124. ISBN 978-3-319-91442-8.

[WHO23rd-13] World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.

[14] "First Generic Drug Approvals". U.S. Food and Drug Administration (FDA). 15 November 2021. Retrieved 30 December 2021.

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