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Compound Detail

CHEMBL1908360

EVEROLIMUS
💊 Approved Drug
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💊 Approved Drug
CO[C@H]1C[C@@H]2CC[C@@H](C)[C@@](O)(O2)C(=O)C(=O)N2CCCC[C@H]2C(=O)O[C@H]([C@H](C)C[C@@H]2CC[C@@H](OCCO)[C@H](OC)C2)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/1C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1908360
Name EVEROLIMUS
Phase Approved
Structure Type MOL
InChI Key HKVAMNSJSFKALM-GKUWKFKPSA-N
Therapeutic ✓ Yes

Known Names

40-o-(2-hydroxyethyl)-rapamycin 42-o-(2-hydroxyethyl)rapamycin Afinitor Afinitor disperz Certican Everolimus RAD 666 RAD-001 RAD-666 RAD001 Rapamycin, 42-o-(2-hydroxyethyl)- Sdz rad +3 more
17
Targets
33
Activities
2
Assay Types
20
PK Parameters
20
Publications
15
Known Names
20
Indications
1
Mechanisms

Molecular Properties

958.2
MW (Da)
6.20
ALogP
14
HBA
3
HBD
204.7
PSA (Ų)
0.13
QED
3
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2009
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -imus
USAN Year 2003

Extended Properties

Molecular Formula C53H83NO14
MW 958.24
Aromatic Rings 0
Heavy Atoms 68
NP-Likeness 1.84

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
FK506-binding protein 1A inhibitor INHIBITOR Peptidyl-prolyl cis-trans isomerase FKBP1A ✓ ✓

Indications

Angiomyolipoma Angiomyolipoma Astrocytoma Astrocytoma Astrocytoma Breast Neoplasms Breast Neoplasms Breast Neoplasms Carcinoma, Renal Cell Carcinoma, Renal Cell Carcinoma, Renal Cell Neoplasms Neoplasms Neuroendocrine Tumors Neuroendocrine Tumors Neuroendocrine Tumors Pancreatic Neoplasms Pancreatic Neoplasms Tuberous Sclerosis Tuberous Sclerosis

ATC Classification

L01EG02
everolimus
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS
L04AH02
everolimus
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: IMMUNOSUPPRESSANTS

Drug Warnings

Black Box Warning
immune system toxicity
Country: United States
Black Box Warning
vascular toxicity
Country: United States
Black Box Warning
nephrotoxicity
Country: United States
Black Box Warning
carcinogenicity
Country: United States
Black Box Warning
infectious disease
Country: United States
Black Box Warning
neurotoxicity
Country: United States
Black Box Warning
musculoskeletal toxicity
Country: United States
Black Box Warning
cardiotoxicity
Country: United States

Activity Summary

IC50 32 meas. best 10.3
Kd 1 meas. best 8.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
mTORC1
CHEMBL4296661
 IC50 10.3 10.225 0.1 2
Cortical neurone
CHEMBL5314314
 IC50 9.82 9.82 0.1 1
Serine/threonine-protein kinase mTOR
CHEMBL2842
 IC50 8.8 7.8 1.6 6
Serine/threonine-protein kinase mTOR
CHEMBL2842
 Kd 8.7 8.7 2.0 1
Bile salt export pump
CHEMBL6020
 IC50 5.7 5.7 2000.0 1
SQ20B
CHEMBL614939
 IC50 5.26 5.2 5500.0 2
DU-145
CHEMBL613508
 IC50 5.1 5.1 8000.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.06 4.99 8700.0 2
ATP-binding cassette sub-family C member 2
CHEMBL5748
 IC50 4.95 4.95 11300.0 1
HCT-116
CHEMBL394
 IC50 4.92 4.92 12000.0 1
CAKI-1
CHEMBL614067
 IC50 4.85 4.85 14000.0 1
HT-29
CHEMBL384
 IC50 4.82 4.82 15000.0 1
OVCAR-3
CHEMBL614213
 IC50 4.8 4.8 16000.0 1
HOP-62
CHEMBL614643
 IC50 4.72 4.72 19000.0 1
COLO 205
CHEMBL614561
 IC50 4.7 4.7 20000.0 1
ATP-binding cassette sub-family C member 3
CHEMBL5918
 IC50 4.08 4.08 84000.0 1
ATP-binding cassette sub-family C member 4
CHEMBL1743128
 IC50 4.02 4.02 95000.0 1
Voltage-gated potassium channel, IKs; KCNQ1(Kv7.1)/KCNE1(MinK)
CHEMBL2221347
 IC50 4.0 4.0 100000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 0.561 uM.hr Homo sapiens
AUC 33636.0 ng.hr.mL-1 Mus musculus
AUC 42267.0 ng.hr.mL-1 Mus musculus
AUC 804.0 ng.hr.mL-1 Mus musculus
AUC 640.0 ng.hr.mL-1 Mus musculus
CL 4.6 mL.min-1.kg-1 Mus musculus
CL 3.75 mL.min-1.kg-1 Mus musculus
CL 171.09 mL.min-1.kg-1 Mus musculus
Cmax 3.464 ug.mL-1 Mus musculus
Cmax 3.941 ug.mL-1 Mus musculus
Cmax 0.057 ug.mL-1 Mus musculus
Cmax 0.043 ug.mL-1 Mus musculus
F 20.0 % Homo sapiens
T1/2 6.5 hr Mus musculus
T1/2 5.7 hr Mus musculus
T1/2 15.8 hr Mus musculus
Tmax 0.5 hr Mus musculus
Tmax 2.0 hr Mus musculus
Tmax 24.0 hr Mus musculus
Tmax 4.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
mTORC1 IC50 = 0.05 nM 10.3 Inhibition of mTORC1 (unknown origin) 35688004
mTORC1 IC50 = 0.07 nM 10.15 Inhibition of mTORC1 in human MDA-MB-468 cells assessed as reduction in P70S6K p... 36533617
Cortical neurone IC50 = 0.15 nM 9.82 Inhibition of oversizing of mouse primary cortical neuron harboring TSC1 deletio... 31955578
Serine/threonine-protein kinase mTOR IC50 = 1.6 nM 8.8 Inhibition of mTOR (unknown origin) 33539089
Serine/threonine-protein kinase mTOR Kd = 2.0 nM 8.7 Binding affinity to mTOR FKBP12 site (unknown origin) 30359003
Serine/threonine-protein kinase mTOR IC50 = 5.0 nM 8.3 Inhibition of mTOR (unknown origin) 32416459
Serine/threonine-protein kinase mTOR IC50 = 5.0 nM 8.3 Inhibition of mTOR in HEK293 cells 32324396
Serine/threonine-protein kinase mTOR IC50 = 5.0 nM 8.3 Inhibition of human mTOR by western blot assay 33650861
Serine/threonine-protein kinase mTOR IC50 = 150.0 nM 6.82 Inhibition of human mTORC1 incubated for 90 mins by Lanthascreen time-resolved F... 38295689
Serine/threonine-protein kinase mTOR IC50 = 530.0 nM 6.28 Inhibition of mTOR (unknown origin) incubated for 1 hr by ELISA analysis 38389871
Bile salt export pump IC50 = 2000.0 nM 5.7 Inhibition of human BSEP overexpressed in Sf9 cell membrane vesicles assessed as... 23956101
SQ20B IC50 = 5500.0 nM 5.26 Cytotoxicity against human SQ20B cells after 72 hrs by MTT assay 24445311
SQ20B IC50 = 7300.0 nM 5.14 Cytotoxicity against human SQ20B cells after 72 hrs by MTT assay 24836070
DU-145 IC50 = 8000.0 nM 5.1 Cytotoxicity against human DU145 cells after 72 hrs by MTT assay 24445311
NON-PROTEIN TARGET IC50 = 8700.0 nM 5.06 Cytotoxicity against human ColoR cells after 72 hrs by MTT assay 24445311
ATP-binding cassette sub-family C member 2 IC50 = 11300.0 nM 4.95 Inhibition of human MRP2 overexpressed in Sf9 cell membrane vesicles assessed as... 23956101
NON-PROTEIN TARGET IC50 = 12000.0 nM 4.92 Cytotoxicity against human SKHEP1 cells after 72 hrs by MTT assay 24445311
HCT-116 IC50 = 12000.0 nM 4.92 Cytotoxicity against human HCT116 cells after 72 hrs by MTT assay 24445311
CAKI-1 IC50 = 14000.0 nM 4.85 Cytotoxicity against human Caki1 cells after 72 hrs by MTT assay 24445311
HT-29 IC50 = 15000.0 nM 4.82 Cytotoxicity against human HT-29 cells after 72 hrs by MTT assay 24445311

Literature References

PubMed DOI Target Context # Activities
- 10.1101/2024.03.28.586928 ADMET 100
33166139 10.1021/acs.jmedchem.0c00620 ADMET 20
23956101 10.1093/toxsci/kft176 Homo sapiens 6
24836070 10.1016/j.ejmech.2014.05.014 mTORC1 6
29191878 10.1126/science.aan4368 Unchecked 5
26176165 10.1021/acs.jnatprod.5b00258 A549 4
28844802 10.1016/j.ejmech.2017.08.007 Homo sapiens 4
33166139 10.1021/acs.jmedchem.0c00620 Unchecked 3
33539089 10.1021/acs.jmedchem.0c01467 Middle East respiratory syndrome-related coronavirus 3
25087753 10.1016/j.vascn.2014.07.002 Voltage-gated inwardly rectifying potassium channel KCNH2 3
36533617 10.1021/acs.jmedchem.2c01658 Unchecked 2
26176165 10.1021/acs.jnatprod.5b00258 Serine/threonine-protein kinase mTOR 2
25087753 10.1016/j.vascn.2014.07.002 Voltage-gated potassium channel, IKs; KCNQ1(Kv7.1)/KCNE1(MinK) 2
25087753 10.1016/j.vascn.2014.07.002 Sodium channel protein type 5 subunit alpha 2
25087753 10.1016/j.vascn.2014.07.002 Voltage-dependent L-type calcium channel subunit alpha-1C 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
24445311 10.1016/j.ejmech.2013.12.020 NON-PROTEIN TARGET 2
- 10.1039/C5MD00493D MCF7 2
36533617 10.1021/acs.jmedchem.2c01658 mTORC1 2
31955578 10.1021/acs.jmedchem.9b01398 Cortical neurone 2

Data from ChEMBL 36 via Core Engine