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Compound Detail

CHEMBL1456

MYCOPHENOLATE MOFETIL
💊 Approved Drug
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💊 Approved Drug
COc1c(C)c2c(c(O)c1C/C=C(\C)CCC(=O)OCCN1CCOCC1)C(=O)OC2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1456
Name MYCOPHENOLATE MOFETIL
Phase Approved
Structure Type MOL
InChI Key RTGDFNSFWBGLEC-SYZQJQIISA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL866

Known Names

Arzip Cellcept Myclausen Mycophenolate mofetil Mycophenolate mofetil teva Mycophenolic acid 2-(4-morpholinyl)ethyl ester Mycophenylate mofetil Myfenax Myhibbin NSC-724229 NSC-758905 RS-61443
9
Targets
19
Activities
2
Assay Types
1
PK Parameters
20
Publications
12
Known Names
20
Indications
1
Mechanisms

Molecular Properties

433.5
MW (Da)
2.52
ALogP
8
HBA
1
HBD
94.5
PSA (Ų)
0.47
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1995
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product Prodrug
USAN Year 1990

Extended Properties

Molecular Formula C23H31NO7
MW 433.50
Aromatic Rings 1
Heavy Atoms 31
NP-Likeness 0.73

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Inosine-5'-monophosphate dehydrogenase (IMPDH) inhibitor INHIBITOR Inosine-5'-monophosphate dehydrogenase (IMPDH) ✓ ✓

Indications

Delayed Graft Function Anti-Neutrophil Cytoplasmic Antibody-Associated Vasculitis Carcinoma, Hepatocellular Cardiovascular Diseases Cystitis, Interstitial Diabetes Mellitus, Type 1 Diabetic Nephropathies Glomerulonephritis, IGA Glomerulonephritis, Membranous Glomerulosclerosis, Focal Segmental Graft vs Host Disease Graft vs Host Disease Granulomatosis with Polyangiitis Heart Diseases Hepatitis C Hodgkin Disease Kidney Diseases Kidney Failure, Chronic Leukemia Leukemia, Myelogenous, Chronic, BCR-ABL Positive

Drug Warnings

Black Box Warning
carcinogenicity
Country: United States
Black Box Warning
immune system toxicity
Country: United States
Black Box Warning
teratogenicity
Country: United States
Black Box Warning
infectious disease
Country: United States
Black Box Warning
gastrointestinal toxicity
Country: United States
Black Box Warning
cardiotoxicity
Country: United States

Activity Summary

IC50 13 meas. best 9.0
EC50 6 meas. best 7.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 9.0 7.08 1.0 7
A549
CHEMBL392
 IC50 7.3 7.3 50.0 1
Vaccinia virus
CHEMBL613493
 EC50 7.0 6.85 100.0 2
Unchecked
CHEMBL612545
 EC50 6.64 6.64 230.0 1
Splenocyte
CHEMBL612422
 EC50 6.32 6.32 480.0 1
Splenocyte
CHEMBL612422
 IC50 6.3 6.15 500.0 2
Human coronavirus OC43
CHEMBL5209665
 EC50 5.8 5.8 1580.0 1
B-cell line
CHEMBL614724
 IC50 5.5 5.5 3200.0 1
Trypanosoma cruzi
CHEMBL368
 EC50 5.16 5.16 7000.0 1
Bile salt export pump
CHEMBL6020
 IC50 4.12 4.12 76000.0 1
ATP-binding cassette sub-family C member 4
CHEMBL1743128
 IC50 4.08 4.08 83000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 19797663.22 ng.hr.mL-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 1.0 nM 9.0 PubChem BioAssay. Colo320 viability from Cell TiterGlo-IC50. (Class of assay: ... -
Unchecked IC50 = 14.7 nM 7.83 PubChem BioAssay. Increased HeLa cells in S-phase-IC50. (Class of assay: confi... -
A549 IC50 = 50.0 nM 7.3 Growth inhibition of human A549 cells 28814374
Unchecked IC50 = 49.8 nM 7.3 PubChem BioAssay. GSK3B-pretreated HCT116 viability from Cell TiterGlo-IC50. (... -
Unchecked IC50 = 67.2 nM 7.17 PubChem BioAssay. HCT116 viability from Cell TiterGlo-IC50. (Class of assay: c... -
Vaccinia virus EC50 = 100.0 nM 7.0 Antiviral activity against Vaccinia virus VG9 infected in African green monkey B... 36961984
Unchecked IC50 = 164.8 nM 6.78 PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: conf... -
Vaccinia virus EC50 = 200.0 nM 6.7 Antiviral activity against Vaccinia virus infected in African green monkey BSC-1... 36961984
Unchecked EC50 = 230.0 nM 6.64 Antiviral activity against HCoV-NL63 infected in Rhesus macaque LLC-MK2 cells in... 32845145
Splenocyte EC50 = 480.0 nM 6.32 Immunosuppressive activity in BALB/c mouse splenocytes assessed as reduction in ... 36596229
Splenocyte IC50 = 500.0 nM 6.3 Immunosuppressive activity in BALB/c mouse splenocytes assessed as inhibition of... 33544615
Splenocyte IC50 = 1000.0 nM 6.0 Immunosuppressive activity in mouse splenocyte assessed as reduction in LPS-indu... 38128907
Unchecked IC50 = 1260.5 nM 5.9 PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area de... -
Human coronavirus OC43 EC50 = 1580.0 nM 5.8 Antiviral activity against wild type HCoV-OC43 infected in BHK-21 cells incubate... 32845145
Unchecked IC50 = 2597.4 nM 5.58 PubChem BioAssay. SW480 viability from Cell TiterGlo-IC50. (Class of assay: co... -
B-cell line IC50 = 3200.0 nM 5.5 Immunosuppressive activity in BALB/c mouse B cells assessed as reduction in LPS-... 32323537
Trypanosoma cruzi EC50 = 7000.0 nM 5.16 Antitrypanosomal activity against Trypanosoma cruzi amastigotes infected in BESM... 20547819
Bile salt export pump IC50 = 76000.0 nM 4.12 Inhibition of human BSEP overexpressed in Sf9 cell membrane vesicles assessed as... 23956101
ATP-binding cassette sub-family C member 4 IC50 = 83000.0 nM 4.08 Inhibition of human MRP4 overexpressed in Sf9 cell membrane vesicles assessed as... 23956101

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 405
- 10.1101/2024.03.28.586928 ADMET 100
- 10.5281/zenodo.13943903 ADMET 88
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
- 10.6019/CHEMBL3301361 No relevant target 4
37770001 10.1016/j.bmcl.2023.129490 Mus musculus 3
32845145 10.1021/acs.jmedchem.0c00626 Unchecked 3
38128907 10.1021/acs.jnatprod.3c00986 Splenocyte 3
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
20014752 10.1021/tx900326k Hepatotoxicity 3
36596229 10.1021/acs.jnatprod.2c00766 Unchecked 2
37468498 10.1038/s41467-023-40064-9 Beta-2 adrenergic receptor 2
36596229 10.1021/acs.jnatprod.2c00766 Splenocyte 2
37468498 10.1038/s41467-023-40064-9 Beta-1 adrenergic receptor 2
23956101 10.1093/toxsci/kft176 Unchecked 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
33544615 10.1021/acs.jnatprod.0c01344 Splenocyte 2

Data from ChEMBL 36 via Core Engine