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Compound Detail

CHEMBL3126004

FOSGEMCITABINE PALABENAMIDE
🧪 Phase III
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🧪 Phase III
C[C@H](NP(=O)(OC[C@H]1O[C@@H](n2ccc(N)nc2=O)C(F)(F)[C@@H]1O)Oc1ccccc1)C(=O)OCc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3126004
Name FOSGEMCITABINE PALABENAMIDE
Phase Phase III
Structure Type MOL
InChI Key NHTKGYOMICWFQZ-KKQYNPQSSA-N

Known Names

Acelarin BIO-1031 CPF-31 CPF31 Fosgemcitabine palabenamide Fosgemcitabine palabenamide, p(rs)- Gemictabine protide Nuc-1031 NUC-1031, (S)-
21
Targets
32
Activities
2
Assay Types
5
PK Parameters
20
Publications
9
Known Names
6
Indications

Molecular Properties

580.5
MW (Da)
2.64
ALogP
11
HBA
3
HBD
164.2
PSA (Ų)
0.23
QED
2
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer
USAN Stem -citabine; fos-
USAN Year 2022

Extended Properties

Molecular Formula C25H27F2N4O8P
MW 580.48
Aromatic Rings 3
Heavy Atoms 40
NP-Likeness 0.35

Indications

Biliary Tract Neoplasms Biliary Tract Neoplasms Ovarian Neoplasms Pancreatic Neoplasms Neoplasms Neoplasms

Activity Summary

IC50 24 meas. best 7.51
EC50 8 meas. best 9.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 9.7 9.425 0.2 2
MM1.S
CHEMBL4296471
 IC50 7.51 7.51 31.1 1
Unchecked
CHEMBL612545
 EC50 7.5 7.34 32.0 2
L1210
CHEMBL386
 IC50 7.46 7.46 35.0 1
Unchecked
CHEMBL612545
 IC50 7.3 7.3 50.0 1
MV4-11
CHEMBL613835
 IC50 7.21 7.21 61.0 1
Human alphaherpesvirus 3
CHEMBL613132
 EC50 7.13 7.09 74.0 2
CCRF-CEM
CHEMBL382
 IC50 7.0 7.0 100.0 1
SK-MES-1
CHEMBL614923
 IC50 6.96 6.96 110.0 1
RT112/84
CHEMBL6066783
 IC50 6.96 6.96 110.0 1
MIA PaCa-2
CHEMBL614725
 IC50 6.92 6.71 120.0 3
CWR22R
CHEMBL612657
 IC50 6.89 6.89 130.1 1
BXPC-3
CHEMBL614530
 IC50 6.82 6.6467 150.0 3
JeKo-1
CHEMBL4296445
 IC50 6.8 6.8 160.1 1
A2780
CHEMBL614004
 IC50 6.57 6.57 270.0 1
Huh-7
CHEMBL614039
 IC50 6.46 6.46 350.3 1
HT-29
CHEMBL384
 IC50 6.32 6.32 480.0 1
MDA-MB-231
CHEMBL400
 IC50 6.0 6.0 1000.0 1
PC-3
CHEMBL390
 IC50 5.96 5.96 1090.0 1
HepG2
CHEMBL395
 IC50 5.94 5.94 1160.0 1
COLO 205
CHEMBL614561
 IC50 5.74 5.74 1820.0 1
PANC-1
CHEMBL614139
 IC50 5.4 5.4 3960.0 1

Pharmacokinetic Data

Parameter Value Units Species
Cmax 475000.0 nM Homo sapiens
T1/2 2.317 hr Homo sapiens
T1/2 8.3 hr Homo sapiens
T1/2 8.3 hr Homo sapiens
T1/2 1.267 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NON-PROTEIN TARGET EC50 = 0.2 nM 9.7 Cytotoxicity against human RT112 cells assessed as cell viability by MTT assay i... 24471998
NON-PROTEIN TARGET EC50 = 0.7 nM 9.15 Cytotoxicity against human RT112 cells assessed as cell viability by MTT assay i... 24471998
MM1.S IC50 = 31.1 nM 7.51 Antiproliferative activity against human MM1.S cells assessed as inhibition of c... 36867101
Unchecked EC50 = 32.0 nM 7.5 Antiviral activity against Human cytomegalovirus Davis infected in human HEL cel... 33479570
L1210 IC50 = 35.0 nM 7.46 Cytostatic activity against mouse L1210 cells after 48 hrs by coulter counter an... 24471998
Unchecked IC50 = 50.0 nM 7.3 Cytotoxicity against human T24/83 cells assessed as inhibition of cell viability... 38547648
MV4-11 IC50 = 61.0 nM 7.21 Antiproliferative activity against human MV4-11 cells assessed as inhibition of ... 36867101
Unchecked EC50 = 66.0 nM 7.18 Antiviral activity against Human cytomegalovirus AD169 infected in human HEL cel... 33479570
Human alphaherpesvirus 3 EC50 = 74.0 nM 7.13 Antiviral activity against thymidine kinase positive Varicella zoster virus OKA ... 33479570
Human alphaherpesvirus 3 EC50 = 89.0 nM 7.05 Antiviral activity against thymidine kinase deficient Varicella zoster virus 07-... 33479570
CCRF-CEM IC50 = 100.0 nM 7.0 Cytostatic activity against human CEM cells after 72 hrs by coulter counter anal... 24471998
RT112/84 IC50 = 110.0 nM 6.96 Cytotoxicity against human RT112/84 cells assessed as inhibition of cell viabili... 38547648
SK-MES-1 IC50 = 110.0 nM 6.96 Cytotoxicity against human SK-MES-1 cells assessed as inhibition of cell viabili... 38547648
MIA PaCa-2 IC50 = 120.0 nM 6.92 Cytotoxicity against human MIA PaCa-2 cells assessed as inhibition of cell viabi... 38547648
CWR22R IC50 = 130.1 nM 6.89 Antiproliferative activity against human 22Rv1 cells assessed as inhibition of c... 36867101
MIA PaCa-2 IC50 = 142.2 nM 6.85 Antiproliferative activity against human MIA PaCa-2 cells assessed as inhibition... 36867101
BXPC-3 IC50 = 150.0 nM 6.82 Cytostatic activity against human BxPC3 cells after 72 hrs by MTS assay 24471998
JeKo-1 IC50 = 160.1 nM 6.8 Antiproliferative activity against human JeKo-1 cells assessed as inhibition of ... 36867101
BXPC-3 IC50 = 230.1 nM 6.64 Antiproliferative activity against human BXPC-3 cells assessed as inhibition of ... 36867101
A2780 IC50 = 270.0 nM 6.57 Cytotoxicity against human A2780 cells assessed as inhibition of cell viability ... 38547648

Literature References

PubMed DOI Target Context # Activities
24471998 10.1021/jm401853a ADMET 7
24471998 10.1021/jm401853a NON-PROTEIN TARGET 7
34085825 10.1021/acs.jmedchem.0c02194 ADMET 5
34085825 10.1021/acs.jmedchem.0c02194 KG-1a 5
36867101 10.1021/acs.jmedchem.3c00006 BXPC-3 5
38547648 10.1016/j.bmc.2024.117696 Unchecked 4
33479570 10.1021/acsmedchemlett.0c00485 Unchecked 4
27559756 10.1021/acs.jmedchem.6b00523 NON-PROTEIN TARGET 4
24471998 10.1021/jm401853a Serum 4
36867101 10.1021/acs.jmedchem.3c00006 CWR22R 3
28792763 10.1021/acs.jmedchem.7b00734 Homo sapiens 3
36867101 10.1021/acs.jmedchem.3c00006 ADMET 3
38547648 10.1016/j.bmc.2024.117696 PANC-1 2
24471998 10.1021/jm401853a Mus musculus 2
38547648 10.1016/j.bmc.2024.117696 MIA PaCa-2 2
33479570 10.1021/acsmedchemlett.0c00485 Vero 2
33479570 10.1021/acsmedchemlett.0c00485 SARS-CoV-2 2
24471998 10.1021/jm401853a BXPC-3 2
33479570 10.1021/acsmedchemlett.0c00485 HEL 2
38547648 10.1016/j.bmc.2024.117696 MOLT-4 2

Data from ChEMBL 36 via Core Engine