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Compound Detail

CHEMBL61

PODOFILOX
💊 Approved Drug
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💊 Approved Drug
COc1cc([C@@H]2c3cc4c(cc3[C@H](O)[C@H]3COC(=O)[C@H]23)OCO4)cc(OC)c1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL61
Name PODOFILOX
Phase Approved
Structure Type MOL
InChI Key YJGVMLPVUAXIQN-XVVDYKMHSA-N
Therapeutic ✓ Yes

Known Names

Condyline Condylox NSC-24818 Podofilox Podophyllotoxin Warticon
95
Targets
547
Activities
4
Assay Types
9
PK Parameters
20
Publications
6
Known Names
3
Indications
1
Mechanisms

Molecular Properties

414.4
MW (Da)
2.41
ALogP
8
HBA
1
HBD
92.7
PSA (Ų)
0.76
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1990
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Topical

Flags

Natural Product
USAN Year 1989

Extended Properties

Molecular Formula C22H22O8
MW 414.41
Aromatic Rings 2
Heavy Atoms 30
NP-Likeness 1.51

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Unknown - - ✓ ✓

Indications

Carcinoma, Squamous Cell Condylomata Acuminata Virus Diseases

ATC Classification

D06BB04
podophyllotoxin
Level 1: DERMATOLOGICALS
Level 2: ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE

Activity Summary

IC50 515 meas. best 10.0
EC50 21 meas. best 8.54
Kd 9 meas. best 7.27
Ki 2 meas. best 6.57

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
MCF7
CHEMBL387
 IC50 10.0 6.4054 0.1 35
KB
CHEMBL398
 IC50 9.3 8.274 0.5 10
L6
CHEMBL614793
 IC50 9.0 7.8344 1.0 100
Unchecked
CHEMBL612545
 IC50 8.7 6.765 2.0 28
Caco-2
CHEMBL614058
 IC50 8.7 7.5 2.0 2
Human immunodeficiency virus 1
CHEMBL378
 EC50 8.54 8.54 2.9 1
HT-29
CHEMBL384
 IC50 8.54 6.7175 2.9 16
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 8.53 6.79 3.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.52 6.6276 3.0 38
1A9
CHEMBL614075
 IC50 8.52 8.52 3.0 1
A549
CHEMBL392
 IC50 8.27 6.4134 5.4 41
P388
CHEMBL389
 IC50 8.23 7.3011 5.9 9
K562
CHEMBL385
 IC50 8.22 7.0243 6.0 7
MG-63
CHEMBL614347
 IC50 8.15 6.445 7.0 2
SH-SY5Y
CHEMBL614910
 IC50 8.15 6.87 7.0 2
CCRF-CEM
CHEMBL382
 IC50 8.14 8.14 7.2 2
FaDu
CHEMBL612250
 IC50 8.14 8.14 7.2 1
HepG2
CHEMBL395
 IC50 8.1 6.1913 8.0 16
MDA-MB-231
CHEMBL400
 IC50 8.1 6.205 8.0 10
Unchecked
CHEMBL612545
 EC50 8.1 7.9233 8.0 3
Bel-7402
CHEMBL614279
 IC50 8.05 7.8083 9.0 6
L6
CHEMBL614793
 EC50 8.05 7.8657 9.0 7
PC-3
CHEMBL390
 IC50 8.0 7.2256 10.0 16
J774.2
CHEMBL614484
 IC50 7.95 7.91 11.3 2
Plasmodium falciparum
CHEMBL364
 EC50 7.92 7.92 12.0 1
Rattus norvegicus
CHEMBL376
 IC50 7.92 7.92 12.0 1
HeLa
CHEMBL399
 IC50 7.92 6.2754 12.0 24
Glucocorticoid receptor
CHEMBL2034
 IC50 7.85 7.85 14.0 1
HUVEC
CHEMBL613979
 IC50 7.85 7.85 14.0 1
MOLT-3
CHEMBL614176
 IC50 7.85 7.85 14.0 4
A2780
CHEMBL614004
 IC50 7.82 7.78 15.0 3
Vero
CHEMBL391
 IC50 7.8 6.988 16.0 5
J774
CHEMBL614123
 IC50 7.79 7.7267 16.4 3
A549
CHEMBL392
 EC50 7.78 7.78 16.5 1
HEK293
CHEMBL614818
 IC50 7.77 6.035 17.0 2
Raji
CHEMBL614628
 IC50 7.75 7.75 18.0 1
MIA PaCa-2
CHEMBL614725
 IC50 7.71 7.71 19.7 1
Paracentrotus lividus
CHEMBL613240
 EC50 7.7 7.1 20.0 3
ADMET
CHEMBL612558
 EC50 7.68 7.14 21.0 2
L02
CHEMBL4296457
 IC50 7.66 6.1688 22.0 8
DMS-79
CHEMBL614286
 IC50 7.64 7.64 23.0 1
NCI-H460
CHEMBL396
 IC50 7.61 7.61 24.6 1
Jurkat
CHEMBL397
 IC50 7.6 7.6 25.0 2
K562/Adr
CHEMBL4296449
 IC50 7.6 7.6 25.0 1
CV-1
CHEMBL613507
 IC50 7.54 7.54 29.0 1
RKO
CHEMBL614879
 IC50 7.54 7.54 29.0 1
LNCaP
CHEMBL612518
 IC50 7.51 7.51 31.0 1
Bel7402/5-FU
CHEMBL4483230
 IC50 7.36 7.36 44.0 1
Human alphaherpesvirus 1
CHEMBL377
 IC50 7.3 7.3 50.0 1
K562/VCR
CHEMBL4296450
 IC50 7.3 7.3 50.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 2.95 ng.hr.mL-1 Rattus norvegicus
CL 56.5 mL.min-1.kg-1 Rattus norvegicus
Cmax 8518.13 nM Rattus norvegicus
Ka 1.8 10'6/M Rattus norvegicus
MRT 0.32 hr Rattus norvegicus
T1/2 24.0 hr -
T1/2 9.8 hr Mus musculus
T1/2 0.21 hr Rattus norvegicus
Tmax 0.1 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
MCF7 IC50 = 0.1 nM 10.0 Cytotoxicity against human MCF7 cells after 48 hrs by SRB assay 25084144
MCF7 IC50 = 0.4 nM 9.4 Cytotoxicity against human MCF7 cells in presence of 10 mM DTT after 48 hrs by S... 25084144
KB IC50 = 0.5 nM 9.3 Cytotoxicity against human KB cells assessed as growth inhibition 21705220
KB IC50 = 0.7 nM 9.15 Cytotoxicity against human KB cells after 72 hrs by Alamar blue assay 24900724
L6 IC50 = 1.0 nM 9.0 Cytotoxicity against rat L6 cells after 72 hrs by Alamar blue assay 24900706
L6 IC50 = 1.7 nM 8.77 Cytotoxicity against rat L6 cells assessed as growth inhibition after 72 hrs by ... 23153330
Unchecked IC50 = 2.0 nM 8.7 Cytotoxicity against human HSF30 cells measured after 72 hrs by sulforhodamine B... 30920216
L6 IC50 = 2.0 nM 8.7 Cytotoxicity against rat L6 cells after 72 hrs by alamar blue assay 26237241
Caco-2 IC50 = 2.0 nM 8.7 Cytotoxicity against human CaCO2 cells after 24 hrs by MTT assay 18586491
HT-29 IC50 = 2.9 nM 8.54 Cytotoxicity against human HT-29 cells 7673931
Human immunodeficiency virus 1 EC50 = 2.9 nM 8.54 Antiviral activity against HIV1 in C8166 cells assessed as inhibition of syncyti... 17317161
NON-PROTEIN TARGET EC50 = 2.97 nM 8.53 Inhibition of colony formation in human T47D cells after 7 days by crystal viole... 27187855
NON-PROTEIN TARGET IC50 = 3.0 nM 8.52 Antiproliferative activity against human HepG2 assessed as reduction in cell via... 27919655
KB IC50 = 3.0 nM 8.52 Cytotoxicity against human KB cells after 48 hrs by alamar blue assay 18215443
1A9 IC50 = 3.0 nM 8.52 Cytotoxicity against human 1A9 cells 18314944
KB IC50 = 3.21 nM 8.49 Antiproliferation activity against human KB cells measured after 72 hrs incubati... 38781920
KB IC50 = 3.6 nM 8.44 Cytotoxicity against KB cell line 16343898
KB IC50 = 4.8 nM 8.32 Cytotoxicity against human KB cells by alamar blue assay 12141852
Unchecked IC50 = 4.8 nM 8.32 PubChem BioAssay. Decreased HeLa cell count-IC50. (Class of assay: confirmator... -
L6 IC50 = 5.0 nM 8.3 Cytotoxicity against rat L6 cells 25547934

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 236
14971901 10.1021/jm030978h HeLa 36
28757065 10.1016/j.bmcl.2017.07.047 MCF7 35
28301815 10.1016/j.ejmech.2017.03.011 Bel7402/5-FU 31
37395092 10.1021/acs.jnatprod.3c00384 NCI-H1975 26
27262599 10.1016/j.bmcl.2016.05.063 MCF7 26
16472241 10.2174/1570163043334794 Hepatotoxicity 18
29678463 10.1016/j.bmcl.2018.04.019 K562/VCR 17
27187855 10.1016/j.ejmech.2016.04.071 NON-PROTEIN TARGET 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
34098082 10.1016/j.bmcl.2021.128174 PC-3M 14
8277312 10.1021/np50100a011 NON-PROTEIN TARGET 11
19880222 10.1016/j.ejmech.2009.09.047 NON-PROTEIN TARGET 11
21916509 10.1021/jm200737s Jurkat 10
18396405 10.1016/j.bmc.2008.03.053 Regulatory protein E2 9
11911206 10.1248/cpb.50.399 Pieris rapae 9
27503681 10.1016/j.bmcl.2016.07.072 K562/Adr 9
30482548 10.1016/j.bmc.2018.10.045 PC-3 8
- 10.1016/0960-894X(95)00172-P Mus musculus 8
19734910 10.1038/nchembio.215 Plasmodium falciparum 7

Data from ChEMBL 36 via Core Engine