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Compound Detail

CHEMBL500576

TEMOPORFIN
💊 Approved Drug
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💊 Approved Drug
Oc1cccc(-c2c3nc(c(-c4cccc(O)c4)c4ccc([nH]4)c(-c4cccc(O)c4)c4nc(c(-c5cccc(O)c5)c5ccc2[nH]5)CC4)C=C3)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL500576
Name TEMOPORFIN
Phase Approved
Structure Type MOL
InChI Key LYPFDBRUNKHDGX-LWQDQPMZSA-N
Therapeutic ✓ Yes

Known Names

EF-9 EF9 Foscan M-thpc Mthpc SML-1707 SML1707 Temoporfin Temoporfina Temoporfine
13
Targets
25
Activities
2
Assay Types
0
PK Parameters
20
Publications
10
Known Names
9
Indications
1
Mechanisms

Molecular Properties

680.8
MW (Da)
9.76
ALogP
6
HBA
6
HBD
138.3
PSA (Ų)
0.11
QED
3
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2001
Availability Unknown
Chirality Achiral

Flags

Natural Product
USAN Stem -porfin
USAN Year 1995

Extended Properties

Molecular Formula C44H32N4O4
MW 680.76
Aromatic Rings 7
Heavy Atoms 52
NP-Likeness 0.15

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Photosensitizer - - ✓ ✓

Indications

Carcinoma, Squamous Cell Carcinoma, Squamous Cell Head and Neck Neoplasms Head and Neck Neoplasms Neoplasms Bile Duct Neoplasms Nasopharyngeal Carcinoma Carcinoma Carcinoma, Non-Small-Cell Lung

ATC Classification

L01XD05
temoporfin
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 21 meas. best 8.12
EC50 4 meas. best 8.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
HCT-116
CHEMBL394
 IC50 8.12 7.8767 7.6 3
West Nile virus
CHEMBL613730
 EC50 8.0 8.0 10.0 1
dengue virus type 2
CHEMBL613966
 EC50 7.7 7.7 20.0 1
Zika virus
CHEMBL4296612
 EC50 7.66 7.66 22.0 1
Nonstructural protein 3
CHEMBL4523954
 EC50 7.66 7.66 22.0 1
HL-60
CHEMBL383
 IC50 7.38 7.38 42.0 1
4T1
CHEMBL612589
 IC50 7.3 6.2167 50.0 3
KYSE-150 cell line
CHEMBL613998
 IC50 7.12 6.435 75.0 2
ECa-109 cell line
CHEMBL614668
 IC50 6.66 6.255 220.0 2
Unchecked
CHEMBL612545
 IC50 6.2 5.8567 630.0 3
A549
CHEMBL392
 IC50 6.15 6.0733 702.0 3
MDA-MB-231
CHEMBL400
 IC50 6.06 5.27 870.0 2
Nonstructural protein 3
CHEMBL4523954
 IC50 5.96 5.96 1100.0 1
HUVEC
CHEMBL613979
 IC50 5.82 5.82 1500.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
HCT-116 IC50 = 7.6 nM 8.12 Cytotoxicity against human HCT116 cell line 16722648
HCT-116 IC50 = 7.6 nM 8.12 Phototoxicity against human HCT116 cells after 24 hrs irradiated with tungsten-h... 19211252
West Nile virus EC50 = 10.0 nM 8.0 Antiviral activity against West Nile virus infected in human A549 cells measured... 34458734
dengue virus type 2 EC50 = 20.0 nM 7.7 Antiviral activity against DENV2 infected in human A549 cells measured after 42 ... 34458734
Nonstructural protein 3 EC50 = 22.0 nM 7.66 Inhibition of Zika virus NS2B-NS3 protease by cell based assay 31980339
Zika virus EC50 = 22.0 nM 7.66 Antiviral activity against Zika virus Puerto Rico strain PRVABC59 infected in hu... 34458734
HCT-116 IC50 = 40.95 nM 7.39 Phototoxicity against human HCT116 cells assessed as nitrite accumulation after ... 19211252
HL-60 IC50 = 42.0 nM 7.38 Phototoxicity against human HL60 cells on exposure to 13.3 J/cm'2 light after 16... 18788727
4T1 IC50 = 50.0 nM 7.3 Phototoxicity against mouse 4T1 cells assessed as reduction in cell viability pr... 32916313
KYSE-150 cell line IC50 = 75.0 nM 7.12 Phototoxicity against human KYSE-150 cell line preincubated for 24 hrs followed ... 38354521
4T1 IC50 = 117.0 nM 6.93 Phototoxicity against mouse 4T1 cells on exposure to 13.3 J/cm'2 light after 16 ... 18788727
ECa-109 cell line IC50 = 220.0 nM 6.66 Phototoxicity against human Eca-109 cells assessed as inhibition of cell growth ... 38056302
Unchecked IC50 = 630.0 nM 6.2 Phototoxicity against human QBC939 cells assessed as reduction in cell viability... 31945666
A549 IC50 = 702.0 nM 6.15 Photodynamic cytotoxicity against human A549 cells assessed as reduction in cell... 31132530
A549 IC50 = 779.0 nM 6.11 Photodynamic cytotoxicity against human A549 cells assessed as reduction in cell... 31132530
MDA-MB-231 IC50 = 870.0 nM 6.06 Phototoxicity against human MDA-MB-231 cells assessed as reduction in cell viabi... 32916313
A549 IC50 = 1099.0 nM 5.96 Photodynamic cytotoxicity against human A549 cells assessed as reduction in cell... 31132530
Nonstructural protein 3 IC50 = 1100.0 nM 5.96 Inhibition of Zika virus NS2B-NS3 protease 31980339
ECa-109 cell line IC50 = 1420.0 nM 5.85 Cytotoxicity against human Eca-109 cells assessed as inhibition of cell growth i... 38056302
Unchecked IC50 = 1460.0 nM 5.84 Phototoxicity against human QBC939 cells assessed as reduction in cell viability... 31945666

Literature References

PubMed DOI Target Context # Activities
19211252 10.1016/j.bmc.2009.01.035 HCT-116 9
31945666 10.1016/j.ejmech.2020.112049 ADMET 8
31132530 10.1016/j.ejmech.2019.05.050 A549 8
31945666 10.1016/j.ejmech.2020.112049 Unchecked 7
32916313 10.1016/j.ejmech.2020.112794 Unchecked 4
38354521 10.1016/j.ejmech.2024.116228 KYSE-150 cell line 4
31980339 10.1016/j.bmcl.2020.126965 Nonstructural protein 3 3
31096157 10.1016/j.ejmech.2019.04.057 Enterococcus faecalis 3
32916313 10.1016/j.ejmech.2020.112794 4T1 2
16722648 10.1021/jm050997m HCT-116 2
32916313 10.1016/j.ejmech.2020.112794 MDA-MB-231 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
32916313 10.1016/j.ejmech.2020.112794 HUVEC 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
38056302 10.1016/j.ejmech.2023.116012 ECa-109 cell line 2
33341498 10.1016/j.bmc.2020.115926 HT-29 2
34458734 10.1039/D1MD00080B West Nile virus 2
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
38354521 10.1016/j.ejmech.2024.116228 ADMET 1
- 10.1039/C1MD00065A No relevant target 1

Data from ChEMBL 36 via Core Engine