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Compound Detail

CHEMBL107

COLCHICINE
💊 Approved Drug
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💊 Approved Drug
COc1cc2c(c(OC)c1OC)-c1ccc(OC)c(=O)cc1[C@@H](NC(C)=O)CC2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL107
Name COLCHICINE
Phase Approved
Structure Type MOL
InChI Key IAKHMKGGTNLKSZ-INIZCTEOSA-N
Therapeutic ✓ Yes

Known Names

(-)-colchicine Colchcine Colchicine Colchicine component of col-probenecid Colchicine component of colbenemid Colchicine component of mitigare Colchicine component of proben-c Colchicinum Colchineos Colchisol Colcrys Gloperba +3 more
168
Targets
1,300
Activities
4
Assay Types
23
PK Parameters
20
Publications
15
Known Names
20
Indications
1
Mechanisms

Molecular Properties

399.4
MW (Da)
2.87
ALogP
6
HBA
1
HBD
83.1
PSA (Ų)
0.83
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1961
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product

Extended Properties

Molecular Formula C22H25NO6
MW 399.44
Aromatic Rings 2
Heavy Atoms 29
NP-Likeness 0.75

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Tubulin inhibitor INHIBITOR Tubulin ✓ ✓

Indications

Familial Mediterranean Fever Gout Arrhythmias, Cardiac Asthma Atrial Fibrillation Cardiovascular Diseases Coronary Disease Heart Failure Liver Cirrhosis, Biliary Lung Diseases Multiple Myeloma Myocardial Infarction Non-ST Elevated Myocardial Infarction Pericarditis Postpericardiotomy Syndrome Reperfusion Injury Severe Acute Respiratory Syndrome Severe Acute Respiratory Syndrome ST Elevation Myocardial Infarction Vasculitis

ATC Classification

M04AC01
colchicine
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: ANTIGOUT PREPARATIONS

Activity Summary

IC50 1,218 meas. best 10.01
EC50 61 meas. best 8.55
Kd 13 meas. best 7.24
Ki 8 meas. best 8.79

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
MCF-10A
CHEMBL614321
 IC50 10.01 9.115 0.1 2
PANC-1
CHEMBL614139
 IC50 10.0 8.2333 0.1 3
T47D
CHEMBL614361
 IC50 9.55 9.55 0.3 1
HaCaT
CHEMBL614392
 IC50 9.52 8.218 0.3 5
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 9.44 7.2301 0.4 100
P388
CHEMBL389
 IC50 9.21 7.908 0.6 5
K562
CHEMBL385
 IC50 9.0 7.3736 1.0 25
MCF7
CHEMBL387
 IC50 9.0 7.1975 1.0 80
HT-1080
CHEMBL614580
 IC50 8.96 8.05 1.1 5
HeLa
CHEMBL399
 IC50 8.89 7.262 1.3 65
MIA PaCa-2
CHEMBL614725
 IC50 8.89 7.776 1.3 5
COLO357
CHEMBL614778
 IC50 8.89 8.095 1.3 4
MV4-11
CHEMBL613835
 IC50 8.8 8.8 1.6 1
Tubulin
CHEMBL2111354
 Ki 8.79 7.015 1.6 2
Unchecked
CHEMBL612545
 IC50 8.77 6.0984 1.7 116
MDA-MB-231
CHEMBL400
 IC50 8.74 7.1125 1.8 32
NCI-H1437
CHEMBL1075513
 IC50 8.7 8.7 2.0 1
MGC-803
CHEMBL3706566
 IC50 8.7 6.8831 2.0 13
HepG2
CHEMBL395
 IC50 8.7 6.8331 2.0 35
MDA-MB-468
CHEMBL614335
 IC50 8.68 7.996 2.1 5
SK-OV-3
CHEMBL614925
 IC50 8.68 7.549 2.1 20
Ramos
CHEMBL614629
 IC50 8.67 8.67 2.1 1
SW-620
CHEMBL612262
 IC50 8.62 8.2567 2.4 3
THP-1
CHEMBL614245
 IC50 8.6 8.6 2.5 1
NIH3T3
CHEMBL614822
 IC50 8.59 7.38 2.6 3
HCT-116
CHEMBL394
 IC50 8.56 7.3845 2.8 42
A-431
CHEMBL614069
 EC50 8.55 8.55 2.8 1
HGC-27
CHEMBL1075463
 IC50 8.52 8.52 3.0 1
Tubulin
CHEMBL2095182
 IC50 8.52 5.7478 3.0 45
B16-F10
CHEMBL612656
 IC50 8.52 6.9891 3.0 11
DU-145
CHEMBL613508
 IC50 8.52 7.6847 3.0 15
COLO 205
CHEMBL614561
 IC50 8.52 7.8975 3.0 4
NCI-H23
CHEMBL614997
 IC50 8.51 8.2 3.1 2
CHL-1
CHEMBL1075422
 IC50 8.44 8.44 3.6 1
HMEC-1
CHEMBL4296433
 IC50 8.42 8.42 3.8 2
BT-474
CHEMBL614529
 IC50 8.42 6.66 3.8 2
NCI-H1299
CHEMBL612255
 IC50 8.4 8.4 4.0 1
ADMET
CHEMBL612558
 IC50 8.4 7.5375 4.0 4
NCI-H358
CHEMBL614135
 IC50 8.4 8.05 4.0 2
SNU-398
CHEMBL614454
 EC50 8.4 8.4 4.0 1
RL
CHEMBL2366175
 IC50 8.36 8.36 4.4 1
MOLM-13
CHEMBL3706572
 IC50 8.33 8.33 4.7 1
SK-BR-3
CHEMBL613834
 IC50 8.3 7.9633 5.0 3
HEK293
CHEMBL614818
 IC50 8.3 7.815 5.0 12
U-937
CHEMBL612794
 IC50 8.28 8.19 5.2 2
NCI-N87
CHEMBL614197
 IC50 8.27 8.27 5.4 1
KB
CHEMBL398
 IC50 8.25 7.813 5.6 20
MDA-MB-453
CHEMBL614334
 IC50 8.24 8.24 5.8 1
ZR-75-1
CHEMBL614393
 EC50 8.22 8.22 6.0 1
LoVo
CHEMBL614721
 IC50 8.22 7.3464 6.0 11

Pharmacokinetic Data

Parameter Value Units Species
CL 2.1 mL.min-1.kg-1 Homo sapiens
CL 4.0 L/hr Homo sapiens
CL 0.384 mL.min-1.g-1 Homo sapiens
F 45.0 % Homo sapiens
F 45.0 % Homo sapiens
Fu 0.61 - -
Fu 0.057 - -
Fu 0.61 - Homo sapiens
Fu 0.61 - Homo sapiens
Ka - - -
Ka 100000000.0 M-1 -
Ka 1.16 10'7/M Bos taurus
Ka 6.7 10^5/M Homo sapiens
MRT 49.0 hr Homo sapiens
T1/2 58.0 hr Homo sapiens
T1/2 35.0 hr Bos taurus
T1/2 14.0 hr Homo sapiens
T1/2 1.0 hr Homo sapiens
T1/2 24.0 hr Bos taurus
t1/2 - - Homo sapiens
T1/2 91.08 hr Homo sapiens
T1/2 1.0 hr Homo sapiens
Vd 7.0 L.kg-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
MCF-10A IC50 = 0.098 nM 10.01 Cytotoxicity against human MCF-10A cells assessed as inhibition of cell prolifer... 37584263
PANC-1 IC50 = 0.1 nM 10.0 Antiproliferative activity against human PANC-1 cells assessed as reduction in c... 32827941
T47D IC50 = 0.28 nM 9.55 Antiproliferative activity against ERalpha positive human T47D cells assessed as... 37584263
HaCaT IC50 = 0.3 nM 9.52 Cytotoxicity against human HaCat cells assessed as reduction in cell growth incu... 32827941
NON-PROTEIN TARGET IC50 = 0.36 nM 9.44 Cytotoxicity against human NCI/ADR cells 25811651
P388 IC50 = 0.62 nM 9.21 The compound was evaluated in vitro for the inhibition of murine leukemia P388D1... -
K562 IC50 = 1.0 nM 9.0 Cytotoxicity against human K562 cells assessed as growth inhibition after 72 hrs... 25091926
MCF7 IC50 = 1.0 nM 9.0 Antiproliferative activity against ERalpha positive human MCF7 cells assessed as... 37584263
HT-1080 IC50 = 1.1 nM 8.96 Antiproliferative activity against human HT1080 cells after 48 hrs by sulforhoda... 21604746
HT-1080 IC50 = 1.1 nM 8.96 Antiproliferative activity against human HT1080 after 48 hrs by SRB assay 21920638
COLO357 IC50 = 1.3 nM 8.89 Cytotoxic activity in human Colo-357 cells assessed as reduction in cell viabili... 29028531
MIA PaCa-2 IC50 = 1.3 nM 8.89 Cytotoxic activity in human MIAPaCa2 cells assessed as reduction in cell viabili... 29028531
COLO357 IC50 = 1.3 nM 8.89 Antiproliferative activity against human COLO357 cells assessed as reduction in ... 32827941
HeLa IC50 = 1.3 nM 8.89 Antiproliferative activity against human HeLa cells assessed as reduction in cel... 32827941
MV4-11 IC50 = 1.58 nM 8.8 Antiproliferative activity against human MV4-11 cells incubated for 72 hrs by MT... 34648295
Tubulin Ki = 1.614 nM 8.79 Binding affinity to pig brain tubulin 23176628
Unchecked IC50 = 1.71 nM 8.77 PubChem BioAssay. Increased HeLa cells with 4N DNA content-IC50. (Class of ass... -
Unchecked IC50 = 1.7 nM 8.77 PubChem BioAssay. Increased HeLa cells with 2N DNA content-IC50. (Class of ass... -
Unchecked IC50 = 1.7 nM 8.77 Displacement of [3H]colchicine from tubulin by scintillation proximity assay 18783207
Unchecked IC50 = 1.73 nM 8.76 PubChem BioAssay. Increased chromatin condensation in HeLa cells-IC50. (Class ... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1505
- 10.6019/CHEMBL3885881 Rattus norvegicus 126
- 10.5281/zenodo.13943903 ADMET 89
30099258 10.1016/j.ejmech.2018.07.043 A-375 26
31653441 10.1016/j.bmc.2019.115144 Unchecked 25
17181164 10.1021/jm0605031 Molecular identity unknown 22
32035399 10.1016/j.ejmech.2020.112105 HT-29 22
17973361 10.1021/jm0708984 Molecular identity unknown 22
19220018 10.1021/jm801338r Molecular identity unknown 22
21051535 10.1124/dmd.110.034629 ADMET 21
37182330 10.1016/j.ejmech.2023.115402 SGC-7901 21
29472126 10.1016/j.bmc.2018.02.013 Rattus norvegicus 17
27912174 10.1016/j.ejmech.2016.11.020 COLO357 13
7241524 10.1021/jm00137a031 Mus musculus 13
12699389 10.1021/jm021012t ATP-dependent translocase ABCB1 13
31653441 10.1016/j.bmc.2019.115144 MCF7 13
27608432 10.1016/j.ejmech.2016.08.041 MDA-MB-231 12
38972078 10.1016/j.ejmech.2024.116649 SK-OV-3 11
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
8133298 10.1021/np50102a009 NON-PROTEIN TARGET 11

Data from ChEMBL 36 via Core Engine