COLCHICINE

Search structure
Trade Names:
Synonyms:
Status: Approved (1961)
Entry Type: Small molecule
Molecule Category: Parent
ATC: M04AC01
UNII: SML2Y3J35T

Structure
InChI Key IAKHMKGGTNLKSZ-INIZCTEOSA-N
Smile COc1cc2c(c(OC)c1OC)-c1ccc(OC)c(=O)cc1[C@@H](NC(C)=O)CC2
InChI
InChI=1S/C22H25NO6/c1-12(24)23-16-8-6-13-10-19(27-3)21(28-4)22(29-5)20(13)14-7-9-18(26-2)17(25)11-15(14)16/h7,9-11,16H,6,8H2,1-5H3,(H,23,24)/t16-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C22H25NO6
Molecular Weight 399.44
AlogP 2.87
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 5.0
Polar Surface Area 83.09
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 29.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Tubulin inhibitor
Primary Target
tubulin beta class I
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 1 Cytochrome P450 family 1A Cytochrome P450 1A2
- - - - 12.4
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C8
- - - - 20.4
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- - - - 11.1
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2D Cytochrome P450 2D6
- - - - 7.7
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- - - - 9.1
Enzyme Hydrolase
- - - - 0.1
Enzyme Kinase Protein Kinase CAMK protein kinase group CAMK protein kinase PIM family
- 4300 - - 65.08
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase JakA family
- - - - 5.7
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase JakB family
- - - - 5.7
Enzyme Transferase
- - - - 16.86-31.49
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- - - - -29.16--3.14
Structural protein
200 3-800000 58-33700 1.614-5750 21.81-100
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - -3.9-101.04
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - 120 31.9
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 298700 - - 8
Unclassified protein
750 - - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Coronary Disease 3 D003327 ClinicalTrials
Heart Failure 3 D006333 ClinicalTrials
Reperfusion Injury 3 D015427 ClinicalTrials
Non-ST Elevated Myocardial Infarction 3 D000072658 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Arrhythmias, Cardiac 3 D001145 ClinicalTrials
Vitreoretinopathy, Proliferative 3 D018630 ClinicalTrials
Multiple Myeloma 3 D009101 ClinicalTrials
Cardiovascular Diseases 3 D002318 ClinicalTrials
Postpericardiotomy Syndrome 3 D011185 ClinicalTrials
Liver Cirrhosis, Biliary 3 D008105 ClinicalTrials
Asthma 3 D001249 ClinicalTrials
Vasculitis 3 D014657 ClinicalTrials
ST Elevation Myocardial Infarction 3 D000072657 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Lung Diseases 3 D008171 ClinicalTrials
Atrial Fibrillation 3 D001281 ClinicalTrials
Myocardial Infarction 3 D009203 ClinicalTrials
Pericarditis 3 D010493 ClinicalTrials
Stomatitis, Aphthous 2 D013281 ClinicalTrials
Acute Coronary Syndrome 2 D054058 ClinicalTrials
Behcet Syndrome 2 D001528 ClinicalTrials
Vascular Diseases 2 D014652 ClinicalTrials
Diabetic Nephropathies 2 D003928 ClinicalTrials
Hepatitis C, Chronic 2 D019698 ClinicalTrials
Heart Diseases 2 D006331 ClinicalTrials
Cholangiocarcinoma 2 D018281 ClinicalTrials
Pneumonia, Viral 2 D011024 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 2 D064129 ClinicalTrials
Renal Insufficiency, Chronic 2 D051436 ClinicalTrials
Hypertension 2 D006973 ClinicalTrials
Intracranial Hemorrhages 2 D020300 ClinicalTrials
Atherosclerosis 2 D050197 ClinicalTrials
Coronavirus Infections 2 D018352 ClinicalTrials
Amyotrophic Lateral Sclerosis 2 D000690 ClinicalTrials
Osteoarthritis, Knee 2 D020370 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials
Liver Cirrhosis 1 D008103 ClinicalTrials
Peripheral Arterial Disease 1 D058729 ClinicalTrials
Urogenital Neoplasms 1 D014565 ClinicalTrials

Related Entries

MCS

Scaffolds

Mixture

Side Effects from Label

Side effects Relative Frequency (%) Labels
Gastrointestinal disorders Diarrhoea 76.9
Gastrointestinal disorders Gastrointestinal disorder 76.9
Gastrointestinal disorders Gastrointestinal disorder 25.7
Gastrointestinal disorders Diarrhoea 23.0
Gastrointestinal disorders Gastrointestinal disorder
Gastrointestinal disorders Nausea 17.3
Gastrointestinal disorders Vomiting 17.3
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Nausea
Metabolism and nutrition disorders Gout 4.05
Metabolism and nutrition disorders Malnutrition 4.05
Gastrointestinal disorders Nausea 4.05
General disorders and administration site conditions Asthenia 3.85
General disorders and administration site conditions Fatigue 3.85
Gastrointestinal disorders Abdominal discomfort
Nervous system disorders Headache
Metabolism and nutrition disorders Malnutrition
Nervous system disorders Nervous system disorder
Respiratory, thoracic and mediastinal disorders Laryngeal pain 3.0
Respiratory, thoracic and mediastinal disorders Laryngeal pain 2.7
Respiratory, thoracic and mediastinal disorders Mediastinal disorder 2.7
Nervous system disorders Headache 1.92
Respiratory, thoracic and mediastinal disorders Laryngeal pain 1.92
Respiratory, thoracic and mediastinal disorders Mediastinal disorder 1.92
Nervous system disorders Nervous system disorder 1.92
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Fatigue
Metabolism and nutrition disorders Gout
General disorders and administration site conditions Asthenia 1.35
General disorders and administration site conditions Fatigue 1.35
Nervous system disorders Headache 1.35
Nervous system disorders Nervous system disorder 1.35

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Injury, poisoning and procedural complications
17.49
General disorders and administration site conditions
16.02
Gastrointestinal disorders
12.46
Musculoskeletal and connective tissue disorders
6.56
Nervous system disorders
5.57
Vascular disorders
4.35
Skin and subcutaneous tissue disorders
4.32
Investigations
4.27
Cardiac disorders
4.18
Metabolism and nutrition disorders
3.36
Psychiatric disorders
3.25
Blood and lymphatic system disorders
3.08
Respiratory, thoracic and mediastinal disorders
2.54
Renal and urinary disorders
2.23
Pregnancy, puerperium and perinatal conditions
2.09

Cross References

Resources Reference
CAS NUMBER 64-86-8
ChEBI 27882
ChEMBL CHEMBL107
DrugBank DB01394
DrugCentral 726
EPA CompTox DTXSID5024845
FDA SRS SML2Y3J35T
Guide to Pharmacology 2367
KEGG C07592
PDB LOC
PharmGKB PA449092
PubChem 6167
SureChEMBL SCHEMBL8469
ZINC ZINC000000621853
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