Identification

Name
Colchicine
Accession Number
DB01394
Type
Small Molecule
Groups
Approved
Description

A major alkaloid from Colchicum autumnale L. and found also in other Colchicum species. Its primary therapeutic use is in the treatment of gout, but it has been used also in the therapy of familial Mediterranean fever (periodic disease). [PubChem]

Structure
Thumb
Synonyms
  • Colchicin
  • Colchicina
  • Colchicinum
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ColchicineCapsule.6 mg/1OralWest Ward Pharmaceutical2014-10-01Not applicableUs
ColchicineTablet0.6 mgOralSandoz Canada Incorporated1974-12-31Not applicableCanada
ColchicineTablet, film coated.6 mg/1OralPrasco, Laboratories2015-01-12Not applicableUs66993 0165 02 nlmimage10 8e404752
ColchicineTablet1 mgOralEuro Pharm International Canada Inc1950-12-312012-06-14Canada
ColchicineTablet, film coated.6 mg/1OralAmerincan Health Packaging2017-07-15Not applicableUs
Colchicine Tab 0.6mgTablet0.6 mgOralOdan Laboratories Ltd1982-12-31Not applicableCanada
Colchicine Tab 0.6mgTablet0.6 mgOralD.C. Labs Limited1969-12-312003-07-11Canada
Colchicine Tab 0.6mgTablet0.6 mgOralAbbott1951-12-312007-07-31Canada
Colchicine Tab 1mgTablet1 mgOralOdan Laboratories Ltd1985-12-312013-03-06Canada
ColcrysTablet, film coated.6 mg/1OralAphena Pharma Solutions Tennessee, Inc.2009-09-01Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ColchicineTablet.6 mg/1OralAmneal Pharmaceuticals of New York Llc2016-09-30Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Probenecid and ColchicineColchicine (.5 mg/1) + Probenecid (500 mg/1)TabletOralAv Kare, Inc.2012-05-082016-02-05Us
Probenecid and ColchicineColchicine (.5 mg/1) + Probenecid (500 mg/1)TabletOralIngenus Pharmaceuticals Nj, Llc2008-05-13Not applicableUs
Probenecid and ColchicineColchicine (.5 mg/1) + Probenecid (500 mg/1)TabletOralWatson Pharmaceuticals1982-10-01Not applicableUs00591 5325 01 nlmimage10 240e1210
Probenecid and ColchicineColchicine (.5 mg/1) + Probenecid (500 mg/1)TabletOralRising Pharmaceuticals2008-05-13Not applicableUs
Verban OntColchicine (100 mg) + Podophyllin (2 g)OintmentTopicalWelcker Lyster Ltd., Division Of Technilab Inc.1963-12-311999-09-17Canada
Categories
UNII
SML2Y3J35T
CAS number
64-86-8
Weight
Average: 399.437
Monoisotopic: 399.168187537
Chemical Formula
C22H25NO6
InChI Key
IAKHMKGGTNLKSZ-UHFFFAOYSA-N
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)
IUPAC Name
N-{3,4,5,14-tetramethoxy-13-oxotricyclo[9.5.0.0²,⁷]hexadeca-1(16),2(7),3,5,11,14-hexaen-10-yl}acetamide
SMILES
COC1=CC2=C(C(OC)=C1OC)C1=CC=C(OC)C(=O)C=C1C(CC2)NC(C)=O

Pharmacology

Indication

For treatment and relief of pain in attacks of acute gouty arthritis.

Structured Indications
Pharmacodynamics

Colchicine is a highly poisonous alkaloid, originally extracted from plants of the genus Colchicum (Autumn crocus, also known as the "Meadow saffron"). Originally used to treat rheumatic complaints and especially gout, it was also prescribed for its cathartic and emetic effects. Its present medicinal use is mainly in the treatment of gout; as well, it is being investigated for its potential use as an anti-cancer drug. It can also be used as initial treatment for pericarditis and preventing recurrences of the condition.

Mechanism of action

The precise mechanism of action has not been completely established. In patients with gout, colchicine apparently interrupts the cycle of monosodium urate crystal deposition in joint tissues and the resultant inflammatory response that initiates and sustains an acute attack. Colchicine decreases leukocyte chemotaxis and phagocytosis and inhibits the formation and release of a chemotactic glycoprotein that is produced during phagocytosis of urate crystals. Colchicine also inhibits urate crystal deposition, which is enhanced by a low pH in the tissues, probably by inhibiting oxidation of glucose and subsequent lactic acid production in leukocytes. Colchicine has no analgesic or antihyperuricemic activity. Colchicine inhibits microtubule assembly in various cells, including leukocytes, probably by binding to and interfering with polymerization of the microtubule subunit tubulin. Although some studies have found that this action probably does not contribute significantly to colchicine's antigout action, a recent in vitro study has shown that it may be at least partially involved.

TargetActionsOrganism
ATubulin beta-1 chain
inhibitor
Human
ATubulin beta chain
inhibitor
Human
Absorption

Colchicine is rapidly absorbed after oral administration, probably from the jejunum and ileum. However, the rate and extent of absorption are variable, depending on the tablet dissolution rate; variability in gastric emptying, intestinal motility, and pH at the absorption site; and the extent to which colchicine is bound to microtubules in gastrointestinal mucosal cells.

Volume of distribution
  • 5 to 8 L/kg [healthy young volunteers]
Protein binding

Low to moderate (30 to 50%).

Metabolism

Probably hepatic. Although colchicine metabolites have not been identified in humans, metabolism by mammalian hepatic microsomes has been demonstrated in vitro.

Route of elimination

In healthy volunteers (n=12) 40 – 65% of 1 mg orally administered colchicine was recovered unchanged in urine. Enterohepatic recirculation and biliary excretion are also postulated to play a role in colchicine elimination.

Half life

Elimination half-life is approximately 1 hour in healthy subjects, although a study with an extended sampling time reported mean terminal elimination half-life values of approximately 9 to 10.5 hours. Other studies have reported half-life values of approximately 2 hours in patients with alcoholic cirrhosis and approximately 2.5 hours in patients with familial Mediterranean fever.

Clearance
  • 0.17 L/hr/kg [familial Mediterranean fever patients with end-stage renal disease]
  • 0.73 L/hr/kg [familial Mediterranean fever patients with normal renal function]
Toxicity

The onset of toxic effects is usually delayed for several hours or more after the ingestion of an acute overdose. Nausea, vomiting, abdominal pain, and diarrhea occur first. The diarrhea may be bloody due to hemorrhagic gastroenteritis. Burning sensations of the throat, stomach, and skin may be prominent symptoms. Extensive vascular damage may result in shock. Kidney damage, evidenced by hematuria and oliguria, may occur. Muscular weakness may be marked, and ascending paralysis of the central nervous system may develop; the patient usually remains conscious. Delirium and convulsions may occur. Death due to respiratory arrest may result. Although death from the ingestion of as little as 7 mg has been reported, much larger doses have been survived .

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AbemaciclibThe serum concentration of Colchicine can be increased when it is combined with Abemaciclib.Approved
AcetaminophenThe serum concentration of Colchicine can be increased when it is combined with Acetaminophen.Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Colchicine.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Colchicine.Experimental
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Colchicine.Approved
AlbendazoleThe serum concentration of Colchicine can be increased when it is combined with Albendazole.Approved, Vet Approved
AlectinibThe serum concentration of Colchicine can be increased when it is combined with Alectinib.Approved
AlfentanilThe serum concentration of Colchicine can be increased when it is combined with Alfentanil.Approved, Illicit
Aluminium clofibrateAluminium clofibrate may increase the myopathic rhabdomyolysis activities of Colchicine.Experimental
AmantadineThe serum concentration of Colchicine can be increased when it is combined with Amantadine.Approved
Aminohippuric acidThe serum concentration of Colchicine can be increased when it is combined with Aminohippuric acid.Approved, Investigational
AmiodaroneThe serum concentration of Colchicine can be increased when it is combined with Amiodarone.Approved, Investigational
AmitriptylineThe serum concentration of Colchicine can be increased when it is combined with Amitriptyline.Approved
AmlodipineThe serum concentration of Colchicine can be increased when it is combined with Amlodipine.Approved
AmodiaquineThe serum concentration of Amodiaquine can be increased when it is combined with Colchicine.Approved, Investigational
AmprenavirThe serum concentration of Colchicine can be increased when it is combined with Amprenavir.Approved
AmsacrineThe serum concentration of Colchicine can be increased when it is combined with Amsacrine.Approved
AprepitantThe serum concentration of Colchicine can be increased when it is combined with Aprepitant.Approved, Investigational
AripiprazoleThe serum concentration of Aripiprazole can be decreased when it is combined with Colchicine.Approved, Investigational
AstemizoleThe serum concentration of Colchicine can be increased when it is combined with Astemizole.Approved, Withdrawn
AtazanavirThe serum concentration of Colchicine can be increased when it is combined with Atazanavir.Approved, Investigational
AtenololThe serum concentration of Colchicine can be increased when it is combined with Atenolol.Approved
AtomoxetineThe serum concentration of Colchicine can be increased when it is combined with Atomoxetine.Approved
AtorvastatinColchicine may increase the myopathic rhabdomyolysis activities of Atorvastatin.Approved
AzelastineThe serum concentration of Colchicine can be increased when it is combined with Azelastine.Approved
AzithromycinThe serum concentration of Colchicine can be increased when it is combined with Azithromycin.Approved
BenzocaineThe serum concentration of Colchicine can be increased when it is combined with Benzocaine.Approved
BepridilThe serum concentration of Colchicine can be increased when it is combined with Bepridil.Approved, Withdrawn
BevacizumabBevacizumab may increase the cardiotoxic activities of Colchicine.Approved, Investigational
BezafibrateBezafibrate may increase the myopathic rhabdomyolysis activities of Colchicine.Approved
BiperidenThe serum concentration of Colchicine can be increased when it is combined with Biperiden.Approved, Investigational
BoceprevirThe serum concentration of Colchicine can be increased when it is combined with Boceprevir.Approved, Withdrawn
BortezomibThe serum concentration of Colchicine can be increased when it is combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Colchicine can be decreased when it is combined with Bosentan.Approved, Investigational
BosutinibThe serum concentration of Colchicine can be increased when it is combined with Bosutinib.Approved
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Colchicine.Approved
BromocriptineThe serum concentration of Colchicine can be increased when it is combined with Bromocriptine.Approved, Investigational
BuprenorphineThe serum concentration of Colchicine can be increased when it is combined with Buprenorphine.Approved, Illicit, Investigational, Vet Approved
BuspironeThe serum concentration of Colchicine can be increased when it is combined with Buspirone.Approved, Investigational
CabazitaxelThe serum concentration of Colchicine can be increased when it is combined with Cabazitaxel.Approved
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Colchicine.Approved
CaffeineThe serum concentration of Colchicine can be increased when it is combined with Caffeine.Approved
CanagliflozinThe serum concentration of Colchicine can be increased when it is combined with Canagliflozin.Approved
CandesartanThe serum concentration of Colchicine can be increased when it is combined with Candesartan.Experimental
Candesartan cilexetilThe serum concentration of Colchicine can be increased when it is combined with Candesartan cilexetil.Approved
CaptoprilThe serum concentration of Colchicine can be increased when it is combined with Captopril.Approved
CarbamazepineThe serum concentration of Colchicine can be increased when it is combined with Carbamazepine.Approved, Investigational
CarvedilolThe serum concentration of Colchicine can be increased when it is combined with Carvedilol.Approved, Investigational
CaspofunginThe serum concentration of Colchicine can be increased when it is combined with Caspofungin.Approved
CeritinibThe serum concentration of Colchicine can be increased when it is combined with Ceritinib.Approved
CerivastatinColchicine may increase the myopathic rhabdomyolysis activities of Cerivastatin.Withdrawn
ChloroquineThe serum concentration of Colchicine can be increased when it is combined with Chloroquine.Approved, Vet Approved
ChlorpromazineThe serum concentration of Colchicine can be increased when it is combined with Chlorpromazine.Approved, Vet Approved
ChlorpropamideThe serum concentration of Colchicine can be increased when it is combined with Chlorpropamide.Approved
ChlorprothixeneThe serum concentration of Colchicine can be increased when it is combined with Chlorprothixene.Approved, Investigational, Withdrawn
CholesterolThe serum concentration of Colchicine can be increased when it is combined with Cholesterol.Experimental, Investigational
Choline C 11The therapeutic efficacy of Choline C 11 can be decreased when used in combination with Colchicine.Approved, Investigational
CilazaprilThe serum concentration of Colchicine can be increased when it is combined with Cilazapril.Approved
CimetidineThe serum concentration of Colchicine can be increased when it is combined with Cimetidine.Approved
CiprofibrateCiprofibrate may increase the myopathic rhabdomyolysis activities of Colchicine.Approved, Investigational
CiprofloxacinThe serum concentration of Colchicine can be increased when it is combined with Ciprofloxacin.Approved, Investigational
CitalopramThe serum concentration of Colchicine can be increased when it is combined with Citalopram.Approved
ClarithromycinThe serum concentration of Colchicine can be increased when it is combined with Clarithromycin.Approved
ClemastineThe serum concentration of Colchicine can be increased when it is combined with Clemastine.Approved
ClofazimineThe serum concentration of Colchicine can be increased when it is combined with Clofazimine.Approved, Investigational
ClofibrateClofibrate may increase the myopathic rhabdomyolysis activities of Colchicine.Approved, Investigational
ClofibrideClofibride may increase the myopathic rhabdomyolysis activities of Colchicine.Experimental
ClomipramineThe serum concentration of Colchicine can be increased when it is combined with Clomipramine.Approved, Vet Approved
ClotrimazoleThe serum concentration of Colchicine can be increased when it is combined with Clotrimazole.Approved, Vet Approved
CobicistatThe serum concentration of Colchicine can be increased when it is combined with Cobicistat.Approved
ColforsinThe serum concentration of Colchicine can be increased when it is combined with Colforsin.Experimental, Investigational
ConivaptanThe serum concentration of Colchicine can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe serum concentration of Colchicine can be increased when it is combined with Crizotinib.Approved
CyanocobalaminThe serum concentration of Cyanocobalamin can be decreased when it is combined with Colchicine.Approved, Nutraceutical
CyclophosphamideThe serum concentration of Colchicine can be increased when it is combined with Cyclophosphamide.Approved, Investigational
CyclosporineThe serum concentration of Colchicine can be increased when it is combined with Cyclosporine.Approved, Investigational, Vet Approved
CymarinCymarin may decrease the cardiotoxic activities of Colchicine.Experimental
Dabigatran etexilateThe serum concentration of the active metabolites of Dabigatran etexilate can be increased when Dabigatran etexilate is used in combination with Colchicine.Approved
DabrafenibThe serum concentration of Colchicine can be decreased when it is combined with Dabrafenib.Approved
DaclatasvirThe serum concentration of Colchicine can be increased when it is combined with Daclatasvir.Approved
DactinomycinThe serum concentration of Colchicine can be increased when it is combined with Dactinomycin.Approved
DarunavirThe serum concentration of Colchicine can be increased when it is combined with Darunavir.Approved
DasatinibThe serum concentration of Colchicine can be increased when it is combined with Dasatinib.Approved, Investigational
DaunorubicinThe serum concentration of Colchicine can be increased when it is combined with Daunorubicin.Approved
DeferasiroxThe serum concentration of Colchicine can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe serum concentration of Colchicine can be increased when it is combined with Delavirdine.Approved
DesipramineThe serum concentration of Colchicine can be increased when it is combined with Desipramine.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Colchicine.Approved
DesloratadineThe serum concentration of Colchicine can be increased when it is combined with Desloratadine.Approved, Investigational
DexamethasoneThe serum concentration of Colchicine can be increased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DextromethorphanThe serum concentration of Colchicine can be increased when it is combined with Dextromethorphan.Approved
DiclofenacThe serum concentration of Colchicine can be increased when it is combined with Diclofenac.Approved, Vet Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Colchicine.Approved, Investigational
DigoxinThe serum concentration of Colchicine can be increased when it is combined with Digoxin.Approved
Digoxin Immune Fab (Ovine)Digoxin Immune Fab (Ovine) may decrease the cardiotoxic activities of Colchicine.Approved
DihydroergocornineThe risk or severity of adverse effects can be increased when Dihydroergocornine is combined with Colchicine.Approved
DihydroergocristineThe risk or severity of adverse effects can be increased when Dihydroergocristine is combined with Colchicine.Experimental
DihydroergocryptineThe risk or severity of adverse effects can be increased when Dihydroergocryptine is combined with Colchicine.Experimental
DihydroergotamineThe serum concentration of Colchicine can be increased when it is combined with Dihydroergotamine.Approved
DiltiazemThe serum concentration of Colchicine can be increased when it is combined with Diltiazem.Approved
DipyridamoleThe serum concentration of Colchicine can be increased when it is combined with Dipyridamole.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Colchicine.Approved, Investigational
DoxazosinThe serum concentration of Colchicine can be increased when it is combined with Doxazosin.Approved
DoxepinThe serum concentration of Colchicine can be increased when it is combined with Doxepin.Approved
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Colchicine.Approved, Investigational
DoxycyclineThe serum concentration of Colchicine can be increased when it is combined with Doxycycline.Approved, Investigational, Vet Approved
DronabinolThe serum concentration of Colchicine can be increased when it is combined with Dronabinol.Approved, Illicit
DronedaroneThe serum concentration of Colchicine can be increased when it is combined with Dronedarone.Approved
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Colchicine.Approved
EnalaprilThe serum concentration of Colchicine can be increased when it is combined with Enalapril.Approved, Vet Approved
EnasidenibThe serum concentration of Colchicine can be increased when it is combined with Enasidenib.Approved
EnzalutamideThe serum concentration of Colchicine can be decreased when it is combined with Enzalutamide.Approved
ErgonovineThe serum concentration of Colchicine can be increased when it is combined with Ergonovine.Approved
ErgotamineThe serum concentration of Colchicine can be increased when it is combined with Ergotamine.Approved
ErythromycinThe serum concentration of Colchicine can be increased when it is combined with Erythromycin.Approved, Vet Approved
EstramustineThe serum concentration of Colchicine can be increased when it is combined with Estramustine.Approved
EtofibrateEtofibrate may increase the myopathic rhabdomyolysis activities of Colchicine.Approved
EtoposideThe serum concentration of Colchicine can be increased when it is combined with Etoposide.Approved
EtravirineThe serum concentration of Colchicine can be increased when it is combined with Etravirine.Approved
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Colchicine.Approved
FelodipineThe serum concentration of Colchicine can be increased when it is combined with Felodipine.Approved, Investigational
FenofibrateFenofibrate may increase the myopathic rhabdomyolysis activities of Colchicine.Approved
Fenofibric acidFenofibric acid may increase the myopathic rhabdomyolysis activities of Colchicine.Approved
FentanylThe serum concentration of Colchicine can be increased when it is combined with Fentanyl.Approved, Illicit, Investigational, Vet Approved
FexofenadineThe serum concentration of Colchicine can be increased when it is combined with Fexofenadine.Approved
FidaxomicinThe serum concentration of Colchicine can be increased when it is combined with Fidaxomicin.Approved
FluconazoleThe serum concentration of Colchicine can be increased when it is combined with Fluconazole.Approved
FluoxetineThe serum concentration of Colchicine can be increased when it is combined with Fluoxetine.Approved, Vet Approved
FlupentixolThe serum concentration of Colchicine can be increased when it is combined with Flupentixol.Approved, Withdrawn
FluphenazineThe serum concentration of Colchicine can be increased when it is combined with Fluphenazine.Approved
FlurazepamThe serum concentration of Colchicine can be increased when it is combined with Flurazepam.Approved, Illicit
FluvastatinColchicine may increase the myopathic rhabdomyolysis activities of Fluvastatin.Approved
FluvoxamineThe serum concentration of Colchicine can be increased when it is combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe serum concentration of Colchicine can be increased when it is combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Colchicine can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Colchicine can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Colchicine can be increased when it is combined with Fusidic Acid.Approved
GefitinibThe serum concentration of Colchicine can be increased when it is combined with Gefitinib.Approved, Investigational
GemfibrozilGemfibrozil may increase the myopathic rhabdomyolysis activities of Colchicine.Approved
GenisteinThe serum concentration of Colchicine can be increased when it is combined with Genistein.Investigational
GitoformateGitoformate may decrease the cardiotoxic activities of Colchicine.Experimental
GlecaprevirThe serum concentration of Colchicine can be increased when it is combined with Glecaprevir.Approved
GlyburideThe serum concentration of Colchicine can be increased when it is combined with Glyburide.Approved
GlycerinThe serum concentration of Colchicine can be increased when it is combined with Glycerin.Approved, Investigational
Gramicidin DThe serum concentration of Colchicine can be increased when it is combined with Gramicidin D.Approved
GrepafloxacinThe serum concentration of Colchicine can be increased when it is combined with Grepafloxacin.Investigational, Withdrawn
HaloperidolThe serum concentration of Colchicine can be increased when it is combined with Haloperidol.Approved
HydrocortisoneThe serum concentration of Colchicine can be increased when it is combined with Hydrocortisone.Approved, Vet Approved
IdelalisibThe serum concentration of Colchicine can be increased when it is combined with Idelalisib.Approved
ImatinibThe serum concentration of Colchicine can be increased when it is combined with Imatinib.Approved
ImipramineThe serum concentration of Colchicine can be increased when it is combined with Imipramine.Approved
IndinavirThe serum concentration of Colchicine can be increased when it is combined with Indinavir.Approved
IndomethacinThe serum concentration of Colchicine can be increased when it is combined with Indomethacin.Approved, Investigational
IsavuconazoniumThe serum concentration of Colchicine can be increased when it is combined with Isavuconazonium.Approved, Investigational
IsradipineThe serum concentration of Colchicine can be increased when it is combined with Isradipine.Approved
ItraconazoleThe serum concentration of Colchicine can be increased when it is combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Colchicine can be increased when it is combined with Ivacaftor.Approved
IvermectinThe serum concentration of Colchicine can be increased when it is combined with Ivermectin.Approved, Vet Approved
KetamineThe serum concentration of Colchicine can be increased when it is combined with Ketamine.Approved, Vet Approved
KetoconazoleThe serum concentration of Colchicine can be increased when it is combined with Ketoconazole.Approved, Investigational
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Colchicine.Experimental
LansoprazoleThe serum concentration of Colchicine can be increased when it is combined with Lansoprazole.Approved, Investigational
LapatinibThe serum concentration of Colchicine can be increased when it is combined with Lapatinib.Approved, Investigational
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Colchicine.Approved
LetermovirThe serum concentration of Colchicine can be increased when it is combined with Letermovir.Approved
LevofloxacinThe serum concentration of Colchicine can be increased when it is combined with Levofloxacin.Approved, Investigational
LidocaineThe serum concentration of Colchicine can be increased when it is combined with Lidocaine.Approved, Vet Approved
LisurideThe risk or severity of adverse effects can be increased when Lisuride is combined with Colchicine.Approved, Investigational
LomitapideThe serum concentration of Colchicine can be increased when it is combined with Lomitapide.Approved
LoperamideThe serum concentration of Colchicine can be increased when it is combined with Loperamide.Approved
LopinavirThe serum concentration of Colchicine can be increased when it is combined with Lopinavir.Approved
LoratadineThe serum concentration of Colchicine can be increased when it is combined with Loratadine.Approved
LosartanThe serum concentration of Colchicine can be increased when it is combined with Losartan.Approved
LovastatinThe serum concentration of Colchicine can be increased when it is combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Colchicine can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Colchicine can be increased when it is combined with Lumacaftor.Approved
Lysergic Acid DiethylamideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Colchicine.Illicit, Investigational, Withdrawn
MaprotilineThe serum concentration of Colchicine can be increased when it is combined with Maprotiline.Approved
MebendazoleThe serum concentration of Colchicine can be increased when it is combined with Mebendazole.Approved, Vet Approved
MefloquineThe serum concentration of Colchicine can be increased when it is combined with Mefloquine.Approved
Megestrol acetateThe serum concentration of Colchicine can be increased when it is combined with Megestrol acetate.Approved, Vet Approved
MeprobamateThe serum concentration of Colchicine can be increased when it is combined with Meprobamate.Approved, Illicit
MetergolineThe risk or severity of adverse effects can be increased when Metergoline is combined with Colchicine.Experimental
MethadoneThe serum concentration of Colchicine can be increased when it is combined with Methadone.Approved
MethylergometrineThe risk or severity of adverse effects can be increased when Methylergometrine is combined with Colchicine.Approved
MethysergideThe risk or severity of adverse effects can be increased when Methysergide is combined with Colchicine.Approved
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Colchicine.Experimental
MetoprololThe serum concentration of Colchicine can be increased when it is combined with Metoprolol.Approved, Investigational
MevastatinColchicine may increase the myopathic rhabdomyolysis activities of Mevastatin.Experimental
MibefradilThe serum concentration of Colchicine can be increased when it is combined with Mibefradil.Investigational, Withdrawn
MiconazoleThe serum concentration of Colchicine can be increased when it is combined with Miconazole.Approved, Investigational, Vet Approved
MidazolamThe serum concentration of Colchicine can be increased when it is combined with Midazolam.Approved, Illicit
MifepristoneThe serum concentration of Colchicine can be increased when it is combined with Mifepristone.Approved, Investigational
MitomycinThe serum concentration of Colchicine can be increased when it is combined with Mitomycin.Approved
MitotaneThe serum concentration of Colchicine can be decreased when it is combined with Mitotane.Approved
MitoxantroneThe serum concentration of Colchicine can be increased when it is combined with Mitoxantrone.Approved, Investigational
MorphineThe serum concentration of Colchicine can be increased when it is combined with Morphine.Approved, Investigational
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Colchicine.Approved
NaltrexoneThe serum concentration of Colchicine can be increased when it is combined with Naltrexone.Approved, Investigational, Vet Approved
NaringeninThe serum concentration of Colchicine can be increased when it is combined with Naringenin.Experimental
NefazodoneThe serum concentration of Colchicine can be increased when it is combined with Nefazodone.Approved, Withdrawn
NelfinavirThe serum concentration of Colchicine can be increased when it is combined with Nelfinavir.Approved
NeostigmineThe serum concentration of Colchicine can be increased when it is combined with Neostigmine.Approved, Vet Approved
NetupitantThe serum concentration of Colchicine can be increased when it is combined with Netupitant.Approved
NevirapineThe serum concentration of Colchicine can be increased when it is combined with Nevirapine.Approved
NicardipineThe serum concentration of Colchicine can be increased when it is combined with Nicardipine.Approved
NicergolineThe risk or severity of adverse effects can be increased when Nicergoline is combined with Colchicine.Approved, Investigational
NifedipineThe serum concentration of Colchicine can be increased when it is combined with Nifedipine.Approved
NilotinibThe serum concentration of Colchicine can be increased when it is combined with Nilotinib.Approved, Investigational
NintedanibThe serum concentration of Nintedanib can be increased when it is combined with Colchicine.Approved
NisoldipineThe serum concentration of Colchicine can be increased when it is combined with Nisoldipine.Approved
NitrazepamThe serum concentration of Colchicine can be increased when it is combined with Nitrazepam.Approved
NitrendipineThe serum concentration of Colchicine can be increased when it is combined with Nitrendipine.Approved, Investigational
OlaparibThe serum concentration of Colchicine can be increased when it is combined with Olaparib.Approved
OleandrinOleandrin may decrease the cardiotoxic activities of Colchicine.Experimental, Investigational
OmeprazoleThe serum concentration of Colchicine can be increased when it is combined with Omeprazole.Approved, Investigational, Vet Approved
OsimertinibThe serum concentration of Colchicine can be increased when it is combined with Osimertinib.Approved
OuabainOuabain may decrease the cardiotoxic activities of Colchicine.Approved
P-NitrophenolThe serum concentration of Colchicine can be increased when it is combined with P-Nitrophenol.Experimental
PaclitaxelThe serum concentration of Colchicine can be increased when it is combined with Paclitaxel.Approved, Vet Approved
PalbociclibThe serum concentration of Colchicine can be increased when it is combined with Palbociclib.Approved
Palmitic AcidThe serum concentration of Colchicine can be increased when it is combined with Palmitic Acid.Approved, Experimental
PantoprazoleThe serum concentration of Colchicine can be increased when it is combined with Pantoprazole.Approved
ParoxetineThe serum concentration of Colchicine can be increased when it is combined with Paroxetine.Approved, Investigational
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Colchicine.Approved
PentobarbitalThe metabolism of Colchicine can be increased when combined with Pentobarbital.Approved, Vet Approved
PergolideThe risk or severity of adverse effects can be increased when Pergolide is combined with Colchicine.Approved, Investigational, Vet Approved, Withdrawn
PerindoprilThe serum concentration of Colchicine can be increased when it is combined with Perindopril.Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Colchicine.Experimental
PhenobarbitalThe metabolism of Colchicine can be increased when combined with Phenobarbital.Approved
PhenytoinThe metabolism of Colchicine can be increased when combined with Phenytoin.Approved, Vet Approved
PibrentasvirThe serum concentration of Colchicine can be increased when it is combined with Pibrentasvir.Approved
PimozideThe serum concentration of Colchicine can be increased when it is combined with Pimozide.Approved
PitavastatinColchicine may increase the myopathic rhabdomyolysis activities of Pitavastatin.Approved
PonatinibThe serum concentration of Colchicine can be increased when it is combined with Ponatinib.Approved
PosaconazoleThe serum concentration of Colchicine can be increased when it is combined with Posaconazole.Approved, Investigational, Vet Approved
PravastatinColchicine may increase the myopathic rhabdomyolysis activities of Pravastatin.Approved
PrazosinThe serum concentration of Colchicine can be increased when it is combined with Prazosin.Approved
PrednisoneThe serum concentration of Colchicine can be increased when it is combined with Prednisone.Approved, Vet Approved
PrimidoneThe metabolism of Colchicine can be increased when combined with Primidone.Approved, Vet Approved
ProbenecidThe serum concentration of Colchicine can be increased when it is combined with Probenecid.Approved
ProgesteroneThe serum concentration of Colchicine can be increased when it is combined with Progesterone.Approved, Vet Approved
PromethazineThe serum concentration of Colchicine can be increased when it is combined with Promethazine.Approved
PropafenoneThe serum concentration of Colchicine can be increased when it is combined with Propafenone.Approved
PropranololThe serum concentration of Colchicine can be increased when it is combined with Propranolol.Approved, Investigational
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Colchicine.Experimental
ProtriptylineThe serum concentration of Colchicine can be increased when it is combined with Protriptyline.Approved
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Colchicine.Approved
QuercetinThe serum concentration of Colchicine can be increased when it is combined with Quercetin.Experimental, Investigational
QuinacrineThe serum concentration of Colchicine can be increased when it is combined with Quinacrine.Approved, Investigational
QuinidineThe serum concentration of Colchicine can be increased when it is combined with Quinidine.Approved
QuinineThe serum concentration of Colchicine can be increased when it is combined with Quinine.Approved
RanitidineThe serum concentration of Colchicine can be increased when it is combined with Ranitidine.Approved
RanolazineThe serum concentration of Colchicine can be increased when it is combined with Ranolazine.Approved, Investigational
ReboxetineThe serum concentration of Colchicine can be increased when it is combined with Reboxetine.Approved, Investigational
RegorafenibThe serum concentration of Colchicine can be increased when it is combined with Regorafenib.Approved
ReserpineThe serum concentration of Colchicine can be increased when it is combined with Reserpine.Approved, Investigational
RibociclibThe serum concentration of Colchicine can be increased when it is combined with Ribociclib.Approved
RifabutinThe metabolism of Colchicine can be increased when combined with Rifabutin.Approved
RifampicinThe serum concentration of Colchicine can be increased when it is combined with Rifampicin.Approved
RifapentineThe metabolism of Colchicine can be increased when combined with Rifapentine.Approved
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Colchicine.Approved, Investigational
RilpivirineThe serum concentration of Colchicine can be increased when it is combined with Rilpivirine.Approved
RitonavirThe serum concentration of Colchicine can be increased when it is combined with Ritonavir.Approved, Investigational
RolapitantThe serum concentration of Colchicine can be increased when it is combined with Rolapitant.Approved
RonifibrateRonifibrate may increase the myopathic rhabdomyolysis activities of Colchicine.Experimental
RosuvastatinColchicine may increase the myopathic rhabdomyolysis activities of Rosuvastatin.Approved
SaquinavirThe serum concentration of Colchicine can be increased when it is combined with Saquinavir.Approved, Investigational
SaxagliptinThe serum concentration of Saxagliptin can be decreased when it is combined with Colchicine.Approved
ScopolamineThe serum concentration of Colchicine can be increased when it is combined with Scopolamine.Approved
SelegilineThe serum concentration of Colchicine can be increased when it is combined with Selegiline.Approved, Investigational, Vet Approved
SertralineThe serum concentration of Colchicine can be increased when it is combined with Sertraline.Approved
SildenafilThe serum concentration of Colchicine can be increased when it is combined with Sildenafil.Approved, Investigational
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Colchicine.Approved
SiltuximabThe serum concentration of Colchicine can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Colchicine can be increased when it is combined with Simeprevir.Approved
SimfibrateSimfibrate may increase the myopathic rhabdomyolysis activities of Colchicine.Experimental
SimvastatinColchicine may increase the myopathic rhabdomyolysis activities of Simvastatin.Approved
SirolimusThe serum concentration of Colchicine can be increased when it is combined with Sirolimus.Approved, Investigational
SorafenibThe serum concentration of Colchicine can be increased when it is combined with Sorafenib.Approved, Investigational
SpironolactoneThe serum concentration of Colchicine can be increased when it is combined with Spironolactone.Approved
St. John's WortThe serum concentration of Colchicine can be decreased when it is combined with St. John's Wort.Investigational, Nutraceutical
StaurosporineThe serum concentration of Colchicine can be increased when it is combined with Staurosporine.Experimental
StiripentolThe serum concentration of Colchicine can be increased when it is combined with Stiripentol.Approved
SulfinpyrazoneThe serum concentration of Colchicine can be increased when it is combined with Sulfinpyrazone.Approved
SulfisoxazoleThe serum concentration of Colchicine can be increased when it is combined with Sulfisoxazole.Approved, Vet Approved
SumatriptanThe serum concentration of Colchicine can be increased when it is combined with Sumatriptan.Approved, Investigational
SunitinibThe serum concentration of Colchicine can be increased when it is combined with Sunitinib.Approved, Investigational
TacrineThe serum concentration of Colchicine can be increased when it is combined with Tacrine.Investigational, Withdrawn
TacrolimusThe serum concentration of Colchicine can be increased when it is combined with Tacrolimus.Approved, Investigational
TamoxifenThe serum concentration of Colchicine can be increased when it is combined with Tamoxifen.Approved
Taurocholic AcidThe serum concentration of Colchicine can be increased when it is combined with Taurocholic Acid.Experimental
TelaprevirThe serum concentration of Colchicine can be increased when it is combined with Telaprevir.Approved, Withdrawn
TelithromycinThe serum concentration of Colchicine can be increased when it is combined with Telithromycin.Approved
TelmisartanThe serum concentration of Colchicine can be increased when it is combined with Telmisartan.Approved, Investigational
TemsirolimusThe serum concentration of Colchicine can be increased when it is combined with Temsirolimus.Approved
TerazosinThe serum concentration of Colchicine can be increased when it is combined with Terazosin.Approved
TerfenadineThe serum concentration of Colchicine can be increased when it is combined with Terfenadine.Withdrawn
TergurideThe risk or severity of adverse effects can be increased when Terguride is combined with Colchicine.Experimental
TestosteroneThe serum concentration of Colchicine can be increased when it is combined with Testosterone.Approved, Investigational
TicagrelorThe serum concentration of Colchicine can be increased when it is combined with Ticagrelor.Approved
TiclopidineThe serum concentration of Colchicine can be increased when it is combined with Ticlopidine.Approved
TipranavirThe serum concentration of Colchicine can be increased when it is combined with Tipranavir.Approved, Investigational
TocilizumabThe serum concentration of Colchicine can be decreased when it is combined with Tocilizumab.Approved
TolvaptanThe serum concentration of Colchicine can be increased when it is combined with Tolvaptan.Approved
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Colchicine.Approved, Investigational
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Colchicine.Approved, Investigational
TrifluoperazineThe serum concentration of Colchicine can be increased when it is combined with Trifluoperazine.Approved
TriflupromazineThe serum concentration of Colchicine can be increased when it is combined with Triflupromazine.Approved, Vet Approved
TrimethoprimThe serum concentration of Colchicine can be increased when it is combined with Trimethoprim.Approved, Vet Approved
TrimipramineThe serum concentration of Colchicine can be increased when it is combined with Trimipramine.Approved
TroleandomycinThe serum concentration of Colchicine can be increased when it is combined with Troleandomycin.Approved
UbidecarenoneColchicine may increase the myopathic rhabdomyolysis activities of Ubidecarenone.Approved, Investigational, Nutraceutical
VelpatasvirThe serum concentration of Colchicine can be increased when it is combined with Velpatasvir.Approved
VenlafaxineThe serum concentration of Colchicine can be increased when it is combined with Venlafaxine.Approved
VerapamilThe serum concentration of Colchicine can be increased when it is combined with Verapamil.Approved
VinblastineThe serum concentration of Colchicine can be increased when it is combined with Vinblastine.Approved
VincristineThe serum concentration of Vincristine can be increased when it is combined with Colchicine.Approved, Investigational
VinorelbineThe serum concentration of Colchicine can be increased when it is combined with Vinorelbine.Approved, Investigational
VoriconazoleThe serum concentration of Colchicine can be increased when it is combined with Voriconazole.Approved, Investigational
VoxilaprevirThe serum concentration of Colchicine can be increased when it is combined with Voxilaprevir.Approved
ZimelidineThe serum concentration of Colchicine can be increased when it is combined with Zimelidine.Withdrawn
ZiprasidoneThe serum concentration of Colchicine can be increased when it is combined with Ziprasidone.Approved
Food Interactions
  • Avoid alcohol since it increases uric acid levels.
  • Drink liberally.
  • Take without regard to meals.

References

Synthesis Reference

Christian Wehrey, "Colchicine derivatives, process for preparing them, products obtained therefrom and use thereof." U.S. Patent US20040138182, issued July 15, 2004.

US20040138182
General References
Not Available
External Links
Human Metabolome Database
HMDB15466
KEGG Drug
D00570
KEGG Compound
C07592
PubChem Compound
2833
PubChem Substance
46505639
ChemSpider
2731
ChEBI
23359
ChEMBL
CHEMBL87
Therapeutic Targets Database
DAP001254
PharmGKB
PA449092
IUPHAR
2367
Guide to Pharmacology
GtP Drug Page
HET
LOC
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Colchicine
ATC Codes
M04AC01 — Colchicine
AHFS Codes
  • 92:16.00 — Antigout Agents
MSDS
Download (74.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedBasic ScienceGout Acute / Hypertriglyceridemias / Pericarditis1
1CompletedBasic ScienceFamilial Mediterranean Fever (FMF )1
1CompletedBasic ScienceHealthy Volunteers6
1CompletedBasic ScienceHealthy Volunteers / Pharmacokinetics1
1CompletedBasic ScienceHealthy; Adult; Volunteer; Colchicine; Pharmacokinetics; Diltiazem; Cytochrome p450 3A4; P-glycoprotein1
1CompletedBasic SciencePharmacokinetics11
1CompletedTreatmentRenal Replacement Therapies1
1RecruitingTreatmentGout Acute1
1Unknown StatusTreatmentLiver Cirrhosis1
1, 2RecruitingTreatmentBMI >30 kg/m2 / Metabolic Diseases1
1, 2RecruitingTreatmentDiabetic Nephropathies1
2CompletedPreventionGout Acute1
2CompletedSupportive CareAtherosclerotic Vascular Diseases1
2CompletedTreatmentBehcet's Syndrome1
2CompletedTreatmentGout Acute3
2CompletedTreatmentGout Acute / Hyperuricemia3
2CompletedTreatmentGout Acute / Moderate Renal Impairment1
2Not Yet RecruitingTreatmentMyocardial Infarction (MI)1
2RecruitingOtherCoronary Artery Disease1
2RecruitingOtherCoronary Artery Disease / Human Immunodeficiency Virus (HIV)1
2RecruitingTreatmentCutaneous Polyarteritis Nodosa / Henoch-Schönlein Purpura / IgA Vasculitis / Primary Cutaneous Vasculitis1
2RecruitingTreatmentHepatocellular,Carcinoma / Invasion / Metastasis1
2RecruitingTreatmentNonvalvular Atrial Fibrillation1
2TerminatedTreatmentChronic Hepatitis C Virus (HCV) Infection1
2Unknown StatusTreatmentDiabetic Nephropathies1
2Unknown StatusTreatmentStomatitis, Aphthous1
2WithdrawnTreatmentProstate Cancer1
2, 3CompletedTreatmentAcute Coronary Syndromes (ACS)1
2, 3CompletedTreatmentKnee Osteoarthritis (Knee OA)1
3CompletedPreventionArrythmias1
3CompletedPreventionNonvalvular Atrial Fibrillation / Thoracic Surgery1
3CompletedPreventionPostpericardiotomy Syndrome1
3CompletedTreatmentGout Acute2
3CompletedTreatmentLiver Cirrhosis, Biliary1
3CompletedTreatmentPericarditis1
3CompletedTreatmentPericarditis / Recurrences1
3Not Yet RecruitingPreventionAtrial Flutter / Nonvalvular Atrial Fibrillation / Thoracic Surgery1
3Not Yet RecruitingPreventionIschemic Attack, Transient / Strokes1
3Not Yet RecruitingTreatmentChondrocalcinosis pyrophosphate1
3Not Yet RecruitingTreatmentST Elevation Myocardial Infarction1
3RecruitingPreventionColchicine Adverse Reaction / Nonvalvular Atrial Fibrillation / Surgery, Cardiac1
3RecruitingPreventionCoronary Artery Disease / Myocardial Infarction (MI)1
3RecruitingPreventionNonvalvular Atrial Fibrillation / Strokes1
3Unknown StatusPreventionNonvalvular Atrial Fibrillation / Pericardial Effusion / Pleural Effusions / Post-pericardiotomy Syndrome / Surgery, Cardiac1
3Unknown StatusTreatmentConstriction / Nonvalvular Atrial Fibrillation / Post-pericardiotomy Syndrome1
3Unknown StatusTreatmentRhegmatogenous Retinal Detachments1
3WithdrawnTreatmentAsthma Bronchial / Chronic Lung Diseases1
4Active Not RecruitingTreatmentGout Acute1
4CompletedBasic ScienceChronic Kidney Disease (CKD)1
4CompletedBasic ScienceHealthy Volunteers1
4CompletedBasic SciencePharmacokinetics1
4CompletedDiagnosticGout Acute1
4CompletedTreatmentElective Coronary Artery Bypass Graft Surgery1
4CompletedTreatmentFamilial Mediterranean Fever (FMF )1
4CompletedTreatmentGout Acute1
4CompletedTreatmentHealthy Volunteers1
4CompletedTreatmentIntercritical Gout1
4CompletedTreatmentPericarditis / Recurrences1
4CompletedTreatmentPrimary Gout1
4RecruitingTreatmentAcute Coronary Syndromes (ACS) / Coronary Artery Disease1
4RecruitingTreatmentAcute Myocardial Infarction (AMI)1
4RecruitingTreatmentCoronary Artery Disease1
4RecruitingTreatmentManipulation Under Anesthesia1
4RecruitingTreatmentMyocardial Infarction (MI)1
4RecruitingTreatmentPericardial Effusion1
4Unknown StatusTreatmentAcute Coronary Syndromes (ACS)1
4Unknown StatusTreatmentAcute Myocardial Infarction (AMI)1
Not AvailableActive Not RecruitingTreatmentDiabetic Nephropathies1
Not AvailableUnknown StatusTreatmentCalcific Tendonitis1
Not AvailableWithdrawnTreatmentNon ST Segment Elevation Myocardial Infarction (NSTEMI)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
TabletOral.6 mg/1
TabletOral1 mg
TabletOral0.6 mg
Tablet, film coatedOral.6 mg/1
TabletOral1.0 mg
CapsuleOral.6 mg/1
TabletOral
OintmentTopical
Prices
Unit descriptionCostUnit
Colchicine powder306.6USD g
Colcrys 0.6 mg tablet5.82USD tablet
Colchicine 0.6 mg tablet0.58USD tablet
Colchicine 1 mg Tablet0.55USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US7601758No2009-02-102029-02-10Us
US7619004No2008-12-032028-12-03Us
US7820681No2009-02-172029-02-17Us
US7906519No2009-02-172029-02-17Us
US7915269No2009-02-172029-02-17Us
US7935731No2008-12-032028-12-03Us
US7964647No2008-10-062028-10-06Us
US7964648No2008-10-062028-10-06Us
US7981938No2008-10-062028-10-06Us
US8093296No2008-10-062028-10-06Us
US8093297No2008-10-062028-10-06Us
US8093298No2008-10-062028-10-06Us
US8097655No2008-10-062028-10-06Us
US8415395No2008-10-062028-10-06Us
US8415396No2008-10-062028-10-06Us
US8440721No2009-02-172029-02-17Us
US8440722No2009-02-172029-02-17Us
US8927607No2013-08-222033-08-22Us
US9399036No2013-08-222033-08-22Us
US9675613No2013-08-222033-08-22Us
US9555029No2013-08-222033-08-22Us
US9789108No2013-08-222033-08-22Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)156 °CPhysProp
water solubility4.5E+004 mg/L (at 25 °C)SEIDELL,A (1941)
logP1.30HANSCH,C ET AL. (1995)
pKa1.85SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.0276 mg/mLALOGPS
logP1.59ALOGPS
logP1.46ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)15.06ChemAxon
pKa (Strongest Basic)-0.038ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area83.09 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity111.38 m3·mol-1ChemAxon
Polarizability42.41 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9856
Blood Brain Barrier+0.7865
Caco-2 permeable+0.5119
P-glycoprotein substrateNon-substrate0.594
P-glycoprotein inhibitor INon-inhibitor0.8007
P-glycoprotein inhibitor IINon-inhibitor0.6956
Renal organic cation transporterNon-inhibitor0.8997
CYP450 2C9 substrateNon-substrate0.8042
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.7359
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7959
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9208
BiodegradationReady biodegradable0.6489
Rat acute toxicity2.3748 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9877
hERG inhibition (predictor II)Non-inhibitor0.7394
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (2.96 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0000900000-c73c5a28a750cece607a
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0049400000-2a76bd81d41e1bc5925c
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0gba-0091000000-fb24bc910ffe7bd74811

Taxonomy

Description
This compound belongs to the class of organic compounds known as tropones. These are compounds containing a tropone ring, which is a cycloheptatrienone ring bearing a ketone group.
Kingdom
Organic compounds
Super Class
Hydrocarbon derivatives
Class
Tropones
Sub Class
Not Available
Direct Parent
Tropones
Alternative Parents
Anisoles / Alkyl aryl ethers / Cyclic ketones / Propargyl-type 1,3-dipolar organic compounds / Carboximidic acids / Organopnictogen compounds / Organonitrogen compounds / Organic oxides
Substituents
Anisole / Tropone / Alkyl aryl ether / Benzenoid / Cyclic ketone / Carboximidic acid / Carboximidic acid derivative / Ether / Organic 1,3-dipolar compound / Propargyl-type 1,3-dipolar organic compound
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
aromatic ether, alkaloid, acetamides, carbotricyclic compound (CHEBI:23359) / an alkaloid (CPD-9785)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Structural constituent of cytoskeleton
Specific Function
Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha chain (By similarity).
Gene Name
TUBB1
Uniprot ID
Q9H4B7
Uniprot Name
Tubulin beta-1 chain
Molecular Weight
50326.56 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Acharya BR, Choudhury D, Das A, Chakrabarti G: Vitamin K3 disrupts the microtubule networks by binding to tubulin: a novel mechanism of its antiproliferative activity. Biochemistry. 2009 Jul 28;48(29):6963-74. doi: 10.1021/bi900152k. [PubMed:19527023]
  4. Li CM, Lu Y, Ahn S, Narayanan R, Miller DD, Dalton JT: Competitive mass spectrometry binding assay for characterization of three binding sites of tubulin. J Mass Spectrom. 2010 Oct;45(10):1160-6. doi: 10.1002/jms.1804. [PubMed:20814887]
  5. Finkelstein Y, Aks SE, Hutson JR, Juurlink DN, Nguyen P, Dubnov-Raz G, Pollak U, Koren G, Bentur Y: Colchicine poisoning: the dark side of an ancient drug. Clin Toxicol (Phila). 2010 Jun;48(5):407-14. doi: 10.3109/15563650.2010.495348. [PubMed:20586571]
  6. Cerquaglia C, Diaco M, Nucera G, La Regina M, Montalto M, Manna R: Pharmacological and clinical basis of treatment of Familial Mediterranean Fever (FMF) with colchicine or analogues: an update. Curr Drug Targets Inflamm Allergy. 2005 Feb;4(1):117-24. [PubMed:15720245]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Ubiquitin protein ligase binding
Specific Function
Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha chain.
Gene Name
TUBB
Uniprot ID
P07437
Uniprot Name
Tubulin beta chain
Molecular Weight
49670.515 Da
References
  1. Yee KW, Hagey A, Verstovsek S, Cortes J, Garcia-Manero G, O'Brien SM, Faderl S, Thomas D, Wierda W, Kornblau S, Ferrajoli A, Albitar M, McKeegan E, Grimm DR, Mueller T, Holley-Shanks RR, Sahelijo L, Gordon GB, Kantarjian HM, Giles FJ: Phase 1 study of ABT-751, a novel microtubule inhibitor, in patients with refractory hematologic malignancies. Clin Cancer Res. 2005 Sep 15;11(18):6615-24. [PubMed:16166440]
  2. Acharya BR, Choudhury D, Das A, Chakrabarti G: Vitamin K3 disrupts the microtubule networks by binding to tubulin: a novel mechanism of its antiproliferative activity. Biochemistry. 2009 Jul 28;48(29):6963-74. doi: 10.1021/bi900152k. [PubMed:19527023]
  3. Li CM, Lu Y, Ahn S, Narayanan R, Miller DD, Dalton JT: Competitive mass spectrometry binding assay for characterization of three binding sites of tubulin. J Mass Spectrom. 2010 Oct;45(10):1160-6. doi: 10.1002/jms.1804. [PubMed:20814887]
  4. Cerquaglia C, Diaco M, Nucera G, La Regina M, Montalto M, Manna R: Pharmacological and clinical basis of treatment of Familial Mediterranean Fever (FMF) with colchicine or analogues: an update. Curr Drug Targets Inflamm Allergy. 2005 Feb;4(1):117-24. [PubMed:15720245]

Enzymes

Details
1. Cytochrome P450 3A4
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent phospholipid efflux translocator that acts as a positive regulator of biliary lipid secretion. Functions as a floppase that translocates specifically phosphatidylcholine (PC) from ...
Gene Name
ABCB4
Uniprot ID
P21439
Uniprot Name
Phosphatidylcholine translocator ABCB4
Molecular Weight
141521.845 Da
References
  1. Vollrath V, Wielandt AM, Acuna C, Duarte I, Andrade L, Chianale J: Effect of colchicine and heat shock on multidrug resistance gene and P-glycoprotein expression in rat liver. J Hepatol. 1994 Nov;21(5):754-63. [PubMed:7890890]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Toxin transporter activity
Specific Function
Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain.
Gene Name
SLC22A3
Uniprot ID
O75751
Uniprot Name
Solute carrier family 22 member 3
Molecular Weight
61279.485 Da
References
  1. Grundemann D, Schechinger B, Rappold GA, Schomig E: Molecular identification of the corticosterone-sensitive extraneuronal catecholamine transporter. Nat Neurosci. 1998 Sep;1(5):349-51. [PubMed:10196521]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. [PubMed:11602674]
  2. Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. [PubMed:12699389]
  3. Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [PubMed:14985103]
  4. Troutman MD, Thakker DR: Novel experimental parameters to quantify the modulation of absorptive and secretory transport of compounds by P-glycoprotein in cell culture models of intestinal epithelium. Pharm Res. 2003 Aug;20(8):1210-24. [PubMed:12948019]
  5. Ambudkar SV, Lelong IH, Zhang J, Cardarelli CO, Gottesman MM, Pastan I: Partial purification and reconstitution of the human multidrug-resistance pump: characterization of the drug-stimulatable ATP hydrolysis. Proc Natl Acad Sci U S A. 1992 Sep 15;89(18):8472-6. [PubMed:1356264]
  6. Bebawy M, Morris MB, Roufogalis BD: A continuous fluorescence assay for the study of P-glycoprotein-mediated drug efflux using inside-out membrane vesicles. Anal Biochem. 1999 Mar 15;268(2):270-7. [PubMed:10075817]
  7. Kuo CC, Hsieh HP, Pan WY, Chen CP, Liou JP, Lee SJ, Chang YL, Chen LT, Chen CT, Chang JY: BPR0L075, a novel synthetic indole compound with antimitotic activity in human cancer cells, exerts effective antitumoral activity in vivo. Cancer Res. 2004 Jul 1;64(13):4621-8. [PubMed:15231674]
  8. Tiwari AK, Sodani K, Wang SR, Kuang YH, Ashby CR Jr, Chen X, Chen ZS: Nilotinib (AMN107, Tasigna) reverses multidrug resistance by inhibiting the activity of the ABCB1/Pgp and ABCG2/BCRP/MXR transporters. Biochem Pharmacol. 2009 Jul 15;78(2):153-61. doi: 10.1016/j.bcp.2009.04.002. Epub 2009 Apr 11. [PubMed:19427995]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Transporter activity
Specific Function
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Stride BD, Grant CE, Loe DW, Hipfner DR, Cole SP, Deeley RG: Pharmacological characterization of the murine and human orthologs of multidrug-resistance protein in transfected human embryonic kidney cells. Mol Pharmacol. 1997 Sep;52(3):344-53. [PubMed:9281595]

Drug created on July 08, 2007 11:02 / Updated on December 10, 2017 17:18