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Colchicine

  CAS No.: 64-86-8   Cat No.: BADC-00004   Purity: >98% HNMR HPLC MS 4.5  

Colchicine, a toxic plant-derived alkaloid extracted from plants of the genus Colchicum, inhibits microtubule polymerization (IC50 = 3.2 μM). It inhibits the growth of MCF-7 human breast carcinoma cells and has anti-inflammatory activity. Colchicine can lower body temperature, inhibit the respiratory center, enhance the effect of sympathomimetic drugs, constrict blood vessels, and raise blood pressure.

Colchicine

Structure of 64-86-8

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Category
ADC Cytotoxin
Molecular Formula
C22H25NO6
Molecular Weight
399.44
Target
Microtubule/Tubulin
Shipping
Tightly closed. Dry. Keep in a well-ventilated place. Light sensitive.

* For research and manufacturing use only. We do not sell to patients.

Size Price Stock Quantity
1 g $298 In stock

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Popular Publications Citing BOC Sciences Products
Synonyms
(S)-N-(5,6,7,9-Tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl)acetamide; (-)-Colchicine; Colchineos; Colchisol; Colcin; Colsaloid; Condylon; NSC 757
IUPAC Name
N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
Canonical SMILES
CC(=O)NC1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC
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
InChIKey
IAKHMKGGTNLKSZ-INIZCTEOSA-N
Density
1.32 g/cm3
Solubility
Slightly soluble in Chloroform, Methanol
Melting Point
150-160°C (dec.)
Appearance
White to Yellow Solid
Quantity
Grams-Kilos
Quality Standard
CP2010
Storage
Tightly closed. Dry. Keep in a well-ventilated place. Light sensitive.
Boiling Point
726.0±60.0°C at 760 mmHg
Form
Powder
NCT NumberTitleCondition Or DiseasePhaseStart DateSponsorStatus
NCT00000577Asthma Clinical Research Network (ACRN)AsthmaPhase 3September 1993Milton S. Hershey Medical CenterWithdrawn
NCT00004368Phase I Study of Colchicine Therapy in Childhood Hepatic CirrhosisCirrhosisPhase 1May 1990National Center for Research Resources (NCRR)Unknown status
NCT00004748Low-Dose Oral Methotrexate Versus Colchicine for Primary Biliary CirrhosisLiver Cirrhosis, BiliaryPhase 3November 1989National Center for Research Resources (NCRR)Completed
NCT00128414Study of Colchicine to Treat and Prevent Recurrent Pericarditis (First Episode)PericarditisPhase 3August 2005Azienda Sanitaria Locale 3, TorinoCompleted
NCT00128427Study of Colchicine to Prevent the Postpericardiotomy SyndromePostpericardiotomy SyndromePhase 3June 2005Azienda Sanitaria Locale 3, TorinoCompleted

Colchicine is a natural alkaloid compound primarily extracted from plants of the genus Colchicum, such as the autumn crocus. It has been used for centuries for its medicinal properties, most notably in the treatment of gout. The compound is known for its anti-inflammatory characteristics, which arise from its ability to disrupt microtubule polymerization. This disruption affects various cellular processes, including cell division, motility, and secretion, rendering colchicine a critical agent in treating inflammatory diseases. Its application in gout therapy is largely due to its capacity to prevent neutrophil-mediated inflammation, thereby alleviating the pain and swelling associated with gout attacks.

Recent advances in drug discovery have highlighted colchicine’s potential beyond gout management. Its ability to inhibit microtubule formation has made it an attractive candidate for cancer research, where it is being studied for its potential to impede the growth and proliferation of cancer cells. Colchicine’s mechanism of binding to tubulin, a key protein in microtubule assembly, allows it to interrupt the mitotic process, potentially leading to cell cycle arrest and apoptosis in rapidly dividing cancer cells. This mechanism has sparked interest in developing colchicine derivatives and analogs that might offer better efficacy and reduced toxicity for oncological applications.

In addition to its emerging applications in oncology, colchicine has been investigated for its role in cardiovascular conditions. Studies have shown promising results in using colchicine to manage pericarditis, a swelling and irritation of the pericardium, as well as to prevent post-operative atrial fibrillation, a common complication following heart surgery. The anti-inflammatory properties of colchicine play a crucial role here by modulating the inflammatory response associated with these cardiovascular issues, which could lead to a reduction in complication rates and improved patient outcomes.

Despite its promising applications, colchicine’s toxicity remains a significant challenge in its therapeutic use. The therapeutic index of colchicine is narrow, meaning the range between effective and toxic doses is small. Overdose can lead to severe consequences including multi-organ failure. Thus, drug development involving colchicine requires careful consideration of dosing regimens and delivery methods to maximize therapeutic benefits while minimizing side effects. Research is ongoing to engineer new forms of colchicine with enhanced safety profiles, which include targeted delivery systems or novel formulations that mitigate systemic exposure.

1.Colchicine Therapy in Acute Coronary Syndrome Patients acts on Caspase-1 to Suppress NLRP3 Inflammasome Monocyte Activation.
Robertson S1, Martinez GJ2, Payet CA3, Barraclough JY4, Celermajer DS4, Bursill C3, Patel S4. Clin Sci (Lond). 2016 Apr 21. pii: CS20160090. [Epub ahead of print]
Rationale<: Inflammasome activation, with subsequent release of pro-inflammatory cytokines IL-1β and IL-18, has recently been implicated in atherosclerosis-associated inflammation.
2.Colchicine aggravates coxsackievirus B3 infection in mice.
Smilde BJ1, Woudstra L2, Fong Hing G1, Wouters D3, Zeerleder S4, Murk JL5, van Ham M3, Heymans S6, Juffermans LJ7, van Rossum AC7, Niessen HW8, Krijnen PA2, Emmens RW9. Int J Cardiol. 2016 Apr 19;216:58-65. doi: 10.1016/j.ijcard.2016.04.144. [Epub ahead of print]
BACKGROUND: There is a clinical need for immunosuppressive therapy that can treat myocarditis patients in the presence of an active viral infection. In this study we therefore investigated the effects of colchicine, an immunosuppressive drug which has been used successfully as treatment for pericarditis patients, in a mouse model of coxsackievirus B3(CVB3)-induced myocarditis.
3.Pyridine Based Antitumour Compounds Acting at the Colchicine Site.
Álvarez R, Aramburu L, Puebla P, Caballero E, González M, Vicente A, Medarde M, Peláez R1. Curr Med Chem. 2016;23(11):1100-30.
Antimitotics binding at the colchicine site of tubulin are important antitumour and vascular disrupting agents. Pyridines and azines are privileged scaffolds in medicinal chemistry and in recent years many colchicine site ligands (CSL) have incorporated them into their structures with the aim of improving their pharmacokinetic and pharmacodynamics properties. CSL have been classified according to their chemical structures and the chemical structures of the pyridine and azine containing antimitotic compounds are described. The designed principles behind the structural modifications and the achieved effect on the biological activity upon inclusion of these heterocycles are also discussed. Lessons from the achievements and failures have been extracted and future perspectives delineated.

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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