Colchicine
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04529 |
| CAS | 64-86-8 |
| Molecular Weight | 399.44 |
| Molecular Formula | C22H25NO6 |
| Purity | >98% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-04529 | 1 g | $298 | In stock |
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Add to cartDescription
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.
Specification
| 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 |
| Storage | Tightly closed. Dry. Keep in a well-ventilated place. Light sensitive. |
| 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 |
| InChI Key | IAKHMKGGTNLKSZ-INIZCTEOSA-N |
Properties
| Appearance | White to Yellow Solid |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 726.0±60.0°C at 760 mmHg |
| Melting Point | 150-160°C (dec.) |
| Density | 1.32 g/cm3 |
| Solubility | Slightly soluble in Chloroform, Methanol |
| LogP | 1.3 |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | 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. |
Reference Reading
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.
Spectrum
LC-MS/MS Spectrum - LC-ESI-QTOF , positive
Experimental Conditions
Instrument Type: LC-ESI-QTOF
Ionization Mode: positive
Ionization Mode: positive
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
