Colchicine | CAS#64-86-8 | Microtubule Inhibitor

MedKoo Cat#: 317563 | Name: (S)-Colchicine

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

(S)-Colchicine is a medication most commonly used to treat gout. Colchicine inhibits microtubule polymerization by binding to tubulin, one of the main constituents of microtubules. Availability of tubulin is essential to mitosis, so colchicine effectively functions as a "mitotic poison" or spindle poison. The mitosis-inhibiting function of colchicine has been of great use in the study of cellular genetics. To see the chromosomes of a cell under a light microscope, it is important that they be viewed near the point in the cell cycle in which they are most dense. This occurs near the middle of mitosis (specifically metaphase), so mitosis must be stopped before it completes.

Chemical Structure

(S)-Colchicine

CAS#64-86-8 (S isomer)

Theoretical Analysis

MedKoo Cat#: 317563

Name: (S)-Colchicine

CAS#: 64-86-8 (S isomer)

Chemical Formula: C22H25NO6

Exact Mass: 399.1682

Molecular Weight: 399.44

Elemental Analysis: C, 66.15; H, 6.31; N, 3.51; O, 24.03

Price and Availability

Size	Price	Availability
100mg	USD 90.00	Ready to ship
200mg	USD 150.00	Ready to ship
500mg	USD 300.00	Ready to ship
1g	USD 500.00	2 Weeks

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Related CAS #

64-86-8 (S isomer) 75520-89-7 （R isomer) 209810-38-8

Synonym

Colchicina; Colchicin; Condylon; Colsaloid; Colchicinum.

IUPAC/Chemical Name

N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide

InChi Key

IAKHMKGGTNLKSZ-INIZCTEOSA-N

InChi Code

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

SMILES Code

CC(=O)N[C@H]1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC

Appearance

White to light yellow solid powder.

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#A23K04S26

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Colchicine is a tubulin inhibitor and a microtubule disrupting agent.

In vitro activity:

Colchicine treatment also caused alterations in Ca2+ responses to chemical depolarization and a moderate, but progressive, increase in the resting intracellular Ca2+ concentration. Nearly all neurons expressed c-Fos after the treatment with colchicine. However, while in part of the cell population c-Fos levels subsequently declined, in the neurons undergoing apoptosis the protein was still expressed, but had an abnormal intracellular localization. An increased expression of the constitutive nitric oxide synthase (NOS-I) was also detected at 12 h and was followed by increased nitrite production. Treatment with 100 nM taxol to stabilize the microtubuli prevented DNA laddering and apoptotic body formation induced by colchicine. Reference: Exp Cell Res. 1995 May;218(1):189-200. https://pubmed.ncbi.nlm.nih.gov/7537689/

In vivo activity:

Colchicine treatment inhibited indomethacin-induced small intestinal injury by 86% (1 mg/kg) and 94% (3 mg/kg) as indicated by the lesion index 24 h after indomethacin administration. Colchicine inhibited the protein expression of cleaved caspase-1 and mature IL-1β, without affecting the mRNA expression of NLRP3 and IL-1β. Although treatment with recombinant IL-1β (0.1 μg/kg) did not change the severity of small intestinal damage, the preventive effects of colchicine were abolished by supplementation with the same dose of recombinant IL-1β. Indomethacin-induced small intestinal damage was reduced by 77%, as determined by the lesion index in NLRP3(-/-) mice, and colchicine treatment failed to inhibit small intestinal damage in NLRP3(-/-) mice. These results demonstrate that colchicine prevents NSAID-induced small intestinal injury by inhibiting activation of the NLRP3 inflammasome. Reference: Sci Rep. 2016 Sep 2;6:32587. https://pubmed.ncbi.nlm.nih.gov/27585971/

	Solvent	mg/mL	mM
Solubility
	DMSO	48.2	120.76
	Ethanol	52.5	131.43
	Water	50.8	127.07

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 399.44 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Muñoz-Montesino C, Burgos CF, Lara CO, Riquelme CR, Flaig D, San Martin VP, Aguayo LG, Fuentealba J, Castro PA, Guzmán L, Yévenes GE, Moraga-Cid G. Inhibition of the Glycine Receptor alpha 3 Function by Colchicine. Front Pharmacol. 2020 Jul 30;11:1143. doi: 10.3389/fphar.2020.01143. PMID: 32903667; PMCID: PMC7438739. 2. Bonfoco E, Ceccatelli S, Manzo L, Nicotera P. Colchicine induces apoptosis in cerebellar granule cells. Exp Cell Res. 1995 May;218(1):189-200. doi: 10.1006/excr.1995.1147. PMID: 7537689. 3. Schwarz N, Fernando S, Chen YC, Salagaras T, Rao SR, Liyanage S, Williamson AE, Toledo-Flores D, Dimasi C, Sargeant TJ, Manavis J, Eddy E, Kanellakis P, Thompson PL, Tan JTM, Snel MF, Bursill CA, Nicholls SJ, Peter K, Psaltis PJ. Colchicine exerts anti-atherosclerotic and -plaque-stabilizing effects targeting foam cell formation. FASEB J. 2023 Apr;37(4):e22846. doi: 10.1096/fj.202201469R. PMID: 36856983. 4. Otani K, Watanabe T, Shimada S, Takeda S, Itani S, Higashimori A, Nadatani Y, Nagami Y, Tanaka F, Kamata N, Yamagami H, Tanigawa T, Shiba M, Tominaga K, Fujiwara Y, Arakawa T. Colchicine prevents NSAID-induced small intestinal injury by inhibiting activation of the NLRP3 inflammasome. Sci Rep. 2016 Sep 2;6:32587. doi: 10.1038/srep32587. PMID: 27585971; PMCID: PMC5009328.

In vitro protocol:

In vivo protocol:

1. Schwarz N, Fernando S, Chen YC, Salagaras T, Rao SR, Liyanage S, Williamson AE, Toledo-Flores D, Dimasi C, Sargeant TJ, Manavis J, Eddy E, Kanellakis P, Thompson PL, Tan JTM, Snel MF, Bursill CA, Nicholls SJ, Peter K, Psaltis PJ. Colchicine exerts anti-atherosclerotic and -plaque-stabilizing effects targeting foam cell formation. FASEB J. 2023 Apr;37(4):e22846. doi: 10.1096/fj.202201469R. PMID: 36856983. 2. Otani K, Watanabe T, Shimada S, Takeda S, Itani S, Higashimori A, Nadatani Y, Nagami Y, Tanaka F, Kamata N, Yamagami H, Tanigawa T, Shiba M, Tominaga K, Fujiwara Y, Arakawa T. Colchicine prevents NSAID-induced small intestinal injury by inhibiting activation of the NLRP3 inflammasome. Sci Rep. 2016 Sep 2;6:32587. doi: 10.1038/srep32587. PMID: 27585971; PMCID: PMC5009328.

1: Yeh LC, Banerjee A, Prasad V, Tuszynski JA, Weis AL, Bakos T, Yeh IT, Ludueña RF, Lee JC. Effect of CH-35, a novel anti-tumor colchicine analogue, on breast cancer cells overexpressing the βIII isotype of tubulin. Invest New Drugs. 2015 Dec 21. [Epub ahead of print] PubMed PMID: 26686345. 2: Kuo MC, Chang SJ, Hsieh MC. Colchicine Significantly Reduces Incident Cancer in Gout Male Patients: A 12-Year Cohort Study. Medicine (Baltimore). 2015 Dec;94(50):e1570. doi: 10.1097/MD.0000000000001570. PubMed PMID: 26683907. 3: Fahim M, Singh M, Kamal YT, Mukhtar HM, Ahmad S. A high performance thin layer chromatographic method for the estimation of colchicine in different formulations. J Pharm Bioallied Sci. 2015 Oct-Dec;7(4):260-3. doi: 10.4103/0975-7406.168021. PubMed PMID: 26681878; PubMed Central PMCID: PMC4678988. 4: Izadi Amoli A, Bozorgi A, HajHossein Talasaz A, Salehi Omran A, Mortazavi SH, Jalali A, Nasirpour S, Jenab Y. Efficacy of colchicine versus placebo for the treatment of pericardial effusion after open-heart surgery: A randomized, placebo-controlled trial. Am Heart J. 2015 Dec;170(6):1195-201. doi: 10.1016/j.ahj.2015.09.020. Epub 2015 Oct 3. PubMed PMID: 26678641. 5: Rohena CC, Telang N, Da C, Risinger A, Sikorski JA, Kellogg GE, Gupton JT, Mooberry SL. Biological Characterization of an Improved Pyrrole-Based Colchicine Site Agent Identified Through Structure-based Design. Mol Pharmacol. 2015 Dec 11. pii: mol.115.101592. [Epub ahead of print] PubMed PMID: 26655304. 6: Imazio M, Gaita F. Colchicine for cardiovascular medicine. Future Cardiol. 2015 Dec 3. [Epub ahead of print] PubMed PMID: 26632860. 7: Ataş H, Cemil BC, Canpolat F, Gönül M. The Effect of Colchicine on Mean Platelet Volume in Behcet's Disease. Ann Clin Lab Sci. 2015 Sep;45(5):545-9. PubMed PMID: 26586706. 8: Solomon DH, Liu CC, Kuo IH, Zak A, Kim SC. Effects of colchicine on risk of cardiovascular events and mortality among patients with gout: a cohort study using electronic medical records linked with Medicare claims. Ann Rheum Dis. 2015 Nov 18. pii: annrheumdis-2015-207984. doi: 10.1136/annrheumdis-2015-207984. [Epub ahead of print] PubMed PMID: 26582823. 9: Portincasa P. Colchicine, Biologic Agents and More for the Treatment of Familial Mediterranean Fever. The Old, the New, and the Rare. Curr Med Chem. 2015 Nov 17. [Epub ahead of print] PubMed PMID: 26572612. 10: Solak Y, Sipahi S. Impact of glomerular filtration rate in colchicine toxicity. Semin Arthritis Rheum. 2015 Oct 22. pii: S0049-0172(15)00248-6. doi: 10.1016/j.semarthrit.2015.09.012. [Epub ahead of print] PubMed PMID: 26564025.