DEMECOLCINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H25NO5
Molecular Weight	371.4269
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN[C@H]1CCC2=C(C(OC)=C(OC)C(OC)=C2)C3=CC=C(OC)C(=O)C=C13

InChI

InChIKey=NNJPGOLRFBJNIW-HNNXBMFYSA-N

InChI=1S/C21H25NO5/c1-22-15-8-6-12-10-18(25-3)20(26-4)21(27-5)19(12)13-7-9-17(24-2)16(23)11-14(13)15/h7,9-11,15,22H,6,8H2,1-5H3/t15-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C21H25NO5
Molecular Weight	371.4269
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27193863
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/2299625 | https://www.ncbi.nlm.nih.gov/pubmed/25654321 |

Demecolcine, also called Colcemid, was isolated from the autumn crocus in 1950 and commercialized by Ciba. Initially, it was explored as a cancer drug due to its low toxicity. Demecolcine depolymerizes microtubules and limits microtubule formation (inactivates spindle fiber formation), thus arresting cells in metaphase and allowing cell harvest and karyotyping to be performed. Today, it is only used as a research tool mainly to overcome limitations of colchicine due to its very slow association and dissociation rate constants. It binds to tubulin at the same site as colchicine, but ~10-fold faster, and it also dissociates faster. Demecolcine main use has been to arrest cells in mitosis for cytogenetic analysis, though to our knowledge it offers no special advantages over other drugs in this application.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Tubulin 69 Target ID: CHEMBL2095182 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7265112	Inhibitor 8504
Tubulin beta chain 8 Target ID: CHEMBL3394 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2299625	Inhibitor 8504		2.4 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Skin cancer 23 Sources: https://www.ncbi.nlm.nih.gov/pubmed/374922	Primary		Withdrawn	Colcemid Approved Use Unknown

PubMed

Title	Date	PubMed
Expression of a dominant negative heat shock factor-1 construct inhibits aneuploidy in prostate carcinoma cells.	2004-07-30	15152009
Development, chromosomal composition, and cell allocation of bovine cloned blastocyst derived from chemically assisted enucleation and cultured in conditioned media.	2004-06	15095340
Microtubule stress modifies intra-nuclear location of Msh2 in mouse embryonic fibroblasts.	2004-05	15044851
Relationship between the host cell mitochondria and the parasitophorous vacuole in cells infected with Encephalitozoon microsporidia.	2004-04-08	15068269
Asymmetric localization of LGN but not AGS3, two homologs of Drosophila pins, in dividing human neural progenitor cells.	2004-03-15	14994339
Detection of mitotic recombination and sex chromosome loss induced by adriamycin, chlorambucil, demecolcine, paclitaxel and vinblastine in somatic cells of Drosophila melanogaster in vivo.	2004-03	14981158
Newborn horizontal cells migrate bi-directionally across the neuroepithelium during retinal development.	2004-03	14973293
Defective control of mitotic and post-mitotic checkpoints in poly(ADP-ribose) polymerase-1(-/-) fibroblasts after mitotic spindle disruption.	2004-03	14726664
Chromosomal analysis of non-small-cell lung cancer by multicolour fluorescent in situ hybridisation.	2004-02-23	14970871
CENP-B interacts with CENP-C domains containing Mif2 regions responsible for centromere localization.	2004-02-13	14612452
Contribution of noncentrosomal microtubules to spindle assembly in Drosophila spermatocytes.	2004-01	14758368
Vertebrate primary cilia: a sensory part of centrosomal complex in tissue cells, but a "sleeping beauty" in cultured cells?	2004	14984760
Brush-like fibers on the human chromosome periphery.	2003-12-31	14696981
Cell cycle checkpoint function in bladder cancer.	2003-12-17	14679155
X-irradiated human lymphocytes with unstable aberrations and their preferential elimination by p53/survivin-dependent apoptosis.	2003-12	14713572
Simultaneous binding of two different drugs in the binding pocket of the human multidrug resistance P-glycoprotein.	2003-10-10	12909621
The ATP-dependent helicase RUVBL1/TIP49a associates with tubulin during mitosis.	2003-10	14506706
Premature chromosome condensation revisited: a novel chemical approach permits efficient cytogenetic analysis of cancers.	2003-10	12939745
The interrelationship between DRIM gene expression and cytogenetic and phenotypic characteristics in human breast tumor cell lines.	2003-09-22	14503924
The role of PAR-1 in regulating the polarised microtubule cytoskeleton in the Drosophila follicular epithelium.	2003-09	12874119
Differential effects of vitamin E and three hydrophilic antioxidants on the actinomycin D-induced and colcemid-accelerated apoptosis in human leukemia CMK-7 cell line.	2003-08	12962151
Delayed arteriolar relaxation after prolonged agonist exposure: functional remodeling involving tyrosine phosphorylation.	2003-08	12714327
S-adenosyl-L-methionine is able to reverse micronucleus formation induced by sodium arsenite and other cytoskeleton disrupting agents in cultured human cells.	2003-07-25	12873724
Mutations in alpha- and beta-tubulin that stabilize microtubules and confer resistance to colcemid and vinblastine.	2003-07	12883031
Possible associations between ELF electromagnetic fields, DNA damage response processes and childhood leukaemia.	2003-06-16	12799640
Permanent activation of the human P-glycoprotein by covalent modification of a residue in the drug-binding site.	2003-06-06	12711602
The rat STSL locus: characterization, chromosomal assignment, and genetic variations in sitosterolemic hypertensive rats.	2003-06-03	12783625
Filament formation of MSF-A, a mammalian septin, in human mammary epithelial cells depends on interactions with microtubules.	2003-05-16	12626509
Substrate-induced conformational changes in the transmembrane segments of human P-glycoprotein. Direct evidence for the substrate-induced fit mechanism for drug binding.	2003-04-18	12609990
Octaploid Meth-A cells are established from a highly polyploidized cell population.	2003-04	12680876
Cloned mice derived from embryonic stem cell karyoplasts and activated cytoplasts prepared by induced enucleation.	2003-04	12606420
Demecolcine-induced oocyte enucleation for somatic cell cloning: coordination between cell-cycle egress, kinetics of cortical cytoskeletal interactions, and second polar body extrusion.	2003-04	12606412
Particulate debris from a titanium metal prosthesis induces genomic instability in primary human fibroblast cells.	2003-02-24	12592368
Involvement of the nonhomologous end joining DNA repair pathway in the bystander effect for chromosomal aberrations.	2003-02	12537532
ATPase inhibitors suppress actinomycin D-induced apoptosis in leukemia cells.	2003-01-18	12530016
Drug binding in human P-glycoprotein causes conformational changes in both nucleotide-binding domains.	2003-01-17	12421806
Bacteriocyte population growth in Blattella germanica.	2003-01	12762657
Different apoptotic responses and patterns in adhering and floating neoplastic cell cultures: effects of microtubule antagonists.	2003-01	12548408
Effect of demecolcine and nocodazole on the efficiency of chemically assisted removal of chromosomes and the developmental potential of nuclear transferred porcine oocytes.	2003	14733755
Production of cloned pigs by using somatic cells as donors.	2003	14733743
Spontaneous chromosome loss and colcemid resistance in lymphocytes from patients with myotonic dystrophy type 1.	2003	14526184
Beta class II tubulin predominates in normal and tumor breast tissues.	2003	12927047
Assays for neoplastic cell enrichment in bone marrow samples.	2003	12710218
In vivo destabilization of dynamic microtubules by HDAC6-mediated deacetylation.	2002-12-16	12486003
Chromosomal radiosensitivity in breast cancer patients with a known or putative genetic predisposition.	2002-12-02	12454765
Effects of polyphenolic anthrone derivatives, resistomycin and hypercin, on apoptosis in human megakaryoblastic leukemia CMK-7 cell line.	2002-11-21	12440735
Binding of hsp90-associated immunophilins to cytoplasmic dynein: direct binding and in vivo evidence that the peptidylprolyl isomerase domain is a dynein interaction domain.	2002-11-19	12427021
Effect of delayed enucleation on the developmental potential of nuclear-transferred oocytes receiving adult and fetal fibroblast cells.	2002-08	12214802
CP248, a derivative of exisulind, causes growth inhibition, mitotic arrest, and abnormalities in microtubule polymerization in glioma cells.	2002-04	12477052
Functional inactivation of pRB results in aneuploid mammalian cells after release from a mitotic block.	2002-03-18	12192596

Patents

Sample Use Guides

In Vivo Use Guide

sheep were treated with Demecolcine at doses 0.22, 0.30, 0.35, and 0.65 mg/kg body weight

Route of Administration: Intravenous

In Vitro Use Guide

The human U251 glioblastoma cell line was used for activity evaluation. U251 cells were seeded at 200 000 cells per 35 mm dish 1 day prior to addition of test compounds (Demecolcine). Cell cycle analyses were performed 24 h after addition of test compounds (Demecolcine, 3 μM), using a Guava Personal Cytometer (EMD Millipore) according to the manufacturer’s protocol for the Guava Cell Cycle Reagent. CytoSoft 2.1.4 software was used to analyze the resulting DNA histograms and calculate the percentage of cells in each phase of the cell cycle, based on a total of 5000 events per sample

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:35:01 GMT 2025` Edited by `admin` on `Mon Mar 31 18:35:01 GMT 2025`
Record UNII	Z01IVE25KI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

C-12669

Preferred Name

English

DEMECOLCINE

Official Name

English

demecolcine [INN]

Common Name

English

DEACETYL-N-METHYLCOLCHICINE

Common Name

English

DEMECOLCINE [MI]

Common Name

English

NSC-3096

Code

English

Demecolcine [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

L01CC01