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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 of DEMECOLCINE

SMILES

CN[C@H]1CCC2=CC(OC)=C(OC)C(OC)=C2C3=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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency
2.4 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Colcemid

PubMed

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
Record UNII
Z01IVE25KI
Record Status Validated (UNII)
Record Version