(-)-demecolcine (CHEBI:4393)

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ChEBI Name	(−)-demecolcine

ChEBI ID	CHEBI:4393

ChEBI ASCII Name	(-)-demecolcine

Definition	A secondary amino compound that is (S)-colchicine in which the N-acetyl group is replaced by an N-methyl group. Isolable from the autumn crocus, Colchicum autumnale, it is less toxic than colchicine and is used as an antineoplastic.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	ChemicalBook:CB3460085, eMolecules:493994, ZINC000003872132

Download	Molfile XML SDF

Wikipedia	License
Demecolcine (INN; also known as colcemid) is a drug used in chemotherapy. It is closely related to the natural alkaloid colchicine with the replacement of the acetyl group on the amino moiety with methyl, but it is less toxic. It depolymerises microtubules and limits microtubule formation (inactivates spindle fibre formation), thus arresting cells in metaphase and allowing cell harvest and karyotyping to be performed. During cell division, demecolcine inhibits mitosis at metaphase by inhibiting spindle formation. Medically, demecolcine has been used to improve the results of cancer radiotherapy by synchronising tumour cells at metaphase, the radiosensitive stage of the cell cycle. In animal cloning procedures, demecolcine makes an ovum eject its nucleus, creating space for insertion of a new nucleus.
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Formula

C21H25NO5

Net Charge

Average Mass

371.42690

Monoisotopic Mass

371.17327

InChI

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

InChIKey

NNJPGOLRFBJNIW-HNNXBMFYSA-N

SMILES

CN[C@H]1CCc2cc(OC)c(OC)c(OC)c2-c2ccc(OC)c(=O)cc12

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	microtubule-destabilising agent Any substance that interacts with tubulin to inhibit polymerisation of microtubules. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. (via alkaloid )

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology
Outgoing	(−)-demecolcine (CHEBI:4393) has role antineoplastic agent (CHEBI:35610) (−)-demecolcine (CHEBI:4393) has role microtubule-destabilising agent (CHEBI:61951) (−)-demecolcine (CHEBI:4393) is a alkaloid (CHEBI:22315) (−)-demecolcine (CHEBI:4393) is a secondary amino compound (CHEBI:50995)

IUPAC Name

(7S)-1,2,3,10-tetramethoxy-7-(methylamino)-6,7-dihydrobenzo[a]heptalen-9(5H)-one

Synonyms	Sources
(−)-colchamine	ChemIDplus
Colcemid	KEGG COMPOUND
N-deacetyl-N-methylcolchicine	ChemIDplus
N-desacetyl-N-methylcolchicine	ChemIDplus
N-methyl-N-deacetylcolchicine	ChemIDplus
N-methyl-N-desacetylcolchicine	ChemIDplus
Reichstein's F	ChemIDplus
Santavy's substance F	ChemIDplus

Citations

Last Modified

22 February 2017