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Revision as of 10:49, 17 February 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: UNII ChEMBL.← Previous edit		Latest revision as of 16:18, 21 September 2024 edit undoCitation bot (talk | contribs)Bots5,424,219 edits Added bibcode. | Use this bot. Report bugs. | Suggested by Whoop whoop pull up | Category:Microtubule inhibitors | #UCB_Category 11/21
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			{{Short description|Chemical compound}}
	{{Drugbox		{{Drugbox
			| Watchedfields = changed
	| verifiedrevid = 396325312		| verifiedrevid = 414414817
	| IUPAC_name = (''S'')-1,2,3,10-Tetramethoxy-7-methylamino-6,7-dihydro-5''H''-benzoheptalen-9-one		| IUPAC_name = (''S'')-1,2,3,10-Tetramethoxy-7-methylamino-6,7-dihydro-5''H''-benzoheptalen-9-one
	| image = Demecolcine.png		| image = Demecolcine.png
			| alt = Skeletal formula of demecolcine
			| image2 = Demecolcine 3D ball.png
			| alt2 = Ball-and-stick model of the demecolcine molecule
			<!--Clinical data-->
			| tradename =
		⚫	| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
		⚫	| pregnancy_US = <!-- A / B / C / D / X -->
		⚫	| pregnancy_category =
		⚫	| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
		⚫	| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
		⚫	| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
		⚫	| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
		⚫	| legal_status =
		⚫	| routes_of_administration =
			<!--Pharmacokinetic data-->
		⚫	| bioavailability =
		⚫	| protein_bound =
		⚫	| metabolism =
		⚫	| elimination_half-life =
		⚫	| excretion =
			<!--Identifiers-->
		⚫	| CAS_number_Ref = {{cascite|correct|??}}
		⚫	| CAS_number = 477-30-5
		⚫	| ATC_prefix = L01
		⚫	| ATC_suffix = CC01
		⚫	| PubChem = 220401
			| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
		⚫	| DrugBank =
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 191135		| ChemSpiderID = 191135
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = Z01IVE25KI		| UNII = Z01IVE25KI
			| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| InChI = 1/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
⚫	| smiles = O=C/1C(\OC)=C/C=C2\C(=C\1)(NC)CCc3c2c(OC)c(OC)c(OC)c3
	| InChIKey = NNJPGOLRFBJNIW-HNNXBMFYBY
⚫	| CASNo_Ref = {{cascite|correct|CAS}}
	| ChEMBL = 312862		| ChEMBL = 312862
			| KEGG_Ref = {{keggcite|correct|kegg}}
			| KEGG = C11250
			| synonyms = Colcemid
			<!--Chemical data-->
		⚫	| C=21 | H=25 | N=1 | O=5
		⚫	| smiles = O=C/1C(\OC)=C/C=C2\C(=C\1)(NC)CCc3c2c(OC)c(OC)c(OC)c3
			| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 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		| StdInChI = 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
			| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = NNJPGOLRFBJNIW-HNNXBMFYSA-N		| StdInChIKey = NNJPGOLRFBJNIW-HNNXBMFYSA-N
⚫	| CAS_number = 477-30-5
⚫	| ATC_prefix = L01
⚫	| ATC_suffix = CC01
⚫	| PubChem = 2832
⚫	| DrugBank =
⚫	| C=21|H=25|N=1|O=5
	| molecular_weight = 371.43 g/mol
⚫	| bioavailability =
⚫	| protein_bound =
⚫	| metabolism =
⚫	| elimination_half-life =
⚫	| excretion =
⚫	| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫	| pregnancy_US = <!-- A / B / C / D / X -->
⚫	| pregnancy_category=
⚫	| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
⚫	| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
⚫	| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
⚫	| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
⚫	| legal_status =
⚫	| routes_of_administration =
	}}		}}
	'''Demecolcine''' is a drug used in ].It is closely related to the natural ] ] with the replacement of the ] group on the ] moiety with ].		'''Demecolcine''' (]; also known as '''colcemid''') is a drug used in ]. It is closely related to the natural ] ] with the replacement of the ] group on the ] moiety with ], but it is less toxic. It ] ] and limits microtubule formation (inactivates ] formation), thus arresting ]s in ] and allowing cell harvest and ] 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.<ref>Brit med J., 1965, 1, 495 – 496</ref>		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.<ref>{{cite journal | vauthors = Sutton M | journal = British Medical Journal | volume = 1 | issue = 5433 | pages = 495–6 | date = February 1965 | pmid = 14238680 | pmc = 2165889 | doi = 10.1136/bmj.1.5433.495 | title = Superior Mediastinal Obstruction Treated with Demecolcine Followed by Radiotherapy }}</ref>
	In animal cloning procedures Demecolcine makes an ovum eject its nucleus, creating space for insertion of a new nucleus.<ref>Reprod Nutr Dev. 2006 Mar-Apr;46(2):219-26</ref>		In animal cloning procedures, demecolcine makes an ovum eject its nucleus, creating space for insertion of a new nucleus.<ref>{{cite journal | vauthors = Hou J, Lei T, Liu L, Cui X, An X, Chen Y | title = Demecolcine-induced enucleation of sheep meiotically maturing oocytes | journal = Reproduction, Nutrition, Development | volume = 46 | issue = 2 | pages = 219–26 | year = 2006 | pmid = 16597428 | doi = 10.1051/rnd:2006002 | doi-access = free }}</ref>
			==Mechanism of action==
			Demecolcine is a microtubule-depolymerizing drug like ]. It acts by two distinct mechanisms. At very low concentration it binds to microtubule plus end to suppress microtubule dynamics.<ref>{{cite journal | vauthors = Jordan MA, Wilson L | s2cid = 10228718 | title = Microtubules as a target for anticancer drugs | journal = Nature Reviews. Cancer | volume = 4 | issue = 4 | pages = 253–65 | date = April 2004 | pmid = 15057285 | doi = 10.1038/nrc1317 }}</ref> Recent study has found at higher concentration demecolcine can promote microtubule detachment from microtubule organizing center. Detached microtubules with unprotected minus end depolymerize with time. Cytotoxicity of the cells seems to correlate better with ] detachment.<ref name=pmid20696757>{{cite journal | vauthors = Yang H, Ganguly A, Cabral F | title = Inhibition of cell migration and cell division correlates with distinct effects of microtubule inhibiting drugs | journal = The Journal of Biological Chemistry | volume = 285 | issue = 42 | pages = 32242–50 | date = October 2010 | pmid = 20696757 | pmc = 2952225 | doi = 10.1074/jbc.M110.160820 | doi-access = free }}</ref> Lower concentration affects microtubule dynamics and cell migration.<ref name=pmid20696757/>
			== Research use==
			Demecolcine is used for scientific research in cells. It is used in a variety of ways, however, until recently, was used mostly for the study of ] in cells. For example, microtubules are necessary for the splitting of cells. More importantly, the movement of chromosomes during the M phase. Demecolcine inhibition of microtubules causes ] in mitotic cells where the microtubules fall apart or are suppressed before they can complete their function of pulling chromosomes into the daughter cell, also known as nondisjunction of chromosomes.<ref>{{cite journal | vauthors = Hashimoto K, Todo T | title = Mitotic slippage underlies the relationship between p53 dysfunction and the induction of large micronuclei by colcemid | journal = Mutagenesis | volume = 28 | issue = 4 | pages = 457–64 | date = July 2013 | pmid = 23702691 | doi = 10.1093/mutage/get021 | doi-access = free }}</ref> Demecolcine, depending on dose, has also been found to cause ] of chromosomes in ] when nondisjunction occurs.<ref>{{cite journal | vauthors = Yamamoto M, Wakata A, Aoki Y, Miyamae Y, Kodama S | title = Chromosome loss caused by DNA fragmentation induced in main nuclei and micronuclei of human lymphoblastoid cells treated with colcemid | journal = Mutation Research | volume = 762 | pages = 10–6 | date = April 2014 | pmid = 24582839 | doi = 10.1016/j.mrfmmm.2014.02.002 | bibcode = 2014MRFMM.762...10Y }}</ref>
	== References ==		== References ==
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	{{Chemotherapeutic agents}}		{{Chemotherapeutic agents}}
			{{Xenobiotic-sensing receptor modulators}}
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	{{antineoplastic-drug-stub}}
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