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Revision as of 12:24, 28 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CASNo').← Previous edit		Latest revision as of 23:26, 4 November 2023 edit undoBuidhe (talk | contribs)Autopatrolled, Extended confirmed users, Page movers, File movers, Mass message senders, New page reviewers, Pending changes reviewers, Template editors136,073 editsm Moving from Category:Protein kinase inhibitors to Category:CDK inhibitors using Cat-a-lot
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	{{chembox		{{chembox
			| Verifiedfields = changed
			| verifiedrevid = 457808081
		⚫	| ImageFile=Flavopiridol.svg
		⚫	| ImageSize=200px
			| ImageFile1=Alvocidib ball-and-stick.png
			| ImageSize1=200px
		⚫	| IUPACName=2′-Chloro-5,7-dihydroxy-8-flavone
			| SystematicName=2-(2-Chlorophenyl)-5,7-dihydroxy-8--4''H''-1-benzopyran-4-one
			| OtherNames=Flavopiridol, HMR 1275, L-868275
		⚫	|Section1={{Chembox Identifiers
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = 45AD6X575G		| UNII = 45AD6X575G
			| IUPHAR_ligand = 5680
⚫	|ImageFile=Flavopiridol.svg
			| CASNo_Ref = {{cascite|changed|??}}
⚫	|ImageSize=200px
			| CASNo=146426-40-6
⚫	|IUPACName=2-(2-chlorophenyl)-5,7-dihydroxy-8--4-chromenone
		⚫	| PubChem= 5287969
	|OtherNames=
			| ChEBI_Ref = {{ebicite|changed|EBI}}
⚫	|Section1={{Chembox Identifiers
			| ChEBI = 47344
	| CASNo = <!-- blanked - oldvalue: 146426-40-6 -->
			| ChEMBL_Ref = {{ebicite|changed|EBI}}
⚫	| PubChem= 5287969
	| ChEMBL = <!-- blanked - oldvalue: 428690 -->		| ChEMBL = 428690
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 4450222		| ChemSpiderID = 4450222
⚫	| StdInChI = 1S/C21H20ClNO5/c1-23-7-6-12(17(27)10-23)19-14(24)8-15(25)20-16(26)9-18(28-21(19)20)11-4-2-3-5-13(11)22/h2-5,8-9,12,17,24-25,27H,6-7,10H2,1H3/t12-,17+/m0/s1
			| KEGG = D09868
			| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
		⚫	| StdInChI = 1S/C21H20ClNO5/c1-23-7-6-12(17(27)10-23)19-14(24)8-15(25)20-16(26)9-18(28-21(19)20)11-4-2-3-5-13(11)22/h2-5,8-9,12,17,24-25,27H,6-7,10H2,1H3/t12-,17+/m0/s1
			| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = BIIVYFLTOXDAOV-YVEFUNNKSA-N		| StdInChIKey = BIIVYFLTOXDAOV-YVEFUNNKSA-N
			| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
	| DrugBank = DB03496		| DrugBank = DB03496
	| SMILES = Clc4ccccc4C=2Oc1c(c(O)cc(O)c1C(=O)C=2)3CCN(C)C3O		| SMILES = Clc4ccccc4C=2Oc1c(c(O)cc(O)c1C(=O)C=2)3CCN(C)C3O
	| MeSHName = Flavopiridol		| MeSHName = Flavopiridol
	}}		}}
	|Section2={{Chembox Properties		|Section2={{Chembox Properties
	| Formula=C<sub>21</sub>H<sub>20</sub>ClNO<sub>5</sub>		| Formula=C<sub>21</sub>H<sub>20</sub>ClNO<sub>5</sub>
	| MolarMass=401.8402		| MolarMass=401.8402
	| Appearance=		| Appearance=
	| Density=		| Density=
	| MeltingPt=		| MeltingPt=
	| BoilingPt=		| BoilingPt=
	| Solubility=		| Solubility=
	}}		}}
	|Section3={{Chembox Hazards		|Section3={{Chembox Hazards
	| MainHazards=		| MainHazards=
	| FlashPt=		| FlashPt=
			| AutoignitionPt =
	| Autoignition=
	}}		}}
	}}		}}
	'''Alvocidib''' (]; also known as '''Flavopiridol''' or '''HMR-1275''') is a cyclin-dependent kinase inhibitor under clinical development for the treatment of ]. It has been studied also for the treatment of ]<ref name="pmid18209094">{{cite journal |author=Sekine C, Sugihara T, Miyake S, ''et al.'' |title=Successful treatment of animal models of rheumatoid arthritis with small-molecule cyclin-dependent kinase inhibitors |journal=J. Immunol. |volume=180 |issue=3 |pages=1954–61 |year=2008 |month=February |pmid=18209094 |doi= |url=http://www.jimmunol.org/cgi/pmidlookup?view=long&pmid=18209094}}</ref> and ] formation <ref name="pmid10441105">{{cite journal |author=Meshel AS, Ruef J, Hu Z, Horaist C, Ballinger CA, Thompson LJ, Subbarao VD, Dumont JA, Patterson C.|title=Flavopiridol inhibits smooth muscle cell proliferation in vitro and neointimal formation In vivo after carotid injury in the rat. |journal=Circulation |volume=10 |issue=100 |pages=659–65 |year=1999 |month=August |pmid=10441105|doi= |url=http://circ.ahajournals.org/cgi/content/short/100/6/659}}</ref>		'''Alvocidib''' (]; also known as '''flavopiridol''') is a ] ] ] under clinical development by Tolero Pharmaceuticals for the treatment of ]. It has been studied also for the treatment of ]<ref name="pmid18209094">{{cite journal | vauthors = Sekine C, Sugihara T, Miyake S, Hirai H, Yoshida M, Miyasaka N, Kohsaka H | title = Successful treatment of animal models of rheumatoid arthritis with small-molecule cyclin-dependent kinase inhibitors | journal = J. Immunol. | volume = 180 | issue = 3 | pages = 1954–61 | year = 2008 | pmid = 18209094 | doi = 10.4049/jimmunol.180.3.1954| doi-access = free }}</ref> and ] formation.<ref name="pmid10441105">{{cite journal | vauthors = Ruef J, Meshel AS, Hu Z, Horaist C, Ballinger CA, Thompson LJ, Subbarao VD, Dumont JA, Patterson C | title = Flavopiridol inhibits smooth muscle cell proliferation in vitro and neointimal formation In vivo after carotid injury in the rat | journal = Circulation | volume = 100 | issue = 6 | pages = 659–65 | year = 1999 | pmid = 10441105 | doi = 10.1161/01.cir.100.6.659| doi-access = free }}</ref> The target of alvocidib is the positive transcription elongation factor ].<ref name="pmid10906320">{{cite journal | vauthors = Chao SH, Fujinaga K, Marion JE, Taube R, Sausville EA, Senderowicz AM, Peterlin BM, Price DH | title = Flavopiridol inhibits P-TEFb and blocks HIV-1 replication | journal = J. Biol. Chem. | volume = 275 | issue = 37 | pages = 28345–8 | year = 2000 | pmid = 10906320 | doi = 10.1074/jbc.C000446200 | doi-access = free }}</ref><ref name="pmid11431468">{{cite journal | vauthors = Chao SH, Price DH | title = Flavopiridol inactivates P-TEFb and blocks most RNA polymerase II transcription in vivo | journal = J. Biol. Chem. | volume = 276 | issue = 34 | pages = 31793–9 | year = 2001 | pmid = 11431468 | doi = 10.1074/jbc.M102306200 | doi-access = free }}</ref> Treatment of cells with alvocidib leads to inhibition of P-TEFb and the loss of ] production.<ref name="pmid22244331">{{cite journal | vauthors = Cheng B, Li T, Rahl PB, Adamson TE, Loudas NB, Guo J, Varzavand K, Cooper JJ, Hu X, Gnatt A, Young RA, Price DH | title = Functional association of Gdown1 with RNA polymerase II poised on human genes | journal = Mol. Cell | volume = 45 | issue = 1 | pages = 38–50 | year = 2012 | pmid = 22244331 | pmc = 3259526 | doi = 10.1016/j.molcel.2011.10.022 }}</ref><ref name="pmid20434984">{{cite journal | vauthors = Rahl PB, Lin CY, Seila AC, Flynn RA, McCuine S, Burge CB, Sharp PA, Young RA | title = c-Myc regulates transcriptional pause release | journal = Cell | volume = 141 | issue = 3 | pages = 432–45 | year = 2010 | pmid = 20434984 | pmc = 2864022 | doi = 10.1016/j.cell.2010.03.030 }}</ref>
			The compound is a synthetic ] of natural product ] which was initially extracted from '']'' (formerly ''Amoora rohituka'', hence the name) and later from '']''.<ref>{{cite journal|last1=Harmon|first1=AD|last2=Weiss|first2=U|last3=Silverton|first3=JV|title=The structure of rohitukine, the main alkaloid of Amoora rohituka (syn.Aphanamixis polystachya) (Meliaceae)|journal=Tetrahedron Lett.|date=1979|volume=20|issue=1|pages=721–724|doi=10.1016/S0040-4039(01)93556-7}}</ref><ref>{{cite journal|last1=Lakdawala|first1=AD|last2=Shirole|first2=MV|last3=Mandrekar|first3=SS|last4=Dohadwalla|first4=AN|title=Immunopharmacological potential of rohitukine: a novel compound isolated from the plant Dysoxylum binectariferum|journal=Asia Pac J Pharmcol.|date=1988|volume=3|issue=1|pages=91–98}}</ref>
			==Orphan drug==
			The FDA has granted ] designation to alvocidib for the treatment of patients with ].<ref>{{cite web | url = http://www.healio.com/hematology-oncology/hematologic-malignancies/news/online/%7B74c6a69e-4529-400d-98e9-d5ee6c602122%7D/fda-grants-orphan-drug-status-to-alvocidib-for-aml | title = FDA grants orphan drug status to Alvocidib for AML}}</ref>
	==References==		==References==
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