Alvocidib: Difference between revisions

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{{Short description|A cyclin-dependent kinase inhibitor used in cancer treatment}}
| Verifiedfields = changed
{{Drugbox
| verifiedrevid = 457808081
| verifiedfields = changed
| ImageFile=Flavopiridol.svg
| verifiedrevid = 477002123
| ImageSize=200px
| IUPAC_name = 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| ImageFile1=Alvocidib ball-and-stick.png
| ImageSize1=200px
| IUPACName=2-(2-chlorophenyl)-5,7-dihydroxy-8-[(3S,4R)-3-hydroxy-1-methyl-4-piperidinyl]-4-chromenone
| OtherNames=Flavopiridol, HMR 1275, L-868275
|Section1={{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 45AD6X575G
| IUPHAR_ligand = 5680
| CASNo_Ref = {{cascite|changed|??}}
| CASNo=146426-40-6
| PubChem= 5287969
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 47344
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 428690
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4450222
| 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
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB03496
| SMILES = Clc4ccccc4C=2Oc1c(c(O)cc(O)c1C(=O)C=2)[C@H]3CCN(C)C[C@H]3O
| MeSHName = Flavopiridol
  }}
|Section2={{Chembox Properties
| Formula=C<sub>21</sub>H<sub>20</sub>ClNO<sub>5</sub>
| MolarMass=401.8402
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
  }}
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
  }}
}}
 
'''Alvocidib''' ([[International Nonproprietary Name|INN]]; also known as '''Flavopiridol''') is a [[flavonoid alkaloid]] [[CDK9]] [[kinase inhibitor]] under clinical development for the treatment of [[acute myeloid leukemia]], by [[Tolero Pharmaceuticals, Inc]]. It has been studied also for the treatment of [[arthritis]]<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}}</ref> and [[atherosclerotic plaque]] 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}}</ref> The target of Flavopiridol is the positive transcription elongation factor [[P-TEFb]].<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 }}</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 }}</ref>  Treatment of cells with Flavopiridol leads to inhibition of P-TEFb and the loss of [[mRNA]] 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 analog of natural product [[rohitukine]] which was initially extracted from ''Amoora rohituka'' [syn. ''[[Aphanamixis polystachya]]''] and later from ''[[Dysoxylum|Dysoxylum binectariferum]]''.<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|accessdate=}}</ref>
 
==Orphan drug==
{{cquote|[[Tolero Pharmaceuticals]] Inc. announced that the FDA has granted [[orphan drug]] designation for Alvocidib, its cyclin-dependent kinase small molecule inhibitor, for the treatment of patients with [[acute myeloid leukemia]].<ref>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</ref>}}
 
==References==
{{Reflist}}
 
{{Intracellular chemotherapeutic agents}}
 
[[Category:Experimental cancer drugs]]
[[Category:Chromones]]
[[Category:Protein kinase inhibitors]]
[[Category:Orphan drugs]]
 
 
{{antineoplastic-drug-stub}}
 
== Alvocidib ==
<gallery>
File:Flavopiridol.svg|Flavopiridol
File:Alvocidib_ball-and-stick.png|Alvocidib ball-and-stick model
</gallery>

Revision as of 19:20, 22 March 2025

A cyclin-dependent kinase inhibitor used in cancer treatment


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