Alvocidib
Basic information
- CAS
146426-40-6- Standard SMILES
CN1CC[C@H](c2c(O)cc(O)c3c(=O)cc(-c4ccccc4Cl)oc23)[C@H](O)C1- InChIKey
BIIVYFLTOXDAOV-YVEFUNNKSA-N- Molecular formula
- C21H20ClNO5
- Average molar mass
- 401.8 g/mol
- Monoisotopic mass
- 401.1030004
Overview
Alvocidib is a synthetic dihydroxyflavone that is 5,7-dihydroxyflavone which is substituted by a 3-hydroxy-1-methylpiperidin-4-yl group at position 8 and by a chlorine at the 2' position (the ()-3S,4R stereoisomer). A cyclin-dependent kinase 9 (CDK9) inhibitor, it has been studied for the treatment of acute myeloid leukaemia, arthritis and atherosclerotic plaque formation. It has a role as an antineoplastic agent, an antirheumatic drug, an apoptosis inducer and an EC 2.7.11.22 (cyclin-dependent kinase) inhibitor. It is a dihydroxyflavone, a hydroxypiperidine, a tertiary amino compound and a member of monochlorobenzenes. It is a conjugate base of an alvocidib(1+).
Names & identifiers
- Preferred name
- Alvocidib
- IUPAC
- 2-(2-chlorophenyl)-5,7-dihydroxy-8-[(3S,4R)-3-hydroxy-1-methylpiperidin-4-yl]chromen-4-one
- English name
- Flavopiridol
- Molecular formula
- C21H20ClNO5
- Molecular weight
- 401.84
Names & synonyms
FlavopiridolAlvocidib146426-40-6Alvocidib freebaseL86-8275L 868275L-868275alvocidibum2-(2-chlorophenyl)-5,7-dihydroxy-8-((3S,4R)-3-hydroxy-1-methylpiperidin-4-yl)-4H-chromen-4-oneHMR 12742-(2-chlorophenyl)-5,7-dihydroxy-8-[(3S,4R)-3-hydroxy-1-methylpiperidin-4-yl]-4H-chromen-4-one2-(2-chlorophenyl)-5,7-dihydroxy-8-[(3S,4R)-3-hydroxy-1-methylpiperidin-4-yl]chromen-4-one
Show more names
CS-180C077990Hmr 1275FlavopirodolHMR-1275
L 86-827545AD6X575G(-)cis-5,7-Dihydroxy-2-(2-chlorophenyl)-8-(4-(3-hydroxy-1-methyl)piperidinyl)-4H-1-benzopyran-4-oneCHEBI:47344DTXSID20904970(-)-cis-5,7-dihydroxy-2-(2-chlorophenyl)-8-(4-(3-hydroxy-1-methyl)piperidinyl)-4H-1-benzopyran-4-oneNSC-6498902-(2-chlorophenyl)-5,7-dihydroxy-8-((3S,4R)-3-hydroxy-1-methylpiperidin-4-yl)chromen-4-one
Database identifiers
- CAS
146426-40-6
Properties
Computed structural properties
- XLogP
- 3.3
- Topological polar surface area
- 90.2 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 2
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 628
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 52.5 °C · 52.5 °C
- Boiling point
- 603.6 · 603.6±55.0 °C(Predicted)
- Density
- 1.448 · 1.448±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 2 O; · insoluble in H2O; ≥40.2 mg/mL in DMSO; ≥85.4 mg/mL in EtOH with gentle warming and ultrasonic
- form
- Yellow powder.
- pka
- 6.16 · 6.16±0.40(Predicted)
- color
- Light yellow to yellow
- InChIKey
- BIIVYFLTOXDAOV-YVEFUNNKSA-N
- SMILES
- C1(C2=CC=CC=C2Cl)OC2=C([C@H]3CCN(C)C[C@H]3O)C(O)=CC(O)=C2C(=O)C=1
- CAS DataBase Reference
- 146426 · 146426-40-6(CAS DataBase Reference)
- FDA UNII
- 45 AD6X575G · 45AD6X575G
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- hs_code
- 2934999090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
Mechanism of ActionInhibits cyclin-dependent kinases, arresting cell division and causing apoptosis in non-small lung cancer cells.
Metabolism/MetabolitesFlavopiridol has known human metabolites that include (2S,3S,4S,5R)-6-[2-(2-chlorophenyl)-5-hydroxy-8-[(3S,4R)-3-hydroxy-1-methylpiperidin-4-yl]-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid.
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Endogenous or exogenous substances which inhibit the normal growth of human and animal cells or micro-organisms, as distinguished from those affecting plant growth (= PLANT GROWTH REGULATORS).
Agents that inhibit PROTEIN KINASES.
Applications
UsesAntineoplastic (cyclin-dependent kinase inhibitor)[Note—The trivial name, flavopiridol, has appeared in literature].
UsesFlavopiridol is a synthetic flavonoid derivative, potent inhibitor of CDKs. Inhibitor of CDK9 as a postexposure drug target for adenoviruses.
Additional notes
DefinitionChEBI: Alvocidib is a synthetic dihydroxyflavone that is 5,7-dihydroxyflavone which is substituted by a 3-hydroxy-1-methylpiperidin-4-yl group at position 8 and by a chlorine at the 2' position (the (-)-3S,4R stereoisomer). A cyclin-dependent kinase 9 (CDK9) inhibitor, it has been studied for the treatment of acute myeloid leukaemia, arthritis and atherosclerotic plaque formation. It has a role as an antineoplastic agent, an EC 2.7.11.22 (cyclin-dependent kinase) inhibitor, an antirheumatic drug and an apoptosis inducer. It is a dihydroxyflavone, a hydroxypiperidine, a member of monochlorobenzenes and a tertiary amino compound. It is a conjugate base of an alvocidib(1+).
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