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Identification
- Name
- Alvocidib
- Accession Number
- DB03496
- Description
Alvocidib is a synthetic flavonoid based on an extract from an Indian plant for the potential treatment of cancer. It works by inhibiting cyclin-dependent kinases, arresting cell division and causing apoptosis in non-small lung cancer cells.
- Type
- Small Molecule
- Groups
- Experimental, Investigational
- Structure
Structure for Alvocidib (DB03496)
- Weight
- Average: 401.84
Monoisotopic: 401.103000462 - Chemical Formula
- C21H20ClNO5
- Synonyms
- alvocidib
- Alvocidib freebase
- Flavopiridol
- External IDs
- L86-8275
Pharmacology
- Indication
Investigated for use/treatment in esophageal cancer, leukemia (lymphoid), lung cancer, liver cancer, and lymphoma (unspecified).
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
- Not Available
- Mechanism of action
Inhibits cyclin-dependent kinases, arresting cell division and causing apoptosis in non-small lung cancer cells.
Target Actions Organism UCyclin-dependent kinase 2 inhibitorHumans UCyclin-dependent kinase 5 Not Available Humans UCyclin-dependent kinase 9 Not Available Humans UCyclin-dependent kinase 1 Not Available Humans UCyclin-dependent kinase 6 Not Available Humans UEpidermal growth factor receptor Not Available Humans UCyclin-dependent kinase 4 Not Available Humans UCyclin-dependent kinase 8 Not Available Humans UCyclin-dependent kinase 7 Not Available Humans UGlycogen phosphorylase, muscle form Not Available Humans UGlycogen phosphorylase, brain form Not Available Humans UGlycogen phosphorylase, liver form Not Available Humans - Absorption
- Not Available
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
- Not Available
- Route of elimination
- Not Available
- Half-life
- Not Available
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAbemaciclib Abemaciclib may decrease the excretion rate of Alvocidib which could result in a higher serum level. Adenine The metabolism of Alvocidib can be decreased when combined with Adenine. Afatinib Afatinib may decrease the excretion rate of Alvocidib which could result in a higher serum level. Alectinib Alectinib may decrease the excretion rate of Alvocidib which could result in a higher serum level. Amitriptyline The metabolism of Alvocidib can be decreased when combined with Amitriptyline. Apalutamide Apalutamide may increase the excretion rate of Alvocidib which could result in a lower serum level and potentially a reduction in efficacy. Atazanavir The metabolism of Alvocidib can be decreased when combined with Atazanavir. Avatrombopag Avatrombopag may decrease the excretion rate of Alvocidib which could result in a higher serum level. Baricitinib Baricitinib may decrease the excretion rate of Alvocidib which could result in a higher serum level. Beclomethasone dipropionate Beclomethasone dipropionate may decrease the excretion rate of Alvocidib which could result in a higher serum level. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Alvocidib hydrochloride D48MS3A6N9 131740-09-5 LGMSNQNWOCSPIK-LWHGMNCYSA-N
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Flavonoids
- Sub Class
- Flavones
- Direct Parent
- Flavones
- Alternative Parents
- 5-hydroxyflavonoids / 7-hydroxyflavonoids / Phenylpiperidines / Chromones / 1-hydroxy-2-unsubstituted benzenoids / Pyranones and derivatives / Aralkylamines / Chlorobenzenes / Aryl chlorides / Heteroaromatic compounds show 10 more
- Substituents
- 1,2-aminoalcohol / 1-benzopyran / 1-hydroxy-2-unsubstituted benzenoid / 5-hydroxyflavonoid / 7-hydroxyflavonoid / Alcohol / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Aryl chloride show 30 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- monochlorobenzenes, hydroxypiperidine, dihydroxyflavone (CHEBI:47344)
Chemical Identifiers
- UNII
- 45AD6X575G
- CAS number
- 146426-40-6
- InChI Key
- BIIVYFLTOXDAOV-YVEFUNNKSA-N
- InChI
- InChI=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
- IUPAC Name
- 2-(2-chlorophenyl)-5,7-dihydroxy-8-[(3S,4R)-3-hydroxy-1-methylpiperidin-4-yl]-4H-chromen-4-one
- SMILES
- CN1CC[[email protected]@H]([[email protected]](O)C1)C1=C(O)C=C(O)C2=C1OC(=CC2=O)C1=CC=CC=C1Cl
References
- Synthesis Reference
Kyoung Soon Kim, "Process for the preparation of chiral ketone intermediates useful for the preparation of flavopiridol and analogs." U.S. Patent US5908934, issued March, 1998.
US5908934- General References
- Not Available
- External Links
- PDB Entries
- 1c8k / 1e1y / 3blr / 3ebp / 4o71
Clinical Trials
- Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.094 mg/mL ALOGPS logP 2.81 ALOGPS logP 2.48 ChemAxon logS -3.6 ALOGPS pKa (Strongest Acidic) 6.71 ChemAxon pKa (Strongest Basic) 7.36 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 90.23 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 107.74 m3·mol-1 ChemAxon Polarizability 40.85 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9932 Blood Brain Barrier - 0.557 Caco-2 permeable + 0.6029 P-glycoprotein substrate Substrate 0.9095 P-glycoprotein inhibitor I Non-inhibitor 0.8213 P-glycoprotein inhibitor II Non-inhibitor 0.7929 Renal organic cation transporter Non-inhibitor 0.6429 CYP450 2C9 substrate Non-substrate 0.7975 CYP450 2D6 substrate Non-substrate 0.6651 CYP450 3A4 substrate Substrate 0.6517 CYP450 1A2 substrate Non-inhibitor 0.6845 CYP450 2C9 inhibitor Non-inhibitor 0.8621 CYP450 2D6 inhibitor Non-inhibitor 0.7374 CYP450 2C19 inhibitor Non-inhibitor 0.7358 CYP450 3A4 inhibitor Non-inhibitor 0.9008 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8937 Ames test Non AMES toxic 0.7686 Carcinogenicity Non-carcinogens 0.9375 Biodegradation Not ready biodegradable 0.9923 Rat acute toxicity 2.7659 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.5312 hERG inhibition (predictor II) Non-inhibitor 0.715
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Metal ion binding
- Specific Function
- Serine/threonine-protein kinase involved in the control of the cell cycle; essential for meiosis, but dispensable for mitosis. Phosphorylates CTNNB1, USP37, p53/TP53, NPM1, CDK7, RB1, BRCA2, MYC, N...
- Gene Name
- CDK2
- Uniprot ID
- P24941
- Uniprot Name
- Cyclin-dependent kinase 2
- Molecular Weight
- 33929.215 Da
References
- Zvelebil MJ: Flavopiridol Hoechst AG. IDrugs. 1998 Jun;1(2):241-6. [PubMed:18465538]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Tau-protein kinase activity
- Specific Function
- Proline-directed serine/threonine-protein kinase essential for neuronal cell cycle arrest and differentiation and may be involved in apoptotic cell death in neuronal diseases by triggering abortive...
- Gene Name
- CDK5
- Uniprot ID
- Q00535
- Uniprot Name
- Cyclin-dependent-like kinase 5
- Molecular Weight
- 33304.125 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transcription regulatory region dna binding
- Specific Function
- Protein kinase involved in the regulation of transcription. Member of the cyclin-dependent kinase pair (CDK9/cyclin-T) complex, also called positive transcription elongation factor b (P-TEFb), whic...
- Gene Name
- CDK9
- Uniprot ID
- P50750
- Uniprot Name
- Cyclin-dependent kinase 9
- Molecular Weight
- 42777.155 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Rna polymerase ii carboxy-terminal domain kinase activity
- Specific Function
- Plays a key role in the control of the eukaryotic cell cycle by modulating the centrosome cycle as well as mitotic onset; promotes G2-M transition, and regulates G1 progress and G1-S transition via...
- Gene Name
- CDK1
- Uniprot ID
- P06493
- Uniprot Name
- Cyclin-dependent kinase 1
- Molecular Weight
- 34095.14 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Cyclin-dependent protein serine/threonine kinase activity
- Specific Function
- Serine/threonine-protein kinase involved in the control of the cell cycle and differentiation; promotes G1/S transition. Phosphorylates pRB/RB1 and NPM1. Interacts with D-type G1 cyclins during int...
- Gene Name
- CDK6
- Uniprot ID
- Q00534
- Uniprot Name
- Cyclin-dependent kinase 6
- Molecular Weight
- 36938.025 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Ubiquitin protein ligase binding
- Specific Function
- Receptor tyrosine kinase binding ligands of the EGF family and activating several signaling cascades to convert extracellular cues into appropriate cellular responses. Known ligands include EGF, TG...
- Gene Name
- EGFR
- Uniprot ID
- P00533
- Uniprot Name
- Epidermal growth factor receptor
- Molecular Weight
- 134276.185 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Cyclin-dependent protein serine/threonine kinase regulator activity
- Specific Function
- Ser/Thr-kinase component of cyclin D-CDK4 (DC) complexes that phosphorylate and inhibit members of the retinoblastoma (RB) protein family including RB1 and regulate the cell-cycle during G(1)/S tra...
- Gene Name
- CDK4
- Uniprot ID
- P11802
- Uniprot Name
- Cyclin-dependent kinase 4
- Molecular Weight
- 33729.55 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Ubiquitin protein ligase activity
- Specific Function
- Component of the Mediator complex, a coactivator involved in regulated gene transcription of nearly all RNA polymerase II-dependent genes. Mediator functions as a bridge to convey information from ...
- Gene Name
- CDK8
- Uniprot ID
- P49336
- Uniprot Name
- Cyclin-dependent kinase 8
- Molecular Weight
- 53283.335 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transcription coactivator activity
- Specific Function
- Serine/threonine kinase involved in cell cycle control and in RNA polymerase II-mediated RNA transcription. Cyclin-dependent kinases (CDKs) are activated by the binding to a cyclin and mediate the ...
- Gene Name
- CDK7
- Uniprot ID
- P50613
- Uniprot Name
- Cyclin-dependent kinase 7
- Molecular Weight
- 39038.005 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Pyridoxal phosphate binding
- Specific Function
- Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known ...
- Gene Name
- PYGM
- Uniprot ID
- P11217
- Uniprot Name
- Glycogen phosphorylase, muscle form
- Molecular Weight
- 97091.265 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Pyridoxal phosphate binding
- Specific Function
- Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known ...
- Gene Name
- PYGB
- Uniprot ID
- P11216
- Uniprot Name
- Glycogen phosphorylase, brain form
- Molecular Weight
- 96695.18 Da
References
- Kaiser A, Nishi K, Gorin FA, Walsh DA, Bradbury EM, Schnier JB: The cyclin-dependent kinase (CDK) inhibitor flavopiridol inhibits glycogen phosphorylase. Arch Biochem Biophys. 2001 Feb 15;386(2):179-87. [PubMed:11368340]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Vitamin binding
- Specific Function
- Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known ...
- Gene Name
- PYGL
- Uniprot ID
- P06737
- Uniprot Name
- Glycogen phosphorylase, liver form
- Molecular Weight
- 97147.82 Da
References
- Kaiser A, Nishi K, Gorin FA, Walsh DA, Bradbury EM, Schnier JB: The cyclin-dependent kinase (CDK) inhibitor flavopiridol inhibits glycogen phosphorylase. Arch Biochem Biophys. 2001 Feb 15;386(2):179-87. [PubMed:11368340]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Steroid binding
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
- Gene Name
- UGT1A1
- Uniprot ID
- P22309
- Uniprot Name
- UDP-glucuronosyltransferase 1-1
- Molecular Weight
- 59590.91 Da
References
- Williams JA, Hyland R, Jones BC, Smith DA, Hurst S, Goosen TC, Peterkin V, Koup JR, Ball SE: Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos. 2004 Nov;32(11):1201-8. doi: 10.1124/dmd.104.000794. Epub 2004 Aug 10. [PubMed:15304429]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
- Gene Name
- ABCG2
- Uniprot ID
- Q9UNQ0
- Uniprot Name
- ATP-binding cassette sub-family G member 2
- Molecular Weight
- 72313.47 Da
References
- Nakanishi T, Karp JE, Tan M, Doyle LA, Peters T, Yang W, Wei D, Ross DD: Quantitative analysis of breast cancer resistance protein and cellular resistance to flavopiridol in acute leukemia patients. Clin Cancer Res. 2003 Aug 15;9(9):3320-8. [PubMed:12960118]
- Nakanishi T, Doyle LA, Hassel B, Wei Y, Bauer KS, Wu S, Pumplin DW, Fang HB, Ross DD: Functional characterization of human breast cancer resistance protein (BCRP, ABCG2) expressed in the oocytes of Xenopus laevis. Mol Pharmacol. 2003 Dec;64(6):1452-62. [PubMed:14645676]
- Shi Z, Parmar S, Peng XX, Shen T, Robey RW, Bates SE, Fu LW, Shao Y, Chen YM, Zang F, Chen ZS: The epidermal growth factor tyrosine kinase inhibitor AG1478 and erlotinib reverse ABCG2-mediated drug resistance. Oncol Rep. 2009 Feb;21(2):483-9. [PubMed:19148526]
Drug created on June 13, 2005 07:24 / Updated on July 02, 2020 07:26
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