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Chemistry

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Also known as: Flavopiridol, 146426-40-6, Alvocidib freebase, L86-8275, L 868275, L-868275
Molecular Formula
C21H20ClNO5
Molecular Weight
401.8  g/mol
InChI Key
BIIVYFLTOXDAOV-YVEFUNNKSA-N
FDA UNII
45AD6X575G

Alvocidib
Alvocidib is the free base form of a synthetic N-methylpiperidinyl chlorophenyl flavone compound. As an inhibitor of cyclin-dependent kinase, alvocidib induces cell cycle arrest by preventing phosphorylation of cyclin-dependent kinases (CDKs) and by down-regulating cyclin D1 and D3 expression, resulting in G1 cell cycle arrest and apoptosis. This agent is also a competitive inhibitor of adenosine triphosphate activity.
1 2D Structure

Alvocidib

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-(2-chlorophenyl)-5,7-dihydroxy-8-[(3S,4R)-3-hydroxy-1-methylpiperidin-4-yl]chromen-4-one
2.1.2 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
2.1.3 InChI Key
BIIVYFLTOXDAOV-YVEFUNNKSA-N
2.1.4 Canonical SMILES
CN1CCC(C(C1)O)C2=C(C=C(C3=C2OC(=CC3=O)C4=CC=CC=C4Cl)O)O
2.1.5 Isomeric SMILES
CN1CC[C@@H]([C@@H](C1)O)C2=C(C=C(C3=C2OC(=CC3=O)C4=CC=CC=C4Cl)O)O
2.2 Other Identifiers
2.2.1 UNII
45AD6X575G
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (-)cis-5,7-dihydroxy-2-(2-chlorophenyl)-8-(4-(3-hydroxy-1-methyl)piperidinyl)-4h-1-benzopyran-4-one

2. Flavopiridol

3. Hmr 1275

4. L 868275

5. L-868275

6. L86-8275

2.3.2 Depositor-Supplied Synonyms

1. Flavopiridol

2. 146426-40-6

3. Alvocidib Freebase

4. L86-8275

5. L 868275

6. L-868275

7. Flavopiridol (alvocidib)

8. Hmr-1275

9. Hmr 1274

10. 131740-09-5

11. L 86-8275

12. 2-(2-chlorophenyl)-5,7-dihydroxy-8-[(3s,4r)-3-hydroxy-1-methylpiperidin-4-yl]-4h-chromen-4-one

13. 2-(2-chlorophenyl)-5,7-dihydroxy-8-[(3s,4r)-3-hydroxy-1-methylpiperidin-4-yl]chromen-4-one

14. Chembl428690

15. 45ad6x575g

16. 2-(2-chlorophenyl)-5,7-dihydroxy-8-((3s,4r)-3-hydroxy-1-methylpiperidin-4-yl)-4h-chromen-4-one

17. 2-(2-chloro-phenyl)-5,7-dihydroxy-8-(3-hydroxy-1-methyl-piperidin-4-yl)-4h-benzopyran-4-one

18. Nsc 649890 Hcl

19. Mdl-107826a

20. 2-(2-chlorophenyl)-5,7-dihydroxy-8-[(3s,4r)-3-hydroxy-1-methyl-4-piperidyl]chromen-4-one

21. Alvocidib [inn]

22. Flavo

23. Flavoperidol

24. 4h-1-benzopyran-4-one, 2-(2-chlorophenyl)-5,7-dihydroxy-8-[(3s,4r)-3-hydroxy-1-methyl-4-piperidinyl]-

25. Alvocidib [usan]

26. L868275

27. Alvocidib [usan:inn]

28. Alvocidibum

29. Unii-45ad6x575g

30. Ccris 9399

31. 4h-1-benzopyran-4-one, 2-(2-chlorophenyl)-5,7-dihydroxy-8-((3s,4r)-3-hydroxy-1-methyl-4-piperidinyl)-

32. (-)cis-5,7-dihydroxy-2-(2-chlorophenyl)-8-(4-(3-hydroxy-1-methyl)piperidinyl)-4h-1-benzopyran-4-one

33. Nsc649890

34. 1c8k

35. 1e1y

36. Alvocidib (usan/inn)

37. Flavopiridol [mi]

38. Alvocidib [mart.]

39. Alvocidib [who-dd]

40. Schembl3652

41. Flavopiridol Hcl; Alvocidib

42. Bdbm5655

43. Gtpl5680

44. Chebi:47344

45. Dtxsid20904970

46. Ex-a1901

47. Flavopiridol,alvocidib, Hmr-1275

48. Hmr-1274

49. Mfcd20501884

50. Nsc799330

51. S1230

52. Zinc21288966

53. Am84422

54. Ccg-268666

55. Db03496

56. Nsc-799330

57. (-)-cis-5,7-dihydroxy-2-(2-chlorophenyl)-8-(4-(3-hydroxy-1-methyl)piperidinyl)-4h-1-benzopyran-4-one

58. 4h-1-benzopyran-4-one, 2-(2-chlorophenyl)-5,7-dihydroxy-8-((3r,4s)-3-hydroxy-1-methyl-4-piperidinyl)-, Rel-(-)-

59. 4h-1-benzopyran-4-one, 2-(2-chlorophenyl)-5,7-dihydroxy-8-(3-hydroxy-1-methyl-4-piperidinyl)-, Cis-(-)-

60. As-74761

61. Hy-10005

62. A25160

63. D09868

64. J-008219

65. Q4063441

66. Brd-k87909389-001-01-2

67. (-)-cis-2-(2-chlorophenyl)-5,7-dihydroxy-8-(3-hydroxy-1-methylpiperidin-4-yl)-4h-1-benzopyran-4-one

68. 2-(2-chlorophenyl)-5,7-dihydroxy-8-((3s,4r)-3-hydroxy-1-methylpiperidin-4-yl)-4h-chromen-4-one;alvocidib

69. 4h-1-benzopyran-4-one, 2-(2-chlorophenyl)-2,3-dihydro-5,7-dihydroxy-8-[(3s,4r)-3-hydroxy-1-methyl-4-piperidinyl]-

70. 5,7-dihydroxy-2-(2-chlorophenyl)-8-(1-methyl-3beta-hydroxypiperidin-4beta-yl)-4h-1-benzopyran-4-one

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 401.8 g/mol
Molecular Formula C21H20ClNO5
XLogP33.3
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count2
Exact Mass401.1030004 g/mol
Monoisotopic Mass401.1030004 g/mol
Topological Polar Surface Area90.2 Ų
Heavy Atom Count28
Formal Charge0
Complexity628
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Investigated for use/treatment in esophageal cancer, leukemia (lymphoid), lung cancer, liver cancer, and lymphoma (unspecified).


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)


Protein Kinase Inhibitors

Agents that inhibit PROTEIN KINASES. (See all compounds classified as Protein Kinase Inhibitors.)


Growth Inhibitors

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). (See all compounds classified as Growth Inhibitors.)


5.2 Metabolism/Metabolites

Flavopiridol 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.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.3 Mechanism of Action

Inhibits cyclin-dependent kinases, arresting cell division and causing apoptosis in non-small lung cancer cells.


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ABOUT THIS PAGE

Alvocidib Manufacturers

A Alvocidib manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Alvocidib, including repackagers and relabelers. The FDA regulates Alvocidib manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Alvocidib API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Alvocidib Suppliers

A Alvocidib supplier is an individual or a company that provides Alvocidib active pharmaceutical ingredient (API) or Alvocidib finished formulations upon request. The Alvocidib suppliers may include Alvocidib API manufacturers, exporters, distributors and traders.

click here to find a list of Alvocidib suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Alvocidib USDMF

A Alvocidib DMF (Drug Master File) is a document detailing the whole manufacturing process of Alvocidib active pharmaceutical ingredient (API) in detail. Different forms of Alvocidib DMFs exist exist since differing nations have different regulations, such as Alvocidib USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Alvocidib DMF submitted to regulatory agencies in the US is known as a USDMF. Alvocidib USDMF includes data on Alvocidib's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Alvocidib USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Alvocidib suppliers with USDMF on PharmaCompass.

Alvocidib GMP

Alvocidib Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Alvocidib GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Alvocidib GMP manufacturer or Alvocidib GMP API supplier for your needs.

Alvocidib CoA

A Alvocidib CoA (Certificate of Analysis) is a formal document that attests to Alvocidib's compliance with Alvocidib specifications and serves as a tool for batch-level quality control.

Alvocidib CoA mostly includes findings from lab analyses of a specific batch. For each Alvocidib CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Alvocidib may be tested according to a variety of international standards, such as European Pharmacopoeia (Alvocidib EP), Alvocidib JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Alvocidib USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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