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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 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 Formula	C₂₁H₂₀ClNO₅
Molecular Weight	401.8 g/mol
XLogP3	3.3
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	2
Exact Mass	401.1030004 g/mol
Monoisotopic Mass	401.1030004 g/mol
Topological Polar Surface Area	90.2 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	628
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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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