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Romidepsin

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ACTIVE PHARMA INGREDIENTS

8 API Suppliers, 5 USDMF, 2 EU WC, 3 NDC API, 5 Listed Suppliers, $ API Reference Price

8 API Suppliers
5 USDMF
2 EU WC
3 NDC API
5 Listed Suppliers
$ API Reference Price

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1 Drugs in Development

1 Drugs in Development

FINISHED DOSAGE FORMULATIONS

5 FDF Dossiers, 4 FDA Orange Book, 1 Canada

5 FDF Dossiers
4 FDA Orange Book
1 Canada

DIGITAL CONTENT

1 DATA COMPILATION #PharmaFlow, 6 NEWS #PharmaBuzz

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1 DATA COMPILATION #PharmaFlow
6 NEWS #PharmaBuzz

GLOBAL SALES INFORMATION

1 US Medicaid Prescriptions, 5 Annual Reports

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1 US Medicaid Prescriptions
5 Annual Reports

MARKET PLACE

1 APIs, 2 FDF Dossiers

marketPlace
1 APIs
2 FDF Dossiers

Synopsis

ACTIVE PHARMA INGREDIENTS

API Suppliers

USDMF

CEP/COS

JDMF

EU WC

KDMF

NDC API

VMF

Listed Suppliers

API REF. PRICE (USD/KG)

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FINISHED DOSAGE FORMULATIONS

FDF Dossiers

FDA Orange Book

Europe

Canada

Australia

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Listed Dossiers

DRUG PRODUCT COMPOSITIONS

REF. STANDARDS OR IMPURITIES

EDQM

USP

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PATENTS & EXCLUSIVITIES

US Patents

US Exclusivities

Health Canada Patents

DIGITAL CONTENT

Data Compilation #PharmaFlow

Stock Recap #PipelineProspector

Weekly News Recap #Phispers

News #PharmaBuzz

GLOBAL SALES INFORMATION

US Medicaid (USD)

544,384

Annual Reports (USD Million)

321

Finished Drug Prices

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Chemistry

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Also known as: Romidepsin, Depsipeptide, Fk228, Chromadax, 128517-07-7, Antibiotic fr 901228

Molecular Formula

C₂₄H₃₆N₄O₆S₂

Molecular Weight

540.7 g/mol

InChI Key

OHRURASPPZQGQM-GCCNXGTGSA-N

FDA UNII

CX3T89XQBK

romidepsin is a natural product found in Chromobacterium violaceum with data available.

Romidepsin is a Histone Deacetylase Inhibitor. The mechanism of action of romidepsin is as a Histone Deacetylase Inhibitor, and Bile Salt Export Pump Inhibitor, and Organic Anion Transporting Polypeptide 1B1 Inhibitor, and Organic Anion Transporting Polypeptide 1B3 Inhibitor, and Organic Anion Transporter 1 Inhibitor, and Organic Cation Transporter 2 Inhibitor.

1 2D Structure

Romidepsin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1S,4S,7Z,10S,16E,21R)-7-ethylidene-4,21-di(propan-2-yl)-2-oxa-12,13-dithia-5,8,20,23-tetrazabicyclo[8.7.6]tricos-16-ene-3,6,9,19,22-pentone

2.1.2 InChI

InChI=1S/C24H36N4O6S2/c1-6-16-21(30)28-20(14(4)5)24(33)34-15-9-7-8-10-35-36-12-17(22(31)25-16)26-23(32)19(13(2)3)27-18(29)11-15/h6-7,9,13-15,17,19-20H,8,10-12H2,1-5H3,(H,25,31)(H,26,32)(H,27,29)(H,28,30)/b9-7+,16-6-/t15-,17-,19-,20+/m1/s1

2.1.3 InChI Key

OHRURASPPZQGQM-GCCNXGTGSA-N

2.1.4 Canonical SMILES

CC=C1C(=O)NC(C(=O)OC2CC(=O)NC(C(=O)NC(CSSCCC=C2)C(=O)N1)C(C)C)C(C)C

2.1.5 Isomeric SMILES

C/C=C\1/C(=O)N[C@H](C(=O)O[C@H]\2CC(=O)N[C@@H](C(=O)N[C@H](CSSCC/C=C2)C(=O)N1)C(C)C)C(C)C

2.2 Other Identifiers

2.2.1 UNII

CX3T89XQBK

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Fk228

2. Fr 901228

3. Fr-901228

4. Fr901228

5. L-valine, N-(3-hydroxy-7-mercapto-1-oxo-4-heptenyl)-d-valyl-d-cysteinyl-(z)-2,3-didehydro-2-aminobutanoyl-, Xi-lactone, Cyclic (1-2)-disulfide, (s-(e))-

6. Romidepsin

2.3.2 Depositor-Supplied Synonyms

1. Romidepsin

2. Depsipeptide

3. Fk228

4. Chromadax

5. 128517-07-7

6. Antibiotic Fr 901228

7. Fr901228

8. Fk 228

9. Fk-228

10. Fr 901228

11. Fr-901228

12. Nsc-630176

13. Chembl343448

14. (1s,4s,7z,10s,16e,21r)-7-ethylidene-4,21-di(propan-2-yl)-2-oxa-12,13-dithia-5,8,20,23-tetrazabicyclo[8.7.6]tricos-16-ene-3,6,9,19,22-pentone

15. Chebi:61080

16. Nsc 630176

17. Nsc630176

18. Nsc754143

19. (1s,4s,7z,10s,16e,21r)-7-ethylidene-4,21-di(propan-2-yl)-2-oxa-12,13-dithia-5,8,20,23-tetraazabicyclo[8.7.6]tricos-16-ene-3,6,9,19,22-pentone

20. C24h36n4o6s2

21. (1s,4s,7z,10s,16e,21r)-7-ethylidene-4,21-bis(propan-2-yl)-2-oxa-12,13-dithia-5,8,20,23-tetraazabicyclo[8.7.6]tricos-16-ene-3,6,9,19,22-pentone

22. Istodax (tn)

23. Romidepsin [usan]

24. Cx3t89xqbk

25. (1s,4s,7z,10s,16e,21r)-7-ethylidene-4,21-bis(1-methylethyl)-2-oxa-12,13-dithia-5,8,20,23-tetraazabicyclo(8.7.6)tricos-16-ene-3,6,9,19,22-pentone

26. Hdinhib_000006

27. Romidepsina

28. Romidepsine

29. Romidepsinum

30. Oxa-12,8,20,23-tetrazabicyclo[8.7.6]tricosane, Cyclic Peptide Deriv.

31. Romidepsin (fk228)

32. Romidepsin; Fk-228

33. Romidepsin [mi]

34. Fk-901228

35. Romidepsin [inn]

36. Romidepsin [jan]

37. Romidepsin [vandf]

38. Probes1_000153

39. Probes2_000337

40. Romidepsin [mart.]

41. Romidepsin [who-dd]

42. Depsipeptide [who-dd]

43. Romidepsin (jan/usan/inn)

44. Schembl677497

45. Gtpl7006

46. Romidepsin [orange Book]

47. Romidepsin, >=98% (hplc)

48. Bdbm19151

49. Romidepsin (fk228 ,depsipeptide)

50. Cyclo((2z)-2-amino-2-butenoyl-l-valyl-(3s,4e)-3-hydroxy-7-mercapto-4-heptenoyl-d-valyl-d-cysteinyl), Cyclic (3->5)-disulfide

51. Zinc3935130

52. Mfcd18433404

53. S3020

54. Api0005301

55. Cs-0985

56. Db06176

57. Nsc-754143

58. Hy-15149

59. D06637

60. Ab01273968-01

61. Sr-01000941579

62. Q7363205

63. Sr-01000941579-1

64. L-valine,3-didehydro-2- Aminobutanoyl-,.xi.-lactone, Cyclic (1.fwdarw.2)-disulfide

65. L-valine,3-didehydro-2-aminobutanoyl-,.xi.-lactone, Cyclic (1.fwdarw.2)-disulfide

66. (1s,4s,7z,10s,16e,21r)-7- Ethylidene-4,21-di(propan-2-yl)-2-oxa-12,13-dithia-5,8,20,23- Tetrazabicyclo[8.7.6]tricos-16-ene-3,6,9,19,22-pentone

67. (1s,4s,7z,10s,16e,21r)-7-ethylidene-4,21-bis(1methylethyl)-2-oxa-12,13-dithia-5,8,20,23-tetraazabicyclo[8.7.6]tricos-16ene-3,6,9,19,22-pentone

68. (e)-(1s,10s,21r)-7-[(z)-ethylidene]-4,21-diisopropyl-2- Oxa-12,13-dithia-5,8,20,23- Tetraazabicyclo[8.7.6]tricos-16-ene-3,6,9,19,22-pentone

69. (e)-(1s,10s,21r)-7-[(z)-ethylidene]-4,21-diisopropyl-2- Oxa-12,13-dithia-5,8,20,23-tetraazabicyclo[8.7.6]tricos-16-ene-3,6,9,19,22-pentone

70. Cyclo((2z)-2-amino-2-butenoyl-l-valyl-(3s,4e)-3-hydroxy-7-mercapto-4-heptenoyl-d-valyl-d-cysteinyl), Cyclic (3->5)-disulphide

71. Cyclo[(2z)-2-amino-2-butenoyl-l-val Yl-(3s,4e)-3-hydroxy-7-mercapto-4-heptenoyl-d-valy L-d-cysteinyl], Cyclic (3-5) Disulfide

72. Cyclo[(2z)-2-amino-2-butenoyl-l-valyl-(3s,4e)-3-hydroxy-7-mercapto-4-heptenoyl-d-valyl-d-cysteinyl], Cyclic (3-5) Disulfide

2.4 Create Date

2006-02-02

3 Chemical and Physical Properties

Molecular Formula	C₂₄H₃₆N₄O₆S₂
Molecular Weight	540.7 g/mol
XLogP3	2.2
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	2
Exact Mass	540.20762723 g/mol
Monoisotopic Mass	540.20762723 g/mol
Topological Polar Surface Area	193 Å²
Heavy Atom Count	36
Formal Charge	0
Complexity	905
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	2
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For the treatment of cutaneous T-cell lymphoma (CTCL) or/and peripheral T-cell lymphoma (PTCL) in patients who have received at least one prior systemic therapy. These indications are based on response rate. Clinical benefit such as improvement in overall survival has not been demonstrated.

FDA Label

treatment of peripheral T-cell lymphoma (PTCL),

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antibiotics, Antineoplastic

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)

Histone Deacetylase Inhibitors

Compounds that inhibit HISTONE DEACETYLASES. This class of drugs may influence gene expression by increasing the level of acetylated HISTONES in specific CHROMATIN domains. (See all compounds classified as Histone Deacetylase Inhibitors.)

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

ROMIDEPSIN

5.2.2 FDA UNII

CX3T89XQBK

5.2.3 Pharmacological Classes

Histone Deacetylase Inhibitor [EPC]; Histone Deacetylase Inhibitors [MoA]; Organic Anion Transporter 1 Inhibitors [MoA]; Organic Anion Transporting Polypeptide 1B1 Inhibitors [MoA]; Organic Anion Transporting Polypeptide 1B3 Inhibitors [MoA]; Organic Cation Transporter 2 Inhibitors [MoA]; Bile Salt Export Pump Inhibitors [MoA]

5.3 ATC Code

L01XX39

L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01X - Other antineoplastic agents

L01XH - Histone deacetylase (hdac) inhibitors

L01XH02 - Romidepsin

5.4 Absorption, Distribution and Excretion

Absorption

Romidepsin exhibited linear pharmacokinetics at standard doses.

Volume of Distribution

44.5L

Clearance

8.4L/h

5.5 Metabolism/Metabolites

Romidepsin undergoes extensive hepatic metabolism in vitro primarily by CYP3A4 with minor contribution from CYP3A5, CYP1A1, CYP2B6 and CYP2C19.

5.6 Biological Half-Life

Approximately 3 hours

5.7 Mechanism of Action

Romidepsin is a prodrug, where it becomes active once taken up into the cell. The active metabolite has a free thiol group, which interacts with zinc ions in the active site of class 1 and 2 HDAC enzymes, resulting in inhibition of its enzymatic activity. Certain tumors have over expressed HDACs and downregulated/mutated histone acetyltransferases. This imbalance of HDAC relative to histone acetyltransferase can lead to a decrease in regulatory genes, ensuing tumorigenesis. Inhibition of HDAC may restore normal gene expression in cancer cells and result in cell cycle arrest and apoptosis.

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API Reference Price

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