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Sobuzoxane

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Chemistry

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Also known as: 98631-95-9, Mst 16, Mst-16, [4-[2-[4-(2-methylpropoxycarbonyloxymethyl)-3,5-dioxopiperazin-1-yl]ethyl]-2,6-dioxopiperazin-1-yl]methyl 2-methylpropyl carbonate, Perazolin, R1308vh37p

Molecular Formula

C₂₂H₃₄N₄O₁₀

Molecular Weight

514.5 g/mol

InChI Key

OCOKWVBYZHBHLU-UHFFFAOYSA-N

FDA UNII

R1308VH37P

Sobuzoxane is the orally available active prodrug of ICRF-154, a bisdioxopiperazine derivative, with cardioprotective and antineoplastic activities. Like other ICRF compounds, sobuzoxane and its active metabolite ICRF-154 interfere with topoisomerase II activity prior to the formation of intermediate cleavable DNA-enzyme complexes during the catalytic cycle resulting in tumor cell growth inhibition. Furthermore, sobuzoxane chelates metal cations thereby limiting the formation of free radical-generating anthracycline-metal complexes and may prevent anthracycline-induced oxidative damage to cardiac and soft tissues.

1 2D Structure

Sobuzoxane

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[4-[2-[4-(2-methylpropoxycarbonyloxymethyl)-3,5-dioxopiperazin-1-yl]ethyl]-2,6-dioxopiperazin-1-yl]methyl 2-methylpropyl carbonate

2.1.2 InChI

InChI=1S/C22H34N4O10/c1-15(2)11-33-21(31)35-13-25-17(27)7-23(8-18(25)28)5-6-24-9-19(29)26(20(30)10-24)14-36-22(32)34-12-16(3)4/h15-16H,5-14H2,1-4H3

2.1.3 InChI Key

OCOKWVBYZHBHLU-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C)COC(=O)OCN1C(=O)CN(CC1=O)CCN2CC(=O)N(C(=O)C2)COC(=O)OCC(C)C

2.2 Other Identifiers

2.2.1 UNII

R1308VH37P

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1,2-bis(4-isobutoxycarbonyloxymethyl-3,5-dioxopiperazin-1-yl)ethane

2. Mst 16

3. Mst-16

2.3.2 Depositor-Supplied Synonyms

1. 98631-95-9

2. Mst 16

3. Mst-16

4. [4-[2-[4-(2-methylpropoxycarbonyloxymethyl)-3,5-dioxopiperazin-1-yl]ethyl]-2,6-dioxopiperazin-1-yl]methyl 2-methylpropyl Carbonate

5. Perazolin

6. R1308vh37p

7. Sobuzoxane (jan)

8. Ncgc00015954-02

9. Sobuzoxane [jan]

10. Sobuzoxano

11. Sobuzoxanum

12. Sobuzoxane [inn:jan]

13. Sobuzoxanum [inn-latin]

14. 4,4'-(1,2-ethanediyl)bis(1-iso-butoxycarbonyloxmethyl-2,6-piperazinedione)

15. Sobuzoxano [inn-spanish]

16. Brn 6031322

17. Unii-r1308vh37p

18. Perazolin (tn)

19. Sobuzoxane [mi]

20. Sobuzoxane [inn]

21. Lopac-s-4692

22. 1,2-bis(4-isobutoxycarbonyloxymethyl-3,5-dioxo-piperazin-1-yl)ethane

23. Sobuzoxane [mart.]

24. 4,4'-ethylenebis(1-(hydroxymethyl)-2,6-piperazinedione) Bis(isobutyl Carbonate) (ester)

25. Dsstox_cid_25203

26. Dsstox_rid_80747

27. Sobuzoxane [who-dd]

28. Dsstox_gsid_45203

29. Lopac0_001094

30. Schembl18416

31. Mls002153414

32. Chembl1256871

33. Dtxsid5045203

34. Chebi:32136

35. Hms2230c04

36. Hms3263k10

37. Hms3369l07

38. Tox21_110265

39. Tox21_501094

40. Mfcd00866498

41. Zinc22032147

42. Sobuzoxane, >=99% (hplc), Solid

43. Ccg-205171

44. Lp01094

45. Sdccgsbi-0051064.p002

46. Ncgc00015954-01

47. Ncgc00015954-03

48. Ncgc00015954-04

49. Ncgc00094367-01

50. Ncgc00094367-02

51. Ncgc00261779-01

52. Carbonic Acid, 1,2-ethanediylbis((2,6-dioxo-4,1-piperazinediyl)methylene)bis(2-methylpropyl) Ester

53. Smr001230790

54. Cas-98631-95-9

55. Eu-0101094

56. 1-n-trityl-imidazole-2-ylpropionicacid

57. D01404

58. F52515

59. S 4692

60. 631s959

61. A839107

62. Sr-01000075401

63. Sr-01000075401-2

64. Q27287640

65. 4,4'-(1,2-ethanediyl)bis(1-isobutoxycarbonyloxmethyl-2,6-piperazinedione)

66. 4,4'-(1,2-ethanediyl)bis(1-isobutoxycarbonyloxymethyl-2,6-piperazinedione)

67. (4,4'-(ethane-1,2-diyl)bis(2,6-dioxopiperazine-4,1-diyl))bis(methylene) Isobutyl Dicarbonate

68. [4-[2-[4-(2-methylpropoxycarbonyloxymethyl)-3,5-bis(oxidanylidene)piperazin-1-yl]ethyl]-2,6-bis(oxidanylidene)piperazin-1-yl]methyl 2-methylpropyl Carbonate

69. [4-[2-[4-(2-methylpropoxycarbonyloxymethyl)-3,5-dioxo-piperazin-1-yl]ethyl]-2,6-dioxo-piperazin-1-yl]methyl 2-methylpropyl Carbonate

70. Carbonic Acid [4-[2-[4-[[2-methylpropoxy(oxo)methoxy]methyl]-3,5-dioxo-1-piperazinyl]ethyl]-2,6-dioxo-1-piperazinyl]methyl 2-methylpropyl Ester

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₃₄N₄O₁₀
Molecular Weight	514.5 g/mol
XLogP3	2
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	15
Exact Mass	514.22749329 g/mol
Monoisotopic Mass	514.22749329 g/mol
Topological Polar Surface Area	152 Å²
Heavy Atom Count	36
Formal Charge	0
Complexity	743
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Antineoplastic Agents

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

Topoisomerase II Inhibitors

Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II. (See all compounds classified as Topoisomerase II Inhibitors.)

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