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Marimastat

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ACTIVE PHARMA INGREDIENTS

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Chemistry

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Also known as: 154039-60-8, Bb-2516, Bb 2516, Bb2516, D5eqv23tds, Nsc-719333

Molecular Formula

C₁₅H₂₉N₃O₅

Molecular Weight

331.41 g/mol

InChI Key

OCSMOTCMPXTDND-OUAUKWLOSA-N

FDA UNII

D5EQV23TDS

a matrix metalloproteinase inhibitor active in patients with advanced carcinoma of the pancreas, prostate, or ovary

1 2D Structure

Marimastat

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R,3S)-N-[(2S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]-N',3-dihydroxy-2-(2-methylpropyl)butanediamide

2.1.2 InChI

InChI=1S/C15H29N3O5/c1-8(2)7-9(10(19)13(21)18-23)12(20)17-11(14(22)16-6)15(3,4)5/h8-11,19,23H,7H2,1-6H3,(H,16,22)(H,17,20)(H,18,21)/t9-,10+,11-/m1/s1

2.1.3 InChI Key

OCSMOTCMPXTDND-OUAUKWLOSA-N

2.2 Other Identifiers

2.2.1 UNII

D5EQV23TDS

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Bb-2516

2.3.2 Depositor-Supplied Synonyms

1. 154039-60-8

2. Bb-2516

3. Bb 2516

4. Bb2516

5. D5eqv23tds

6. Nsc-719333

7. Gi5712

8. Kb-r 8898

9. Ta2516

10. Gi-5712

11. Ta-2516

12. (2s,3r)-3-(((1s)-2,2-dimethyl-1-(methylcarbamoxy)propyl)carboyl)-2-hydroxy-5-methylhexanohydroxamic Acid

13. Chebi:50662

14. Dtxsid20165524

15. Nsc689451

16. Nsc719333

17. Marimistat

18. (2s,3r)-n-[(1s)-2,2-dimethyl-1-(methylcarbamoyl)propyl]-n',2-dihydroxy-3-(2-methylpropyl)butanediamide

19. Marimastatum

20. (2s,3r)-n-((1s)-2,2-dimethyl-1-(methylcarbamoyl)propyl)-n',2-dihydroxy-3-(2-methylpropyl)butanediamide

21. Refchem:810621

22. Dtxcid3088015

23. (2s,3r)-3-((s)-(2,2-dimethyl-1-(methylcarbamoyl) Propyl)carbamoyl)-2-hydroxy-5-methylhexanohydroxamic Acid

24. Marimastat (bb-2516)

25. (2r,3s)-n1-((s)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)-n4,3-dihydroxy-2-isobutylsuccinamide

26. (2r,3s)-n-[(2s)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]-n',3-dihydroxy-2-(2-methylpropyl)butanediamide

27. Mfcd00866242

28. Bb2516;ta2516

29. Chembl279785

30. Marimastat [usan]

31. (2s,3r)-3-(((1s)-2,2-dimethyl-1-(methylcarbamoyl)propyl)carbamoyl)-2-hydroxy-5-methylhexanohydroxamic Acid

32. (2s,3r)-n(4)-[(2s)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]-n(1),2-dihydroxy-3-(2-methylpropyl)butanediamide

33. (2r)-n-[(1s)-2,2-dimethyl-1-(methylcarbamoyl)propyl]-2-[(1s)-1-hydroxy-2-(hydroxyamino)-2-oxo-ethyl]-4-methyl-pentanamide

34. (2s,3r)-n~4~-[(1s)-2,2-dimethyl-1-(methylcarbamoyl)propyl]-n~1~,2-dihydroxy-3-(2-methylpropyl)butanediamide

35. Butanediamide, N4-((1s)-2,2-dimethyl-1-((methylamino)carbonyl)propyl)-n1,2-dihydroxy-3-(2-methylpropyl)-, (2s,3r)-

36. Butanediamide, N4-[(1s)-2,2-dimethyl-1-[(methylamino)carbonyl]propyl]-n1,2-dihydroxy-3-(2-methylpropyl)-, (2s,3r)-

37. Smr002530328

38. Marimastat (usan/inn)

39. Unii-d5eqv23tds

40. Marimastat [usan:inn:ban]

41. (2s,3r)-3-[[(1s)-2,2-dimethyl-1-(methylcarbamoyl)propyl]carbamoyl]-2-hydroxy-5-methylhexanohydroxamic Acid

42. Butaneamide,2-dimethyl-1-[(methylamino)carbonyl]propyl]- N1,2-dihydroxy-3-(2-methylpropyl)-, (2s,3r)-

43. 3hy7

44. Marimastat [mi]

45. Marimastat [inn]

46. D03795

47. Marimastat [mart.]

48. Marimastat [who-dd]

49. Schembl34033

50. Mls003899230

51. Mls006010669

52. Cid_119031

53. Gtpl5220

54. Orb1300377

55. Marimastat, >=98% (hplc)

56. Ex-a643

57. Glxc-06760

58. Bdbm50063917

59. S7156

60. Akos024457206

61. Ccg-267821

62. Cs-3456

63. Db00786

64. Gi 5712

65. Nsc 719333

66. Nsc-689451

67. Ta 2516

68. Marimastat - Cas 154039-60-8

69. (2s,3r)-n'-[(1s)-2,2-dimethyl-1-(methylcarbamoyl)propyl]-n,2-dihydroxy-3-(2-methylpropyl)butanediamide

70. Ac-35828

71. As-57129

72. Butanediamide, N(sup 4)-(2,2-dimethyl-1-((methylamino)carbonyl)propyl)-n(sup 1),2-dihydroxy-3-(2-methylpropyl)-, (2s-(n(sup 4)(r*),2r*,3s*))-

73. Butanediamide, N4-(2,2-dimethyl-1-((methylamino)carbonyl)propyl)-n1,2-dihydroxy-3-(2-methylpropyl)-, (2s-(n4(r*),2r*,3s*))-

74. Fm161188

75. Hy-12169

76. Ns00068619

77. Q6763659

78. Brd-k21396683-001-04-8

79. (2s,3r)-n4-[(1s)-2,2-dimethyl-1-[(methylamino)carbonyl]propyl]-n1,2-dihydroxy-3-(2-methylpropyl)butanediamide;bb 2516;ta 2516

80. Butanediamide, N(sup 4)-(2,2-dimethyl-1-((methylamino)carbonyl)propyl)-n1,2-dihydroxy-3-(2-methylpropyl)-, (2s-(n4(r*),2r*,3s*))-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₂₉N₃O₅
Molecular Weight	331.41 g/mol
XLogP3	0.5
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	8
Exact Mass	Da
Monoisotopic Mass	Da
Topological Polar Surface Area	128
Heavy Atom Count	23
Formal Charge	0
Complexity	431
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
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

For the treatment of various cancers

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Enzyme Inhibitors

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.

5.2 Mechanism of Action

Marimastat is a broad spectrum matrix metalloprotease inhibitor. It mimics the peptide structure of natural MMP substrates and binds to matrix metalloproteases, thereby preventing the degradation of the basement membrane by these proteases. This antiprotease action prevents the migration of endothelial cells needed to form new blood vessels. Inhibition of MMPs also prevents the entry and exit of tumor cells into existing blood cells, thereby preventing metastasis.

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