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DSSTox_CID_3706

DSSTox_CID_3706

Synopsis, Chemistry

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Also known as: 13647-35-3, Modrenal, Vetoryl, Desopan, Modrastane, Trilostanum

Molecular Formula

C₂₀H₂₇NO₃

Molecular Weight

329.4 g/mol

InChI Key

KVJXBPDAXMEYOA-CXANFOAXSA-N

FDA UNII

L0FPV48Q5R

Trilostane is a synthetic derivative of androstane with adrenocortical suppressive properties. Trilostane reversibly inhibits 3 beta-hydroxysteroid dehydrogenase delta 5-4 isomerase in the adrenal cortex, resulting in the decreased synthesis of mineralocorticoids and glucocorticoids and the decreased conversion of pregnenolone to progesterone. (NCI04)

1 2D Structure

DSSTox_CID_3706

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1S,2R,6R,8S,11S,12S,15S,16S)-5,15-dihydroxy-2,16-dimethyl-7-oxapentacyclo[9.7.0.02,8.06,8.012,16]octadec-4-ene-4-carbonitrile

2.1.2 InChI

InChI=1S/C20H27NO3/c1-18-7-6-14-12(13(18)3-4-15(18)22)5-8-20-17(24-20)16(23)11(10-21)9-19(14,20)2/h12-15,17,22-23H,3-9H2,1-2H3/t12-,13-,14-,15-,17+,18-,19+,20+/m0/s1

2.1.3 InChI Key

KVJXBPDAXMEYOA-CXANFOAXSA-N

2.1.4 Canonical SMILES

CC12CCC3C(C1CCC2O)CCC45C3(CC(=C(C4O5)O)C#N)C

2.1.5 Isomeric SMILES

C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CC[C@]45[C@@]3(CC(=C([C@H]4O5)O)C#N)C

2.2 Other Identifiers

2.2.1 UNII

L0FPV48Q5R

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4alpha,5-epoxy-17beta-hydroxy-3-oxoandrostane-2-carbonitrile

2. Modrenal

3. Win 24,540

2.3.2 Depositor-Supplied Synonyms

1. 13647-35-3

2. Modrenal

3. Vetoryl

4. Desopan

5. Modrastane

6. Trilostanum

7. Trilostano

8. Win-24540

9. Win 24,540

10. Chebi:32260

11. L0fpv48q5r

12. Win 24540

13. Androst-2-ene-2-carbonitrile, 4,5-epoxy-3,17-dihydroxy-, (4alpha,5alpha,17beta)-

14. Nsc-758904

15. Dsstox_cid_3706

16. Androst-2-ene-2-carbonitrile, 4,5-epoxy-3,17-dihydroxy-, (4a,5a,17b)-

17. Dsstox_rid_77157

18. Dsstox_gsid_23706

19. (1ar,4ar,4bs,6as,7s,9as,9bs,11as)-2,7-dihydroxy-4a,6a-dimethyl-1a,4,4a,4b,5,6,6a,7,8,9,9a,9b,10,11-tetradecahydrocyclopenta[7,8]phenanthro[1,10a-b]oxirene-3-carbonitrile

20. (1s,2r,6r,8s,11s,12s,15s,16s)-5,15-dihydroxy-2,16-dimethyl-7-oxapentacyclo[9.7.0.0^{2,8}.0^{6,8}.0^{12,16}]octadec-4-ene-4-carbonitrile

21. Modrenal (tn)

22. (1ar,4ar,4bs,6as,7s,9as,9bs,11as)-2,7-dihydroxy-4a,6a-dimethyl-1a,4,4a,4b,5,6,6a,7,8,9,9a,9b,10,11-tetradecahydrocyclopenta[7,8]phenanthro[1,10a-b]oxirene-3-carbonitrile.

23. (1s,2r,6r,8s,11s,12s,15s,16s)-5,15-dihydroxy-2,16-dimethyl-7-oxapentacyclo[9.7.0.02,8.06,8.012,16]octadec-4-ene-4-carbonitrile

24. Desopan (tn)

25. Cas-13647-35-3

26. Trilostane (jan/usan)

27. Trilostanum [inn-latin]

28. Trilostano [inn-spanish]

29. Unii-l0fpv48q5r

30. Androst-2-ene-2-carbonitrile, 4,5-epoxy-3,17-dihydroxy-, (4.alpha.,5.alpha.,17.beta.)-

31. Trilostane [usan:inn:ban:jan]

32. Ncgc00274061-01

33. Einecs 237-133-0

34. Mfcd00199295

35. Win 24450

36. Trilostane [mi]

37. Trilostane [inn]

38. Trilostane [jan]

39. Trilostane [usan]

40. Trilostane [vandf]

41. (4alpha,5alpha,17beta)-3,17-dihydroxy-4,5-epoxyandrost-2-ene-2-carbonitrile

42. Schembl7517

43. Trilostane [mart.]

44. Trilostane [who-dd]

45. Gtpl6850

46. Trilostane [green Book]

47. Chembl1200907

48. Dtxsid9023706

49. Trilostane [orange Book]

50. Trilostane, >=98% (hplc)

51. 4.alpha.,5-epoxy-3,17.beta.-dihydroxy-5.alpha.-androst-2-ene-2-carbonitrile

52. Hms3884a15

53. Bcp04132

54. Tox21_112454

55. Tox21_302406

56. 4-alpha,5-epoxy-3,17-dihydroxy-5-alpha-androst-2-ene-2-carbonitrile

57. Ac-927

58. Bdbm50247882

59. S1404

60. 3,17beta-dihydroxy-4alpha,5-epoxy-5alpha-androst-2-ene-2-carbonitrile

61. 4alpha,5-epoxy-3,17beta-dihydroxy-5alpha-androst-2-ene-2-carbonitrile

62. Akos015964043

63. Akos032947221

64. Tox21_112454_1

65. Zinc100038546

66. Ccg-267803

67. Cs-1707

68. Db01108

69. Ks-1414

70. Nsc 758904

71. (2-alpha,4-alpha,5-alpha,17-beta)-4,5-epoxy-17-hydroxy-3-oxoandrostane-2-carbonitrile

72. 4-alpha-5-epoxy-17-beta-hydroxy-3-oxo-5-alpha-androstane-2-alpha-carbonitrile

73. Androstane-2-carbonitrile, 4,5-epoxy-17-hydroxy-3-oxo-, (2-alpha,4-alpha,5-alpha,17-beta)-

74. Ncgc00255201-01

75. Hy-14281

76. Bcp0726000098

77. D01180

78. Ab01274788-01

79. Ab01274788_02

80. 647t353

81. A886681

82. Q907313

83. Q-201884

84. Z1563146079

85. Trilostane; 13647-35-3; Vetoryl; Modrenal; Modrastane

86. (4a,5a,17b)-3,17-dihydroxy-4,5-epoxyandrost-2-ene-2-carbonitrile

87. 5-alpha-androstane-2-alpha-carbonitrile, 4-alpha,5-epoxy-17-beta-hydroxy-3-oxo-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₂₇NO₃
Molecular Weight	329.4 g/mol
XLogP3	2.9
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	0
Exact Mass	329.19909372 g/mol
Monoisotopic Mass	329.19909372 g/mol
Topological Polar Surface Area	76.8 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	692
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
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

Used in the treatment of Cushing's syndrome. It is normally used in short-term treatment until permanent therapy is possible.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Trilostane blocks an enzyme involved in the production of several steroids including cortisol. Inhibiting this enzyme inhibits the production of cortisol. In Cushing's syndrome, the adrenal gland overproduces steroids. Although steroids are important for various functions of the body, too much can cause problems. Trilostane reduces the amount of steroids produced by the adrenal gland. This product was withdrawn from the U.S. market in April 1994.

5.2 MeSH Pharmacological Classification

Abortifacient Agents, Steroidal

Steroidal compounds with abortifacient activity. (See all compounds classified as Abortifacient Agents, Steroidal.)

Antineoplastic Agents

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

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. (See all compounds classified as Enzyme Inhibitors.)

5.3 ATC Code

H - Systemic hormonal preparations, excl. sex hormones and insulins

H02 - Corticosteroids for systemic use

H02C - Antiadrenal preparations

H02CA - Anticorticosteroids

H02CA01 - Trilostane

5.4 Metabolism/Metabolites

Hepatic.

5.5 Biological Half-Life

8 hours.

5.6 Mechanism of Action

Trilostane produces suppression of the adrenal cortex by inhibiting enzymatic conversion of steroids by 3-beta-hydroxysteroid dehydrogenase/delta 5,4 ketosteroid isomerase, thus blocking synthesis of adrenal steroids.