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Triptolide

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Also known as: 38748-32-2, Nsc-163062, 19ald1s53j, Dtxsid5041144, (1s,2s,4s,5s,7r,8r,9s,11s,13s)-8-hydroxy-1-methyl-7-propan-2-yl-3,6,10,16-tetraoxaheptacyclo[11.7.0.02,4.02,9.05,7.09,11.014,18]icos-14(18)-en-17-one, (1s,2s,4s,5s,7r,8r,9s,11s,13s)-8-hydroxy-1-methyl-7-propan-2-yl-3,6,10,16-tetraoxaheptacyclo(11.7.0.02,4.02,9.05,7.09,11.014,18)icos-14(18)-en-17-one

Molecular Formula

C₂₀H₂₄O₆

Molecular Weight

360.4 g/mol

InChI Key

DFBIRQPKNDILPW-CIVMWXNOSA-N

FDA UNII

19ALD1S53J

also has antiangiogenic, anti-inflammatory, and neuroprotective activities; a phytogenic antineoplastic agent; a tri-epoxide phenanthrene from Chinese herb, Tripterygium wilfordii; structure

1 2D Structure

Triptolide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1S,2S,4S,5S,7R,8R,9S,11S,13S)-8-hydroxy-1-methyl-7-propan-2-yl-3,6,10,16-tetraoxaheptacyclo[11.7.0.02,4.02,9.05,7.09,11.014,18]icos-14(18)-en-17-one

2.1.2 InChI

InChI=1S/C20H24O6/c1-8(2)18-13(25-18)14-20(26-14)17(3)5-4-9-10(7-23-15(9)21)11(17)6-12-19(20,24-12)16(18)22/h8,11-14,16,22H,4-7H2,1-3H3/t11-,12-,13-,14-,16+,17-,18-,19+,20+/m0/s1

2.1.3 InChI Key

DFBIRQPKNDILPW-CIVMWXNOSA-N

2.2 Other Identifiers

2.2.1 UNII

19ALD1S53J

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 38748-32-2

2. Nsc-163062

3. 19ald1s53j

4. Dtxsid5041144

5. (1s,2s,4s,5s,7r,8r,9s,11s,13s)-8-hydroxy-1-methyl-7-propan-2-yl-3,6,10,16-tetraoxaheptacyclo[11.7.0.02,4.02,9.05,7.09,11.014,18]icos-14(18)-en-17-one

6. (1s,2s,4s,5s,7r,8r,9s,11s,13s)-8-hydroxy-1-methyl-7-propan-2-yl-3,6,10,16-tetraoxaheptacyclo(11.7.0.02,4.02,9.05,7.09,11.014,18)icos-14(18)-en-17-one

7. Refchem:192024

8. Dtxcid3021144

9. (1s,2s,4s,5s,7r,8r,9s,11s,13s)-8-hydroxy-1-methyl-7-(propan-2-yl)-3,6,10,16-tetraoxaheptacyclo(11.7.0.0^(2,4).0^(2,9).0^(5,7).0^(9,11).0^(14,18))icos-14(18)-en-17-one

10. 683-214-2

11. Pg490

12. Triptolid

13. Mfcd00210565

14. Nsc 163062

15. Chebi:9747

16. Chembl463763

17. Pg-490

18. (5bs,6as,7as,8r,8ar,9as,9bs,10as,10bs)-8-hydroxy-8a-isopropyl-10b-methyl-1,5,5b,6,6a,8,8a,9a,9b,10b-decahydrotris(oxireno)[2',3':4b,5;2'',3'':6,7;2''',3''':8a,9]phenanthro[1,2-c]furan-3(2h)-one

19. (3bs,4as,5as,6r,6ar,7as,7bs,8as,8bs)-6-hydroxy-8b-methyl-6a-(propan-2-yl)-3b,4,4a,6,6a,7a,7b,8b,9,10-decahydrotrisoxireno[6,7:8a,9:4b,5]phenanthro[1,2-c]furan-1(3h)-one

20. (6as,7as,8r,8ar,9as,9bs,10as,10bs)-8-hydroxy-8a-isopropyl-10b-methyl-1,5,5b,6,6a,8,8a,9a,9b,10b-decahydrotris(oxireno)[2',3':4b,5;2'',3'':6,7;2''',3''':8a,9]phenanthro[1,2-c]furan-3(2h)-one.

21. Smr000466307

22. Unii-19ald1s53j

23. Triptolide?

24. Triptolide, 1

25. Trisoxireno[6,7:8a,9:4b,5]phenanthro[1,2-c]furan-1(3h)-one, 3b,4,4a,6,6a,7a,7b,8b,9,10-decahydro-6-hydroxy-8b-methyl-6a-(1-methylethyl)-, (3bs,4as,5as,6r,6ar,7as,7bs,8as,8bs)-

26. Pg 490

27. Cpd000466307

28. Triptolide [mi]

29. Triptolide [who-dd]

30. Bspbio_001595

31. Kbiogr_000315

32. Kbioss_000315

33. Mls000759410

34. Mls001424107

35. Mls006010844

36. Schembl413634

37. Orb1306199

38. Ex-a7744a

39. Kbio2_000315

40. Kbio2_002883

41. Kbio2_005451

42. Kbio3_000629

43. Kbio3_000630

44. Bio2_000315

45. Bio2_000795

46. Glxc-06921

47. Hms1361p17

48. Hms1791p17

49. Hms1989p17

50. Hms2051n13

51. Hms3402p17

52. Msk40281

53. Bdbm50241049

54. Nsc163062

55. Nsc839303

56. S3604

57. Akos022168197

58. Ccg-100957

59. Cs-0286

60. Db12025

61. Ft28581

62. Nc00207

63. Nsc-839303

64. Idi1_034065

65. Ncgc00163411-01

66. Ncgc00163411-02

67. Ncgc00163411-03

68. Ncgc00163411-07

69. Bp-25386

70. Bs-16697

71. Hy-32735

72. Nci60_001223

73. Trisoxireno(4b,5:6,7:8a,9)phenanthro(1,2-c)furan-1(3h)-one, 3b,4,4a,6,6a,7a,7b,8b,9,10-decahydro-6-hydroxy-8b-methyl-6a-(1-methylethyl)-, (3bs,4as,5as,6r,6ar,7as,7bs,8as,8bs)-

74. Ns00018025

75. T2899

76. C09204

77. Ab00639938-06

78. Ab00639938-08

79. 748t322

80. F557653

81. Q906351

82. Brd-k39484304-001-02-5

83. Brd-k39484304-001-06-6

84. Brd-k39484304-001-16-5

85. Triptolide, Tripterygium Wilfordii - Cas 38748-32-2

86. (1s,2s,4s,5s,7r,8r,9s,11s)-8-hydroxy-1-methyl-7-propan-2-yl-3,6,10,16-tetraoxaheptacyclo[11.7.0.02,4.02,9.05,7.09,11.014,18]icos-14(18)-en-17-one

87. (1s,2s,4s,5s,7r,8r,9s,11s,13s)-8-hydroxy-7-isopropyl-1-methyl-3,6,10,16-tetraoxaheptacyclo[11.7.0.02,4.02,9.05,7.09,11.014,18]icos-14(18)-en-17-one

88. (3bs,4as,5as,6r,6ar,7as,7bs,8as,8bs)-3b,4,4a,6,6a,7a,7b,8b,9,10-decahydro-6-hydroxy-6a-isopropyl-8b-methyltrisoxireno(6,7:8a,9:4b,5)phenanthro(1,2-c)furan-1(3h)-one

89. (3bs,4as,5as,6r,6ar,7as,7bs,8as,8bs)-3b,4,4a,6,6a,7a,7b,8b,9,10-decahydro-6-hydroxy-8b-methyl-6a-(1-methylethyl)trisoxireno(4b,5:6,7:8a,9)phenanthro(1,2-c)furan-1(3h)-one

90. (5bs,6as,7as,8r,8ar,9as,9bs,10as,10bs)-8-hydroxy-8a-isopropyl-10b-methyl-2,5,5b,6,6a,8,8a,9a,9b,10b-decahydrotris(oxireno)[2',3':4b,5;2'',3'':6,7;2''',3''':8a,9]phenanthro[1,2-c]furan-3(1h)-one

91. Pg 490; (3bs,4as,5as,6r,6ar,7as,7bs,8as,8bs)-6-hydroxy-6a-isopropyl-8b-methyl-3b,4,4a,6,6a,7a,7b,8b,9,10-decahydrotrisoxireno[6,7:8a

92. Trisoxireno[4b,7:8a,9]phenanthro[1,2-c]furan-(3h)-one, 3b,4,4a,6,6a,7a,7b,8b,9,10-decahydro-6-hydroxy-8b-methyl-6a-(1-methylethyl)-, [3br-(3b.alpha.,4a.alpha.,5as*,6.beta.,6a.beta.,7a.beta.,7b.alpha.,8as*,8b.beta.)]-

93. Trisoxireno[4b,7:8a,9]phenanthro[1,2-c]furan-1(3h)-one, 3b,4,4a,6,6a,7a,7b,8b,9,10-decahydro-6-hydroxy-8b-methyl-6a-(1-methylethyl)-, [3br-(3b.alpha.,4a.alpha.,5as*,6.beta.,6a.beta.,7a.beta.,7b.alpha.,8as*,8b.beta.)]-

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₂₄O₆
Molecular Weight	360.4 g/mol
XLogP3	0.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	1
Exact Mass	Da
Monoisotopic Mass	Da
Topological Polar Surface Area	84.1
Heavy Atom Count	26
Formal Charge	0
Complexity	819
Isotope Atom Count	0
Defined Atom Stereocenter Count	9
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

Antispermatogenic Agents

Agents, either mechanical or chemical, which destroy spermatozoa in the male genitalia and block spermatogenesis.

Immunosuppressive Agents

Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging.

Antineoplastic Agents, Alkylating

A class of drugs that differs from other alkylating agents used clinically in that they are monofunctional and thus unable to cross-link cellular macromolecules. Among their common properties are a requirement for metabolic activation to intermediates with antitumor efficacy and the presence in their chemical structures of N-methyl groups, that after metabolism, can covalently modify cellular DNA. The precise mechanisms by which each of these drugs acts to kill tumor cells are not completely understood. (From AMA, Drug Evaluations Annual, 1994, p2026)

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