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Cepharanthine

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Chemistry

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Also known as: 481-49-2, Cepharanthin, (+)-cepharanthine, O-methylcepharanoline, Cepharantin, Cepharanthine [jan]

Molecular Formula

C₃₇H₃₈N₂O₆

Molecular Weight

606.7 g/mol

InChI Key

YVPXVXANRNDGTA-WDYNHAJCSA-N

FDA UNII

7592YJ0J6T

(14S,27R)-22,33-dimethoxy-13,28-dimethyl-2,5,7,20-tetraoxa-13,28-diazaoctacyclo[25.6.2.2,.1,.1,.0,.0,.0,]nonatriaconta-1(34),3,8,10(39),16,18,21(36),22,24,31(35),32,37-dodecaene is a natural product found in Stephania sinica, Stephania cephalantha, and other organisms with data available.

1 2D Structure

Cepharanthine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(14S,27R)-22,33-dimethoxy-13,28-dimethyl-2,5,7,20-tetraoxa-13,28-diazaoctacyclo[25.6.2.216,19.13,10.121,25.04,8.031,35.014,39]nonatriaconta-1(33),3(39),4(8),9,16(38),17,19(37),21,23,25(36),31,34-dodecaene

2.1.2 InChI

InChI=1S/C37H38N2O6/c1-38-13-11-24-18-31(41-4)33-20-27(24)28(38)16-23-7-10-30(40-3)32(17-23)44-26-8-5-22(6-9-26)15-29-35-25(12-14-39(29)2)19-34-36(37(35)45-33)43-21-42-34/h5-10,17-20,28-29H,11-16,21H2,1-4H3/t28-,29+/m1/s1

2.1.3 InChI Key

YVPXVXANRNDGTA-WDYNHAJCSA-N

2.1.4 Canonical SMILES

CN1CCC2=CC3=C(C4=C2C1CC5=CC=C(C=C5)OC6=C(C=CC(=C6)CC7C8=CC(=C(C=C8CCN7C)OC)O4)OC)OCO3

2.1.5 Isomeric SMILES

CN1CCC2=CC3=C(C4=C2[C@@H]1CC5=CC=C(C=C5)OC6=C(C=CC(=C6)C[C@@H]7C8=CC(=C(C=C8CCN7C)OC)O4)OC)OCO3

2.2 Other Identifiers

2.2.1 UNII

7592YJ0J6T

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 6',12'-dimethoxy-2,2'-dimethyl-6,7-(methylenebis(oxy))oxyacanthan

2. Cepharanthin

2.3.2 Depositor-Supplied Synonyms

1. 481-49-2

2. Cepharanthin

3. (+)-cepharanthine

4. O-methylcepharanoline

5. Cepharantin

6. Cepharanthine [jan]

7. 6',12'-dimethoxy-2,2'-dimethyl-6,7-(methylenebis(oxy))oxyacanthan

8. Nsc-623442

9. Chebi:3546

10. 7592yj0j6t

11. Nsc623442

12. Cepharanthine (jan)

13. (14s,27r)-22,33-dimethoxy-13,28-dimethyl-2,5,7,20-tetraoxa-13,28-diazaoctacyclo[25.6.2.216,19.13,10.121,25.04,8.031,35.014,39]nonatriaconta-1(33),3(39),4(8),9,16(38),17,19(37),21,23,25(36),31,34-dodecaene

14. Oxyacanthan, 6',12'-dimethoxy-2,2'-dimethyl-6,7-(methylenebis(oxy))-

15. Ecaene (non-preferred Name)

16. Dsstox_cid_25957

17. Dsstox_rid_81253

18. Dsstox_gsid_45957

19. 22,33-dimethoxy-13,28-dimethyl-2,5,7,20-tetraoxa-13,28-diazaoctacyclo[25.6.2.216,19.13,10.121,25.04,8.031,35.014,39]nonatriaconta-1(33),3(39),4(8),9,16(38),17,19(37),21,23,25(36),31,34-dodecaene

20. Cas-481-49-2

21. Ccris 6539

22. Sr-01000779734

23. Nsc 623442

24. Brn 0075231

25. Unii-7592yj0j6t

26. Cepharanthin,(s)

27. Ncgc00095194-01

28. (14s,27r)-22,33-dimethoxy-13,28-dimethyl-2,5,7,20-tetraoxa-13,28-diazaoctacyclo[25.6.2.2~16,19~.1~3,10~.1~21,25~.0~4,8~.0~14,39~.0~31,35~]nonatriaconta-1(33),3,8,10(39),16,18,21(36),22,24,31,34,37-dod

29. Cepharanthine (tn)

30. Spectrum2_000832

31. Spectrum3_001963

32. 12-o-methylcepharanoline

33. Cepharanthine [mi]

34. Upcmld-dp054

35. Bspbio_003563

36. 4-27-00-09061 (beilstein Handbook Reference)

37. Mls000728518

38. Schembl154545

39. Spectrum1505322

40. Spbio_000783

41. Cepharanthine [who-dd]

42. Chembl449782

43. Dtxsid6045957

44. Upcmld-dp054:001

45. Kbio3_002909

46. Cepharanthine, >=95% (hplc)

47. Cepharanthine, >=98% (hplc)

48. Hms1922j12

49. Hms2232f21

50. Pharmakon1600-01505322

51. Hy-n6972

52. Tox21_111483

53. Bbl030154

54. Bdbm50423643

55. Ccg-40294

56. Mfcd00210482

57. Nsc758965

58. S4238

59. Stk801907

60. Zinc30726863

61. Akos004119865

62. Tox21_111483_1

63. Nsc-758965

64. Sdccgmls-0066893.p001

65. Ncgc00161621-01

66. Ncgc00161621-02

67. Ncgc00161621-03

68. Ncgc00161621-05

69. Ncgc00161621-13

70. Ac-15206

71. As-17451

72. Smr000445632

73. Sbi-0207049.p001

74. Cs-0007138

75. M2968

76. C09391

77. D01035

78. Ab00643356_08

79. Ab00643356_09

80. 481c492

81. A871948

82. Q-100524

83. Sr-01000779734-3

84. Sr-01000779734-4

85. Brd-k96194081-001-06-0

86. Q15410888

87. (14s,27r)-22,33-dimethoxy-13,28-dimethyl-2,5,7,20-tetraoxa-13,28-diazaoctacyclo[25.6.2.2(16,19).1(3,10).1(21,25).0(4,8).0(14,39).0(31,35)]nonatriaconta-1(33),3,8,10(39),16,18,21(36),22,24,31,34,37-dodecaene

88. (14s,27r)-22,33-dimethoxy-13,28-dimethyl-2,5,7,20-tetraoxa-13,28-diazaoctacyclo[25.6.2.2??,??.1?,??.1??,??.0?,?.0??,??.0??,??]nonatriaconta-1(33),3,8,10(39),16,18,21(36),22,24,31,34,37-dodecaene

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₃₇H₃₈N₂O₆
Molecular Weight	606.7 g/mol
XLogP3	6.5
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	2
Exact Mass	606.27298694 g/mol
Monoisotopic Mass	606.27298694 g/mol
Topological Polar Surface Area	61.9 Å²
Heavy Atom Count	45
Formal Charge	0
Complexity	994
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
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

Anti-Inflammatory Agents, Non-Steroidal

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

Radiation-Protective Agents

Drugs used to protect against ionizing radiation. They are usually of interest for use in radiation therapy but have been considered for other purposes, e.g. military. (See all compounds classified as Radiation-Protective Agents.)

Antineoplastic Agents, Phytogenic

Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. (See all compounds classified as Antineoplastic Agents, Phytogenic.)

Drugs in Development