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2 Methoxyestradiol

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Also known as: 362-07-2, Panzem, 2-methoxyestradiol-17beta, 2-hydroxyestradol 2-methyl ether, 2-me2, 2me2

Molecular Formula

C₁₉H₂₆O₃

Molecular Weight

302.4 g/mol

InChI Key

CQOQDQWUFQDJMK-SSTWWWIQSA-N

FDA UNII

6I2QW73SR5

A metabolite of estradiol that lacks estrogenic activity and inhibits TUBULIN polymerization. It has antineoplastic properties, including inhibition of angiogenesis and induction of APOPTOSIS.

1 2D Structure

2-Methoxyestradiol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(8R,9S,13S,14S,17S)-2-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol

2.1.2 InChI

InChI=1S/C19H26O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-16(20)17(22-2)10-14(11)12/h9-10,12-13,15,18,20-21H,3-8H2,1-2H3/t12-,13+,15-,18-,19-/m0/s1

2.1.3 InChI Key

CQOQDQWUFQDJMK-SSTWWWIQSA-N

2.1.4 Canonical SMILES

CC12CCC3C(C1CCC2O)CCC4=CC(=C(C=C34)OC)O

2.1.5 Isomeric SMILES

C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=CC(=C(C=C34)OC)O

2.2 Other Identifiers

2.2.1 UNII

6I2QW73SR5

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (17 Beta)-2-methoxyestra-1,3,5(10)-triene-3,17-diol

2. 2 Methoxyestradiol

3. 2 Methoxyestradiol 17 Beta

4. 2 Methoxyoestradiol

5. 2-(methyl-11c)methoxyestradiol

6. 2-methoxyestradiol, (17alpha)-isomer

7. 2-methoxyestradiol-17 Beta

8. 2-methoxyoestradiol

9. Panzem

2.3.2 Depositor-Supplied Synonyms

1. 362-07-2

2. Panzem

3. 2-methoxyestradiol-17beta

4. 2-hydroxyestradol 2-methyl Ether

5. 2-me2

6. 2me2

7. 2-meoe2

8. Estradiol, 2-methoxy-

9. 2-methoxyestradiol (2-meoe2)

10. 2-methoxyoestradiol

11. 2-hydroxyestradiol 2-methyl Ether

12. 2-methoxy-17beta-estradiol

13. Nsc-659853

14. (17beta)-2-methoxyestra-1,3,5(10)-triene-3,17-diol

15. 2-methoxyestra-1,3,5(10)-triene-3,17beta-diol

16. 2-methoxy-estradiol

17. 2-methoxy-beta-estradiol

18. Mls000028819

19. 6i2qw73sr5

20. Chembl299613

21. Chebi:28955

22. Estra-1,3,5(10)-triene-3,17-diol, 2-methoxy-, (17beta)-

23. Panzem Ncd

24. 1,3,5(10)-estratrien-2,3,17-beta-triol 2-methyl Ether

25. 2-methoxy-estra-1,3,5(10)-triene-3,17beta-diol

26. Estra-1,3,5(10)-triene-3,17beta-diol, 2-methoxy-

27. (8r,9s,13s,14s,17s)-2-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol

28. (8r,9s,13s,14s,17s)-2-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6h-cyclopenta[a]phenanthrene-3,17-diol

29. Smr000058478

30. Estra-1,3,5(10)-triene-3,17-diol, 2-methoxy-, (17b)-

31. (17beta)-2-methoxyestra-1(10),2,4-triene-3,17-diol

32. Pulmolar

33. 2-methoxy-.beta.-estradiol

34. Nsc 659853

35. Unii-6i2qw73sr5

36. Ccris 9405

37. 1lhw

38. Mfcd00010489

39. Opera_id_634

40. 2-methoxyestradiol Powder

41. 2-methoxyestradiol, Powder

42. 2-methoxy 17?-estradiol

43. M 6383

44. Schembl8796

45. 2-meo-e2

46. Lopac0_000739

47. Mls001076279

48. Mls006010142

49. Dtxsid3040938

50. Gtpl12058

51. Hms2230l22

52. Hms3262c20

53. Hms3412h22

54. Hms3676h22

55. Bcp02076

56. Zinc3818826

57. 2-methoxyestradiol [who-dd]

58. 2-methoxyoestradiol [mart.]

59. Tox21_500739

60. Bdbm50060957

61. Lmst02010035

62. S1233

63. Akos015901723

64. 2-methoxyestradiol, Analytical Standard

65. Bcp9000109

66. Ccg-204824

67. Cs-0176

68. Db02342

69. Lp00739

70. Sdccgsbi-0050717.p002

71. Smp2_000045

72. Ncgc00094082-03

73. Ncgc00094082-04

74. Ncgc00094082-13

75. Ncgc00261424-01

76. Ac-32086

77. As-19175

78. Bp-25393

79. Hy-12033

80. Eu-0100739

81. M2530

82. C05302

83. C74863

84. Ab00639611-09

85. Ab00639611_10

86. Sr-01000076000

87. 2-methoxy-1,3,5 (10)-estratriene-3,17beta-diol

88. 2-methoxyestra-1,3,5(10)-triene-3,17-diol #

89. Q4596897

90. Sr-01000076000-1

91. Brd-k44408410-001-20-0

92. (17?)-2-methoxyestra-1(10),2,4-triene-3,17-diol

93. (17?)-2-methoxyestra-1,3,5(10)-triene-3,17-diol

94. 17beta-2-methoxyestra-1,3,5(10)-triene-3,17-diol

95. Estra-1,3,5(10)-triene-3,17.beta.-diol, 2-methoxy-

96. Estra-1(10),2,4-triene-3,17-diol, 2-methoxy-, (17beta)-

97. (14beta,17beta)-2-methoxyestra-1(10),2,4-triene-3,17-diol

98. (17.beta.)-2-methoxyestra-1,3,5(10)-triene-3,17-diol

99. B3c40b85-1733-48fe-8418-a39011910d19

100. Estra-1,3,5(10)-triene-3,17-diol, 2-methoxy-, (17.beta.)-

2.4 Create Date

2005-06-08

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₂₆O₃
Molecular Weight	302.4 g/mol
XLogP3	4
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	1
Exact Mass	302.18819469 g/mol
Monoisotopic Mass	302.18819469 g/mol
Topological Polar Surface Area	49.7 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	425
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
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 breast cancer and inflammatory diseases such as rheumatoid arthritis.

5 Pharmacology and Biochemistry

5.1 Pharmacology

2-Methoxyestradiol belongs to the family of drugs called angiogenesis inhibitors. It also acts as a vasodilator.

5.2 MeSH Pharmacological Classification

Tubulin Modulators

Agents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES. (See all compounds classified as Tubulin Modulators.)

Antineoplastic Agents

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

5.3 Metabolism/Metabolites

In vivo metabolism, assessed using 24-h collections of urine from cancer patients treated with 2ME2 revealed that <0.01% of the total administered dose of 2ME2 is excreted unchanged in urine and about 1% excreted as glucuronides. Collectively, this suggests that glucuronidation and subsequent urinary excretion are elimination pathways for 2ME2.

2-O-methoxyestradiol has known human metabolites that include 2-Methoxy-estradiol-17beta 3-glucuronide.

2-O-methoxyestradiol is a known human metabolite of 2-hydroxyestradiol.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

5.4 Mechanism of Action

2-Methoxyestradiol is an angiogenesis inhibitor, and has been shown to attack both tumor cells and their blood supply in preclinical testing. 2-methoxyestradiol is a naturally occurring estrogen metabolite but has no undesired estrogenic activity.

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