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Synopsis

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Data Compilation #PharmaFlow

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Chemistry

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Also known as: 117091-64-2, Etopofos, Etopophos, Etopophos preservative free, Bmy 40481, Vepeside

Molecular Formula

C₂₉H₃₃O₁₆P

Molecular Weight

668.5 g/mol

InChI Key

LIQODXNTTZAGID-OCBXBXKTSA-N

FDA UNII

528XYJ8L1N

Etoposide Phosphate is a phosphate salt of a semisynthetic derivative of podophyllotoxin. Etoposide binds to the enzyme topoisomerase II, inducing double-strand DNA breaks, inhibiting DNA repair, and resulting in decreased DNA synthesis and tumor cell proliferation. Cells in the S and G2 phases of the cell cycle are most sensitive to this agent. (NCI04)

1 2D Structure

Etoposide Phosphate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[4-[(5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-8-oxo-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-9-yl]-2,6-dimethoxyphenyl] dihydrogen phosphate

2.1.2 InChI

InChI=1S/C29H33O16P/c1-11-38-9-20-27(42-11)23(30)24(31)29(43-20)44-25-14-7-17-16(40-10-41-17)6-13(14)21(22-15(25)8-39-28(22)32)12-4-18(36-2)26(19(5-12)37-3)45-46(33,34)35/h4-7,11,15,20-25,27,29-31H,8-10H2,1-3H3,(H2,33,34,35)/t11-,15+,20-,21-,22+,23-,24-,25-,27-,29+/m1/s1

2.1.3 InChI Key

LIQODXNTTZAGID-OCBXBXKTSA-N

2.1.4 Canonical SMILES

CC1OCC2C(O1)C(C(C(O2)OC3C4COC(=O)C4C(C5=CC6=C(C=C35)OCO6)C7=CC(=C(C(=C7)OC)OP(=O)(O)O)OC)O)O

2.1.5 Isomeric SMILES

C[C@@H]1OC[C@@H]2[C@@H](O1)[C@@H]([C@H]([C@@H](O2)O[C@H]3[C@H]4COC(=O)[C@@H]4[C@@H](C5=CC6=C(C=C35)OCO6)C7=CC(=C(C(=C7)OC)OP(=O)(O)O)OC)O)O

2.2 Other Identifiers

2.2.1 UNII

528XYJ8L1N

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Bmy 40481-30

2. Bmy-40481

3. Bmy-40481-30

4. Etophos

5. Etopofos

6. Etopophos

2.3.2 Depositor-Supplied Synonyms

1. 117091-64-2

2. Etopofos

3. Etopophos

4. Etopophos Preservative Free

5. Bmy 40481

6. Vepeside

7. Etoposide Phosphate [usan]

8. Bmy-40481

9. 528xyj8l1n

10. Vp16

11. Etophos

12. Etoposide Phosphate (usan)

13. Etoposide 4'-phosphate

14. Unii-528xyj8l1n

15. Etoposide-phosphate

16. Etopophos (tn)

17. Ncgc00185753-01

18. Eposin Etopophos Vepesid Vp16

19. Etoposide Phosphate (etopophos)

20. Chembl1200645

21. Etoposide Phosphate [mi]

22. Schembl13318053

23. Chebi:135867

24. Etoposide Phosphate [vandf]

25. Etoposide Phosphate [mart.]

26. Ex-a3595

27. Zinc3920020

28. Bdbm50247889

29. Etoposide Phosphate [usp-rs]

30. Etoposide Phosphate [who-dd]

31. Mfcd00270859

32. Akos025311200

33. Etoposide Phosphate [orange Book]

34. Ncgc00185753-04

35. 4'-demethylepipodophyllotoxin 9-(4,6-o-(r)-ethylidene-beta-d-glucopyranoside), 4'-(dihydrogen Phosphate)

36. As-12896

37. Hy-13630

38. Etoposide Phosphate [usp Monograph]

39. Cs-0007496

40. D04107

41. 091e642

42. J-003505

43. Q27260984

44. [4-[(5s,5ar,8ar,9r)-5-[[(2r,4ar,6r,7r,8r,8as)-7,8-dihydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-8-oxo-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[5,6-f][1,3]benzodioxol-9-yl]-2

45. 4'-demethylepipodophyllotoxin 9-(4,6-o-(r)-ethylidene-.beta.-d-glucopyranoside), 4'-(dihydrogen Phosphate)

46. Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5ah)-one, 5-(3,5-dimethoxy-4-(phosphonooxy)phenyl)-9-((4,6-o-ethylidene-.beta.-d-glucopyranosyl)oxy)-5,8,8a,9-tetrahydro-, (5r-(5.alpha.,5a.beta.,8a.alpha.,9.beta.(r*)))-

47. Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5ah)-one, 5-(3,5-dimethoxy-4-(phosphonooxy)phenyl)-9-((4,6-o-ethylidene-beta-d-glucopyranosyl)oxy)-5,8,8a,9-tetrahydro-, (5r-(5alpha,5abeta,8aalpha,9beta(r*)))-

2.4 Create Date

2006-07-28

3 Chemical and Physical Properties

Molecular Formula	C₂₉H₃₃O₁₆P
Molecular Weight	668.5 g/mol
XLogP3	-0.7
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	16
Rotatable Bond Count	7
Exact Mass	668.15062196 g/mol
Monoisotopic Mass	668.15062196 g/mol
Topological Polar Surface Area	207 Å²
Heavy Atom Count	46
Formal Charge	0
Complexity	1140
Isotope Atom Count	0
Defined Atom Stereocenter Count	10
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1