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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
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 Weight 668.5 g/mol
Molecular Formula C29H33O16P
XLogP3-0.7
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count16
Rotatable Bond Count7
Exact Mass668.15062196 g/mol
Monoisotopic Mass668.15062196 g/mol
Topological Polar Surface Area207 Ų
Heavy Atom Count46
Formal Charge0
Complexity1140
Isotope Atom Count0
Defined Atom Stereocenter Count10
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Antineoplastic Agents

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


4.2 FDA Pharmacological Classification
4.2.1 Pharmacological Classes
Topoisomerase Inhibitors [MoA]; Topoisomerase Inhibitor [EPC]

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