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ACTIVE PHARMA INGREDIENTS

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Chemistry

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Also known as: 149882-10-0, Osi-211, Lurtotecan [inn], 4j1l80t08i, Gg-211, Nx-211

Molecular Formula

C₂₈H₃₀N₄O₆

Molecular Weight

518.6 g/mol

InChI Key

RVFGKBWWUQOIOU-NDEPHWFRSA-N

FDA UNII

4J1L80T08I

Lurtotecan is a semisynthetic analogue of camptothecin with antineoplastic activity. Lurtotecan selectively stabilizes the topoisomerase I-DNA covalent complex and forms an enzyme-drug-DNA ternary complex. As a consequence of the formation of this complex, both the initial cleavage reaction and religation steps are inhibited and subsequent collision of the replication fork with the cleaved strand of DNA results in inhibition of DNA replication, double strand DNA breakage and triggering of apoptosis. Independent from DNA replication inhibition, lurtotecan also inhibits RNA synthesis, multi-ubiquitination and degradation of topoisomerase I and chromatin reorganization.

1 2D Structure

Lurtotecan

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(18S)-18-ethyl-18-hydroxy-2-[(4-methylpiperazin-1-yl)methyl]-6,9,20-trioxa-13,24-diazahexacyclo[12.11.0.03,12.05,10.015,24.017,22]pentacosa-1,3,5(10),11,13,15,17(22)-heptaene-19,23-dione

2.1.2 InChI

InChI=1S/C28H30N4O6/c1-3-28(35)20-11-22-25-18(14-32(22)26(33)19(20)15-38-27(28)34)17(13-31-6-4-30(2)5-7-31)16-10-23-24(12-21(16)29-25)37-9-8-36-23/h10-12,35H,3-9,13-15H2,1-2H3/t28-/m0/s1

2.1.3 InChI Key

RVFGKBWWUQOIOU-NDEPHWFRSA-N

2.1.4 Canonical SMILES

CCC1(C2=C(COC1=O)C(=O)N3CC4=C(C5=CC6=C(C=C5N=C4C3=C2)OCCO6)CN7CCN(CC7)C)O

2.1.5 Isomeric SMILES

CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=C(C5=CC6=C(C=C5N=C4C3=C2)OCCO6)CN7CCN(CC7)C)O

2.2 Other Identifiers

2.2.1 UNII

4J1L80T08I

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 7-(4-methylpiperazinomethylene)-10,11-ethylenedioxy-20(s)-camptothecin

2. Gg-211

3. Gg211

4. Gi 147211

5. Gi-147211

6. Gi147211

7. Gl 147211c

8. Gl-147211c

9. Gl147211c

10. Nx 211

11. Nx-211

12. Nx211 Cpd

13. Osi 211

14. Osi-211

15. Osi211

2.3.2 Depositor-Supplied Synonyms

1. 149882-10-0

2. Osi-211

3. Lurtotecan [inn]

4. 4j1l80t08i

5. Gg-211

6. Nx-211

7. Gi-147211

8. Gg 211; Gi 147211; Lurtotecan; Nx 211; Osi 211

9. Chembl341028

10. (s)-8-ethyl-8-hydroxy-15-((4-methylpiperazin-1-yl)methyl)-11,14-dihydro-2h-[1,4]dioxino[2,3-g]pyrano[3',4':6,7]indolizino[1,2-b]quinoline-9,12(3h,8h)-dione

11. Osi 211

12. Gg 211

13. Nx 211

14. Gi 147211

15. Unii-4j1l80t08i

16. Nx211 Cpd

17. Lurtotecan [who-dd]

18. Schembl19208

19. Chembl305666

20. Osi211

21. Dtxsid30164422

22. Gg211

23. Gl147211c

24. Gl 147211c

25. Bdbm50036130

26. Gw-211

27. Zinc22010625

28. Db12222

29. Gl-147211c

30. 11h-1,4-dioxino(2,3-g)pyrano(3',4':6,7)indolizino(1,2-b)quinoline-9,12(8h,14h)-dione, 8-ethyl-2,3-dihydro-8-hydroxy-15-((4-methyl-1-piperazinyl)methyl)-, (8s)-

31. Gi147211

32. Hy-13670

33. Cs-0007547

34. A936765

35. Q6704977

36. D-myo-inositol2,4,5-trisphosphate,hexaammoniumsalt

37. 7-(4-methylpiperazinomethylene)-10,11-ethylenedioxy-20(s)-camptothecin

38. (18s)-18-ethyl-18-hydroxy-2-[(4-methylpiperazin-1-yl)methyl]-6,9,20-trioxa-13,24-diazahexacyclo[12.11.0.03,12.05,10.015,24.017,22]pentacosa-1,3,5(10),11,13,15,17(22)-heptaene-19,23-dione

39. (8s)-8-ethyl-2,3-dihydro-8-hydroxy-15-((4-methyl-1-piperazinyl)methyl)-11h-p-dioxino(2,3-g)pyrano(3',4':6,7)indolizino(1,2-b)quinoline-9,12(8h,14h)-dione

40. (s)-8-ethyl-8-hydroxy-15-((4-methylpiperazin-1-yl)methyl)-2,3,11,14-tetrahydro-12h-[1,4]dioxino[2,3-g]pyrano[3',4':6,7]indolizino[1,2-b]quinoline-9,12(8h)-dione

41. 11h-1,4-dioxino(2,3-g)pyrano(3',4':6,7)indolizino(1,2-b)quinoline-9,12(8h,14h)-dione, 8-ethyl-2,3-dihydro-8-hydroxy-15-((4-methyl-1-piperazinyl)methyl)-, (s)

42. 8-ethyl-8-hydroxy-15-(4-methylhexahydro-1-pyrazinylmethyl)-(8s)-2,3,8,9,12,14-hexahydro-11h-[1,4]dioxino[2,3-g]pyrano[3'',4'':6,7]indolizino[1,2-b]quinoline-9,12-dione With Trifluoroaceticacid

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₂₈H₃₀N₄O₆
Molecular Weight	518.6 g/mol
XLogP3	0.3
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	3
Exact Mass	518.21653469 g/mol
Monoisotopic Mass	518.21653469 g/mol
Topological Polar Surface Area	105 Å²
Heavy Atom Count	38
Formal Charge	0
Complexity	1070
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1